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Grafton Manour Estate—A Rare Chesapeake Waterfront Legacy. Embrace the quiet grandeur of Grafton Manour Estate, an 86±-acre peninsula wrapped by approximately 1.5± miles of shoreline with panoramic water views in every direction. Bordered by Briary Cove to the east, Harris Creek to the southeast, and Waterhole Cove to the west, this extraordinary property blends pastoral elegance with true Chesapeake Bay access. Property Highlights: 86± acres with sweeping water vistas, open fields, and meticulously manicured lawns. Varied shoreline: riprap, sandy beaches, and natural grasses. Deep-water pier with 7' MLW, suitable for larger boats and sailboats; direct access to the Chesapeake Bay. Two subdivided, waterfront lots included: Lot 2: 6± acres on Briary Cove (east side), with prior SDA approval for a 4-bedroom home (re-evaluation required). Lot 3: 5.5± acres is located on Waterhole Cove (west side), with prior SDA approval for a 4-bedroom home (re-evaluation required). Historic Lowes Family Cemetery on the west side, dating to the 1700s. Land mix: approximately 60± acres tillable; balance in timber and lawns along the eastern shoreline. Main Residence: Custom-built in 2004, approx. 7,400 sq ft, four en suite bedrooms. Primary suite in the main-floor north wing with private laundry, library, office/workout room, and sunroom. Dramatic great room and dining room with vaulted ceiling, chestnut beams, cedar ceiling, and a raised-hearth stone fireplace. Signature silo feature: 1st and 2nd floors: full baths serving two bedrooms. 3rd floor: window-lined observatory with 360° views across the estate. Wide-plank wood floors milled from the same chestnut as the great room beams. Exceptional craftsmanship throughout; a must-see for discerning buyers. Guest/Farmhouse: Approx. 2,000 sq ft with three bedrooms and one bath. Two wood-burning fireplaces (living room and dining room). Charming and versatile for guests, caretakers, or rental income. Barns and Outbuildings: Large heated barn with concrete floors, three overhead doors, expansive workbench, and open-loft recreation room. Attached a conditioned office/hunters’ lodge with full bath and hookups for laundry and kitchenette. Adjacent irrigated, fenced raised-bed garden; nearby small apple orchard. Additional smaller barn for equipment or livestock. Lifestyle and Possibilities: Ideal for a family compound, equestrian pursuits, or an exclusive retreat. Premier sporting opportunities: shoreline waterfowl, whitetail deer, and turkey. Ample acreage and infrastructure for hobby farming, vineyards, or conservation. A once-in-a-generation opportunity to own an iconic waterfront estate where open water, open sky, and open fields meet. Follow the country road home to the place you belong—Grafton Manour Estate. By appointment only. Do not enter the property by water or land without the listing agent. The property is monitored by camera surveillance 24/7.

22101 Grafton Manour Ln, Wittman

Listing courtesy of Meredith Fine Properties. Contact: 4107458060

$5,295,000

First time offering in Morgans Point. Custom built estate designed by architect Lauren Dianich of Atelier 11, this elegant Georgian-style brick and shingle residence offers over 5,200± square feet of thoughtfully designed living space filled with natural light and panoramic water views of the Tred Avon River. Set on 5± acres, the home is crafted for both refined entertaining and private, relaxed waterfront living. The heart of the home is the River Room, surrounded by windows that frame sweeping views of the Tred Avon River. Hardwood floors by Universal Floors in D.C. feature an inlaid compass medallion that points to magnetic north, creating a distinctive focal point. A fireplace anchors the space, with a screened-in porch with its own fireplace just beyond, perfect for enjoying chilly evenings. The chef’s kitchen is equipped with professional-grade appliances including a Wolf range and double wall ovens, Sub-Zero refrigerator, Asko full-size dishwasher, and Fisher & Paykel dishwasher drawers. A large island offers a wine fridge and illuminated display cabinetry, while the butler’s pantry—complete with an additional refrigerator and charming porthole windows framing water views—enhances the home’s functionality. Additionally, a custom-built oval wet bar with a two-drawer Sub-Zero refrigerator offers substantial cabinetry. This space provides a natural gathering point for entertaining. A large mudroom with powder room provides convenience for busy households. Also on the main level are a library with floor-to-ceiling shelving and a wood-burning fireplace, a fitness room with water vistas, a formal half-bath, and a first-floor en-suite bedroom ideal for guests. A dedicated utility entrance allows for discreet service and maintenance without entering the main living spaces. A 25kW standby generator provides reliable backup power for the main residence, offering peace of mind during outages. Upstairs, the primary suite with a gas fireplace serves as a retreat, with its spacious bathroom offering a shower, jetted soaking tub, and two walk-in closets—one with its own half-bath. Additional bedrooms include an upper-level en-suite and family-friendly accommodations, all supported by a conveniently located laundry room. Completing this floor is a private office with a gas fireplace and panoramic river views, offering an inspiring space for work or study. A generously sized, detached three-car garage includes a second-floor guest quarters with a kitchenette, washer and dryer, and en-suite bedroom, where windows capture tranquil water views. Outdoors, enjoy resort-like amenities including a heated pool with a fully retractable cover and a pool pavilion with its own bathroom and outdoor shower. The grounds are beautifully landscaped and designed for relaxation, with serene river views visible from nearly every room of the property. This rare offering seamlessly blends architectural pedigree, modern luxury, and a spectacular setting on the Tred Avon River—an exceptional opportunity to experience Eastern Shore living at its finest.

4 Beds ⋅ 7 Baths

First time offering in Morgans Point. Custom built estate designed by architect Lauren Dianich of Atelier 11, this elegant Georgian-style brick and shingle residence offers over 5,200± square feet of thoughtfully designed living space filled with natural light and panoramic water views of the Tred Avon River. Set on 5± acres, the home is crafted for both refined entertaining and private, relaxed waterfront living. The heart of the home is the River Room, surrounded by windows that frame sweeping views of the Tred Avon River. Hardwood floors by Universal Floors in D.C. feature an inlaid compass medallion that points to magnetic north, creating a distinctive focal point. A fireplace anchors the space, with a screened-in porch with its own fireplace just beyond, perfect for enjoying chilly evenings. The chef’s kitchen is equipped with professional-grade appliances including a Wolf range and double wall ovens, Sub-Zero refrigerator, Asko full-size dishwasher, and Fisher & Paykel dishwasher drawers. A large island offers a wine fridge and illuminated display cabinetry, while the butler’s pantry—complete with an additional refrigerator and charming porthole windows framing water views—enhances the home’s functionality. Additionally, a custom-built oval wet bar with a two-drawer Sub-Zero refrigerator offers substantial cabinetry. This space provides a natural gathering point for entertaining. A large mudroom with powder room provides convenience for busy households. Also on the main level are a library with floor-to-ceiling shelving and a wood-burning fireplace, a fitness room with water vistas, a formal half-bath, and a first-floor en-suite bedroom ideal for guests. A dedicated utility entrance allows for discreet service and maintenance without entering the main living spaces. A 25kW standby generator provides reliable backup power for the main residence, offering peace of mind during outages. Upstairs, the primary suite with a gas fireplace serves as a retreat, with its spacious bathroom offering a shower, jetted soaking tub, and two walk-in closets—one with its own half-bath. Additional bedrooms include an upper-level en-suite and family-friendly accommodations, all supported by a conveniently located laundry room. Completing this floor is a private office with a gas fireplace and panoramic river views, offering an inspiring space for work or study. A generously sized, detached three-car garage includes a second-floor guest quarters with a kitchenette, washer and dryer, and en-suite bedroom, where windows capture tranquil water views. Outdoors, enjoy resort-like amenities including a heated pool with a fully retractable cover and a pool pavilion with its own bathroom and outdoor shower. The grounds are beautifully landscaped and designed for relaxation, with serene river views visible from nearly every room of the property. This rare offering seamlessly blends architectural pedigree, modern luxury, and a spectacular setting on the Tred Avon River—an exceptional opportunity to experience Eastern Shore living at its finest.

5381 Morgans Point Dr, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$4,650,000

Substantial 27,000+ sq. ft. warehouse in a prime commercial/light industrial location, one-mile from Route 50 and downtown Easton, MD. Subject to current lease.

8880 Mistletoe Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$3,495,000

Rare opportunity to acquire a well-appointed home with immense views and convenient proximity to St Michaels. Ideally located by land and sea in Chance Hope Farm on the Miles River at the confluence of Eastern Bay, this stunning, classic eastern shore brick colonial has everything the most decerning buyer needs. This Daffin custom-built home features a generous, main-level primary suite featuring a spa-like bath with heated floors, a large soaking tub and separate shower, and two walk-in closets. The kitchen is a chef’s dream, featuring high-end stainless-steel appliances, a wine cooler, a warming drawer, and a massive island. There are also formal living and dining rooms, two office spaces, a recreation room, and a river room that enjoys views of Eastern Bay and beyond. The park-like lot has 220+/- feet of rip-rapped shoreline, a private pier with 3’ of MLW, lush landscaping, and a waterside deck with an outdoor kitchen.

Rare opportunity to acquire a well-appointed home with immense views and convenient proximity to St Michaels. Ideally located by land and sea in Chance Hope Farm on the Miles River at the confluence of Eastern Bay, this stunning, classic eastern shore brick colonial has everything the most decerning buyer needs. This Daffin custom-built home features a generous, main-level primary suite featuring a spa-like bath with heated floors, a large soaking tub and separate shower, and two walk-in closets. The kitchen is a chef’s dream, featuring high-end stainless-steel appliances, a wine cooler, a warming drawer, and a massive island. There are also formal living and dining rooms, two office spaces, a recreation room, and a river room that enjoys views of Eastern Bay and beyond. The park-like lot has 220+/- feet of rip-rapped shoreline, a private pier with 3’ of MLW, lush landscaping, and a waterside deck with an outdoor kitchen.

24678 New Post Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$3,250,000

Experience tranquil waterfront living in this stunning 4BR/4.5 BA home sited on .68 acres overlooking the Miles River. This cottage-style home was completely renovated by Focus Construction Featuring exquisite architectural and interior design details throughout and include custom built-ins, and a large dual-sided gas fireplace. The open floor plan offers breathtaking river views from nearly every room and the main living spaces are perfectly suited for family living and entertaining. The first floor boasts a gourmet kitchen with high-end stainless and custom cabinetry, quartz counters, a scullery, and an adjacent dining area with sweeping waterfront views. Relax by the dual-sided fireplace in the living room, which connects seamlessly to the waterside sunroom. The spacious first floor primary suite offers a luxurious ensuite bath with a dual vanity, glass-enclosed walk-in shower, large walk-in closet. There is an upstairs Primary Suite and a separate guest bedroom and bath. Additionally, there is a private suite with dedicated staircase, large efficiency-style layout with bedroom and sitting area and private bathroom/closet. Completing the property is an oversized attached 2+car garage, providing additional storage and functionality. On the waterside of the home, there is a wall of glass doors leading out to a waterside deck and an inground pool. The property is further improved with a fenced in backyard, mature landscaping, a concrete bulkheaded, a private dock with boat lift (8,000 lbs.). Minutes to downtown Saint Michaels and a short drive to Easton, this exceptional property combines waterfront beauty and a turn-key situation in one of Saint Michaels most desirable neighborhoods.

Experience tranquil waterfront living in this stunning 4BR/4.5 BA home sited on .68 acres overlooking the Miles River. This cottage-style home was completely renovated by Focus Construction Featuring exquisite architectural and interior design details throughout and include custom built-ins, and a large dual-sided gas fireplace. The open floor plan offers breathtaking river views from nearly every room and the main living spaces are perfectly suited for family living and entertaining. The first floor boasts a gourmet kitchen with high-end stainless and custom cabinetry, quartz counters, a scullery, and an adjacent dining area with sweeping waterfront views. Relax by the dual-sided fireplace in the living room, which connects seamlessly to the waterside sunroom. The spacious first floor primary suite offers a luxurious ensuite bath with a dual vanity, glass-enclosed walk-in shower, large walk-in closet. There is an upstairs Primary Suite and a separate guest bedroom and bath. Additionally, there is a private suite with dedicated staircase, large efficiency-style layout with bedroom and sitting area and private bathroom/closet. Completing the property is an oversized attached 2+car garage, providing additional storage and functionality. On the waterside of the home, there is a wall of glass doors leading out to a waterside deck and an inground pool. The property is further improved with a fenced in backyard, mature landscaping, a concrete bulkheaded, a private dock with boat lift (8,000 lbs.). Minutes to downtown Saint Michaels and a short drive to Easton, this exceptional property combines waterfront beauty and a turn-key situation in one of Saint Michaels most desirable neighborhoods.

601 Cove Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$2,995,000

Nestled on just over 3 picturesque acres along the Miles River, this exceptional waterfront estate is the epitome of Eastern Shore charm. Renovated in 2017, the beautifully appointed residence is designed to maximize its stunning setting, with breathtaking water views from most rooms and an abundance of natural light throughout. The thoughtfully designed kitchen serves as the heart of the home and is ideal for both everyday living and entertaining. Featuring a large center island, high-end stainless steel appliances, custom cabinetry, and generous workspace, the kitchen flows seamlessly into the dining area and inviting river room, where expansive windows frame the spectacular waterfront views. The outdoor living spaces are equally impressive. A stunning negative-edge pool with elegant fire features creates a private resort-like atmosphere, while impeccably maintained grounds provide the perfect backdrop for relaxing or hosting family and friends. The rip-rapped shoreline leads to a private dock equipped with two boat lifts and approximately five feet of mean low water, offering easy access to the Miles River and the Chesapeake Bay beyond. Multiple sheds and large barn provide for storage of your boat and more. Whether you're working remotely, enjoying a weekend retreat, or seeking a year-round residence, this property offers exceptional convenience. High-speed Easton Velocity internet makes working from home effortless, while the property's location provides quick access to Easton Airport, the Easton Bypass, and the shops, restaurants, and waterfront attractions of St. Michaels. This extraordinary offering presents a rare opportunity to experience the very best of waterfront living on Maryland's Eastern Shore.

3 Beds ⋅ 5 Baths

Nestled on just over 3 picturesque acres along the Miles River, this exceptional waterfront estate is the epitome of Eastern Shore charm. Renovated in 2017, the beautifully appointed residence is designed to maximize its stunning setting, with breathtaking water views from most rooms and an abundance of natural light throughout. The thoughtfully designed kitchen serves as the heart of the home and is ideal for both everyday living and entertaining. Featuring a large center island, high-end stainless steel appliances, custom cabinetry, and generous workspace, the kitchen flows seamlessly into the dining area and inviting river room, where expansive windows frame the spectacular waterfront views. The outdoor living spaces are equally impressive. A stunning negative-edge pool with elegant fire features creates a private resort-like atmosphere, while impeccably maintained grounds provide the perfect backdrop for relaxing or hosting family and friends. The rip-rapped shoreline leads to a private dock equipped with two boat lifts and approximately five feet of mean low water, offering easy access to the Miles River and the Chesapeake Bay beyond. Multiple sheds and large barn provide for storage of your boat and more. Whether you're working remotely, enjoying a weekend retreat, or seeking a year-round residence, this property offers exceptional convenience. High-speed Easton Velocity internet makes working from home effortless, while the property's location provides quick access to Easton Airport, the Easton Bypass, and the shops, restaurants, and waterfront attractions of St. Michaels. This extraordinary offering presents a rare opportunity to experience the very best of waterfront living on Maryland's Eastern Shore.

27625 Parkway Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$2,995,000

"Cypress Lodge" - Tucked away on a private waterfront lot along the Tred Avon River, this striking contemporary-style residence offers expansive water views, exceptional privacy, and thoughtfully designed indoor-outdoor living. The 3-bedroom, 5-bath home features an open floorplan filled with natural light, highlighted by soaring vaulted cathedral ceilings and clean architectural lines that create a bright, airy feel throughout. Designed to embrace its waterfront setting, the home seamlessly connects spacious living areas with multiple outdoor entertaining spaces overlooking the river. The well-thought-out outdoor living space was designed to fully maximize the property’s incredible waterfront setting, complete with a pool, outdoor fireplace, and covered pavilion overlooking both the pool and the water. Whether hosting guests or enjoying a quiet evening at home, the outdoor spaces offer a seamless extension of the home’s contemporary design and relaxed Eastern Shore lifestyle. Additional exterior amenities include a private dock, private tennis court, and hot tub, all surrounded by mature landscaping and a peaceful setting that enhances the property’s sense of seclusion. Ideally located just outside of Easton, the property provides convenient access to Washington, D.C., Baltimore, and Philadelphia, making it an exceptional full-time residence or weekend getaway within reach of several major metropolitan areas.

3 Beds ⋅ 5 Baths

"Cypress Lodge" - Tucked away on a private waterfront lot along the Tred Avon River, this striking contemporary-style residence offers expansive water views, exceptional privacy, and thoughtfully designed indoor-outdoor living. The 3-bedroom, 5-bath home features an open floorplan filled with natural light, highlighted by soaring vaulted cathedral ceilings and clean architectural lines that create a bright, airy feel throughout. Designed to embrace its waterfront setting, the home seamlessly connects spacious living areas with multiple outdoor entertaining spaces overlooking the river. The well-thought-out outdoor living space was designed to fully maximize the property’s incredible waterfront setting, complete with a pool, outdoor fireplace, and covered pavilion overlooking both the pool and the water. Whether hosting guests or enjoying a quiet evening at home, the outdoor spaces offer a seamless extension of the home’s contemporary design and relaxed Eastern Shore lifestyle. Additional exterior amenities include a private dock, private tennis court, and hot tub, all surrounded by mature landscaping and a peaceful setting that enhances the property’s sense of seclusion. Ideally located just outside of Easton, the property provides convenient access to Washington, D.C., Baltimore, and Philadelphia, making it an exceptional full-time residence or weekend getaway within reach of several major metropolitan areas.

6906 Travelers Rest Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$2,795,000

Absolutely stunning mid-century contemporary estate offering a private , park-like setting, with heated swimming pool, pavilion, luxurious fully equipped outdoor- kitchen, outdoor shower, in -ground hot tub ,tennis court, and maintenance -free Azek pier with new 30K lb. boat lift. Meticulously maintained inside and out! Professionally landscaped with WiFi controlled front/rear irrigation system.The superbly designed and crafted home offers an open floor-plan with 4 bedrooms and an office, 3.5 designer baths with heated floors,, a magnificent gourmet kitchen, upper and lower level living areas providing outstanding functionality. Breathtaking water- views and protected shoreline! This is an outstanding turn-key property that comes beautifully furnished !

Absolutely stunning mid-century contemporary estate offering a private , park-like setting, with heated swimming pool, pavilion, luxurious fully equipped outdoor- kitchen, outdoor shower, in -ground hot tub ,tennis court, and maintenance -free Azek pier with new 30K lb. boat lift. Meticulously maintained inside and out! Professionally landscaped with WiFi controlled front/rear irrigation system.The superbly designed and crafted home offers an open floor-plan with 4 bedrooms and an office, 3.5 designer baths with heated floors,, a magnificent gourmet kitchen, upper and lower level living areas providing outstanding functionality. Breathtaking water- views and protected shoreline! This is an outstanding turn-key property that comes beautifully furnished !

5837 Irish Creek Rd, Royal Oak

Listing courtesy of TTR Sotheby's International Realty. Contact:

$2,450,000

This exceptional waterfront estate was thoughtfully designed and custom built by its current owner after years of meticulous research and planning, drawing architectural inspiration from the timeless elegance of Colonial Williamsburg. Constructed with an uncompromising commitment to quality and authenticity, this remarkable residence is a true showcase of enduring craftsmanship. Offering 6 bedrooms, 5 full baths, 1 half bath, and an impressive 7 fireplaces, the home is rich with period-inspired architectural details. From the Flemish Bond brickwork and cypress plank siding to the one-of-a-kind, 2.5-inch-thick solid cherry and mahogany entry door, every element was carefully selected to reflect both beauty and longevity. Exceptional custom woodwork is found throughout the home, complemented by stunning Brazilian Teak, Brazilian Cherry, and White Oak hardwood flooring. Adding to the home’s distinction are custom light fixtures crafted by Virginia MetalCrafters, among the final pieces ever produced by the renowned Virginia manufacturer. The chef’s kitchen was designed with both elegance and functionality in mind, featuring custom cherry cabinetry, dual sinks, dual dishwashers, dual Sub-Zero refrigerator and freezer units, and abundant workspace for entertaining or everyday living. The inviting living room showcases custom built-in cabinetry and a magnificent fireplace designed to accommodate both a traditional open hearth and a wood-burning stove. The spacious first-floor primary suite offers a private retreat complete with a luxurious en-suite bath featuring a jetted soaking tub, walk-in shower, and generous walk-in closet. Upstairs, five additional bedrooms enjoy abundant natural light, southern exposure, and beautiful water views. Nearly every principal living space throughout the home captures breathtaking southern-facing waterfront vistas, creating a seamless connection between the interior and its spectacular setting. Outdoor living is equally impressive. A gracious waterside patio with elegant bifurcated brick steps leads to the expansive 720-square-foot swimming pool, creating an ideal space for relaxing or entertaining. Beyond, the riprap-protected shoreline leads to a custom private dock with approximately 3 feet of water depth at mean low water (MLW), providing convenient access to the water. A rare offering on Maryland’s Eastern Shore, this extraordinary waterfront home blends historic architectural inspiration with modern comfort and exceptional craftsmanship. Designed and built to stand the test of time, it is a legacy property meant to be enjoyed for generations.

6 Beds ⋅ 6 Baths

This exceptional waterfront estate was thoughtfully designed and custom built by its current owner after years of meticulous research and planning, drawing architectural inspiration from the timeless elegance of Colonial Williamsburg. Constructed with an uncompromising commitment to quality and authenticity, this remarkable residence is a true showcase of enduring craftsmanship. Offering 6 bedrooms, 5 full baths, 1 half bath, and an impressive 7 fireplaces, the home is rich with period-inspired architectural details. From the Flemish Bond brickwork and cypress plank siding to the one-of-a-kind, 2.5-inch-thick solid cherry and mahogany entry door, every element was carefully selected to reflect both beauty and longevity. Exceptional custom woodwork is found throughout the home, complemented by stunning Brazilian Teak, Brazilian Cherry, and White Oak hardwood flooring. Adding to the home’s distinction are custom light fixtures crafted by Virginia MetalCrafters, among the final pieces ever produced by the renowned Virginia manufacturer. The chef’s kitchen was designed with both elegance and functionality in mind, featuring custom cherry cabinetry, dual sinks, dual dishwashers, dual Sub-Zero refrigerator and freezer units, and abundant workspace for entertaining or everyday living. The inviting living room showcases custom built-in cabinetry and a magnificent fireplace designed to accommodate both a traditional open hearth and a wood-burning stove. The spacious first-floor primary suite offers a private retreat complete with a luxurious en-suite bath featuring a jetted soaking tub, walk-in shower, and generous walk-in closet. Upstairs, five additional bedrooms enjoy abundant natural light, southern exposure, and beautiful water views. Nearly every principal living space throughout the home captures breathtaking southern-facing waterfront vistas, creating a seamless connection between the interior and its spectacular setting. Outdoor living is equally impressive. A gracious waterside patio with elegant bifurcated brick steps leads to the expansive 720-square-foot swimming pool, creating an ideal space for relaxing or entertaining. Beyond, the riprap-protected shoreline leads to a custom private dock with approximately 3 feet of water depth at mean low water (MLW), providing convenient access to the water. A rare offering on Maryland’s Eastern Shore, this extraordinary waterfront home blends historic architectural inspiration with modern comfort and exceptional craftsmanship. Designed and built to stand the test of time, it is a legacy property meant to be enjoyed for generations.

7250 Maxmore Creek Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$2,395,000

Waterfront Living Reimagined in San Domingo Cove! Coastal influences, exceptional craftsmanship and meticulous attention to detail define this immaculate custom waterfront home. Dramatic two-story family room, soaring ceilings, walls of windows and an open staircase with stainless steel cable railings create a striking architectural statement. The second-story catwalk and loft overlook the main living area, while expansive windows frame the pool and water views beyond. Designed for both everyday living and entertaining, the chef's kitchen features quartz countertops, stainless steel appliances and extensive soft-close cabinetry. An oversized island provides generous prep space and seating, while the bright eat-in dining area and separate beverage station offer exceptional space for casual dining and entertaining. Bamboo flooring extends throughout the living spaces, adding warmth and continuity to the home's contemporary coastal design. The thoughtfully designed floor plan includes a first-floor primary suite overlooking the pool and San Domingo Creek, two additional ensuite bedrooms and a spacious bonus room with a full bath, ideal as a guest suite, home office, studio, media room or fourth bedroom. Outside, beautifully landscaped grounds frame the waterside pool and expansive patio, while the shared private pier with a boat lift and floating dock provides easy access for boating, kayaking and paddleboarding. An oversized three-car garage offers ample space for vehicles, storage and recreational equipment. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the St. Michaels Nature Trail. This distinctive property combines waterfront privacy with convenient access to the shops, restaurants, marinas and waterfront attractions of St. Michaels.

Waterfront Living Reimagined in San Domingo Cove! Coastal influences, exceptional craftsmanship and meticulous attention to detail define this immaculate custom waterfront home. Dramatic two-story family room, soaring ceilings, walls of windows and an open staircase with stainless steel cable railings create a striking architectural statement. The second-story catwalk and loft overlook the main living area, while expansive windows frame the pool and water views beyond. Designed for both everyday living and entertaining, the chef's kitchen features quartz countertops, stainless steel appliances and extensive soft-close cabinetry. An oversized island provides generous prep space and seating, while the bright eat-in dining area and separate beverage station offer exceptional space for casual dining and entertaining. Bamboo flooring extends throughout the living spaces, adding warmth and continuity to the home's contemporary coastal design. The thoughtfully designed floor plan includes a first-floor primary suite overlooking the pool and San Domingo Creek, two additional ensuite bedrooms and a spacious bonus room with a full bath, ideal as a guest suite, home office, studio, media room or fourth bedroom. Outside, beautifully landscaped grounds frame the waterside pool and expansive patio, while the shared private pier with a boat lift and floating dock provides easy access for boating, kayaking and paddleboarding. An oversized three-car garage offers ample space for vehicles, storage and recreational equipment. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the St. Michaels Nature Trail. This distinctive property combines waterfront privacy with convenient access to the shops, restaurants, marinas and waterfront attractions of St. Michaels.

965 San Domingo, Saint Michaels

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$2,295,000

With its central Talbot County location and effortless one‑story layout, this move‑in ready waterfront retreat offers a rare blend of convenience, comfort, and stunning natural beauty. Set on more than two acres on Trippe Creek with 185' of water frontage—directly across from Talbot Country Club—the property enjoys an elevated vantage point with broad water views, a private pier, and a heated pool and hot tub all just minutes from the amenities of both Oxford and Easton. The 3,100‑plus square‑foot home is designed for easy living, with sweeping waterside views and a newly renovated primary suite featuring a luxurious private bath with a steam shower. Two additional bedrooms, a bunkroom plus three full baths provide ample space for guests. The gourmet eat‑in kitchen, formal dining room, large living room with fireplace, separate family room create a warm, flexible layout for everyday living and entertaining. A screened porch offers the perfect spot to enjoy the breeze off the creek. Thoughtful updates throughout the home preserve its beautiful hardwood floors, moldings, and character while introducing a fresh coastal palette, contemporary kitchen and baths, new roof and Hardie board siding, and numerous additional improvements. The grounds are exceptional—one of the most beautiful settings in the county—with mature specimen trees, curated landscaping, full yard and garden sprinkler system, invisible dog fence and uncommon topography that enhances both privacy and views. The dedicated nature preserve directly across the street ensures no future building. A waterfront property of this quality, setting, and convenience with no flood insurance required is a rare find. Added bonus--enjoy a front row seat without leaving your own property to enjoy TCC's incredible 4th of July fireworks! Don’t miss the opportunity to make 5920 Oxford Road your own.

3 Beds ⋅ 6 Baths

With its central Talbot County location and effortless one‑story layout, this move‑in ready waterfront retreat offers a rare blend of convenience, comfort, and stunning natural beauty. Set on more than two acres on Trippe Creek with 185' of water frontage—directly across from Talbot Country Club—the property enjoys an elevated vantage point with broad water views, a private pier, and a heated pool and hot tub all just minutes from the amenities of both Oxford and Easton. The 3,100‑plus square‑foot home is designed for easy living, with sweeping waterside views and a newly renovated primary suite featuring a luxurious private bath with a steam shower. Two additional bedrooms, a bunkroom plus three full baths provide ample space for guests. The gourmet eat‑in kitchen, formal dining room, large living room with fireplace, separate family room create a warm, flexible layout for everyday living and entertaining. A screened porch offers the perfect spot to enjoy the breeze off the creek. Thoughtful updates throughout the home preserve its beautiful hardwood floors, moldings, and character while introducing a fresh coastal palette, contemporary kitchen and baths, new roof and Hardie board siding, and numerous additional improvements. The grounds are exceptional—one of the most beautiful settings in the county—with mature specimen trees, curated landscaping, full yard and garden sprinkler system, invisible dog fence and uncommon topography that enhances both privacy and views. The dedicated nature preserve directly across the street ensures no future building. A waterfront property of this quality, setting, and convenience with no flood insurance required is a rare find. Added bonus--enjoy a front row seat without leaving your own property to enjoy TCC's incredible 4th of July fireworks! Don’t miss the opportunity to make 5920 Oxford Road your own.

5920 Oxford Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$2,250,000

Experience the best of Eastern Shore Living at this stunning waterfront retreat. Set on 8+ private acres, this solid brick Dutch Colonial offers timeless architecture, exceptional privacy and spectacular waterfrontage on San Domingo Creek. A long tree lined drive welcomes you to over 4400 square feet of thoughtfully designed living space. Additional highlights include a 2 car garage, paved parking, mature landscaping, pool, 4+ mlw water depth and pier. A short 5 minute drive to downtown St. Michaels. Please see notes about the ALARM.

5 Beds ⋅ 2 Baths

Experience the best of Eastern Shore Living at this stunning waterfront retreat. Set on 8+ private acres, this solid brick Dutch Colonial offers timeless architecture, exceptional privacy and spectacular waterfrontage on San Domingo Creek. A long tree lined drive welcomes you to over 4400 square feet of thoughtfully designed living space. Additional highlights include a 2 car garage, paved parking, mature landscaping, pool, 4+ mlw water depth and pier. A short 5 minute drive to downtown St. Michaels. Please see notes about the ALARM.

8209 Tricefield, Saint Michaels

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$2,195,000

LOCATION, CHARM, and beautifully RENOVATED!!!Set on 2.32 glorious acres overlooking Dixon Creek, this beautifully and lovingly maintained 1915 residence offers timeless character, refined comfort, and exceptional waterfront living. Original hardwood floors run throughout much of the home, while expansive windows bathe the traditional floor plan in natural light and frame expansive water views from nearly every room. The main level features gracious formal living and dining rooms, a gourmet kitchen with a beautiful center island and top-tier stainless appliances, and a welcoming family room with wood-burning fireplace. Custom built-ins are thoughtfully integrated throughout the home, reflecting quality craftsmanship and attention to detail. Upstairs, the waterside primary suite offers a fireplace, dual walk-in closets and a luxurious ensuite bath with soaking tub and glass-enclosed shower. Two additional guest bedrooms include one with an ensuite bath and another with access to the hall bath. The third level provides a small loft style BR /flexible bonus room, ideal for an office or studio. Outdoor living is equally inviting, with a waterside screened porch, a poolside screened porch with wet bar, and an additional open deck off the dining room—perfect for enjoying the tranquil setting. The beautifully landscaped grounds feature mature trees, lush plantings, and extensive hardscaping, anchored by a gunite pool with expansive deck and surrounding gardens. Additional structures include a charming former icehouse (currently used as a storage shed) and a larger outbuilding once used as tenant quarters. An attached 2-car garage and a full encapsulated basement offer excellent functionality and versatility. With 280 feet of natural shoreline, a private pier with two slips, boat lift, and 3.5–4' MLW, this property captures the essence of Eastern Shore waterfront living. *Roof- 2011, new siding, new boiler, renovated kitchen and primary bath, encapsulated basement, redecked pier, plus more1!-Septic replaced in 2020 and is for 4 bedrooms-owners have plans for proposed first floor primary suite where existing south side porch currently is.

LOCATION, CHARM, and beautifully RENOVATED!!!Set on 2.32 glorious acres overlooking Dixon Creek, this beautifully and lovingly maintained 1915 residence offers timeless character, refined comfort, and exceptional waterfront living. Original hardwood floors run throughout much of the home, while expansive windows bathe the traditional floor plan in natural light and frame expansive water views from nearly every room. The main level features gracious formal living and dining rooms, a gourmet kitchen with a beautiful center island and top-tier stainless appliances, and a welcoming family room with wood-burning fireplace. Custom built-ins are thoughtfully integrated throughout the home, reflecting quality craftsmanship and attention to detail. Upstairs, the waterside primary suite offers a fireplace, dual walk-in closets and a luxurious ensuite bath with soaking tub and glass-enclosed shower. Two additional guest bedrooms include one with an ensuite bath and another with access to the hall bath. The third level provides a small loft style BR /flexible bonus room, ideal for an office or studio. Outdoor living is equally inviting, with a waterside screened porch, a poolside screened porch with wet bar, and an additional open deck off the dining room—perfect for enjoying the tranquil setting. The beautifully landscaped grounds feature mature trees, lush plantings, and extensive hardscaping, anchored by a gunite pool with expansive deck and surrounding gardens. Additional structures include a charming former icehouse (currently used as a storage shed) and a larger outbuilding once used as tenant quarters. An attached 2-car garage and a full encapsulated basement offer excellent functionality and versatility. With 280 feet of natural shoreline, a private pier with two slips, boat lift, and 3.5–4' MLW, this property captures the essence of Eastern Shore waterfront living. *Roof- 2011, new siding, new boiler, renovated kitchen and primary bath, encapsulated basement, redecked pier, plus more1!-Septic replaced in 2020 and is for 4 bedrooms-owners have plans for proposed first floor primary suite where existing south side porch currently is.

8075 Leehaven Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$1,795,000

Offered for the first time in over 50 years, this 13+/- acre waterfront property on Broad Creek presents a rare opportunity to own an expansive estate with exceptional shoreline frontage. With more than 960+/- feet of waterfront, the setting provides unobstructed water views and a private pier, offering direct access to the creek and surrounding natural landscape. A tree-lined private driveway leads to the residence, positioned to take full advantage of its waterfront location. The home features 6 bedrooms and 4 full/1 half baths. The main level includes a screened-in porch entry, welcoming foyer, spacious living room with fireplace, formal dining room with a second fireplace, and a flexible study or office with built-in shelving and water views. The updated eat-in kitchen is equipped with granite countertops, a large breakfast bar, gas cooktop, stainless steel appliances, and a spacious pantry. A main-level half bath completes the floor. Both a primary staircase and a secondary staircase provide access to the upper levels. All six bedrooms are located on the second floor. The owner’s suite includes a fireplace, ensuite bath, and access to a front-facing balcony. Front-facing secondary bedrooms also have balcony access. The third level offers additional living space, including a large bonus room, entertainment room, three additional rooms, completed drywall and electrical work, and a full bath with shower. Additional property features include a detached garage with parking and storage, an externally accessed basement for storage, a wide exterior pad suitable for boat or RV storage, hardwood floors, a waterside deck, and a private pier. This property combines acreage, extensive waterfront frontage, and a spacious residence ready for its next owner.

6 Beds ⋅ 5 Baths

Offered for the first time in over 50 years, this 13+/- acre waterfront property on Broad Creek presents a rare opportunity to own an expansive estate with exceptional shoreline frontage. With more than 960+/- feet of waterfront, the setting provides unobstructed water views and a private pier, offering direct access to the creek and surrounding natural landscape. A tree-lined private driveway leads to the residence, positioned to take full advantage of its waterfront location. The home features 6 bedrooms and 4 full/1 half baths. The main level includes a screened-in porch entry, welcoming foyer, spacious living room with fireplace, formal dining room with a second fireplace, and a flexible study or office with built-in shelving and water views. The updated eat-in kitchen is equipped with granite countertops, a large breakfast bar, gas cooktop, stainless steel appliances, and a spacious pantry. A main-level half bath completes the floor. Both a primary staircase and a secondary staircase provide access to the upper levels. All six bedrooms are located on the second floor. The owner’s suite includes a fireplace, ensuite bath, and access to a front-facing balcony. Front-facing secondary bedrooms also have balcony access. The third level offers additional living space, including a large bonus room, entertainment room, three additional rooms, completed drywall and electrical work, and a full bath with shower. Additional property features include a detached garage with parking and storage, an externally accessed basement for storage, a wide exterior pad suitable for boat or RV storage, hardwood floors, a waterside deck, and a private pier. This property combines acreage, extensive waterfront frontage, and a spacious residence ready for its next owner.

7421 Quaker Neck Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$1,650,000

Prime Development Opportunity in Downtown Easton – Part of the original 1963 Calvert Terrace subdivision, offers an exceptional in-town development prospect just two blocks from Route 50/Ocean Gateway and minutes from downtown Easton. Situated adjacent to an established residential neighborhood, this land combines location and potential for a variety of development projects. The property includes an existing stormwater management facility and is sold in its entirety, encompassing multiple parcels of record, stormwater retention ponds, and associated easements. Conceptual drawings, including a Planned Unit Development (PUD) and the original engineered plat, are available for review, providing valuable insights into potential layouts and uses. Ideal for developers and investors, this offering is one of the few remaining large parcels in Easton’s town limits, with immediate access to major transportation routes and community amenities. Note: Current tax information does not reflect the total for all existing parcels.

Calvert Street, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$1,625,000

Welcome to White Barn at Middlespring, a remarkable 8-acre Eastern Shore estate offering the perfect blend of historic charm, modern updates, privacy, and country living. Set at the end of a quarter-mile private drive surrounded by picturesque farmland, this exceptional property features three distinctive structures: a beautifully restored 1824 manor home, a 3-car detached garage with finished bonus space above, and a historic 40' x 63' barn. Additional highlights include a new metal roof, new windows, composite decking, updated kitchens and bathrooms, irrigation for the rear lawn and landscape beds, landscape lighting, and thoughtfully renovated living spaces, creating a truly move-in-ready retreat just minutes from downtown Easton. Built in 1824 on land first patented in 1663, the manor home has been thoughtfully renovated to preserve its historic character while embracing modern comfort. Wide-plank pine floors, original architectural details, and three wood-burning fireplaces create warmth and timeless elegance throughout. At the heart of the home, the beautifully renovated farmhouse kitchen is designed for gathering, featuring a large center island, professional 8-burner range, farmhouse sink, and recently updated fixtures that blend seamlessly with the home's period character. All kitchen and bathroom fixtures throughout the home have been thoughtfully updated within the past three years, offering today's conveniences while preserving the home's historic integrity. A spacious mudroom with utility sink adds everyday functionality, while the newly constructed sunroom addition showcases exposed wood beams and a cozy propane stove, creating the perfect space to relax and enjoy the surrounding landscape in every season. Outside, enjoy peaceful mornings from the composite deck overlooking eight scenic acres. The beautifully maintained rear lawn and landscape beds are serviced by an irrigation system, while landscape lighting highlights the mature trees, historic outbuilding, and walkways, creating an inviting setting well into the evening. Offered fully furnished, the home includes a beautifully curated collection of furnishings and lighting from Restoration Hardware, Arhaus, and Pottery Barn, allowing the next owner to enjoy a seamless transition into the Eastern Shore lifestyle.

Welcome to White Barn at Middlespring, a remarkable 8-acre Eastern Shore estate offering the perfect blend of historic charm, modern updates, privacy, and country living. Set at the end of a quarter-mile private drive surrounded by picturesque farmland, this exceptional property features three distinctive structures: a beautifully restored 1824 manor home, a 3-car detached garage with finished bonus space above, and a historic 40' x 63' barn. Additional highlights include a new metal roof, new windows, composite decking, updated kitchens and bathrooms, irrigation for the rear lawn and landscape beds, landscape lighting, and thoughtfully renovated living spaces, creating a truly move-in-ready retreat just minutes from downtown Easton. Built in 1824 on land first patented in 1663, the manor home has been thoughtfully renovated to preserve its historic character while embracing modern comfort. Wide-plank pine floors, original architectural details, and three wood-burning fireplaces create warmth and timeless elegance throughout. At the heart of the home, the beautifully renovated farmhouse kitchen is designed for gathering, featuring a large center island, professional 8-burner range, farmhouse sink, and recently updated fixtures that blend seamlessly with the home's period character. All kitchen and bathroom fixtures throughout the home have been thoughtfully updated within the past three years, offering today's conveniences while preserving the home's historic integrity. A spacious mudroom with utility sink adds everyday functionality, while the newly constructed sunroom addition showcases exposed wood beams and a cozy propane stove, creating the perfect space to relax and enjoy the surrounding landscape in every season. Outside, enjoy peaceful mornings from the composite deck overlooking eight scenic acres. The beautifully maintained rear lawn and landscape beds are serviced by an irrigation system, while landscape lighting highlights the mature trees, historic outbuilding, and walkways, creating an inviting setting well into the evening. Offered fully furnished, the home includes a beautifully curated collection of furnishings and lighting from Restoration Hardware, Arhaus, and Pottery Barn, allowing the next owner to enjoy a seamless transition into the Eastern Shore lifestyle.

32137 Discovery Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$1,495,000

Nestled on a picturesque country setting, this exceptional and thoughtfully designed estate is perfect for both everyday living and entertaining. Featureing a beautifully appointed four-bedroom main residence, a private guest apartment, an inviting outdoor living area, and a spacious pole barn. The heart of the home is the stunning gourmet kitchen, complete with high-end appliances including a Viking range, a wine refrigerator, and an expansive center island with seating. The open design creates a seamless flow into the adjoining living and dining spaces, making it ideal for gatherings of any size. The luxurious main-level primary suite provides a peaceful retreat, while the covered front porch and screened porch offer the perfect places to enjoy the surrounding landscape throughout the seasons.Step outside to discover an extraordinary outdoor oasis featuring an in-ground pool, a charming pool house, and a covered outdoor kitchen and living area designed for effortless entertaining. Whether hosting family and friends or enjoying a quiet evening at home, the outdoor amenities create an unmatched resort-like atmosphere. Guests will appreciate the detached one-bedroom apartment, complete with a kitchenette and a cozy wood-burning stove, providing both privacy and comfort. A large pole barn offers abundant storage space and endless possibilities for hobbies, equipment, or workshop use. New GAF roof on main house, pole barn and garage has a fully transferable 50-year warranty on materials and a 30 year workmanship warranty. Offering an exceptional combination of elegance, functionality, and timeless appeal, this remarkable property presents a rare opportunity to enjoy the very best of Eastern Shore living.

5 Beds ⋅ 6 Baths

Nestled on a picturesque country setting, this exceptional and thoughtfully designed estate is perfect for both everyday living and entertaining. Featureing a beautifully appointed four-bedroom main residence, a private guest apartment, an inviting outdoor living area, and a spacious pole barn. The heart of the home is the stunning gourmet kitchen, complete with high-end appliances including a Viking range, a wine refrigerator, and an expansive center island with seating. The open design creates a seamless flow into the adjoining living and dining spaces, making it ideal for gatherings of any size. The luxurious main-level primary suite provides a peaceful retreat, while the covered front porch and screened porch offer the perfect places to enjoy the surrounding landscape throughout the seasons.Step outside to discover an extraordinary outdoor oasis featuring an in-ground pool, a charming pool house, and a covered outdoor kitchen and living area designed for effortless entertaining. Whether hosting family and friends or enjoying a quiet evening at home, the outdoor amenities create an unmatched resort-like atmosphere. Guests will appreciate the detached one-bedroom apartment, complete with a kitchenette and a cozy wood-burning stove, providing both privacy and comfort. A large pole barn offers abundant storage space and endless possibilities for hobbies, equipment, or workshop use. New GAF roof on main house, pole barn and garage has a fully transferable 50-year warranty on materials and a 30 year workmanship warranty. Offering an exceptional combination of elegance, functionality, and timeless appeal, this remarkable property presents a rare opportunity to enjoy the very best of Eastern Shore living.

4401 Grove Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$1,295,000

Harris Creek Waterfront. This 3 bedroom, 2 bath well maintained brick one story house is the perfect getaway. Nestled on 1.63+/- acres it is the perfect blend of privacy and community. This home features a large kitchen with several entertaining areas including a cozy living room complete with a fireplace and a large living room that overlooks the huge screen porch and Harris Creek and a gracious waterside paver patio. The water frontage is spectacular complete with additional seating areas on the shoreline to enjoy the river and a dock with 4' MLW with a newer lift. The two car garage has an additional half bath and plenty of room for cars and additional storage. Carpet and paint have just been completed - this is a turnkey house just in time for the season.

Harris Creek Waterfront. This 3 bedroom, 2 bath well maintained brick one story house is the perfect getaway. Nestled on 1.63+/- acres it is the perfect blend of privacy and community. This home features a large kitchen with several entertaining areas including a cozy living room complete with a fireplace and a large living room that overlooks the huge screen porch and Harris Creek and a gracious waterside paver patio. The water frontage is spectacular complete with additional seating areas on the shoreline to enjoy the river and a dock with 4' MLW with a newer lift. The two car garage has an additional half bath and plenty of room for cars and additional storage. Carpet and paint have just been completed - this is a turnkey house just in time for the season.

9251 Mallard Point Ct, Mcdaniel

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$1,285,000

Tucked in a lovely Oxford location just steps from in-town amenities, this completely redone 4 bedroom, 3.5-bath residence offers quaint Eastern Shore living with exceptional charm and flexibility. The light-filled main home features a formal dining room, private office/bedroom, inviting family room with gas fireplace and wet bar with custom built-ins, and a top-of-the-line gourmet kitchen with cathedral ceiling, generous cabinetry, center island, and an adjacent mudroom with additional appliances. Upstairs, the spacious primary suite overlooks the beautifully landscaped rear grounds , pool and features vaulted ceilings, custom built-ins, and a walk-in closet. There is a comfortable guest bedroom and full bath. Outdoor living features a fabulous rear deck overlooking an in-ground swimming pool and manicured gardens—perfect for entertaining or quiet relaxation. A separate guest cottage with murphy bed, full bath and kitchenette adds even more versatility, ideal for guests, extended stays, or a private retreat. Only a couple blocks to town owned waterfront, shops, restaurants, parks, marinas and the local market. Move in ready home.

Tucked in a lovely Oxford location just steps from in-town amenities, this completely redone 4 bedroom, 3.5-bath residence offers quaint Eastern Shore living with exceptional charm and flexibility. The light-filled main home features a formal dining room, private office/bedroom, inviting family room with gas fireplace and wet bar with custom built-ins, and a top-of-the-line gourmet kitchen with cathedral ceiling, generous cabinetry, center island, and an adjacent mudroom with additional appliances. Upstairs, the spacious primary suite overlooks the beautifully landscaped rear grounds , pool and features vaulted ceilings, custom built-ins, and a walk-in closet. There is a comfortable guest bedroom and full bath. Outdoor living features a fabulous rear deck overlooking an in-ground swimming pool and manicured gardens—perfect for entertaining or quiet relaxation. A separate guest cottage with murphy bed, full bath and kitchenette adds even more versatility, ideal for guests, extended stays, or a private retreat. Only a couple blocks to town owned waterfront, shops, restaurants, parks, marinas and the local market. Move in ready home.

103 Tred Avon Ave, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$1,250,000

Presenting 47+ acres of stunning land just minutes from Easton, perfectly positioned at the intersection of Unionville Road and Miles River Road, extending along Anchorage Road. This expansive property is currently leased for farming and hunting, offering both income potential and recreational opportunities. While it has not been perc tested, the property holds potential for multiple lots, subject to required approvals. A rare investment opportunity with endless possibilities in a highly desirable location.

Unionville Rd, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4107458060

$1,200,000

Unique Tilghman Island Property. Zoned Residential-Commercial. Situated on a 2.74 acre fenced yard. This 2450 sq ft Stone Rancher has many upgrades, new 2 car garage and 24 new commercial slips. The possibilities are endless....... Vacation Rental, 24 brand new slips, typically rent from 175.00-225.00 monthly. Develop a new fishing center, crabbing tours, sunsets cruises. Let's see what you can dream up??

Unique Tilghman Island Property. Zoned Residential-Commercial. Situated on a 2.74 acre fenced yard. This 2450 sq ft Stone Rancher has many upgrades, new 2 car garage and 24 new commercial slips. The possibilities are endless....... Vacation Rental, 24 brand new slips, typically rent from 175.00-225.00 monthly. Develop a new fishing center, crabbing tours, sunsets cruises. Let's see what you can dream up??

21441 Dogwood Cove Rd, Tilghman

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$1,195,000

Welcome to downtown living in Easton, Maryland. Located on one of the most desirable streets in historic Downtown Easton, this charming Victorian-style home offers 4 bedrooms, 3 full baths, and a powder room, with convenient access to downtown Easton restaurants, shopping, parks, entertainment, and local attractions. Inside, the home features a fully finished third floor offering flexible additional living space, along with an unfinished basement providing ample storage. Outside, enjoy meticulously maintained gardens, patio hardscaping, off-street parking, a newly installed garden shed, and a whole-yard irrigation system. Recent improvements include (but not limited to) a new roof with Lifetime Timberline HDZ architectural shingles and enlarged gutters in 2024, as well as updated wood siding, gable trim, and flashing. Thoughtfully maintained while preserving its historic character, 9 Brookletts Avenue is a special opportunity to own a classic Victorian home in the heart of Downtown Easton.

Welcome to downtown living in Easton, Maryland. Located on one of the most desirable streets in historic Downtown Easton, this charming Victorian-style home offers 4 bedrooms, 3 full baths, and a powder room, with convenient access to downtown Easton restaurants, shopping, parks, entertainment, and local attractions. Inside, the home features a fully finished third floor offering flexible additional living space, along with an unfinished basement providing ample storage. Outside, enjoy meticulously maintained gardens, patio hardscaping, off-street parking, a newly installed garden shed, and a whole-yard irrigation system. Recent improvements include (but not limited to) a new roof with Lifetime Timberline HDZ architectural shingles and enlarged gutters in 2024, as well as updated wood siding, gable trim, and flashing. Thoughtfully maintained while preserving its historic character, 9 Brookletts Avenue is a special opportunity to own a classic Victorian home in the heart of Downtown Easton.

9 Brookletts Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$1,190,000

Presenting 925 Riverview Terrace, a move in ready, charming home ideally located in the sought after Bentley Hay neighborhood just minutes from historic downtown St. Michaels. This beautifully renovated & meticulously maintained home offers Miles River views, a saltwater pool, 1st floor primary bedroom, attached 2 car garage, screened in porch, hardwood floors, gardens, home office, fiber optic cable, new roof, new HVAC & encapsulated crawlspace. Enter the impressive two-story foyer and enjoy a direct view through the home to the pool beyond. The open living room features a dramatic vaulted shiplap ceiling, built in bookcases, entertainment cabinet & gas fireplace. Off the living room is a custom 2 desk, dedicated office with storage cabinets. Enjoy cooking in the elegantly renovated kitchen with French Blue cabinetry, granite & marble countertops, cutting board topped island, stainless steel appliances including a CAFE range with copper handles. The first-floor primary suite is open & spacious with high ceilings with views of the pool & backyard. The primary bathroom has designer tile walk-in shower & flooring with a double sink vanity with marble countertop. The 2nd floor features a wonderful family room with oversize windows & waterviews over the Miles River, 2 large, lovely bedrooms, full bath & walk in attic. Enjoy the screened-in porch overlooking the inviting saltwater pool with durable Trex decking, relax in your private, fenced backyard, with raised gardens & vegetable beds—perfect for entertaining, gardening, or simply enjoying the Eastern Shore lifestyle. The property is zoned to allow short-term rentals with County approval, offering added flexibility as a primary residence, second home, or investment opportunity. This home checks all the boxes!

Presenting 925 Riverview Terrace, a move in ready, charming home ideally located in the sought after Bentley Hay neighborhood just minutes from historic downtown St. Michaels. This beautifully renovated & meticulously maintained home offers Miles River views, a saltwater pool, 1st floor primary bedroom, attached 2 car garage, screened in porch, hardwood floors, gardens, home office, fiber optic cable, new roof, new HVAC & encapsulated crawlspace. Enter the impressive two-story foyer and enjoy a direct view through the home to the pool beyond. The open living room features a dramatic vaulted shiplap ceiling, built in bookcases, entertainment cabinet & gas fireplace. Off the living room is a custom 2 desk, dedicated office with storage cabinets. Enjoy cooking in the elegantly renovated kitchen with French Blue cabinetry, granite & marble countertops, cutting board topped island, stainless steel appliances including a CAFE range with copper handles. The first-floor primary suite is open & spacious with high ceilings with views of the pool & backyard. The primary bathroom has designer tile walk-in shower & flooring with a double sink vanity with marble countertop. The 2nd floor features a wonderful family room with oversize windows & waterviews over the Miles River, 2 large, lovely bedrooms, full bath & walk in attic. Enjoy the screened-in porch overlooking the inviting saltwater pool with durable Trex decking, relax in your private, fenced backyard, with raised gardens & vegetable beds—perfect for entertaining, gardening, or simply enjoying the Eastern Shore lifestyle. The property is zoned to allow short-term rentals with County approval, offering added flexibility as a primary residence, second home, or investment opportunity. This home checks all the boxes!

925 Riverview Terrace, Saint Michaels

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$995,000

Extremely well maintained, inside and out, 3 bedroom 2 1/2 bath house with an oversized 2 car detached garage, huge back yard and within walking distance to downtown St. Michael's! Since the owner purchased this house there has been a primary first floor master addition, all new windows throughout, updated stainless appliances, professional interior designer decorating, all new extensive landscaping with full irrigation and so much more!

Extremely well maintained, inside and out, 3 bedroom 2 1/2 bath house with an oversized 2 car detached garage, huge back yard and within walking distance to downtown St. Michael's! Since the owner purchased this house there has been a primary first floor master addition, all new windows throughout, updated stainless appliances, professional interior designer decorating, all new extensive landscaping with full irrigation and so much more!

101 Seymour, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$989,000

Just Listed! Beautifully renovated, this turn-of-the-century home is ideally situated on Brookletts Avenue in Easton's sought-after Historic District. Designed to maximize natural light and fresh air, the home features a welcoming wraparound porch, along with a beautifully landscaped, fully fenced backyard complete with perennial gardens, a patio, and access to a two-car carriage/garage house with a renovated space to use for home office, gym, children's playroom, plus additional alley parking. Inside, you'll find gracious living spaces that flow seamlessly while maintaining distinct, inviting rooms. Rich hardwood floors, soaring ceilings, classic architectural moldings, original hardware, custom built-ins, closets design by California Closets, and a stunning staircase showcase the home's timeless character. The renovated kitchen perfectly blends style and functionality with custom-finished concrete countertops, premium appliances, a farmhouse sink, a spacious island, and thoughtfully designed storage. The charming powder room makes a statement with hand-painted Portuguese tile and a one-of-a-kind custom concrete sink. Upstairs, a unique staircase landing provides privacy by separating the primary suite from the front bedrooms. The primary bathroom has been freshly updated with stunning details to be admired by sophisticated buyers. The third bedroom features a Murphy bed which gives this room multiple uses. The guest bathroom is beautiful with carefully selected finishes that complement the home's historic charm. This home has been meticulously maintained, with new boiler, HVAC and hot water heater, and newer dishwasher these added updates should give a new buyer peace of mind. The low-maintenance exterior features durable vinyl and cement board siding. A rare opportunity to own a beautifully restored historic home with modern conveniences in one of Easton's most desirable neighborhoods. Schedule your private showing today!

Just Listed! Beautifully renovated, this turn-of-the-century home is ideally situated on Brookletts Avenue in Easton's sought-after Historic District. Designed to maximize natural light and fresh air, the home features a welcoming wraparound porch, along with a beautifully landscaped, fully fenced backyard complete with perennial gardens, a patio, and access to a two-car carriage/garage house with a renovated space to use for home office, gym, children's playroom, plus additional alley parking. Inside, you'll find gracious living spaces that flow seamlessly while maintaining distinct, inviting rooms. Rich hardwood floors, soaring ceilings, classic architectural moldings, original hardware, custom built-ins, closets design by California Closets, and a stunning staircase showcase the home's timeless character. The renovated kitchen perfectly blends style and functionality with custom-finished concrete countertops, premium appliances, a farmhouse sink, a spacious island, and thoughtfully designed storage. The charming powder room makes a statement with hand-painted Portuguese tile and a one-of-a-kind custom concrete sink. Upstairs, a unique staircase landing provides privacy by separating the primary suite from the front bedrooms. The primary bathroom has been freshly updated with stunning details to be admired by sophisticated buyers. The third bedroom features a Murphy bed which gives this room multiple uses. The guest bathroom is beautiful with carefully selected finishes that complement the home's historic charm. This home has been meticulously maintained, with new boiler, HVAC and hot water heater, and newer dishwasher these added updates should give a new buyer peace of mind. The low-maintenance exterior features durable vinyl and cement board siding. A rare opportunity to own a beautifully restored historic home with modern conveniences in one of Easton's most desirable neighborhoods. Schedule your private showing today!

204 Brookletts Ave, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$925,000

Set on a peaceful two-acre lot in Wye Mills, 28715 Jacks Field Road has been thoughtfully updated from top to bottom, offering the space, functionality, and modern finishes today’s buyers are looking for. This spacious five-bedroom, three-bath home features a newly reimagined interior with new flooring throughout, custom blinds, and a series of high-impact upgrades that elevate both everyday living and entertaining. The kitchen serves as the heart of the home, showcasing brand-new stainless steel appliances, a gas cooktop with downdraft, double ovens, new countertops, and an oversized center island with new cabinetry. Part of the kitchen and dining area has been remodeled to create a more open, connected floor plan, complemented by updated lighting throughout the kitchen, dining area, office, laundry room, and four bedrooms. The primary suite offers a relaxing retreat with heated floors in the master bath and a newly installed walk-in closet organizer. Two additional bathrooms have been completely remodeled, providing fresh, modern finishes throughout the home. Major system upgrades include two brand-new HVAC heat pump systems with new exterior components and a new asphalt driveway, ensuring both comfort and peace of mind. Practical features abound with new laundry room cabinetry, ample storage, and flexible spaces for work, guests, or hobbies. Outside, the property truly shines. A 20’ x 20’ brick-lined patio seamlessly matches the existing covered patio, creating an ideal setting for outdoor entertaining. The expansive backyard is anchored by a 16’–20’ diameter gas fire pit with stone surround, perfect for gatherings under the stars. In addition to the two-car attached garage with walk-up attic storage, the property also includes a two-car detached garage, offering exceptional storage and workspace options. With its generous acreage, extensive updates, and move-in-ready condition, 28715 Jacks Field Road delivers a rare blend of privacy, functionality, and modern comfort in a sought-after Eastern Shore setting.

5 Beds ⋅ 3 Baths

Set on a peaceful two-acre lot in Wye Mills, 28715 Jacks Field Road has been thoughtfully updated from top to bottom, offering the space, functionality, and modern finishes today’s buyers are looking for. This spacious five-bedroom, three-bath home features a newly reimagined interior with new flooring throughout, custom blinds, and a series of high-impact upgrades that elevate both everyday living and entertaining. The kitchen serves as the heart of the home, showcasing brand-new stainless steel appliances, a gas cooktop with downdraft, double ovens, new countertops, and an oversized center island with new cabinetry. Part of the kitchen and dining area has been remodeled to create a more open, connected floor plan, complemented by updated lighting throughout the kitchen, dining area, office, laundry room, and four bedrooms. The primary suite offers a relaxing retreat with heated floors in the master bath and a newly installed walk-in closet organizer. Two additional bathrooms have been completely remodeled, providing fresh, modern finishes throughout the home. Major system upgrades include two brand-new HVAC heat pump systems with new exterior components and a new asphalt driveway, ensuring both comfort and peace of mind. Practical features abound with new laundry room cabinetry, ample storage, and flexible spaces for work, guests, or hobbies. Outside, the property truly shines. A 20’ x 20’ brick-lined patio seamlessly matches the existing covered patio, creating an ideal setting for outdoor entertaining. The expansive backyard is anchored by a 16’–20’ diameter gas fire pit with stone surround, perfect for gatherings under the stars. In addition to the two-car attached garage with walk-up attic storage, the property also includes a two-car detached garage, offering exceptional storage and workspace options. With its generous acreage, extensive updates, and move-in-ready condition, 28715 Jacks Field Road delivers a rare blend of privacy, functionality, and modern comfort in a sought-after Eastern Shore setting.

28715 Jacks Field Rd, Wye Mills

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$898,000

Designed to optimize water views of the Tred Avon and access to the community kayak launch and beach area is this to be built home. Centrally located between Easton and St Michaels and just a stone's throw from the Oxford Bellevue Ferry on the Tred Avon, one of Talbot County's premier waterfront communities with 13 half acre to 1.5 acre home sites. The community features its own private beach and kayak launch with nearby public park with playground and marina. Additional floor plans, options, and upgrades available. Some photos and renderings are for illustrative purposes only and may include additional upgrades.