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$1,450,000
5 Beds ⋅ 3 Baths
A rare chance to own 44.28± acres of productive farmland located in the sought-after Chapel School District, just minutes northeast of Easton, Maryland. In a county where quality agricultural ground is rarely brought to market, this property presents a valuable opportunity for farmers, investors, and ag-focused buyers. The farm offers approximately 30± acres of tillable land, well-suited for row crops or rotational planting, along with 6± acres of timber and the remaining acreage in the homesite and agricultural improvements. The operation includes substantial infrastructure designed for dairy use: - 70± stall main barn with pasture access - Dry cow barn - 120' x 50' heifer barn - 10-cow swing parlor - 800-gallon milk tank - 350,000-gallon Slurrystone tank A 3,878± square-foot farmhouse (5 BR, 3 BA) accompanies the farm, offering ample space for family or farm staff. Both the residence and farm structures are sold As Is, giving the buyer an opportunity to repurpose or expand. Please note: Only the real property conveys. Cattle, machinery, and creamery processing equipment are available separately, outside of the property sale. With its tillable acreage, extensive dairy facilities, and prime Talbot County location, this is a rare opportunity to secure agricultural ground in one of Maryland’s most sought-after farming regions.

10380 Chapel Road, Easton

Listing courtesy of The Land Group. Contact:

Selling Office: .

$1,450,000
4 Beds ⋅ 4 Baths
Waterfront Retreat in Cooke’s Hope – Perfectly positioned along Easton’s sought-after Oxford Road corridor, this custom waterfront home in Cooke’s Hope offers timeless design and a relaxed Eastern Shore lifestyle just minutes from downtown Easton. Designed by Pam Gardner, the home features 3 bedrooms, 2.5 baths and an open floor plan filled with natural light and beautiful water views. A dramatic two-story foyer leads to the vaulted waterfront living room with skylights and wood floors, creating an inviting setting for everyday living and entertaining. The waterside primary suite offers a private retreat with a fireplace and spa-inspired bath featuring a steam shower and soaking tub. The kitchen is designed for both everyday living and entertaining with granite countertops, bar seating and casual dining space. A private den with built-ins and fireplace offers a comfortable office or reading retreat, while the light-filled cupola room provides flexible space for a studio, lounge or creative escape. A separate bedroom wing ensures privacy for family or guests while a detached one-bedroom guest apartment offers additional accommodations. Outdoor living includes a screened porch and waterside deck overlooking the tranquil setting. A two-car garage provides excellent storage for vehicles and waterfront gear. The leased boat slip with water and electric at the community pier (available 2026) offers easy access to the surrounding waterways. A rare opportunity to enjoy waterfront living just minutes from Easton, Oxford and St. Michaels!

6780 Cookes Hope Road, Easton

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

Selling Office: .

$1,395,000
3 Beds ⋅ 3 Baths
121 West Chestnut Street is a true gem among the historic houses in St. Michaels. First time offered in a decade, the 1890 colonial embodies all the desirable features of an older home on the exterior – an inviting covered front porch, wood shingle siding, a two-bay center hall two story architecture, bracing chimneys on each end and true divided double hung windows in the front. Once inside, this home surprises with a light filled open interior and a seamlessly flowing floor plan. The important historic features, such as wood flooring, built ins and fireplace have been well preserved, but with its well thought out renovations and a sizable addition, the house now features large open rooms, an impressive gourmet kitchen and an attractive modern primary bedroom with walk-in closet and bath. The kitchen opens to the back yard and features a large island with seating for five, farm sink, five burner gas cooktop with faucet, wall oven and convection microwave, ample cabinet space, and granite and quartz counters. The adjacent dining room includes built ins with a beverage refrigerator and a decorative fireplace that could be converted to electric or gas. The living room is anchored by a gas fireplace, built in cabinets, and shelving. The home offers four bedrooms, one of which currently serves as an office, accessible from both the primary and secondary staircase. The living area is rounded out by a dedicated laundry room with access to the backyard, and a sitting room. The lot has alley access from the back and while currently not in place, could have parking at the rear. A sizable outbuilding offers plenty of space for storage. This home is just steps away from the park and public dock on San Domingo Creek, and the St. Michaels Nature Trail.

121 W Chestnut, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$1,350,000
3 Beds ⋅ 4 Baths
Beyond the white picket fence, a storybook garden unfolds—lush, curated, and unmistakably Oxford. Perfectly positioned just moments from the beach, ferry, and waterfront park, 208 Factory Street offers a rare blend of timeless village charm and sophisticated modern comfort. Thoughtfully enhanced with updated mechanical systems since 2019, this three-bedroom residence has been meticulously maintained and beautifully reimagined for effortless living. Sunlight pours into the airy, open- concept living, dining, and kitchen spaces, where hardwood flooring flows seamlessly throughout and every room feels connected to the outdoors. Designed with exceptional flexibility, the home features two private primary suites—one conveniently located on the main level and a second occupying the upper floor. The upstairs retreat serves as a true sanctuary, complemented by a beautifully renovated spa-inspired bath featuring a glass-enclosed porcelain tile steam shower. The main-level suite offers its own renovated bath and charming loft area, creating an equally inviting private escape. Just off the kitchen, a dedicated office provides the ideal work-from-home setting, while multiple outdoor living spaces invite relaxation and entertaining throughout the seasons. Enjoy quiet mornings on the intimate sitting porch overlooking the pool, gather with friends on the screened porch, or simply savor the beauty of the impeccably landscaped cottage gardens that envelop the property. Completing the offering is a detached one-car garage and an enviable location in the heart of Oxford. A home that captures the very essence of Eastern Shore living—elegant yet approachable, refined yet welcoming, and perfectly connected to one of Maryland’s most treasured waterfront communities. Here, every detail has been thoughtfully curated to create a lifestyle as beautiful as its surroundings. ---{Luxury & Special Features} Electric retractable awnings | Heated floor in second-floor primary bath | Glass-enclosed steam shower with rain shower in second-floor primary bath | Towel warmer in second-floor primary bath | Tesla charger in detached garage | Moen smart water shutoff valve | Water pressure booster pump | Lawn irrigation system | Updated mechanical systems since 2019 | Hardwood flooring throughout | Two primary suites, including a main-level primary | Dedicated office/flex room | Screened porch | Poolside sitting porch | Detached one-car garage | Cottage gardens and white picket fence setting |

208 Factory Street, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$1,325,000
5 Beds ⋅ 5 Baths
Some homes check the boxes. Others create a lifetime of memories......Welcome Home to 28091 Oaklands Circle Perfectly situated on over 2.5 beautifully landscaped acres in the highly desirable Oaklands community, this exceptional five-bedroom, four-and-a-half-bath custom home offers the rare combination of luxury, comfort, privacy, and a truly move-in-ready lifestyle. From the moment you arrive, you’ll appreciate the mature trees, manicured landscaping, fresh mulch, and natural privacy that surround this beautifully maintained property. Every detail reflects years of thoughtful care and pride of ownership. Inside, timeless craftsmanship meets thoughtful updates. Rich hardwood flooring flows throughout the home, complemented by replacement windows, recessed LED lighting, custom built-in shelving, window seats with hidden storage, and pocket doors that add both character and functionality. At the heart of the home is the beautifully updated kitchen featuring granite countertops, generous island workspace, coffee bar, breakfast area with lots of natural light and an inviting layout designed for everything from family dinners to holiday gatherings. With five spacious bedrooms, 4 1/2 bathrooms, great room, formal areas, and a fully finished bonus room above the attached three-car garage, the flexible floor plan easily accommodates growing, blended, or multi generational families, overnight guests, a home office, fitness room, or recreation space. Comfort can be found in every season. Enjoy the warmth of both a gas fireplace and a traditional wood-burning fireplace, or gather around the fire pit on cool evenings during cooler months. Just outside you will discover your own private retreat. Relax on the screened-in covered porch, multiple decks, spend afternoons and weekends lounging by the sparkling swimming pool with diving board, featuring a new pool cover and new pool pumps. Explore the custom tree fort and zip line, or simply enjoy the open green space that makes this property so special. Relax on any one of the multiple deck spaces overlooking the peaceful backyard or just simply soak up the AC in the summertime. A large storage shed provides plenty of room for lawn equipment, tools, and outdoor gear. Significant improvements—including replacement windows, approximately three-quarters of the roof replaced, and a whole-house backup generator—offer lasting value and peace of mind. A state-of-the-art security, alarm, and surveillance system adds another level of comfort for today’s homeowners. Located just minutes from historic downtown Easton or the waterfront town of Oxford, both with outstanding restaurants, boutique shopping, access to local healthcare, schools, and the waterfront lifestyle of Maryland’s Eastern Shore, this home offers the perfect balance of convenience and tranquility. Beautifully updated, meticulously maintained, and designed for everyday living as well as unforgettable entertaining, 28091 Oaklands Circle is more than a home—it’s where birthdays are celebrated, holidays are shared, and lifelong memories are made. Come experience the warmth, quality, and lifestyle that make this remarkable property truly one of Easton’s finest.

28091 Oaklands Circle, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$1,280,000
2 Beds ⋅ 3 Baths
Prime waterfront home in Oxford’s beautiful historic district, faces west overlooking the Tred Avon River. Offering the best in Oxford waterfront with prevailing SW summer breezes, fantastic year-round sunsets, a long dock, patio, old growth large trees, extensive hardscape and off-street parking make this property unique. It has a carport and is located on a significant tree-lined street and lies with the “X” zone on the flood maps. On the first floor is an open, well equipped kitchen that opens to the great room with views overlooking the patio, gardens and the river. One full bath on the first floor with a library/den and front entrance. There is a primary bedroom suite on the second level adjoining a screened porch and deck with views to the Tred Avon beyond. The views are extraordinary! In addition, there is a second bedroom and bath on this level.

102 Tred Avon Avenue, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$1,270,000
4 Beds ⋅ 4 Baths
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 Avenue, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$1,250,000
The owner must approve all showings, advance notice is preferred. REAL ESTATE ONLY FOR SALE. Positioned in the heart of downtown St. Michaels, 208 N Talbot Street offers a rare opportunity to acquire a premier mixed-use commercial property in one of the Eastern Shore’s most desirable waterfront communities. This 4,111-square-foot building features outstanding visibility along Talbot Street, benefiting from strong pedestrian traffic and close proximity to the waterfront, marinas, boutique shops, and established dining destinations. The property is ideally suited for a restaurant or hospitality concept, featuring a fully built-out commercial kitchen and an impressive total seating capacity of approximately 158 guests across indoor and outdoor dining areas. This allows a new owner to open and operate with minimal additional build-out—an increasingly rare opportunity in this market. A standout feature is the inclusion of 12 dedicated parking spaces, a significant advantage in downtown St. Michaels, enhancing accessibility for both customers and staff. The second level, which has outside access, offers a spacious three-bedroom, three-bathroom apartment, providing excellent flexibility for owner occupancy or future rental income. The apartment kitchen is currently unfinished, needs some remodelling, upstairs offering the opportunity for customization while adding additional long-term value once completed. Whether positioned as a signature dining establishment, boutique hospitality concept, or mixed-use investment, this property delivers a compelling combination of location, infrastructure, and upside potential in a market where inventory remains limited. The property is sold as is. Recommend each individual buyer check with the Town Office for uses for 2nd level.

208 N Talbot, Saint Michaels

Listing courtesy of Keller Williams Select Realtors of Easton. Contact:

Selling Office: .

$1,250,000
4 Beds ⋅ 3 Baths
A storybook waterfront home with privacy, and timeless old-world charm. This Tilghman Island waterfront property carries a gracious, welcoming spirit: peaceful, and full of character. Large rooms, tall presence, mature trees, and a beautiful wraparound porch give the home a timeless, almost cinematic quality. Set down a long private driveway on Broad Cove, which connects to Harris Creek, this secluded 4-bedroom, 2.5-bath home offers 3,037 square feet of generous living space, 438+ feet of shoreline and a swimming pool. Inside, the home offers expansive gathering spaces, including a large living room with a grand wood-burning fireplace, a spacious family room, a kitchen with a wood stove, and a generous primary bedroom with its own wood-burning fireplace. There is warmth and scale throughout. Old charm, big rooms, and the kind of relaxed elegance that is hard to recreate. A dock is in place and in need of repair, offering the next owner the opportunity to restore and customize the waterfront experience. Gracious, private, and full of soul, this rare Broad Cove property offers the presence and romance of a true dream home. Note: Original section of home has asbestos-cement exterior shingles.

21408 Broad Cove Lane, Tilghman

Listing courtesy of Compass. Contact:

Selling Office: .

$1,250,000
Prime 82.54± Acre Eastern Shore Farm With Tillable Ground And Hunting This 82.54-acre property in Talbot County, Maryland, offers a highly desirable opportunity to own productive Eastern Shore farmland with strong agricultural value, recreational appeal, and future homesite potential. Situated in a well-regarded farming region, this tract offers a balanced combination of income-producing capability, land investment potential, and outdoor enjoyment. The property is zoned agricultural, allowing continued row-crop production, long-term land ownership, and flexibility for future use. A large portion of the acreage is tillable, supported by soils consisting primarily of Hambrook Sassafras complex and Ingleside sandy loam. These soil types are well known throughout the region for their productivity and drainage, making the farm suitable for consistent agricultural operations. In addition to its farming attributes, the property includes a smaller wooded section that enhances privacy, natural diversity, and wildlife habitat. This wooded section also includes a designated forest conservation area, as shown on the recorded plat. This area represents only a small portion of the overall property and contributes to long-term environmental stewardship while maintaining the farms overall usability and value. Portions of the property were previously enrolled in CRP, offering the potential to further utilize income-producing opportunities on the property while continuing current agricultural practices. The property benefits from excellent access and layout, with road frontage along Bambury Road on the eastern boundary and Kates Point Road along the northern boundary. This dual frontage provides convenient entry points and supports efficient movement for farming operations. A drainage and utility easement is present on the property, typical for farms in the area near county roads, and does not detract from its overall usability. From a recreational standpoint, this property offers exceptional hunting potential. The combination of productive tillable ground, natural edge habitat, and surrounding agricultural landscape creates an ideal environment for attracting and holding whitetail deer and migratory geese. The property has a strong history of producing quality whitetail deer, with the area known for harvesting mature bucks. The layout supports multiple stand and blind locations, allowing for effective setups across different wind directions and seasons. The property also offers strong potential for a future homesite, making it an excellent option for those looking to build a private residence, farmhouse, or retreat surrounded by productive farmland and natural beauty. This blend of usability, privacy, and location creates an appealing setting for both investment and lifestyle buyers. For buyers seeking expansion, this tract is also available in combination with the adjacent 90-acre home farm, creating the potential for a larger, contiguous farming operation with additional improvements. This Talbot County property offers a rare combination of productive farmland, recreational value, and long-term potential in one of Marylands most sought-after rural regions. Property taxes shall be based on the acreage as determined by the Buyer’s survey and the acreage conveyed. Taxes will be prorated proportionally from the total parent tract of 582 acres.

3750-B Windy Hill Road, Trappe

Listing courtesy of LPT Realty, LLC. Contact:

Selling Office: .

$1,225,000
2 Beds ⋅ 3 Baths
Luxury Restoration in the Heart of Historic St. Michaels Welcome to 106 E. Chestnut Street, where historic charm and modern luxury come together in one of the Eastern Shore’s most beloved waterfront towns. Completely renovated down to the studs, this exceptional home has been thoughtfully reimagined to preserve its classic character while introducing high-end systems, refined finishes, and modern conveniences throughout. Inside, a bright open-concept floor plan creates an inviting atmosphere ideal for both everyday living and entertaining. The beautifully designed kitchen with all-new appliances flows seamlessly into the main living spaces, while tastefully updated bathrooms and carefully curated details reflect the quality of this full-scale restoration. The home offers the comfort and efficiency of geothermal HVAC, a central vacuum system, new roof, and a fully encapsulated crawl space, providing peace of mind alongside modern performance. The primary suite is a private retreat, featuring a luxurious bathroom, plenty of closet space, and a walk-out rooftop deck overlooking the backyard—the perfect place to enjoy quiet mornings with coffee or unwind under the evening sky. Outdoors, the property continues to impress with a generous yard enhanced by natural walkways, native plants, and thoughtfully designed landscaping, creating a serene garden-like setting. Additional highlights include a one-car garage with workbench and storage, along with a separate workshop that offers flexible space for hobbies, studio use, or potential guest accommodations. Ideally located within walking distance to St. Michaels’ charming harbor, boutique shops, galleries, and renowned restaurants, this home offers the rare opportunity to enjoy historic town living with the comfort of a completely modernized residence. A truly exceptional offering in the heart of St. Michaels.

106 E Chestnut E Street, Saint Michaels

Listing courtesy of Taylor Properties. Contact:

Selling Office: .

$1,190,000
4 Beds ⋅ 4 Baths
Welcome to this exceptional William Poole–designed Tidewater Colonial, gracefully sited on approximately 2.3 acres in the desirable community of Waverly Island Estates, just three miles from the Town of Easton. Offering a refined blend of classic coastal architecture and modern comfort, this property provides a private retreat on Maryland’s Eastern Shore. NEW ROOF and Pool Equipment 2026, HVAC 2019 & 2021. Inside, the home features a well-designed floor plan with abundant natural light and timeless appeal. The open kitchen connects seamlessly to a casual dining and living area highlighted by a vaulted ceiling, creating an inviting space for everyday living and entertaining. Formal living and dining rooms offer elegant settings for gatherings, while the expansive deck, fenced backyard, and in-ground pool extend the living space outdoors. The first-floor primary suite provides convenience and privacy. Upstairs, you’ll find spacious guest suites, a dedicated office, and a flexible family room ideal for work, relaxation, or hobbies. A large walk-up attic offers excellent storage and future expansion potential. Ideally positioned within the Oxford corridor, this home allows easy access to the waterfront town of Oxford and the shopping, dining, and cultural amenities of Easton. Enjoy the best of rural living with proximity to modern conveniences, all within a peaceful and sought-after neighborhood.

28028 Playtor Road, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$1,187,500
3 Beds ⋅ 3 Baths

344 Perry Cabin Drive, Saint Michaels

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

Selling Office: .

$1,175,000
6 Beds ⋅ 6 Baths
Set on 2.14 beautifully maintained acres, this exceptional 6-bedroom home offers the perfect blend of space, comfort, and outdoor living. A thoughtfully designed layout features a desirable first-floor master suite, providing privacy and convenience with generous proportions and serene views of the surrounding landscape. The home’s expansive interior includes multiple living and entertaining areas, ideal for both everyday living and hosting guests. Large windows throughout invite natural light and showcase the property’s stunning grounds. Step outside to your own private retreat, complete with a sparkling pool and extensive landscaping that creates a peaceful, park-like setting. Whether relaxing poolside or enjoying the open green space, this property offers endless opportunities for outdoor enjoyment. A detached two-car garage adds functionality and additional storage, complementing the home’s impressive features. With six spacious bedrooms and ample acreage, this property provides flexibility for a variety of lifestyles—all in a picturesque and private setting.

8464 Aveley Farm Road, Easton

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: .

$1,152,500
3 Beds ⋅ 3 Baths
The George E. Shockley House (c. 1890) is a rare historic gem in the heart of St. Michaels, just moments from the harbor, fine dining, unique shops, walking trails, and the renowned Chesapeake Bay Maritime Museum. Beautifully preserved and enhanced with significant structural improvements by Victor MacSorley, this distinguished residence blends period charm with modern comfort and is notably not subject to St. Michaels Historic District regulations. The home features an exceptional main-level primary suite with vaulted ceiling, three walk-in closets, en suite bath, and serene views of the private yard; an updated kitchen with large center island, granite countertops, stainless steel appliances, abundant storage, and casual dining overlooking the gardens; three main-level living spaces including a bright sunroom/library, spacious family room with brick fireplace, and the original welcoming living room; along with a formal dining room and powder room. Upstairs are two additional bedrooms and a full bath. The fenced backyard offers a patio beneath a magnificent magnolia, and a detached structure with a half bath provides the perfect space for a private office, studio, or creative retreat, complemented by a potting shed and additional storage. Off-street parking from both New Lane and E. Chew completes this exceptional in-town offering.

114 E Chew Avenue, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$1,150,000
4 Beds ⋅ 4 Baths
This home checks ALL the boxes! Over 400ft of waterfront overlooking Bolingbroke Creek with Pier and Floating jet ski dock. Beautiful and Inviting Front Porch that leads into this Custom-built Cape Cod located on Very Private 12.77 acres with many recent upgrades. Features include 4 Bedrooms, 3-1/2 Baths. This open floor plan features large kitchen with Granite countertops and plenty of cabinets and Lots of Storage. Primary Bedroom on the first floor with Full Bath, deck and Hot Tub overlooking the water. Family Room with wood burning Fireplace. Waterside glassed in porch and first floor laundry with built-in Pet Bathing Station. Separate Dining Room / Office. Gorgeous Luxury Vinyl Planking floors throughout. Upstairs you will find...3 Bedrooms, 1 Full Bath, Large Rec Room, and a Breezeway that leads you to Finished Space above Garage-Currently a bonus room with Full Bath. Room could easily be a Workout Room / Office / Game Room. Outdoor Features Include... Geothermal HVAC, Shed, Fire Pit, Entertaining Space surrounded by Beautiful Landscaping. Custom walkway to the water for all your boating and Fishing needs. Minutes to Scenic Choptank River, Sand Bar, and all Cambridge has to offer. In addition, there is plenty of acreage for Hunting or Gardening which includes a Garage w/ lean to attached and a small Greenhouse. Currently a Perc pending for additional dwelling. Home is situated within 15 minutes to Easton or Cambridge. One hour to Maryland and Delaware Beaches. Call Today!! You will not be disappointed.

2195 Quail Run Drive, Trappe

Listing courtesy of Brenton Realty Group. Contact:

Selling Office: .

$1,138,000
2 Beds ⋅ 2 Baths
Gorgeous waterfront home! Rancher, one level living on over 2 acres in Royal Oak. Get ready, properties like these don't come around too often!

6706 Thorneton Road, Royal Oak

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

$1,135,000
2 Beds ⋅ 2 Baths
Welcome to 107 E. Chestnut, a beautifully restored circa-1870 residence nestled in the heart of St. Michaels. From the moment you step inside, you are greeted by the perfect blend of timeless character and modern sophistication, where original architectural details have been thoughtfully preserved and seamlessly integrated with extensive renovations. The spacious entry combines an elegant living and dining area, featuring wood floors, a gas fireplace flanked by custom built-ins, and custom shutters have been added to each window. Throughout this home you will find historic charm and craftsmanship are evident at every turn. At the rear of the home is a full bath and designer kitchen that opens to the family room highlighted by soaring ceilings and an abundance of windows that fill the space with natural light year round. This inviting area flows to the screened-in porch and brick patio, creating the perfect setting for indoor-outdoor living. Beyond the patio lies a garden oasis featuring lush landscaping, colorful perennials, pond and large detached shed/storage building. The current owner has worked with the Town of St. Michaels to obtain approvals for converting this structure into a separate guest suite, and architectural plans are available for the next owner. The second level offers two generously sized bedrooms and a beautifully redesigned full bath. The rear bedroom includes an overlook of the family room, which offers additional space that could easily be transformed into a private sitting area, dressing room or walk-in closet. The front bedroom features a dedicated dressing room and oversized closet, providing the potential to create an en-suite bath. Both rooms offer cathedral ceilings with exposed rafters adding to the rooms architectural interest and charm. This is a true gem in historic St. Michaels that includes off street parking. Don't miss this exceptional opportunity to own a home in the one of the most popular towns on the Eastern Shore.

107 E Chestnut, Saint Michaels

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

Selling Office: .

$1,100,000
4 Beds ⋅ 3 Baths
Beautifully updated home on Easton's premier residential block. a short distance to the downtown, Idlewild Park the "Y", and the Academy Art Museum. Brick and flagstone walkways. Traditional center-hall colonial with 9 ft ceilings and oak floors. Oversize crown moldings in LR, DR and PBR. Living Room with fireplace. Dining Room, with built in corner cupboards. Eat-in kitchen with top-of-the-line refrigerator, decorative tiles. Cheery sunroom with south bay window. Three or four Bedrooms, 2 1/2 baths. Principal Bedroom has four closets, and newly remodeled principal Bath has heated tile floor, marble shower surround. Third story can be utilized as a large home office or as a dormitory. Central A/C. Third story and sunroom heated/cooled by mini-split heat pump supplemented by e.b.b. heat Third story is 20' x 31', irregular dimensions. . Hardwood floors. Newly installed "Levelor" privacy blinds. Screened porch. Detached garage, beautiful flower garden with fenced yard. Brick and flagstone walkways. Alley in rear.

221 S Harrison Street, Easton

Listing courtesy of Shoreline Realty. Contact:

Selling Office: .

$1,055,000
3 Beds ⋅ 3 Baths
Experience exceptional waterfront living in this custom-built home set on a private, 3-acre lot. Designed to maximize comfort and connection to the outdoors. The spacious floor plan includes a dedicated office, a cozy den and a gourmet kitchen. The oversized garage and separate laundry room are an added bonus to this perfect property. This custom designed and built - one of a kind home is conveniently located between Easton and St. Michaels. Large primary bedroom with ensuite bath. Every bedroom features direct access to the expansive deck, creating a seamless indoor–outdoor lifestyle and offering the perfect place to enjoy quiet moments. Step outside to your own resort-like escape. The very large deck provides ample room for dining, relaxing, and entertaining, while the in-ground pool invites you to enjoy warm days in total privacy. A rare combination of craftsmanship, serenity, and recreation, this waterfront property delivers an unparalleled living experience—perfect as a year-round residence or private retreat.

7605 Pendleton Farm Lane, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$1,050,000
4 Beds ⋅ 4 Baths
Welcome to this one-of-a-kind custom-built home by Paquin Design Build, ideally situated in the sought-after waterfront access community of Easton Village. This exceptional 4-bedroom, 3.5-bath home with a bonus room and office showcases high-end craftsmanship and extensive post-construction upgrades throughout. Interior highlights include a gourmet kitchen with an oversized waterfall-edge island, high-end inset cabinets extending up to the 10ft ceilings, pantry, and stainless-steel appliances. The kitchen opens to a spacious family room with a gas fireplace and built-in storage. There is a primary suite on both the first and second floor, and the second floor suite includes a private balcony, wood-paneled ceiling, and a spa-inspired bath. A sunroom enhanced by custom windows fills the home with natural light, while solid core doors, Cat6 wiring, and a Control4 whole-home audio/visual system elevate everyday living. Outdoor spaces are equally impressive, featuring a welcoming front porch with swing and fan, a professionally designed backyard complete with an extended brick patio, pergola, fire pit with custom sitting wall and a natural gas grill. The Control4 audio extends to the outdoor living areas/porches and the landscaped yard is upgraded with uplighting and WiFi-controlled irrigation. Additional highlights include an encapsulated crawlspace with waterproofing, dual-zone HVAC, Rinnai tankless water heater, and an epoxy-coated garage floor with Gorilla Track storage system. This is a rare opportunity to own a custom-built, impeccably designed home in one of Easton's premier communities. Enjoy all that Easton Village has to offer, including waterfront access with community boat slips, kayak launch, clubhouse and outdoor pool, walking trails, and scenic green spaces along the Tred Avon River. Conveniently located just minutes from downtown Easton's shops, dining, and cultural attractions, this home offers the perfect blend of luxury, comfort and Eastern Shore lifestyle.

8099 Fox Squirrel Way, Easton

Listing courtesy of ERA Martin Associates. Contact:

Selling Office: .

$1,050,000
3 Beds ⋅ 2 Baths
Waterfront living on Glebe Creek! Set on 1.7 elevated acres overlooking scenic Glebe Creek, this updated 3-bedroom, 2-bath rancher offers expansive southern-facing water views and effortless Eastern Shore living. The single-story layout is designed for comfort and connection to the outdoors, with large windows throughout that capture natural light and sweeping creek views. The heart of the home features a fully renovated kitchen with new cabinetry, stainless steel appliances, quartz countertops, tile flooring, and a stylish backsplash, opening into inviting living spaces with refinished hardwood floors, custom built-ins, and a charming gas fireplace. One of the standout spaces is the expansive rear sunroom, complete with vaulted ceilings, exposed beams, luxury vinyl plank flooring, and walls of windows that flood the room with natural light while framing peaceful water views. Recent improvements throughout the home include a brand-new roof (2026), fresh interior paint, refinished hardwood floors, a renovated shared bath with new tile and shower, making this home move-in ready. Outside, enjoy the best of waterfront living with a private dock and boat lift, perfect for exploring Glebe Creek and beyond. The property also includes a detached 2-car garage connected by a breezeway, offering convenience and additional storage. Just a short drive from both downtown Saint. Michaels and downtown Easton​, this property provides the ideal blend of waterfront tranquility and access to the Eastern Shore’s restaurants, shops, and amenities.

8987 Glebe Creek Road, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$1,050,000
3 Beds ⋅ 3 Baths
Exquisitely designed renovation incorporating high end finishes makes this waterfront 3BR, 3B cottage the perfect retreat! Large great room w/dining area, fireplace & multiple seating areas gives you ample spaces to enjoy the broad, westerly views of the bay. The gourmet kitchen & pantry is a chef's dream. Screen room, private pier, separate garage w/ guest house.

6050 Sunset Lane, Tilghman

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

Selling Office: .

$1,049,000
3 Beds ⋅ 2 Baths
Privately situated along the Oxford Road corridor, Heron Rest is a custom Pam Gardner–designed waterfront home that beautifully blends Eastern Shore charm with modern functionality. Built in 1995 and set on approximately two acres overlooking Peachblossom Creek, this property embodies the essence of relaxed waterfront living. The home features cathedral ceilings and hardwood floors throughout the great room and dining area, anchored by a striking wood-burning marble fireplace. The spacious kitchen is equipped with double wall ovens, a gas cooktop, generous cabinetry, and a walk-in pantry with wine storage. A butler’s pantry, laundry room, and mudroom/side entry add convenience and thoughtful flow to the layout. The primary suite includes an adjoining library with custom built-ins and a vaulted ceiling, while two additional bedrooms share a hall bath. A large screened porch features tile floors, rattan shades, and a gas fireplace, an inviting retreat with tranquil water views. A detached three-car garage includes second floor storage for an office or studio. The waterside deck and gently sloping lawn lead to a private pier on Peachblossom Creek. Located just minutes from downtown Easton and Oxford, Heron Rest offers a rare combination of privacy, craftsmanship, and timeless Eastern Shore beauty.

28701 Edgemere Road, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$1,048,000
3 Beds ⋅ 3 Baths
Historic Charm Meets Endless Potential in Easton Welcome to this beautifully renovated home situated on a highly desirable, deep double corner lot in Easton's Historic District. Inside, you are greeted by bright, airy spaces that perfectly balance historic character with modern flair, featuring gorgeous hardwood floors, classic moldings, and elegant fireplaces. Main House Highlights: Inviting Living Spaces: Multiple sitting areas offer cozy fireplaces and glass doors that seamlessly blend indoor and outdoor living. Brand new HVAC. Chef’s Kitchen: A large, fully equipped kitchen boasts crisp white cabinetry, stainless steel appliances, a center island with seating, and striking granite countertops, flowing easily into a separate dining room. Versatile Upper Level: Features spacious bedrooms (including a bold, stylish primary suite), flexible space for a dedicated home office, and a beautiful sunroom bathed in natural light from three sides. Updated Baths: Two charming and light-filled bathrooms complete the interior. Outdoor Oasis: Step outside to enjoy a very private, fenced yard complete with a patio, a relaxing side porch, extensive landscaping, greenhouses, landscape lighting, and the convenience of off-street parking. The home also features Lutron lighting throughout to perfectly set the mood. The Bonus Opportunity—A Ready-to-Build Guest House: The property includes an existing barn/shop outbuilding, and the current owners have already done the heavy lifting to envision its future. Schematic architectural plans for a complete barn conversion by John Hutchison Architecture are available for the new owner! The Vision: The proposed design transforms the space into a stunning guest house or accessory dwelling. First Floor: Designed to feature a living area with a gas fireplace, a kitchenette, and two bathrooms. Second Floor: Expertly planned to accommodate custom built-in beds and bunks. Premium Finishes: Planned materials include James Hardie vertical board and batten siding, Andersen 400 series windows, and engineered hardwood flooring. Turnkey Potential: A comprehensive construction estimate from KRM Construction is also on file, making this an easy, ready-to-execute project for the visionary buyer. (Further adding to the property's incredible potential, existing condition architectural plans have also been drafted for a future main house addition.)

209 Goldsborough Street, Easton

Listing courtesy of Compass. Contact:

Selling Office: .

$1,035,000
5 Beds ⋅ 4 Baths
Welcome to Pin Oak House, an Easton Federal style white-washed brick property proud to feature the Grand Champion Pin Oak of Talbot County within the confines of its iron-fenced front yard. The spacious corner lot also offers fine gardens, providing colorful foliage nearly year-round. Roses, honeysuckle, tulips, a glorious crepe myrtle, gazebo, irises, stone hardscaping, and a koi pond with waterfall feature are among the many surprises of the enchanting, fairytale-like backyard. The front and backyards are on a multi-zone irrigation system. This property provides ample off street parking for three cars as well as a sizable storage facility that can be converted into a garage if desired. The backyard and main parking area is monitored 24/7 by a Nest Cam security system. The recently installed uplighting in the front and back of the property further adds to the elegance of the home. Enter inside the red solid wood front door and you are greeted by new custom closets and wood doors, new crown molding, a just installed custom sisal stair runner in the foyer; a stunning formal dining room with designer wallpaper and custom window treatments, a beautiful kitchen with granite, dual ovens, a gas stove, new plantation shutters, stainless appliances, and a wet bar/coffee bar; a sizable living room inclusive of custom built in bookcases and a working wood burning fireplace; a cozy family room with a brick floor and warm grasscloth wallpaper; and a darling period-inspired powder room. On the second and third floors are five bedrooms (one being used as an office), three full baths, new paint, designer toile wallpaper, a new custom herringbone runner, new plantation shutters/window treatments, and custom built ins. The entire house offers ample closet space on each floor. Additionally, the dry basement (which is accessible from either inside the home or from the exterior) offers many storage racks, a washer/dryer, a large laundry sink, and sump pump. The backyard is fully fenced with privacy trees along Earle Avenue, so the space cooperates with dog lovers and truly feels like a private, quiet escape in the heart of town. This property is diagonal across the street from the Historic District so is not subject to the restrictions of the town's historic requirements, however, the white-washed Federal style brick blends in seamlessly with the look of the district. The property is a short walk to Easton's renowned restaurants, shops, galleries, downtown events such as Waterfowl Festival, museums, as well as in the opposite direction to Idlewild Park, the YMCA and Rails to Trails. Full list of upgrades can be found in the agent remarks. Owner is a licensed realtor in Maryland.

301 S Washington S Street, Easton

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: .

$1,025,000
3 Beds ⋅ 2 Baths
A lovely waterfront home located in Sailors Retreat. Three bedrooms and two and half baths. primary bedroom, sunroom, and family room have a beautiful view of Island Creek. Nice deck and patio for relaxing Two car garage with walk upstairs to the attic. The dock can accommodate two boats with a water depth of 3'-4' MLW. Buyer must verify the water depth

4752 Sailors Retreat Road, Oxford

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: .

$1,009,009
Well-maintained 8-unit apartment building offering immediate income and a history of consistent occupancy. Ideally located approximately one block from Route 50, providing convenient access for commuters while maintaining a neighborhood setting. The property consists of eight 1-bedroom, 1-bath units, including two larger units at approximately 711 sq ft and six units at approximately 650 sq ft . Each unit features a functional layout with open living areas, separate bedrooms, and efficient kitchens. Flooring is a mix of hardwood, carpet, and laminate, with new carpet installed (common areas) throughout both upper and lower levels in 2024. Each apartment is equipped with its own mini-split system for heating and air conditioning, as well as a dedicated hot water heater.

142 Calvert Street, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$1,000,000
5 Beds ⋅ 3 Baths
Welcome to 5520 Leeward Lane, a private waterfront estate tucked away at the end of a quiet, tree-lined drive on Tilghman Island—a rare opportunity to own a stunning piece of Maryland’s Eastern Shore. This expansive home features panoramic water views from almost every room and delivers the ultimate blend of luxury, comfort, and natural beauty. The grand foyer sets a graceful tone, leading into a spacious main-level layout designed to impress. The expansive living room is flooded with natural light and flanked by a formal dining area, a warm and inviting den, and a breakfast nook with vaulted ceilings—all connected by elegant sight lines and polished hardwoods. A true chef’s kitchen anchors the heart of the home, outfitted with a commercial-grade gas stove, a commercial refrigerator, two dishwashers, granite countertops, and an oversized island perfect for entertaining or casual morning coffee. The main-level primary suite is a private retreat, offering dual walk-in closets, a spa-inspired bath with soaking tub and glass shower, and serene views of the surrounding landscape. A conveniently placed laundry room with a half bath adds thoughtful utility to the main floor, while the upstairs offers flexibility with four generous bedrooms, a shared full bath, and a secondary living space complete with its own kitchenette—ideal for extended guests or multigenerational living. From nearly every room, you're drawn to the shimmering water just beyond the windows. Whether enjoying sunsets from the deck, stargazing from the rooftop deck above the three-car garage, or savoring peaceful mornings with the birdsong of the bay, this home embraces its setting with elegance and ease. Attic storage above the garage ensures ample space for seasonal gear or future creative use. Tilghman Island itself is a captivating enclave, celebrated for its maritime heritage, vibrant wildlife, and relaxed coastal vibe. Here, you’ll enjoy unmatched privacy, historic charm, and proximity to waterfront dining, boutique shops, and world-class boating—just far enough to escape, yet close enough to stay connected. 5520 Leeward Lane isn’t just a home—it’s a lifestyle. A sanctuary where land, sea, and sky converge in perfect harmony. Schedule your private showing and experience Eastern Shore living redefined.

5520 Leeward Lane, Tilghman

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: .

$995,000
3 Beds ⋅ 3 Baths
Affordable Talbot County, MD waterfront home. Just a 12-minute drive beyond St. Michaels, this well-built 3 bedroom, 2.5 bath home faces west across the waters of Cummings Creek. Great sunset views from the waterside screened porch! The 1.92-acre lot is well-elevated (flood insurance is not required by mortgage lenders). The house features generous-sized rooms, including a spacious kitchen/dining room. Efficient hot-water baseboard heat and 2-zone AC. In addition to an attached garage, there is a detached 3-bay garage/workshop. Asphalt driveway and parking area. Substantial pier w/two boat slips. By boat, Tilghman Island and the open waters of Chesapeake are a short, scenic cruise downstream from the dock. This location is known for great fishing and crabbing!

8684 Sewell Point Road, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .