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296 Devon Dr, Ruther Glen
$270,000
3 Beds ⋅ 2 Baths
Welcome to the Lake Land Or! This 3 bedroom, 2 bath charming ranch style home offering is a charm! Located in a gated community including amenities lakes and ponds, clubhouse, pool, tennis courts and so much more! Inside; new vinyl plank flooring (2022), updated white cabinets, newer stainless steel appliances, and upgraded fixtures. Stackable washer/dryer (2022), new roof (2022), new HVAC system (2024) and new refrigerator (2024). Hot water replaced (2020). Eat-in kitchen leading to private back deck leading to a large backyard. Master bedroom has its own en-suite bathroom. There are two additional bedrooms with access to the hall bathroom. This home is ready for you!

296 Devon Dr, Ruther Glen

Listing courtesy of CENTURY 21 New Millennium. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

306 S Main St, Federalsburg
$270,000
4 Beds ⋅ 2 Baths
Bring Your Fishing Pole! Nestled along the tranquil waters of Marshyhope Creek, this waterfront retreat offers peaceful views and the rare opportunity to fish or kayak directly from your own private shoreline. This charming 2,820 sq. ft. Victorian home features 4 spacious, freshly painted bedrooms and 1.5 baths and is ready for you to add your special touches. Begin your mornings with coffee on the inviting front porch or host memorable gatherings with family and friends in the generous outdoor living space. Inside, the thoughtfully designed layout offers expansive rooms ideal for everyday living and entertaining. Enjoy cozy evenings by the gas fireplace in the living room, relax in the separate family room, or find inspiration in the sun-filled sunroom, perfect for a home office or reading nook. Additional highlights include a dedicated office and flexible living areas that easily adapt to your lifestyle. Ideally located just minutes from a public boat ramp, walking trails, pavilion, playground, and basketball courts, this home is great for nature lovers and those with active lifestyles.

306 S Main St, Federalsburg

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

Selling Office: Brenton Realty Group.

132 Hobbs St, Greensboro
$269,990
2 Beds ⋅ 2 Baths
**Red Tag Sales Event now through January 25, 2026! Was $268,490 Now: $265,790! Home must close on or before 3/31/2026.** Discover the Perry in Kinnamon Meadows, a 1,059 square foot open concept cottage-style ranch home, offering two bedrooms and two bathrooms at 132 Hobbs Street in Greensboro, MD. A welcoming front porch leads you into the spacious living room that seamlessly flows into the kitchen, creating a perfect space for entertaining guests or enjoying family time. The well-equipped kitchen is complete with modern gray cabinetry, granite countertops, stainless steel appliances, a spacious peninsula island with room for seating, and a corner pantry. The large main bedroom is a retreat in the back of the home; its private bathroom has a double bowl vanity, shower, and an impressive walk-in closet. The second generously sized bedroom is in the front of the home along with a full bathroom and linen closet. The laundry room is tucked away near the entrance of the home. The included white blinds and an innovative Smart Home® package will give you complete peace of mind living in your new home. Pictures, artist renderings, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Image representative of plan only and may vary as built. Images are of model home and include custom design features that may not be available in other homes. Furnishings and decorative items not included with home purchase.

132 Hobbs St, Greensboro

Listing courtesy of D.R. Horton Realty of Virginia, LLC. Contact:

Selling Office: Clark & Co Realty, LLC.

2697 Choptank Main St, Preston
$262,000
2 Beds ⋅ 2 Baths
Charming Renovated Home in Choptank, Preston MD. This home currently has a fresh coat of interior paint, new kitchen appliances. Luxury vinyl flooring installed in the Living Room. Updated bath vanities and many more updates. It is turn key and ready and waiting for you. Situated on a large double lot with mature landscaping. Don’t miss this beautifully completely renovated 2-bedroom, 2-bath home located in the quaint and peaceful community of Choptank. Every inch of this home has been thoughtfully updated from top to bottom, blending modern finishes with classic Eastern Shore charm. Pella windows. Heat pump. Updated Septic. Previously used as a rental home, this home offers investment potential or the perfect retreat. Walking distance to Choptank Marina. Enjoy local crabbing, fishing, and boating nearby. Peaceful, small-town setting on Maryland’s scenic Eastern Shore. Whether you’re looking for a primary residence, weekend getaway, or income-producing property, this move-in-ready home offers it all.

2697 Choptank Main St, Preston

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Douglas Realty LLC.

315 Main St, Greensboro
$261,150
3 Beds ⋅ 1 Baths
Charming Greensboro bungalow ready to welcome you home! This 3-bedroom, 1-bathroom property offers a warm blend of character and modern updates throughout. The dining area features a beautiful wood‑burning fireplace, creating a cozy focal point for gatherings. The remodeled 2024 kitchen brings fresh style and functionality, while the new roof (2019) and all‑new flooring add peace of mind and comfort. A partial basement provides additional storage and houses the laundry area. Outside, enjoy the convenience of a one‑car detached garage and a lovely yard perfect for relaxing or outdoor hobbies. This well‑maintained home is the perfect place to settle in and enjoy small‑town Eastern Shore living.

315 Main St, Greensboro

Listing courtesy of Brenton Realty Group. Contact:

Selling Office: Keller Williams Realty.

14192 Devils Three Jump Rd, Milford
$260,500
2 Beds ⋅ 2 Baths
COUNTRY CHARM AWAITS! Nestled on a picturesque 2+ acre lot, this cozy ranch-style home offers peaceful one-level living with a welcoming full front porch overlooking mature hardwoods and open pasture views. Inside, you’ll find warm hardwood floors, charming country touches, and a comfortable layout perfect for everyday living. Multiple outbuildings provide endless possibilities for hobbies, storage, or workshop space — including one with electric already in place. Recent updates include a new HVAC system and newer water heater. Whether you’re a first-time home buyer, looking to downsize, or simply craving a little space and serenity, this property is full of potential and opportunity. Although no known issues, property conveyed as-is.

14192 Devils Three Jump Rd, Milford

Listing courtesy of Coldwell Banker Elite. Contact:

Selling Office: Blue and Gray Realty,LLC.

103 Williamson St, Preston
$260,000
3 Beds ⋅ 2 Baths
Welcome home to this beautifully remodeled 3-bedroom, 2-bath home situated on nearly a half-acre lot in the charming town of Preston. This move-in ready property features beautiful hardwood floors, a spacious kitchen with abundant cabinetry, granite countertops, new appliances, and new carpet throughout. The inviting living room showcases gleaming hardwood floors and a cozy gas fireplace, creating the perfect space for relaxing or entertaining. Enjoy peaceful mornings or quiet evenings on the welcoming front porch while sipping your favorite beverage. For added peace of mind and year-round comfort, the home is equipped with a Generac whole-house generator, ensuring reliable power when you need it most. Don't miss the opportunity to own this beautifully updated home with plenty of space both inside and out!

103 Williamson St, Preston

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

Selling Office: Benson & Mangold, LLC.

719 Lake Caroline Dr, Ruther Glen
$257,000
2 Beds ⋅ 1 Baths
Back on the market due to buyer financing falling through. Their loss is your opportunity. Nestled within the sought-after Lake Caroline community, this charming home offers something buyers are struggling to find today: affordability, functionality, and access to an incredible lifestyle. Step inside and you'll immediately notice how spacious the home feels. Warm hardwood floors flow throughout the main living areas, while natural light fills the space and creates an inviting atmosphere from the moment you walk through the door. An arched doorway adds character and architectural interest, setting this home apart from the ordinary. The living room offers a comfortable gathering space that feels open yet welcoming, making it equally suited for quiet evenings at home or entertaining family and friends. Just beyond, the kitchen provides ample cabinet storage, practical workspace, and an easy connection to the living areas that keeps everyone part of the conversation. With two bedrooms and one full bath, the layout is efficient, comfortable, and ideal for first-time buyers, downsizers, weekend lake enthusiasts, or anyone looking for a smart investment in a growing community. Outside, the oversized rear deck expands your living space and creates the perfect setting for morning coffee, summer cookouts, or relaxing evenings under the stars. Positioned on a corner lot, the property offers additional yard space, privacy, and room to enjoy the outdoors. But the real magic is the lifestyle that comes with Lake Caroline ownership. Residents enjoy private lake access, a sandy beach, swimming pool, basketball courts, playgrounds, picnic areas, and year-round recreational opportunities. Whether you're spending the day on the water, meeting neighbors at community events, or simply enjoying the peaceful surroundings, Lake Caroline offers far more than just a place to live. Homes at this price point with access to amenities like these are becoming increasingly difficult to find. If you've been waiting for an opportunity to enjoy lake community living without the waterfront price tag, this is one worth seeing. The previous buyer's financing fell through. The home did not. Now it's ready for its next owner.

719 Lake Caroline Dr, Ruther Glen

Listing courtesy of Lake Anna Island Realty. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

705 S 2nd St, Denton
$250,000
2 Beds ⋅ 2 Baths
Welcome to 705 S 2nd St, a spacious home set on a .46-acre corner lot in one of Denton’s most desirable areas. Offering approximately 2,000 square feet, this property presents a fantastic opportunity for buyers looking to personalize a home and add long-term value. The main level features a large living room, formal dining area, and an open kitchen layout, along with a bright rear sunroom that overlooks the pool. A versatile den provides additional living space and could easily function as a home office, guest room, or potential third bedroom. The home currently offers 2 bedrooms and 2 full bathrooms with space to expand. Upstairs, a finished attic space—previously used as a craft room—adds even more flexibility, along with additional unfinished space ideal for storage or future use. Outside, the property includes an in-ground pool, pool shed, and two additional outbuildings, offering a variety of possibilities for storage, hobbies, or outdoor enjoyment. This home offers a solid footprint, flexible layout, and a prime location—making it an excellent opportunity for those ready to bring their vision to life and create something special.

705 S 2nd St, Denton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Wilson Realty & Staging LLC.

4 Maple Ave, Ridgely
$250,000
2 Beds ⋅ 1 Baths
Step into this cozy home tucked away in a peaceful, established neighborhood. Designed for easy living, it’s an affordable, low maintenance option perfect as a starter or downsize. Inside, you’ll find fresh paint and updated flooring which creates a modern feel from the moment you enter. The living room offers a welcoming space to relax and entertain. Enjoy year round comfort with central air installed in 2025, adding peace of mind and efficiency. Outside, the spacious lot features a fully fenced backyard, fire pit and deck perfect for privacy and outdoor enjoyment. Conveniently located in the heart of Ridgely, you’ll enjoy easy access to local favorites, nearby parks, and the charm of a close knit community. With quick connections to Route 404, commuting to work over the By Bride, surrounding towns and the Eastern Shore’s beaches is a breeze. With thoughtful updates, a functional layout, and convenient location, this home is truly move in ready. See this home before someone scoops it up first!!

4 Maple Ave, Ridgely

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Douglas Realty LLC.

502 W Sunset Ave, Greensboro
$249,900
3 Beds ⋅ 2 Baths
✨ Renovated & Move-In Ready with Detached 2-Car Garage! ✨ Welcome to this beautifully updated 3-bedroom, 1.5-bath home where modern style meets everyday comfort. From the moment you step inside, you’ll notice the fresh, clean feel created by brand-new LVP flooring, recessed lighting, fresh paint throughout, and a completely renovated kitchen and bathroom designed with today’s buyer in mind. The kitchen features stylish and modern vibe — with black and white quartz countertop, glossy black subway tile backsplash, stainless steel appliances perfect for entertaining or enjoying your morning coffee. The bathrooms have been fully refreshed with a contemporary look that feels both polished and timeless. Detached 2-Car Garage The spacious detached garage is a standout feature — ideal for contractors, car enthusiasts, hobbyists, storage, a workshop, or whatever your heart dreams of. Whether you need space for tools, toys, or projects, this flexible area adds incredible value and versatility. With three comfortable bedrooms, 1.5 baths, and a layout that feels both functional and inviting. Enjoy small-town charm while staying conveniently connected. Located within easy driving distance to Dover Air Force Base, this home offers an excellent option for military personnel or base employees. You’ll also appreciate quick access to major commuting routes including Maryland Route 404 and U.S. Route 13, making travel to Delaware beaches, Annapolis, or surrounding cities simple and convenient. Move right in and start your next chapter — this one is ready for you.

502 W Sunset Ave, Greensboro

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Clark & Co Realty, LLC.

222 S 3rd St, Denton
$249,000
3 Beds ⋅ 2 Baths
Discover the timeless appeal of this classic Cape Cod, ideally situated just moments from the heart of historic Denton. Lovingly maintained over the years, this three-bedroom, two-bath home offers enduring character, thoughtful updates, and an exceptional backyard retreat rarely found at this price point. The inviting floor plan is filled with natural light and includes comfortable gathering spaces, while the rear Florida room provides the perfect vantage point for overlooking the backyard. Step outside to discover your own private oasis featuring an in-ground swimming pool, expansive concrete patio, covered entertaining area, fenced yard, and pool house with electricity—an ideal setting for summer entertaining, weekend relaxation, and creating lasting memories with family and friends. Significant improvements reflect years of attentive ownership and include replacement siding and many replacement windows in 2011, a new roof installed in 2021, and a regularly maintained heating system. The pool is open and operational, allowing the next owner to enjoy one of the property's signature amenities from day one. Located just minutes from Denton's charming historic downtown, you'll enjoy easy access to locally owned restaurants, shopping, medical services, parks, and community events. Convenient access to Routes 404 and 50 makes commuting to Easton, Annapolis, Dover, and the Delaware beaches practical while allowing you to enjoy the relaxed lifestyle and small-town charm of Maryland's Eastern Shore. Whether you're searching for a place to call home or an opportunity to personalize a property with lasting appeal, this well-cared-for Cape Cod offers comfort, character, and exceptional outdoor living in a convenient in-town location. Estate sale. Property is being sold strictly "As Is, Where Is"

222 S 3rd St, Denton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

207 Bloomingdale Ave, Federalsburg
$240,000
3 Beds ⋅ 2 Baths
Discover this inviting 3-bedroom, 2-bath home on a 0.27-acre lot in the heart of Federalsburg. Enter to a spacious living room filled with natural light and a cozy fireplace, perfect for relaxing or entertaining. Adjacent, the family room features stunning wood-paneled walls, built-in shelving, a second fireplace, and access to both the outdoors and the kitchen and dining areas, creating a seamless flow throughout the home. The kitchen is equipped with generous cabinetry, providing ample storage and functionality. Two generously sized bedrooms include a primary bedroom with abundant natural light and built-in storage. A bright sunroom adds extra living space, ideal for morning coffee or quiet relaxation. Outside, enjoy a detached garage and a covered carport, offering plenty of parking and storage options. Situated in a welcoming community, this home is close to local shops, parks, and recreational amenities, providing both convenience and charm. With its blend of character, functionality, and comfort, this property is ready to become your next home.

207 Bloomingdale Ave, Federalsburg

Listing courtesy of The Parker Group. Contact:

Selling Office: Fairfax Realty Premier.

231 Oldtown Rd, Goldsboro
$235,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully remodeled 3 bedroom, 2 bath home offering 1192 +/- sq ft of stylish, move-in ready living! Fully remodeled down to the studs, this home combines modern finishes, thoughtful design, and energy-efficient comfort throughout. Step inside to find an open-concept layout featuring durable LVP flooring, recessed lighting, and a spacious living area highlighted by a stunning custom green accent wall. The kitchen is designed to impress with butcher block countertops, white shaker cabinets, all new appliances, beautiful backsplash, and a center island perfect for entertaining or everyday dining. The home offers three comfortable bedrooms and two updated bathrooms, including a beautifully finished custom tile shower with pebble stone flooring. Enjoy year-round comfort with 5 mini-split systems providing efficient heating and cooling throughout the home. A dedicated laundry area comes complete with front load washer and dryer for added convenience. Outside, the charming farmhouse-style exterior features a covered front porch, low-maintenance metal siding and roofing, plus a storage shed offering plenty of additional space. Situated on a spacious lot with room to enjoy the outdoors, this property is ideal as a primary residence, weekend getaway, or investment opportunity. Priced at $249,500, this fully renovated home is turnkey and ready for its next owner!

231 Oldtown Rd, Goldsboro

Listing courtesy of Taylor Properties. Contact:

Selling Office: Samson Properties.

302 Vernon Ave, Federalsburg
$230,000
3 Beds ⋅ 1 Baths
Fully Updated & Move-In Ready: Charming Corner-Lot Bungalow Near Downtown! Property Overview Welcome to 302 Vernon Ave, a charming and beautifully refreshed 3-bedroom one bath bungalow that is completely move-in ready! The loft is currently set up for a bed room, but could easily be used as an office or rec room. Situated on a desirable corner lot close to downtown Federalsburg, this home perfectly blends classic bungalow character with extensive modern updates. The property boasts a beautifully landscaped yard that elevates its exceptional curb appeal. Every major system has been recently upgraded, offering the next homeowner ultimate peace of mind and years of maintenance-free living. Key Upgrades (Completed 2023–2025)

302 Vernon Ave, Federalsburg

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

121 E Central Ave, Federalsburg
$230,000
4 Beds ⋅ 2 Baths
Step into the timeless charm of 121 E Central Avenue, a stately four-bedroom, two-full-bathroom residence that perfectly captures the essence of classic Eastern Shore living. Situated in the heart of Federalsburg, this home makes a grand first impression with its expansive wrap-around front porch, offering the ideal vantage point to enjoy refreshing breezes and peaceful water views of the nearby Marshyhope Creek. The exterior's crisp white siding and traditional architecture reflect a sense of enduring character that continues the moment you cross the threshold. Inside, the home unfolds into a series of impressively large rooms characterized by soaring ceilings and rich wood floors that run throughout the main living areas. The formal dining room, bathed in natural light from generous windows, provides an elegant space for hosting large gatherings, while the spacious kitchen combines functionality with a bright, airy atmosphere featuring white cabinetry and modern stainless steel appliances. Adjacent to the main living spaces, the entryway showcases a beautiful staircase with a striking black banister, further highlighting the home's historic appeal and attention to detail. Comfort meets versatility across the two levels of this residence, with four well-proportioned bedrooms providing ample space for family, guests, or a dedicated home office. The two full bathrooms are conveniently situated to serve the household with ease. Beyond the interior, the property extends into a level, fenced-in backyard that offers a secure and private retreat for outdoor activities, gardening, or relaxing under the shade of mature trees. With its blend of historic charm, generous square footage, and a prime location near the water, this Federalsburg gem is ready to welcome its next chapter.

121 E Central Ave, Federalsburg

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: LPT Realty, LLC.

no property photo
$230,000
This 21.55-acre Rural Preservation parcel in western Caroline County answers a common land search question: Is there acreage available for a private homesite, homestead, small farm, or weekend retreat with quick access to I-95 and Lake Anna? The property features a desirable mix of open pasture and wooded land, offering flexibility for buyers who value privacy, usable acreage, and a peaceful country setting. Surrounded by residential, forested and agricultural parcels, the land feels rooted in the rural character that draws people to this part of Virginia while still keeping everyday travel convenient. I-95 is approx.10 minutes away, making north/south commutes more manageable. The main marina at Lake Anna is about 25 minutes away for boating, fishing, and easy weekend escapes. This is the kind of tract that can appeal to buyers seeking room to build, create a hobby farm, enjoy outdoor recreation, or hold land as a long-term investment. Buyers should complete their own due diligence regarding intended use, access, well and septic approvals, and any development requirements with Caroline County. Seven acres open and level with 14 acres wooded with a gentle descent in the back woods to a seasonal stream/swale. DO NOT DRIVE IN FIELD.

19075 Chilesburg Rd, Beaverdam

Listing courtesy of EXP REALTY LLC, - RICHMOND. Contact:

Selling Office: UnrepresentedBuyer.