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$375,000
2 Beds 1 Baths
COUNTRY LIVING AT IT'S VERY BEST! THIS ADORABLE COTTAGE NESTLED ON OVER 4 ACRES OF LEVEL FIELD SURROUNDED BY MATURE TREES & SHRUBBERY IN CAROLINE COUNTY BEAUTIFUL COUNTRYSIDE! THIS CUTE HOUSE HAS BEAUTIFUL HARDWOOD FLOORING, 2 BEDROOMS, LIVING ROOM, KITCHEN & LARGE BATHROOM- LAUNDRY AREA. CEILING FANS THROUGHOUT, UPDATED KITCHEN, QUAINT FRONT PORCH & SIDE PORCH STOOP. BEAUTIFUL WOODED SCENERY FROM EVERY WINDOW BRINGING THE OUTSIDE IN! MAJORITY OF THE LAND IS OPEN FIELDS WITH WOODED AREA IN THE REAR OF THE HOME. 2 LARGE UTILITY SHEDS CONVEY WITH THIS PROPERTY. BRING YOUR HORSES & CHICKENS & LOTS OF ROOM FOR A GARDENING PARADISE. LOCATED NOT FAR FROM I-95 FOR COMMUTERS ALL AROUND RVA, DC & MD - GREAT STARTER HOME WITH ROOM TO ADD ON. COME CHECK IT OUT NOW!

18214 Minor Ln, Ruther Glen

Listing courtesy of Hometown Realty Services, Inc.. Contact:

$375,000
5 Beds 3 Baths
Imagine what you could create here—and turn this house into a home that’s entirely your own! Priced almost $60,000 below tax-assessed value, this spacious rambler offers almost 2,100 square feet, 5 bedrooms, 3 full baths, an oversized 2-car garage, a 0.55 acre double lot, and an exciting opportunity to make it your own while building equity from day one. The open living area flows into a generously sized kitchen already featuring granite countertops, abundant cabinetry, stainless steel appliances, and a center island. The large primary bedroom suite includes a walk-in closet and en-suite bathroom with soaking tub and separate shower. Choose your colors, finishes, and style to completely transform the space. Ramblers this large in Lake Caroline are rare—especially with a two-car garage—and this home offers considerably more space than the typical one-level. A 2-year-old deck and separate storage shed add even more value. Bring your ideas, see the potential, and transform this spacious home into something truly special! Home is being sold as-is.

151 Yorktown Dr, Ruther Glen

Listing courtesy of Samson Properties. Contact: (703) 378-8810

$99,000
3 Beds 2 Baths
AS IS! GREAT INVESTMENT PROPERTY! This charming 3-bedroom, 1-bathroom traditional home, built in 1944, offers a solid investment opportunity with its AS IS condition gives you a blank slate to modernize this home to fit your needs! The traditional floor plan maximizes space, creating a warm and inviting atmosphere perfect for comfortable living. With a manageable lot size of 0.09 acres, maintenance is simplified, allowing for a focus on maximizing rental income or future resale value. The property features off-street parking, enhancing convenience for tenants or guests. Investors will appreciate the potential for appreciation in this desirable area, coupled with the opportunity to enhance the property further through updates or renovations. This home is not just a residence; it's a canvas for future growth and profitability. Don't miss the chance to add this gem with all its potential to your portfolio!

101 S University Ave, Federalsburg

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$955,000
3 Beds 3 Baths
Private Waterfront Retreat on the Choptank River Experience the best of Eastern Shore waterfront living in this exceptional home built in 2021, where modern luxury, privacy, and serene views come together on one remarkable property. Situated on 8.15± private acres with approximately 600 feet of Choptank River frontage and deep water access, this stunning retreat offers the perfect balance of refined living and peaceful seclusion. Featuring 2,376± square feet of beautifully designed living space with modern finishes throughout, this home was thoughtfully crafted for effortless entertaining and everyday comfort. The open concept design seamlessly connects the kitchen, dining, and living areas, including a spacious sunroom with expansive windows for a bird's eye view of the river frontage. The main floor also includes an easily accessible large primary suite. Two additional bedrooms, full bath, and a dedicated pocket office or potential walk in closet can be found on the second level. Over the large garage, a full staircase provides access to a spacious bonus room, providing storage space currently, though could potentially serve as flexible space for guests, a media room, home gym, or playroom, per county approval. Step outside to discover a true waterfront oasis. Fresh landscaping complements the natural beauty of the property, while three acres of manicured lawn blend seamlessly into five acres of mature woods, creating ideal privacy and a picturesque setting. Whether hosting gatherings with family or friends, enjoying dinner or cocktails on the patio or dock, or relaxing with your morning coffee overlooking the peaceful scenery, every moment is enhanced by the tranquil surroundings. A new private pier with approximately 12 feet of water depth offers outstanding access to the Choptank River, making it easy to spend your days boating, fishing, kayaking, paddleboarding, or simply taking in spectacular sun painted skies from your own backyard. Ideally located near the town of Denton with lovely shops and restaurants, the location of this sanctuary is just a short drive to the Eastern Shore's most desirable destinations where there is convenient access to the boutique shopping, award winning restaurants, galleries, and downtown charm of Easton, the historic waterfront town of St. Michaels, and even excellent ocean beaches only one hour away. This property provides the perfect blend of privacy while keeping you close to everything that makes Maryland's Eastern Shore so special. More than just a home, this is a lifestyle where every day feels like a getaway and every season brings new opportunities to relax, entertain, and enjoy the beauty of private waterfront living.

8851 New Bridge Rd, Denton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$170,000
2 Beds 1 Baths
Escape the noise and reconnect with what matters most. Nestled on a peaceful 1-acre country setting surrounded by mature trees and open skies, this charming cottage offers the perfect opportunity to embrace the simplicity and serenity of tiny home living. Whether you’re searching for a full-time residence, a weekend retreat, or a place to slow down and enjoy nature, this property delivers a lifestyle that’s becoming increasingly hard to find. Thoughtfully cared for and recently improved, the home features updated insulation, an upgraded electrical box, several newer windows, and the added comfort of a wall-mounted propane heater, providing a secondary heat source for cozy winter days. Outside, you’ll find endless possibilities with three detached outbuildings. Two are ideal workshop spaces for woodworking, hobbies, crafting, or storing equipment, while the detached one-car garage provides additional parking and storage. The expansive yard offers room for gardening, outdoor entertaining, or simply enjoying the sights and sounds of the surrounding countryside. Located just a short drive from historic downtown Denton, you’ll enjoy local restaurants, shops, community events, parks, the Choptank River, Martinak State Park, kayaking, fishing, hiking, and easy access to Maryland’s Eastern Shore attractions while still coming home to the peace and privacy of rural living. If you’ve been dreaming of a slower pace, simpler living, and a place where nature becomes part of your everyday routine, this inviting country cottage is ready to welcome you home. Conventional or cash sale only due to ceiling height.

6140 Laurel Grove Rd, Denton

Listing courtesy of Compass. Contact: 3022029855

$429,499
6 Beds 3 Baths
LOVELY Tidewater Farms home with a light, open layout and plenty of space to enjoy. The main level features a spacious breakfast room, open kitchen and great room with a center island, eat-at bar, and gas fireplace. There is also a 19' x 15' bonus room and convenient upstairs laundry. The primary suite offers walk-in closets, a soaking tub, separate shower, and double sink vanity. Outside, enjoy the patio, storage shed, and white panel fence. The home has a brand-new roof from last year, HVAC upgraded approximately five years ago, brand-new washer and dryer, good plumbing, and a finished crawl space. Appliances are under warranty. The sellers are in the process of transitioning into their new home, so buyers should plan for a few months before possession. Reach out for additional information and pictures of the property!

304 Tidewater Cir, Preston

Listing courtesy of Samson Properties. Contact: 3018500255

$310,000
3 Beds 4 Baths
Welcome to 18436 Congressional Circle, Ruther Glen, VA, located in the desirable Pendleton Golf Community. This three-level townhome offers a functional floor plan with spacious living areas, a bright kitchen with ample cabinet space, a private primary suite, and a finished lower level that provides additional living or recreation space. The home is ready to be loved and offers an excellent opportunity for buyers to add their own personal touches while building equity. Enjoy all that the Pendleton HOA has to offer, including an 18-hole golf course, community pool, walking trails, parks, playgrounds, pickleball courts, dog park, and beautifully maintained common areas. Conveniently located just minutes from I-95, shopping, dining, and local amenities, this home combines value, convenience, and a fantastic community lifestyle. Don't miss this opportunity!

18436 Congressional Cir, Ruther Glen

Listing courtesy of Samson Properties. Contact: (703) 378-8810

$435,000
3 Beds 2 Baths
Possibilities! This Caroline County 3-bedroom 2 bath Victorian sitting on almost 4 acres with fencing and plenty of usable buildings in a country setting. Nearby points of interest include Tuckahoe state park with equestrian trails, hiking trails, even a lake to paddle or fish. Gooden Airpark is just down the road along with a few boat ramps to the Choptank River. The property offers several mechanical upgrades including a recent new boiler for the hot water and heating system, recent BATT septic system installation, recent cooling system upgrades, a car charging hookup with upgraded service. The property is offered in as-is condition. Let's set up an appointment to take a look

13166 Oakland Rd, Ridgely

Listing courtesy of The Land Group. Contact: (410) 934-3478

$629,900
4 Beds 3 Baths
Private waterfront retreat less than 90 minutes from Washington DC & Richmond in amenity rich Lake Caroline. Fully renovated home with private lakefront living on one of the community’s most desirable DOUBLE Lots (nearly one acre w/space for parking, RV, detached garage etc.) This beautifully remodeled home offers over 120 feet of private water frontage w/your own dock, creating a perfect backdrop for boating, fishing, or soaking in peaceful views. This home features a new roof, new HVAC, and luxury vinyl plank flooring throughout. Stunning chef’s kitchen, complete with custom cabinetry, under-cabinet lighting, quartz countertops, a spacious island, wine cooler, and a premium KitchenAid gas cooktop with electric oven—designed to impress and built for entertaining. The open dining area captures picturesque lake views, while the all-brick gas fireplace adds warmth to the living space. Redesigned mudroom/laundry area offers custom built-ins for added convenience, along with a large half bath and a versatile 4th bedroom—perfect for guests, a home office, or flex space. The primary suite is features a beautifully updated bathroom w/modern finishes and a tiled walk-in shower. Upgraded fully encapsulated crawl space w/dehumidifier & alarm making a moisture free added storage area. Enjoy lake life w/gatherings on the expansive back deck, relax in the fenced backyard, or explore your green thumb with the custom-built 12x12 greenhouse, mature landscaping, fruit trees, & thoughtfully designed garden beds leading down to the water. Freshly painted storage shed. This expansive lot has incredible potential—add a detached garage, or create your dream outdoor oasis. All of this is located within the amenity-rich Lake Caroline community, offering a pool, clubhouse, tennis and basketball courts, security, and more. This is more than a home—it’s a Lake lifestyle. Enjoy boating, fishing, paddleboarding, gas powered boats and jet skis permitted. INCLUDES FREE HOME WARRANTY & 1 YEAR HOA PREPAID DUES! Don't miss this rare opportunity!

448 Lake Caroline Dr, Ruther Glen

Listing courtesy of Real Broker, LLC. Contact: 8504500442

$435,000
3 Beds 2 Baths
Possibilities! This Caroline County 3-bedroom 2 bath Victorian sitting on almost 4 acres with fencing and plenty of usable buildings in a country setting. Nearby points of interest include Tuckahoe state park with equestrian trails, hiking trails, even a lake to paddle or fish. Gooden Airpark is just down the road along with a few boat ramps to the Choptank River. The property offers several mechanical upgrades including a recent new boiler for the hot water and heating system, recent BATT septic system installation, recent cooling system upgrades, a car charging hookup with upgraded service. The property is offered in as-is condition. Let's set up an appointment to take a look

13166 Oakland Rd, Ridgely

Listing courtesy of The Land Group. Contact: (410) 934-3478

$274,950
25.5± acres on Ladysmith Road in Caroline County offering an excellent opportunity for residential, recreational, or investment use just 4 miles west of I-95 Exit 110 (Ladysmith) and just down the road from Land Landor. With over 400 feet of road frontage along Ladysmith Road, the property provides multiple options for driveway access and future homesites. The tract is completely wooded and features a naturally regenerated forest after the timber was harvested in 2006. Today, the property offers a diverse mix of pines, young hardwoods, and scattered mature oaks, creating excellent wildlife habitat while allowing the next owner to enjoy a healthy, growing timber stand. The land gently rolls from the road toward the rear, where a seasonal creek provides natural drainage and seasonal water source for wildlife. Tax Map 51-A-44 may be divided one time as a minor subdivision, subject to Caroline County regulations, with a minimum lot size of 10 acres (buyer to verify). No soil studies or perc testing have been completed; however, USDA soil maps indicate the property may be suitable for a conventional septic system. Buyers should conduct their own due diligence regarding soils, subdivision potential, and intended use. Whether you're looking to build a custom home, establish a small farm, enjoy a private hunting property, or purchase land as a long-term investment, this property offers exceptional versatility. The regenerating timber, abundant deer and turkey sign, and gently rolling topography provide the perfect setting for trails, food plots, gardens, or future pastureland. Conveniently located approximately 40 minutes from both Richmond and Fredericksburg, this property offers the peace and privacy of country living while remaining close to I-95, shopping, dining, and employment centers. Shown by appointment only. Parking instructions in the attachments.

25.5 Acres Ladysmith, Ruther Glen

Listing courtesy of Coldwell Banker Avenues. Contact:

$269,000
3 Beds 2 Baths
Welcome home to Bowling Green! This charming 3-bedroom, 2-bath ranch offers a wonderful opportunity for buyers looking for an affordable home with plenty of potential. Whether you're a first-time homebuyer, an investor, or simply looking for a place to make your own, this property provides a solid foundation to create the home you've been dreaming of. The functional one-level floor plan offers comfortable everyday living, while the spacious yard provides room for outdoor entertaining, gardening, pets, or simply relaxing. Conveniently located just minutes from shopping, restaurants, schools, and major commuter routes including Route 301 and I-95, you'll enjoy the perfect balance of small-town charm and accessibility. This property is being offered as a short sale, presenting an excellent opportunity to purchase at a competitive price. The sale is subject to lender approval, and additional time may be required to complete the approval process. The home is being sold As Is, and the seller will make no repairs. If you've been searching for a home with value, potential, and a convenient location, this is one you won't want to miss. Schedule your private tour today and discover all that this Bowling Green home has to offer!

16064 Chester Ln, Bowling Green

Listing courtesy of Samson Properties. Contact: (703) 378-8810

$2,500,000
This valuable commercial property consists of 10.4 level acres that fronts two roads. It is located on the corner of Blades Farm Rd and Sharp Rd. Blades Farm Rd runs parallel with RT 404 with a traffic light at the intersection of Rt 404 and Deep Shore Rd. There is also access from Rt 404 to Sharp Rd. The site is mainly open crop land, however it currently has a 1983 home on it. The property is in the town limits and will require the buyer to hook up to town water and sewer. Sharp Rd has access to the Food Lion shopping center along with two banks and a Medical Center. It also adjoins a large residential community and the Denton Elementary School to the back of the property. To the left of the property is another Medical Center and Horizon Farm Credit Bank. Across the highway you will find two car dealerships, Aldi’s, Petco, Dollar Tree, Verizon, Walgreens and of course Walmart, Dunkin Donuts, Taco Bell and Wendy's to name a few. May be possible to divide. A commercial property like this doesn't come along often!

1120 Blades Farm Rd, Denton

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

$699,000
3 Beds 2 Baths
Searching for your own private oasis with endless possibilities? Welcome to a rare 16.29-acre offering made up of four separate parcels, thoughtfully improved and ready for whatever vision you bring. Whether you dream of a hobby farm, a multi-use homestead, or a private retreat, this property delivers space, versatility, and infrastructure you won’t find anywhere else. Across the acreage you’ll find multiple outbuildings and specialized structures, including: 40x80 shop with three overhead doors; 30x40 heated and cooled workshop with two overhead doors and water; 15x48 kennel building with dedicated office space; 24x24x32 barn with four stalls; Poultry and roosting sheds; Established gun range area; Small animal paddocks; Two large fenced pastures; Fenced duck pond; Additional storage sheds throughout the property The main home offers comfortable one-level living with a split-bedroom layout, featuring an open kitchen/dining/living area anchored by a cozy wood stove. With 3 bedrooms, 2 bathrooms, and approximately 1,200 sq. ft., it’s the perfect base for enjoying the land that surrounds you. Bring your animals, your imagination, and your offer — opportunities like this don’t come around often. Your private retreat with unlimited potential is waiting.

14540 Drapers Mill Rd, Goldsboro

Listing courtesy of Brenton Realty Group. Contact: 4104794663

$575,000
4 Beds 3 Baths
Photos Coming Soon. You'll love this custom home nestled on 2.13 private acres, offering nearly 2,500 square feet of thoughtfully designed living space with 4 bedrooms and 2.5 baths. The open floor plan is highlighted by rich Brazilian hardwood floors, cathedral ceiling, and a welcoming great room anchored by a dramatic floor-to-ceiling brick fireplace. The spacious kitchen opens seamlessly to the great room and features an island, abundant cabinetry, generous counter space, and a built-in breakfast area. The formal dining room provides the perfect setting for holiday meals and special occasions. Relax in the spacious family room or the bright four-season room that overlooks the backyard. Designed for both entertaining and everyday enjoyment, the outdoor living space features a private in-ground pool. Whether taking a refreshing swim or relaxing on the screened porch while family and friends enjoy the pool, this backyard provides the perfect setting for summer gatherings or peaceful evenings at home. The oversized two-car garage offers exceptional space for hobbies, projects, or additional storage. This home combines quality craftsmanship, spacious living areas, and exceptional indoor and outdoor amenities, offering the perfect balance of privacy and comfort. 2 zones, 2 heat pumps, 3 and 8 yrs old. Solar is leased. Last years Solar lease bill plus electric bill averaged $228 a month. Roof is less then 5 years old

22733 Squire Ln, Queen Anne

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

$649,900
INCOME PRODUCING PROPERTY!! Live in one house and rent the other one out for $2400. Rare opportunity to own two fully renovated single-family homes on one property! The main house offers 4 bedrooms, 3 full bathrooms, and 2,092 finished square feet, while the second house features 3 bedrooms, 2 full bathrooms, and approximately 1,000 finished square feet. Both homes have been completely remodeled with new flooring, fresh paint, updated kitchens, new cabinetry, countertops, fixtures, renovated bathrooms with new vanities, new HVAC systems, and new roofs and gutters. The modern open floor plans create a bright and inviting atmosphere, while the peaceful country setting provides privacy and space to enjoy. This unique property is perfect for multi-generational living, accommodating in-laws, or generating rental income to help offset your mortgage. Whether you're looking for additional living space, an investment opportunity, or both, this property offers exceptional flexibility and value. Two homes for the price of one—don't miss this incredible opportunity!

12469 Paige Rd, Woodford

Listing courtesy of Samson Properties. Contact: (703) 378-8810

$465,000
3 Beds 2 Baths
Eastern Shore living at its finest! Nestled in the desirable Tuckahoe Springs subdivision, this beautifully maintained home offers the perfect blend of comfort, style, and serene outdoor living. Step inside to an inviting foyer that leads to a dedicated laundry area and an expansive, well‑appointed kitchen featuring cabinetry galore, upgraded stainless‑steel appliances, and quartz countertops. The kitchen flows seamlessly into a bright dining area accented with custom shiplap, creating an ideal space for everyday meals or entertaining. The formal living room is a true showstopper—anchored by a whitewashed brick wood fireplace and bathed in natural light, it’s the perfect place to unwind. Down the hall, you’ll find a guest bathroom, two comfortable bedrooms, and the private primary suite. The full basement expands your living possibilities with additional recreational space, thoughtfully divided into a potential living area and a generous storage section. Off the dining room, the spacious sunroom provides year‑round enjoyment, offering peaceful views of the backyard oasis. Outdoors, tranquility awaits. The backyard has been thoughtfully transformed with multiple gathering spaces including a cozy fire pit area, dedicated grilling zones, garden beds, and a private yard that captures the true Eastern Shore peace and quiet. The neighborhood also provides a private community water access to the Tuckahoe Creek with a picnic area and dock. This is your chance to experience a home that offers comfort, character, and the lifestyle you’ve been searching for. Don’t miss the opportunity to make this incredible property yours. Roof, HVAC, Septic and multiple other upgrades completed since 2022, providing the peace of mind you want in your next home!

23118 Tuckahoe Springs Dr, Denton

Listing courtesy of Brenton Realty Group. Contact: 4104794663

$374,900
4 Beds 2 Baths
Move-in ready and full of charm! Enjoy the freedom of country living with NO HOA! This beautifully updated home offers 4 spacious bedrooms, 2 updated bathrooms, and an open-concept floor plan designed for comfortable everyday living and effortless entertaining. The large backyard provides the perfect space for gatherings, cookouts, or simply relaxing outdoors, complete with a storage shed and oversize detached garage. Recent updates include a newer roof, stylish shaker-style cabinetry, stainless steel appliances, granite countertops, fresh interior paint, new carpet and luxury vinyl flooring throughout, upgraded lighting and fixtures, and much more. Don't miss your opportunity to own this home with modern updates and plenty of space. Schedule your private showing today!

17122 New Baltimore Rd, Milford

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 5403717653

$524,500
4 Beds 3 Baths
Welcome to your own private retreat! Situated on 4 peaceful acres, this well-maintained 4-bedroom, 2.5-bath home offers the perfect combination of comfort, privacy, and functionality. Inside, you'll find a spacious and inviting floor plan with generous living areas, an updated kitchen, and plenty of room for family and guests. Step outside to the enormous rear deck, an ideal space for entertaining, grilling, or simply relaxing while enjoying the peaceful surroundings. One of the property's standout features is the incredible heated and air-conditioned pole barn. This impressive building includes a finished second floor and half bath, making it perfect for a home-based business, workshop, hobby space, gym, recreational area, additional storage, or countless other possibilities. Located just minutes from Tuckahoe State Park, you'll enjoy easy access to miles of hiking and horseback riding trails, kayaking, fishing, camping, and some of the Eastern Shore's best outdoor recreation while still being conveniently close to shopping, dining, and major commuter routes. Whether you're looking for room to spread out, a place to store equipment and toys, or simply a private country setting with exceptional amenities, this property delivers. Also included are the paid off solar panels. So crank up the AC and still have low electric bills with no lease or purchase fee. Don't miss this rare opportunity to own a versatile property that truly has it all. Schedule your private showing today!

22845 Peaviner Rd, Ridgely

Listing courtesy of CR Realty. Contact: 4104900460