Caroline County, VA 55+ Community Homes for Sale

Absolutely beautiful rancher, priced below appraised value! Why wait for new construction? Completed in 2025, this custom-built, move-in ready rancher offers 1,436 square feet of thoughtfully designed, single-level living--with no HOA. The bright, open-concept living, dining, and kitchen area features nine-foot ceilings, solid hardwood flooring and recessed LED lighting. The kitchen is finished with granite countertops, all-wood cabinetry, Samsung stainless-steel appliances, a Moen faucet and an instant hot-water system. Propane lines are already in place should the next owner prefer a gas range. The spacious primary suite includes a walk-in closet and private bath with a tiled walk-in shower and granite vanity. Two additional bedrooms, a second full bath, washer & dryer, window treatments, and ceiling fans make this home truly ready for its next owner. Each bedroom is prewired for television and internet service. Quality construction continues behind the scenes with a 200+ amp electrical service, energy-efficient appliances, spray-foam and batt insulation, floored attic storage, and a professionally encapsulated crawlspace with concrete flooring, lighting, dehumidifier, French drains, and sump pump. Outside, enjoy welcoming front and rear porches, a level backyard with privacy fencing, parking for up to six vehicles and convenient hot & cold exterior water connections plus an electric hookup for a camper or RV. This is not a basic builder-grade home -- it is a carefully constructed, nearly new home with upgrades, storage and practical features already in place. Schedule your private showing and see the difference for yourself. Come see this exceptional home today and become the new owners in just a few weeks!

110 N School St, Greensboro

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

$499,999

Beautiful to be built new construction on 1.8 acres just outside Denton. This home offers 4 bedrooms, 2 full baths, great open kitchen with island, pantry, separate laundry room, large family room plus dining area. The crawl space will be conditioned for total peace of mind. The garage is huge measuring 32x22 and will be fully insulated with R19 Batts insulation. There will be a slider leading to the huge back yard. Buyers can still choose colors and finishes. Welcome Home!

25660 Cherry Blossom Ln, Denton

Listing courtesy of Keller Williams Realty. Contact:

$314,000

5 Beds ⋅ 2 Baths

This is 222 S. 2nd Street, a recently renovated home with historic charm. Original wood flooring, and architectural details such as moldings and antique door knobs highlight the home's history. Though it embraces the past, the house has been updated with all new appliances, new quartz kitchen countertops, newly painted walls and new siding. The house offers something that many two-story homes do not - a spacious first floor bedroom with a full bathroom nearby. Kids and guests will have the privacy of their own floor with 4 bedrooms and a full bathroom upstairs. The walk up attic, air-conditioned and heated, provides storage and an opportunity to create more living space. The partial basement offers storage plus utility access. Outdoor lovers can relax on the screened porch, or in the fenced backyard that is big enough for activities, but small enough for easy maintenance. And it’s a short walk to the library, restaurants, and shops. Check out 222 S. 2nd St. and see what it has to offer you.-- Within walking distance to Shops, Restaurants, Library, and Parks. Minutes to Public Boat ramp, Choptank River, and State Parks. Come check this out... You won't be disappointed!

222 S 2nd St, Denton

Listing courtesy of Brenton Realty Group. Contact:

$295,000

Welcome home to this charming 3-bedroom, 1.5‑bath property located in the amenity‑rich community of Lake Land’ Or. The inviting front porch welcomes you in, while the cozy screened back porch offers the perfect spot to unwind and enjoy peaceful evenings. A large fenced yard provides plenty of room for outdoor fun, pets, gardening, or weekend gatherings — a true extension of your living space. Living in Lake Land’ Or means access to incredible amenities including lakes, beaches, pools, playgrounds, walking trails, security, and more. And for even more fun and adventure, you’re just a short drive from the Kalahari Resort, giving you access to world‑class entertainment, dining, and one of the largest indoor waterparks around. Seller will pay the HOA fees through 2026, offering added value and peace of mind for the new owner. This home blends comfort, outdoor living, and unbeatable community perks — a wonderful opportunity you won’t want to miss.

733 Canterbury Dr, Ruther Glen

Listing courtesy of Samson Properties. Contact:

$335,000

NEW PRICE! RECENTLY REDUCED BY NEARLY $40,000! AN INCREDIBLE OPPORTUNITY TO ENJOY EASTERN SHORE LIVING! Welcome to 23116 Gilpin Point Road in Preston, an updated Eastern Shore rancher offering the perfect blend of one-level living, privacy, history, and a water-oriented lifestyle. Beautifully situated in the historic Gilpin Point area, this inviting home provides a peaceful country backdrop with convenient access to nearby towns, commuter routes, and the Choptank River. Steeped in the heritage of the Gilpin Point estate area, the property offers a special connection to one of the Eastern Shore’s historic riverfront communities. Inside, enjoy the ease and comfort of true one-level living with a thoughtful layout designed for everyday convenience. The spacious living area is an inviting place to gather and unwind, while the eat-in kitchen offers comfortable dining space and easy flow to the main living areas. The private owner’s suite features its own full bath, and additional bedrooms offer flexibility for guests, a home office, craft room, or hobbies. A large laundry and utility area provides valuable storage and practical convenience, all on one level. Generous room sizes and a comfortable layout make this home an appealing choice for buyers seeking convenient living without sacrificing space or charm. Outside, the recently refreshed landscaping enhances the home's welcoming curb appeal and highlights its peaceful Eastern Shore setting. Mature trees, open outdoor space, and room to make the yard your own create opportunities for future flower beds, a vegetable garden, outdoor entertaining, or simply relaxing in the fresh air. Whether you envision a fire pit, boat storage, raising chickens, or space for your favorite projects, this property offers flexibility to suit your lifestyle. Fenced areas, greenhouse space, a storage shed with electric, and additional outbuilding space provide options for recreation, hobbies, and storage. Generous parking and room to spread out complete the setting. Less than five blocks away, Ganey’s Wharf provides access to the beautiful Choptank River, with opportunities for boating, fishing, kayaking, crabbing, picnics, or simply enjoying waterfront views. This is more than a home—it is an Eastern Shore lifestyle. Private, peaceful, updated, and full of Eastern Shore charm, 23116 Gilpin Point Road offers one-level living, generous outdoor space, nearby river access, historic character, and everyday comfort. Conveniently located for access to Easton, Denton, Cambridge, Annapolis, Baltimore, Washington, D.C., Middletown, Dover, Dover Air Force Base, Routes 50 and 301, the Bay Bridge, Kent Island, and Delaware shopping. An exceptional opportunity to enjoy Eastern Shore living at a newly improved price!

23116 Gilpin Point Rd, Preston

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$280,000

5 Beds ⋅ 2 Baths

Charming 5BR detached home, located in a quiet neighborhood in Greensboro. Experience the great outdoors in your own backyard on a nearly 1/2 acre lot, adjacent to 140 acres of farmland. Enjoy the 'Sunset' from the 320 sf sunroom with sliding glass doors, or sit outside to watch the sunrise on the new 230 sf wooden front porch. Several updates include replacement windows, upgraded plumbing & electrical, new flooring & paint, jacuzzi, and much more. OWNER FINANCING AVAILABLE. Call for details.

407 W Sunset Ave, Greensboro

Listing courtesy of R&R Executive Realty. Contact:

$359,000

4 Beds ⋅ 4 Baths

Welcome to this spacious three-level home offering flexible living space and a functional floor plan! The main level features a bright living room that flows in the open kitchen. Separate dining room for those family gatherings. Also, on this level is a half bath and a small guest bedroom or turn into your reading area or an office space. Upstairs, you'll find three additional bedrooms and the laundry room conveniently located on the same level. The finished lower level provides endless possibilities and can be customized to fit your needs -family room, home office, gym, recreation area or additional living space. Enjoy outdoor living on the large rea deck overlooking the fenced backyard, while the covered front porch provides a welcoming place to relax and unwind. Plenty of room to make this home your own. Solar panels complete this amazing home.

410 Wood Duck Dr, Greensboro

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

$89,900

2 Beds ⋅ 1 Baths

Investor Alert!! This rancher, situated on over half an acre, is packed with value-add potential! With some TLC and the right vision, this property could be transformed into a strong income-producing asset or profitable flip in no time. Whether you’re looking to renovate and rent or resell, the opportunity here is undeniable—especially with a motivated seller ready to make a deal. Located in Caroline County, you’ll benefit from an area known for its affordability, growth, and rural charm. Larger lot sizes, fewer restrictions, and strong rental demand make this a smart choice for investors. Plus, you’re conveniently positioned within driving distance to Annapolis, Easton, and Dover, giving you access to major hubs while still enjoying a quieter, more laid-back setting. If you’ve been waiting for your next project with upside potential in a growing area—this is it.

305 Old Denton Rd, Federalsburg

Listing courtesy of Keller Williams Realty Delmarva. Contact:

$299,500

3 Beds ⋅ 1 Baths

Seller $5,000 credit being offered to buyer. Welcome to 7397 Cedar Fork Rd in Ruther Glen, a charming country home offering a peaceful setting, comfortable living spaces, and plenty of room to enjoy both indoors and out. Surrounded by mature trees and seasonal blooms, this property provides the quiet feel of country living while remaining conveniently located between Fredericksburg and Richmond. The main level features two bedrooms and one full bathroom, along with a spacious living room, dining area, kitchen, and laundry area. The living and dining spaces flow comfortably together, creating an inviting setting for everyday living and entertaining. Large windows throughout the home bring in plenty of natural light and showcase views of the surrounding greenery. The kitchen offers ample cabinetry and counter space along with a Frigidaire refrigerator purchased new in January 2025 and a Frigidaire range featuring a gas cooktop and electric oven. Just off the kitchen is a convenient laundry area with a GE stackable washer and dryer purchased new in January 2025. One of the home's standout features is the entire upper level, which adds a third bedroom along with a versatile sitting/bonus area and walk-in closet. Whether used as a private retreat, home office, exercise area, music space, reading room, or combination of uses, this flexible second floor provides valuable additional living space and character. Outside, the home offers multiple places to relax and enjoy the peaceful surroundings. Start your morning on the covered front porch or gather with friends and family on the spacious rear deck, perfect for cookouts and outdoor entertaining. The property is surrounded by mature trees and comes alive throughout the seasons with established flowers including daffodils, peonies, lilies, baby's breath, and wild roses. Additional outdoor features include a storage shed and a chicken coop, providing extra space and versatility for those who enjoy gardening, outdoor projects, or a more country-oriented lifestyle. Important improvements include a JES crawl space encapsulation and support system, which conveys with a two-year service plan and lifetime warranty. The home is served by a Trane HVAC system, Ruud water heater, private well, and central heating powered by propane through Tiger Fuel, with the propane tank conveying with an almost full tank. The location offers a great balance between privacy and convenience. Enjoy the peaceful surroundings of Ruther Glen while still being within easy reach of shopping, dining, and entertainment in Fredericksburg and Ashland. Kings Dominion is approximately 15 minutes away, with the new Kalahari indoor water park also nearby. Local favorites in the Ladysmith area include restaurants, thrift and consignment shopping, and everyday conveniences. If you've been searching for a home with country charm, flexible living space, inviting outdoor areas, and convenient access to major cities, 7397 Cedar Fork Rd offers a wonderful opportunity to enjoy a quieter pace without feeling disconnected from everything you need.

7397 Cedar Fork Rd, Ruther Glen

Listing courtesy of Keller Williams Capital Properties. Contact:

$225,000

4 Beds ⋅ 1 Baths

4 bedrooms 1 bathroom bungalow being sold "AS IS". 16,700 sq. ft. lot with detached garage. Priced to Sell. Updated 200. amp electric service.

5258 Preston Rd, Federalsburg

Listing courtesy of Marshy Hope Realty LLC. Contact:

$629,000

Welcome to 132 Deep Shore Rd—an inviting homestead set on more than 3 acres of beautifully maintained gardens, thoughtfully designed outdoor spaces, and versatile outbuildings. From greenhouse and herb beds to a dedicated drying room and casual nooks for lounging, every corner invites you to savor the seasons. Inside, this spacious home offers over 2,700 sq ft with 4 bedrooms and 2.5 baths. An open den with brick tile flooring flows to a charming side porch with a swing—perfect for evening breezes and views of the yard. Warm hardwood floors carry through the dining room and into the kitchen and family room, creating an easy, open flow ideal for everyday living and entertaining. The family room centers around a gas fireplace with a handcrafted black walnut mantel, while a granite-topped built-in serves as a convenient entertainment hub. The chef’s kitchen features quartz countertops, double ovens, a gas cooktop with hood, and generous storage. Three well-appointed bedrooms sit on one side of the home—one showcasing a custom bedframe with built-in storage, another featuring a clever Murphy bed and its own half bath. The private primary suite is tucked on the opposite side and includes a walk-in closet with custom built-ins and an en suite bath. Outdoors, the property is a hobbyist’s dream. You’ll find multiple outbuildings for storage and projects, along with 5 frost-proof yard spigots plus 2 additional spigots on the home for effortless garden care. A 50' x 30' garage is paired with an attached 10' x 30' sunroom. The main shop includes a large storage area, parking, a substantial wood shop, and an additional garage bay equipped with a 7,000 lb. lift. Enjoy all the comforts of home in the shop and sunroom as they offer Heat and Air. Electric as well in all other outbuildings as well. Location is the finishing touch: directly across from the front entrance to Martinek State Park, offering camping, trails, a playground, picnic areas, a public boat ramp, and fishing on Watts Creek with direct access to the Choptank River. Here, you’re surrounded by nature, recreation, and room to grow—an exceptional blend of comfort, craft, and country living at 132 Deep Shore Rd.

132 Deep Shore Rd, Denton

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$435,000

RENOVATED ONE-LEVEL LIVING WITH YOUR OWN BACKYARD ENTERTAINMENT SPACE! Welcome to 25485 Hignutt Road, where a beautifully updated 3-bedroom, 2.5-bath home meets nearly half an acre of peaceful country surroundings—just minutes from Denton’s shopping, dining, and everyday conveniences. Move right in and enjoy a bright, modern interior featuring luxury vinyl plank flooring, beautifully renovated bathrooms, and a spacious living room with custom built-ins and an updated fireplace with a granite hearth. Comfortable one-level living keeps daily essentials within easy reach, while an encapsulated basement adds to the home’s extensive improvements. The appeal continues outside. Extensive tree work has opened up the yard, creating more usable space for gardening, outdoor gatherings, or simply enjoying the setting. The renovated detached outbuilding is a standout feature, complete with a custom bar and entertainment space. Host game day, invite friends over, or make it your own place to unwind. POTENTIAL SAVINGS ON YOUR INITIAL MORTGAGE PAYMENTS! With an acceptable offer, the sellers will consider contributing toward a temporary interest-rate buydown, which could reduce your monthly mortgage payments during the initial buydown period. Subject to loan program and lender approval—ask your agent and lender for details. An updated home, room to enjoy the outdoors, and an entertainment space that sets it apart—schedule your showing and experience everything Hignutt Road has to offer!

25485 Hignutt Rd, Denton

Listing courtesy of Taylor Properties. Contact:

$310,000

The seller is motivated and covering your first full year of HOA fees. Now let's talk about the house. Every detail inside 3 Boston Cove has been thought through. This home has been fully renovated down to the crawl space... the seller spent real time and money making sure it was in tip-top shape so you're not worrying about structural surprises down the road. The kitchen is all new and open, but still has good separation from the main living space. You're not going to hear the dishwasher running while you're watching a movie. The full bath has modern, elegant finishes that are easy on the eyes with plenty of room to move around. The half bath shares with the laundry, which means you've got a built-in drop zone for the yard clothes after a day outside. And no millennial gray here. The seller went with 2026 finishes instead of that played-out 2020 gray. It feels current without trying too hard. Entertaining is easy. Circle driveway with plenty of parking, tucked in a cul-de-sac off the main road. Welcoming brick exterior. One level. A cute rancher that works whether you're just starting out or you're an empty nester looking for some community fun on the lake. Gated Lake Caroline community with lake access, a pool, and the kind of summers that keep people here. Under 10 minutes to I-95, easy access to Fredericksburg, Richmond, and historic Bowling Green. Caroline County schools. This one rewards the people who walk through the door

3 Boston Cv, Ruther Glen

Listing courtesy of EXP Realty, LLC. Contact:

$299,000

Charming 3-bedroom, 2-bath rancher located in Ridgely! Inside, you’ll find comfortable one-level living with a functional open layout connecting the living room and kitchen, complete with stainless steel appliances. The spacious primary suite features a large en-suite bath and private doors leading directly to the backyard deck. Two additional generously sized bedrooms provide plenty of space for family, guests, or a home office. Step outside to enjoy the spacious backyard offering a patio and plenty of room for entertaining, gardening, or relaxing. Move-in ready and conveniently located close to town amenities.

208 Oriole Ave, Ridgely

Listing courtesy of Benson & Mangold, LLC. Contact:

$494,999

NEW Construction Only 2 remain - Ready to move in today! Below Market financing available. This ranch-style model home includes an inviting great room with fireplace and a well-designed kitchen with stainless-steel appliances, tile backsplash, hardwood flooring, a built-in pantry and an adjacent dining room. The luxurious primary suite offers a roomy walk-in closet and lavish bath with double sinks. You'll also appreciate the private study, extended covered deck and unfinished basement. Lot backs to trees!

7106 Braxton Ct, Ruther Glen

Listing courtesy of LPT Realty, LLC. Contact:

$484,999

Amazing Corner Homesite - NEW Construction ready for Move-IN. 2 story - 3 Beds w/ a loft -2 car Garage - Deck included Only 2 homes remain in this amazing Golf Course Community. Schedule your appointment today.

7099 Resolution Way, Ruther Glen

Listing courtesy of LPT Realty, LLC. Contact:

$199,900

Located in the heart of Preston, this classic 1900-built home offers a solid opportunity for both homeowners and investors alike. Inside, the home features 3 bedrooms and1.5 bathrooms and a functional layout that includes a combined laundry room, bath, and mudroom with direct access to the back deck—adding everyday practicality. The kitchen has been updated with durable luxury vinyl plank (LVP) flooring, offering a clean and low-maintenance foundation for the space. Enjoy outdoor living from both the covered front porch and the rear porch, providing comfortable areas to relax or entertain. With its central location and existing rental history, this property presents a strong investment opportunity or a chance to make it your own.

156 Main St, Preston

Listing courtesy of Benson & Mangold, LLC. Contact:

$225,000

ATTENTION INVESTORS -- Incredible opportunity in the heart of Denton - Roomy DUPLEX with tons of potential - renovate and hold, fix and flip, or create a long-term income-producing asset. Featuring 2 separate units, each level includes 2 bedrooms and 1 full bathroom, ideal for rental income or multi-family living - OR - convert this home back to its original colonial charm as a single-family home. Denton is a quintessential Eastern Shore town on the banks of the Choptank River. Minutes to the best that Denton and Caroline County offers - great local restaurants, boutique and big-box store shopping, arts + culture, history galore, plenty of public launches and marinas, boating, world-class fishing, crabbing, hunting, wildlife estuaries, incredible state parks - a true paradise for nature lovers, photographers, boaters, fishermen and anyone who wants to enjoy the more relaxed pace on the Eastern Shore - from the beaches to the bays and beyond! Great central location on the Delmarva Peninsula -- 15mi to Easton, 30mi to the Bay Bridge or Cambridge, 40mi to Annapolis's Downtown, about an hour to the Delaware Beaches or Newark, half hour more to Ocean City's Boardwalk. Sizes, taxes, distances approximate

522 Market St, Denton

Listing courtesy of EXP Realty, LLC. Contact:

$374,900

Don’t miss this opportunity to build a brand-new 3-bedroom, 2-bath home on a .25-acre lot in the heart of the Town of Port Royal. This thoughtfully designed floor plan offers approximately 1,300+ square feet of easy, one-level living, complete with a one-car garage. The open-concept layout features a spacious great room that flows seamlessly into the dining area and kitchen—ideal for both everyday living and entertaining. The home comes standard with a welcoming front porch and a rear deck, with the option to upgrade to a covered deck for additional outdoor living space. Quality standard features include low-maintenance vinyl siding, architectural shingles, modern-finish oak cabinetry, attractive laminate countertops, and stainless steel appliances. Enjoy a comfortable blend of finishes with carpet in the bedrooms and durable luxury vinyl flooring throughout the main living and wet areas. Since this home is to be built, buyers have the opportunity to select colors, finishes, and upgrades to truly make it their own. Estimated build time is approximately 90 days from contract and permits. Build your new home exactly the way you want it—while still keeping the process simple and efficient.

624 Market St, Port Royal

Listing courtesy of Holt For Homes, Inc.. Contact:

$415,000

Welcome to 1709 Cattail Commons Way, located in the highly desirable Savannah Overlook community in Denton, MD. This beautifully maintained 4-bedroom, 2.5-bath home offers a spacious open floor plan, modern upgrades, and move-in ready convenience—perfect for today’s buyer seeking comfort, functionality, and style. The main level features a bright and open layout ideal for both everyday living and entertaining. The gourmet kitchen serves as the heart of the home, complete with an oversized island, stainless steel appliances, a newer refrigerator and microwave (just 3 years old), and a huge walk-in pantry with custom wood shelving. The kitchen flows seamlessly into the family room, where a cozy gas fireplace and views of the fully fenced backyard create an inviting atmosphere. A dedicated home office and convenient powder room complete the first floor. Upstairs, you’ll find a versatile second living area—perfect for a media room, playroom, or additional lounge space. All four bedrooms are located on this level, including a spacious primary suite featuring a tiled walk-in shower with glass doors, a deep soaking tub, double vanities, and a large walk-in closet. Two full bathrooms upstairs provide ease for daily living. This home is loaded with valuable upgrades, including a whole-home soft water system and an under-the-counter reverse osmosis system for high-quality drinking water. The separate laundry room includes a brand new washer and dryer along with custom shelving for added storage. Additional features include a two-car garage and no carpet throughout the home. Situated on a premium corner lot, the outdoor space is designed for enjoyment with a fully fenced yard, a large Trex deck with solar lighting, and a storage shed—perfect for entertaining, pets, or relaxing evenings. Located just minutes from the Choptank River, enjoy easy access to boating, fishing, and waterfront activities—all while being outside of a flood zone. Denton offers a charming small-town atmosphere with local shops, restaurants, and community events, while still providing convenient access for commuters. The Chesapeake Bay Bridge is approximately 35–45 minutes away, and Delaware beaches such as Rehoboth, Lewes, and Bethany are within about 55–65 miles. If you're searching for a move-in ready home in Denton, MD with modern upgrades, flexible living space, and a prime location near the water, 1709 Cattail Commons Way is a must-see.

1709 Cattail Commons Way, Denton

Listing courtesy of Benson & Mangold, LLC. Contact:

$215,000

3 Beds ⋅ 1 Baths

Tenant-occupied property offering an excellent investment opportunity with immediate rental income. Current lease in place through July 31, 2027. The property is well-maintained and conveniently located near local amenities, schools, and major routes. Please allow adequate notice for all showings.

105 Lincoln, Greensboro

Listing courtesy of Taylor Properties. Contact:

$374,000

*Ignore DOM. Home in Excellent Condition. Previous buyer financing fell through after a lot of time wasted** Move-In Ready One-Level Ranch in Bowling Green – $30K+ Updates! NOW AVAILABLE! This beautifully updated 2021 DR Horton Lismore model at 16032 Grant Ct offers 1,531 sqft of comfortable one-level living with 3 bedrooms and 2 full baths. Fresh custom paint throughout and over $30,000 in recent upgrades (2022-2023 luxury vinyl plank flooring, stone paver patio & walkway, aluminum fencing, generator rough-in, new AC unit, and more) make this home truly turnkey. Highlights Include: Open Kitchen & Living: Granite counters, upgraded stainless appliances, oversized island, spacious pantry—perfect for entertaining or everyday meals. Primary Suite: Private bath with walk-in closet for ultimate convenience. Outdoor Oasis: Fully fenced rear yard with paver patio, irrigation system—ideal for pets, relaxation, or BBQs. Practical Perks: 2-car garage, main-level laundry with washer/dryer included, functional layout ideal for starters, downsizers, or commuters. Located minutes from downtown Bowling Green shops, restaurants (try Mixing Bowl Bakery!), and with easy access to I-95 (quick trips to Fredericksburg or Richmond) and Route 17. Enjoy the upcoming Kalahari Resorts & Conventions—Virginia’s largest indoor waterpark just 15 minutes away! Priced at $374,000 with low HOA ( $47/mo). Don’t miss this opportunity—schedule your showing today and move right in! *Some photos staged using AI*

16032 Grant Ct, Bowling Green

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$497,740

5 Beds ⋅ 4 Baths

The Verona is a 5 bedroom, 3.5 bathroom plan offering 2199 square feet. It features an open-concept floorplan, with a large great room, kitchen, laundry/mud room and powder room on the first floor. The chef-inspired kitchen offers a large peninsula and walk-in pantry, and flows into the expansive open-concept dining area and living room with plenty of room for entertaining. The second level includes a large owner's suite, with double vanities, water closet and an oversized walk-in closet. Th second level offers three more spacious bedrooms and a full bathroom. On the third level, an additional bedroom suite and finished storage space complete the home. Renderings and photos are from builder's library, actual finishes and features may vary.

6289 Sterling Way, Ruther Glen

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

$174,000

Move-In Ready & Beautifully Remodeled! This charming 3-bedroom, 1.5-bath home offers the perfect blend of comfort and convenience. Enjoy a spacious living room, separate dining area, and a dedicated laundry room for added functionality. The kitchen is designed for both everyday living and entertaining, featuring dual bar seating areas with open views to the living and dining spaces. One bedroom includes a private half bath—ideal for guests or added flexibility. Relax on the inviting front porch, perfect for evening unwinding. Conveniently located near shopping, grocery stores, a public boat ramp, park, and walking trails—with the added bonus of tax-free shopping just a short drive away in Delaware. A must-see home ready for its new owners!

107 Smith St, Federalsburg

Listing courtesy of Mabry Real Estate LLC. Contact:

$285,000

Nearly new ranch style home with large front porch. Three bedrooms and two full baths plus spacious laundry room enhance this home. Large kitchen with center island with stainless appliances and granite countertops are a focal point of this open floor plan. This home has no HOA or Front Foot Fees to add to payment! Great value for the price. Move in ready and waiting for you.

506 Pintail St, Greensboro

Listing courtesy of Keller Williams Realty. Contact:

$225,000

Hurry before it’s gone! This is an opportunity to buy in the sold out community of Riverwalk Terrace. The owner stayed at the home a few times some of the appliances never used. Open floor plan 1365 square feet , 3 bedrooms and 2.5 baths easy living. Only 2 years young this unit feels like new, was never a rental barley lived in. also backs up to the woods the private side of the community. Another perk to this location is has a back yard, some of the units do not have the ability to have a yard. Easy location to jump onto main roads, short distance to down town Federalsburg and shopping.

103 Riverwalk Ter, Federalsburg

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

$369,900

2 Acre cleared lot. Great opportunity for a fixer upper. Home needs a fair amount of work but it has a great layout. Main level primary, office/den separate dining room. Additional main level bedroom and full bath on main level. Spacious living room with access to the large screened porch. Corner eat-in kitchen & main level laundry. Cash or 203(K). ***The property is being sold in its current “as-is” condition, and Seller will not be responsible for any costs related to the repair, improvement, or modification of the property, including but not limited to any lender-required repairs.

25331 Adams Landing Rd, Denton

Listing courtesy of Keller Williams Realty. Contact:

$669,000

Price Reduction! Motivated Seller. Welcome to 1108 Camp Street, sits on over 14 acres of land where modern comfort meets elegant design through an extensive list of upgrades that enhance both functionality and style. Secluded in a great location for Dirt biking, bow hunting. The included outbuilding is great for car enthusiast. This home features stunning stone work on both the front and back, framing the house in natural beauty and providing a warm welcome. The meticulously crafted stone walls create an inviting outdoor ambiance. Venture beneath the home and discover a 4-foot rat trap encapsulated crawl space, ensuring a clean and dry environment for your peace of mind. The home includes a spacious full-size garage attached garage equipped with a stand-up freezer, making it easy to store extra food and supplies. Step into luxury in the master bath, which boasts a steam shower and a freestanding tub, perfect for unwinding after a long day. The home is designed with accessibility in mind, featuring ADA-compliant doors and hallways for ease of movement. Never worry about power outages again with the whole-house generator, powered by underground propane that activates automatically when there is a power outage. Throughout the home, ceiling fans grace each bedroom and the dining area, providing comfort and a refreshing breeze. The kitchen is a chef’s dream, showcasing soft-close cabinets, a double full-size Frigidaire oven, a General Electric flat-top stove, a Whirlpool microwave, and a sleek Samsung refrigerator with a freezer, complete with four ice settings and a convenient water dispenser. All appliances are stainless steel, adding a modern touch to your culinary space. The unique kitchen sink is Embossed Stainless Steel Nano Black raindance Waterfall Drop in sink with pressurizing cup washer and two waterfalls. 29.5 x 18 For added luxury, towel warmers are installed in the bathrooms, ensuring a cozy experience year-round. The home's smart features include Bluetooth-enabled thermostats, providing efficient climate control, while two thermostats manage temperature zones for optimal comfort. Access to the home is convenient with a combo/key access front door. The living area is designed with practicality in mind, featuring electrical outlets conveniently located on the floor—no more stretching cords across the room! Motion detector lights outside enhance security and illuminate your outdoor spaces. The property also boasts a three-car detached garage, complete with windows and a wood-burning stove, perfect for hobbies or storage. Additionally, there are two storage sheds on the property, providing ample space for all your belongings. Horses ok. Limit on number of chickens. Experience the perfect blend of luxury, convenience, and practicality at 1108 Camp Street, where every upgrade has been thoughtfully selected to enhance your living experience. Come see for yourself and discover your new home! The back porch is ready to be converted to a three season room. Has outlet for fan, sprinklers and connections for tv.

1108 Camp Rd, Denton

Listing courtesy of Coldwell Banker Premier - Rehoboth. Contact:

$1,099,900

Sunny Side Up Farm at 1815 Country Road is the kind of property farm and land buyers are always hoping to find! Priced under appraised value, this property has beautiful infrastructure, level usable acreage, and a classic farmhouse that has been thoughtfully updated over the years. Set on 12.15 acres of open pasture and mature hardwoods, the property offers both functionality and charm, with nine total stalls across multiple barn structures, making it well-equipped for equestrian use or a variety of farm lifestyles. At the heart of the property stands one of the most beautiful and custom barns you will see. The impressive 58x50 pole barn built in 2020 was designed with both craftsmanship and practicality in mind. Inside, the barn features four big stalls with rubber mats, Nelson temperature-controlled automatic waterers, a wash stall, and a well-appointed tack room with utility sink, washer and dryer, and a 40-gallon water heater. The structure has its own dedicated 1,000-gallon septic system, allowing for tremendous flexibility in use. What truly sets this barn apart is the beautifully finished lower-level living space attached to the stalls that is designed with the same attention to detail as the rest of the structure. The space includes a fully appointed kitchen with stainless appliances, a full bath, HVAC, and comfortable living area, making it ideal for a barn apartment, guest quarters, farm manager residence, private office, or studio space. It is rare to find a barn setup with this level of finish and versatility. Above the barn is an expansive upper level already plumbed and wired, providing excellent potential for additional finished space such as an apartment, office suite, or creative workspace overlooking the farm. Additional equestrian infrastructure includes a nostalgic original barn with four stalls and integrated office, along with a classic corn crib with flanking stalls ideal for hay storage, bringing the property’s stall count to nine total. Multiple additional outbuildings include garages, a cinderblock workshop with sliding doors and concrete floor, a gardening room, and ample storage for equipment and tools. The 12.15 acres are a standout feature—level, open, and highly usable with a wonderful mix of pasture and mature hardwoods. The property includes four-board fencing along the road frontage with an electric black aluminum gate, two paddocks with run-in shelters, and expansive back fields that make up nearly two-thirds of the acreage. Centrally positioned on the property is a classic farmhouse with circa-1930s roots that has been updated and renovated throughout the years. Surrounded by gardens, a peaceful fishpond, and mature pecan and walnut trees, the home blends historic charm with modern improvements completed since 2014. Updates include cedar siding (painted in 2025), Thompson Creek windows with transferable warranty, a Trane HVAC system with new ductwork and humidity control, Mitsubishi split system upstairs, updated plumbing and septic, upgraded electrical ready for solar, and encapsulated basement and porch areas for conditioned storage. Inside, the home offers warm and welcoming spaces including a bright family room wrapped in windows, a cozy parlor, dining room with tin chandelier, and a spacious kitchen with oak cabinetry, black granite countertops, butcher block workspace, stainless appliances, and hardwood floors. Upstairs are three bedrooms and a full bath, including an expansive primary suite with cedar closet. A large back porch overlooks the surrounding pastureland where wildlife often passes through, creating the peaceful rhythm that defines life on this special property. With nine stalls, beautiful barns, multiple outbuildings, level acreage, and a lovingly updated farmhouse, Sunny Side Up Farm is a rare and complete farm offering within approximately 15 minutes of Lake Anna, shopping, dining, and I-95.

1815 Country Rd, Beaverdam

Listing courtesy of Porch & Stable Realty, LLC. Contact:

$359,000

Major Reduction! Sellers are ready to move on! Homes like this is what they use for Christmas cards, large wrap around porch, entry foyer, detailed fireplaces, hard wood floors, and so much more. This is waiting for the right owner to continue the 126 years this home has stood. Everything in this home is in grand size. Large rooms, make this an easy home for a large family . The house current owners have the house set up as a six bedroom home. These rooms cannot be considered bedroom's to lack of closets. Located in historic Denton which sits on the Choptank River. A short walk to the 4th Street park with a playground for children , tennis and pickleball for adults and a picnic area. Additional parks are Martinak and Tuckahoe, which offer camping, walking trails, and access to the Choptank River. A public boat ramp is in town as well as in the park. Shopping is minutes away with a vast and fast growing commercial district offering a healthy mix of options. The surrounding area is full of nature lovers options, multiple farmers markets, small entrepreneurial businesses, which includes our local pub, a brewery, a bakery, and a culinary school just to name a few. This really is a special house and a special area. May be subject to a short sale.

112 S 5th Ave, Denton

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

$2,500,000

3 Beds ⋅ 1 Baths

Federalsburg

Listing courtesy of The Land Group. Contact:

$230,000

***NEWLY ADJUSTED PRICE***Come on in to explore this beautifully maintained 3-level home offering the perfect blend of modern convenience and comfortable living. This beauty features 3 spacious bedrooms and 2.5 baths, with an open floor plan that creates an inviting flow throughout the main living areas. The home has been updated with fresh paint, new appliances and more to ensure it's move-in ready for you. Each level offers its own distinct living space providing flexibility for various lifestyle needs. Location is everything, and this home delivers convenience. Situated in a premium location with ideal access to both Route 404 and Route 50 for effortless commuting and easy access to shopping, dining and entertainment. Whether you're headed to work or exploring the area, everything you need is just minutes away.

1204 Blue Heron Dr, Denton

Listing courtesy of Shore Results Realty. Contact:

$220,000

Step back in time with this early 1900s home. This home is full of character, from the detail in the trim work to the upper level 'porch.' This home offers great potential to be returned to the early 1900s with a little TLC and vision. Located in the heart of Preston, it is 15 minutes from historic Easton with all its amenities. Come take a look and see the vision.

126 Maple Ave, Preston

Listing courtesy of Marshy Hope Realty LLC. Contact:

$279,900

This exquisite Colonial-style home, thoughtfully renovated in 2019, seamlessly blends classic charm with modern luxury. Spanning 1,791 square feet, this residence offers a warm and inviting atmosphere, perfect for creating lasting memories. Step inside to discover a beautifully designed interior featuring engineered luxury vinyl plank flooring that exudes elegance and durability. The heart of the home is the gourmet kitchen, equipped with high-end appliances including a sleek electric oven/range, a spacious refrigerator, and a convenient dishwasher, making meal preparation a delight. With three generously sized bedrooms and one and a half bathrooms, this home provides ample space for relaxation and rejuvenation. The layout is designed for comfort, ensuring that every corner feels like a retreat. The property sits on a charming 0.15-acre lot, providing a cozy outdoor space for gatherings or quiet evenings under the stars. Enjoy the convenience of driveway parking, ensuring easy access for you and your guests. This home is not just a place to live; it's a lifestyle choice that embodies comfort, elegance, and modern convenience. Experience the perfect blend of luxury and warmth in this exceptional property, where every detail has been curated for your enjoyment.

309 N Main St, Greensboro

Listing courtesy of Benson & Mangold, LLC. Contact:

$289,000

2 Beds ⋅ 2 Baths

Back on the market, buyer didn't qualify for their loan. Welcome to 211 Bloomingdale Ave. This custom‑built Brick Williamsburg‑style colonial showcases true craftsmanship, featuring beautiful hardwood floors throughout, custom built‑ins, and detailed moldings. The spacious living room offers an inviting wood‑burning fireplace, while the large great room with its vaulted ceiling provides flexible living space and could easily be converted into a third bedroom if desired. The bright, well‑appointed kitchen is ideal for anyone who loves to cook, offering ample room for a kitchen table and direct access to a separate formal dining room—perfect for hosting guests. A convenient half bath is located on the main level, with a full bath upstairs along with two generously sized bedrooms and a large walk‑in storage area. Outside, a concrete driveway leads to an attached garage. There is a brick walkway from house to the town sidewalk. Spacious private backyard with mature trees and a newer roof. This home is truly move‑in ready and waiting for you to enjoy.

211 Bloomingdale Ave, Federalsburg

Listing courtesy of Meredith Fine Properties. Contact:

$450,000

1 Beds ⋅ 3 Baths

Back on the market!! A Unique Opportunity on Marylands Eastern Shore. This prime location tucked away between Easton & Denton, is this remarkable and beautifully maintained, 6.18 acre property that combines the tranquility of a pastoral countryside. Set on 6.18 acres of gently rolling land, this is One Lot, divided into 2 parcels, (one 2 .18 Acre and one 4 acre parcel). The 2.18 acre parcel hosts an impressive 1,596 Sq. Ft. building, impeccably maintained and beautifully finished. Beautiful wood floors and Oak Ceilings. Lots of skylights! Kitchen, SS appliances. Top of the line ceramic tile shower room and loft bedroom. This building offers flexibility to serve as a residence, or guest quarters. ...and the crawlspace is fully encapsulated! The adjoining 4 acre parcel is ready to build, if so desired. The grounds are partially wooded, with majestic mature trees and a peaceful pond, creating a picturesque setting that inspires both productivity and relaxation. Additional amenities include a spacious Workshop, ample storage, a fabulous fenced garden area, greenhouse, fenced firewood supply area, a fully fenced lot and a full home generator for convenience and peace of mind. Whether you are an entrepreneur, a creative professional, or someone who values space and serenity, this property delivers a rare balance of beauty and purpose. Take the opportunity to come and see for yourself.

23629 Willow Pond Rd, Denton

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

$58,000

2 Beds ⋅ 1 Baths

If you looking for a place to built your dream homes, in the charming town of Bowling Green You must see this piece of property, conveniently located near schools, shopping dining, and commuter routes. The existing building is not safe to enter but it has a septic in the property . The value is in the land. Great Location. Buyer to do the due diligences about utilities and anything else pertaining to this property.

160 Chase St, Bowling Green

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

$155,000

1 Beds ⋅ 1 Baths

House is of little to no value, existing well and septic. This house includes an additional parcel of 7 acres, tax id, 0601012428 for a total of 7.27 acres. Property being SOLD AS IS.

26355 Marydel Rd, Marydel

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

23348 Tidewater Trl, Rappahannock Academy

$5,500,000

4 Beds ⋅ 5 Baths

ROSE HILL ESTATE — 352 ACRES OF HISTORIC ELEGANCE AND AN ELEVATED COUNTRY LIFESTYLE Featured in Architectural Digest, this Amelia T. Handegan–designed residence anchors one of Virginia’s most distinguished country estates. Encompassing 352.24 acres, the property offers timeless elegance, masterful restoration, and unparalleled privacy. Designed for those who value both heritage and luxury, every detail reflects refined craftsmanship and enduring beauty. The estate’s remarkable grounds and gardens were further recognized with the 2016 ASLA Virginia Chapter Merit Award, honoring the property’s exceptional landscape architecture and stewardship. Protected under conservation easement, the estate’s rolling landscape unfolds through two gated entrances across open fields, century-old hardwoods, formal gardens, and a stocked pond—offering a rare balance of seclusion, scale, and natural beauty. Originally built in 1799, the residence was comprehensively restored in 2011 by Tidewater Preservation, Inc., under the direction of acclaimed Charleston designer Amelia T. Handegan. The result is a seamless blend of historic integrity and modern sophistication, enhanced by geothermal climate control and radiant floor heating. The 5,431-square-foot main residence features 4 bedrooms, each with an ensuite bath, and a collection of gracious living spaces defined by hardwood floors, intricate crown molding, chair railing, and custom French wallpaper. Formal rooms include a dining room with fireplace, an elegant living room with built-ins, and a distinctive octagonal music room with English windows and hand-painted geometric floors. The chef’s eat-in kitchen pairs historic character with professional-grade function, offering custom wood cabinetry, a wood-burning fireplace, marble-topped island, Wolf range, paneled appliances, wine refrigerator, and ice machine. A well-appointed mudroom with built-ins and laundry provides convenient access to the gardens. The main-level primary suite is a private retreat, featuring a fireplace, sitting room with built-ins, walk-in closet, and direct access to the outdoors, along with a marble-clad bath complete with dual vanities, soaking tub, and walk-in shower. Additional bedroom suites offer fireplaces, built-ins, and beautifully appointed baths, each capturing sweeping views of the rolling countryside, pond, or historic gardens. Beyond the main residence, a guest cottage with exposed beams, marble finishes, and a fireplace offers refined accommodations for visitors. A Pennsylvania bank barn, relocated in 2009, has been thoughtfully reimagined to include a gym, office with full bath, and loft. Distinctive architectural elements include a Thomas Jefferson–inspired dovecote with Birmingham Rollers and a newly constructed folly overlooking the pond. Outdoor amenities are equally exceptional, featuring a tennis court with pavilion, croquet lawn, riding trails, and formal gardens that have been showcased in Garden Club tours, filled with hydrangeas, peonies, fruit trees, and rose of Sharon. A working barn supports a herd of Belted Galloway cattle, further enhancing the estate’s pastoral character. Utilities include well water, septic, geothermal HVAC, propane heat (two owned tanks: 500 and 1,000 gallons), radiant floor heating, and four hot water tanks. A rare and significant offering, Rose Hill Estate embodies a legacy property—where history, land, and lifestyle converge in extraordinary form.

23348 Tidewater Trl, Rappahannock Academy

Listing courtesy of Coldwell Banker Elite. Contact:

$21,000

2 Beds ⋅ 1 Baths

Investor special! This property is being sold AS-IS and is priced for land value or a full renovation. The existing structure requires extensive repairs or complete tear-down—ideal for experienced builders, contractors, or savvy investors looking for a project. Buyer to verify zoning, permits, potential use. Buyer Broker/Agent and/or Buyer must do their own due diligence to verify if the existing structure or land is suitable for building.. No warranties, guarantees, or repairs will be made by seller.

204 Academy Ave, Federalsburg

Listing courtesy of Keller Williams Realty Delmarva. Contact:

$3,300,000

2 Beds ⋅ 2 Baths

Amazing Opportunity, Owner Financing may be an option. Call me Today-Your Business Ideas, with a 2 plus Area Corner Lot on Route1. New Development on Every Corner. Prime 2.3-Acre Corner Lot on Route 1! Location: Route 1 – High-Visibility Corner Lot with Two Road Frontages Property Features:

12439 Us Route 1st Hwy, Woodford

Listing courtesy of Samson Properties. Contact:

$25,000

Build your dream home on this available lot in Preston, Md. Old home on property - either tear down or restore. Buyer to complete due diligence with County

23547 Jonestown Ln, Preston

Listing courtesy of Mabry Real Estate LLC. Contact:

$349,900

Custom Brick rancher, close to town on large lot. Open floor plan, spacious kitchen, stainless steel appliances, large island. 3 bedrooms, 2 baths, sunroom overlooking yard. Upgrades include new windows, CAC, new roof new electric service and plumbing New Septic and Well, Closing help will be considered

22403 Marsh Creek Rd, Preston

Listing courtesy of Results Realty Inc.. Contact:

$399,000