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$350,000
4 Beds ⋅ 2 Baths
Welcome to this stunning Victorian gem built in 1900, gracefully resting on three combined lots totaling .76 acres of mature, beautifully planted grounds. From the moment you arrive, the home's presence is unmistakable; a sweeping wrap-around front porch invites you in, while a fully enclosed back porch offers a quiet retreat overlooking the private backyard. Step inside to discover soaring high ceilings and generously proportioned rooms that speak to a bygone era of craftsmanship. Original hardwood floors, pocket doors, and period fixtures and hardware remain lovingly preserved throughout, offering that rare, authentic character today's buyers dream of. Two separate staircases lead to the second floor, where you'll find four spacious bedrooms and a beautifully updated full bathroom. The home has been thoughtfully modernized where it counts most- a stylishly updated kitchen anchors the main level, complemented by a fully updated main-floor bathroom, so timeless charm meets everyday comfort. Recent mechanical updates provide additional peace of mind, including new heat pumps installed in 2020 and 2021, a new roof, and chimney repairs completed in 2022. Outdoor space is just as impressive as the home itself. The grounds include two outbuildings- a small horse barn with stall and a versatile storage shed with workshop area- along with an expansive 5-bay garage/shop, perfect for cars, boats, hobbies, or storage of every kind. This is a rare opportunity to own a true piece of history, thoughtfully updated for modern living, on nearly three-quarters of an acre of storybook grounds. Homes with this much land, character, and versatility simply don't come along often. Welcome home.

22040 Main St, Hillsboro

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$680,000
4 Beds ⋅ 4 Baths
A home where timeless Colonial Williamsburg architecture meets the flexibility and modern features today's buyers are searching for on 1 acre. Perfectly located in the heart of Bowling Green, this one-of-a-kind property offers the ideal blend of character, functionality, and income potential, all in a peaceful neighborhood with convenient access to shopping, dining, and commuter routes to Fredericksburg, Richmond, and beyond. From the moment you arrive, the home's classic curb appeal and inviting front elevation make a lasting first impression. Inside, rich hardwood flooring, elegant architectural details, and thoughtfully designed living spaces create a warm and welcoming atmosphere throughout. The kitchen is the heart of the home, featuring granite countertops, custom refinished walnut cabinetry, stainless steel appliances, a pantry, breakfast nook, and formal dining room, perfect for everything from weeknight dinners to holiday gatherings. Two beautiful masonry wood-burning fireplaces anchor both the formal living room and the spacious family room, where custom built-in cabinetry adds warmth and functionality. The sunroom provides a light-filled retreat to enjoy every season, while the main-level office and adjacent full bathroom offer exceptional flexibility for a guest suite, fifth bedroom, or private work-from-home space. Upstairs, the spacious primary suite serves as a true retreat with an adjoining bonus room ideal for a sitting area, nursery, fitness space, or second home office, along with a private en-suite bathroom. Two additional generously sized bedrooms and another full bathroom complete the upper level. One of this property's most valuable features is the approximately 900-square-foot detached apartment above the three-car garage. Complete with its own private entrance, full kitchen, laundry, and living space, it offers exceptional versatility as an income-producing rental, Airbnb, multigenerational living space, private guest suite, home business, or ultimate recreation room. Step outside onto the premium Brazilian hardwood deck, where you'll enjoy outdoor dining, entertaining, or simply relaxing while overlooking the peaceful surroundings. Whether you're searching for a home with room to grow, multigenerational living, rental income potential, or simply a property with timeless character and modern conveniences, this exceptional Bowling Green residence delivers a lifestyle that is increasingly difficult to find.

120 Lacy Ln, Bowling Green

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 5407359176
$390,000
3 Beds ⋅ 1 Baths
This charming ranch-style home, built in 2004, offers a cozy retreat on over 11 acres of serene land, adjoining the picturesque Marshyhope Creek with 3800 acres of Idlewild WMA just across the creek. Inside, discover a traditional floor plan featuring three inviting bedrooms and a country-style kitchen perfect for gatherings. Enjoy the warmth of luxury vinyl plank and carpet flooring throughout. Step outside to find a welcoming porch and patio, ideal for relaxing or entertaining. The property includes a detached 40x24, 2 Car garage with workshop for ample storage. Nature enthusiasts will appreciate the wooded surroundings, stream access, and opportunities for fishing and hunting right at your doorstep. Located in a peaceful, rural setting, this home is just a short drive from local parks and community amenities. Embrace the tranquility and beauty of this unique property, where comfort meets nature.

4455 Smithville Rd, Federalsburg

Listing courtesy of RE/MAX Executive. Contact:

$399,900
3 Beds ⋅ 2 Baths
Welcome home to this 3-bedroom, 2-bathroom home located in the sought-after gated community of Lake Caroline in Caroline County! Can you believe this house sits on just over an acre of land? As you arrive, you'll be welcomed by a circular driveway that provides both convenience and curb appeal. Inside, you'll find 3 bedrooms upstairs, with access to the full hall bathroom from the primary bedroom. The main-level living room features a bay window, allowing natural daylight to brighten the space. Downstairs, you'll find an additional family room with a fireplace and another full bathroom! The mudroom includes a built-in desk and additional storage space. One of the standout features of this property is the detached two-car garage, complete with a finished room above. Whether you're looking for a dedicated home office, art studio, fitness room, hobby space, or private retreat, this versatile bonus area offers endless possibilities. Enjoy all that Lake Caroline has to offer, including gated security, a beautiful 277-acre lake, sandy beaches, swimming, boating, fishing, tennis courts, playgrounds, and year-round community events. If you've been searching for a home that offers peaceful living with exceptional amenities, this is one you won't want to miss. Schedule your showing today!

71 Lake Caroline Dr, Ruther Glen

Listing courtesy of Belcher Real Estate, LLC.. Contact: (540) 300-9669
$265,000
3 Beds ⋅ 3 Baths
**Seller is offering $7,500 towards buyers closing costs with an acceptable offer** Welcome home to this beautifully updated 3-bedroom, 2.5-bath home built by Gemcraft Homes in 2002. Freshly painted throughout in 2026, this move-in-ready home also features brand-new luxury vinyl plank flooring on the main level and new carpet throughout the second floor, offering a fresh, modern feel from the moment you step inside. The main level offers a bright and inviting living room that flows into the open dining area and kitchen, creating an ideal layout for both everyday living and entertaining. A convenient half bath completes the main level. The kitchen boasts ample cabinet space, features a brand new refrigerator (2025), and provides direct access to the backyard through a sliding glass door. Upstairs, the spacious primary suite showcases soaring vaulted ceilings, a private en-suite bath, and a walk-in closet. Two additional generously sized bedrooms, a second full bathroom, and a dedicated laundry area complete the upper level. The washing machine was replaced in 2024 as an added bonus. Step outside to enjoy the fully fenced backyard featuring a newer vinyl privacy fence (2023), an attached storage shed, and additional side yard space, perfect for gardening, pets, or outdoor activities. Enjoy peace of mind with numerous major upgrades, including a new A/C condenser (2026), new heat pump (2026), and energy-saving blown-in insulation (2026), all added to improve year-round comfort and efficiency. Conveniently located near Routes 313, 480, and 314, this home offers easy access to commuting, shopping, dining, and everyday conveniences. Don't miss your opportunity to own this thoughtfully updated, move-in-ready home!

530 Vaughn Ave, Greensboro

Listing courtesy of Hyatt & Company Real Estate, LLC. Contact:

$330,000
3 Beds ⋅ 3 Baths
Ready to own without the stress? Move in and start your life, not your renovation. This fully renovated home is one your friends will be drooling over. The kitchen steals the show: soft-close navy cabinets with gold hardware and quartz countertops, stainless steel appliances, a deep kitchen sink, stylish floating shelves, and a crisp white tile backsplash. It's the kind of space that makes cooking and gathering feel effortless. The first-floor primary bedroom is your sanctuary—walk-in closet, walk-in tile shower that feels like a spa, beautiful quartz vanity. Wide plank LVP flooring keeps the whole home feeling fresh and connected. The two-car detached garage is insulated, has electric, and includes a storage room—practical space that actually works. The 0.325-acre lot sits across from Chambers Park, where you can enjoy a ball game, walking path, or tennis courts. Paved driveway, plenty of parking, and a home that's honestly ready for you. This is what move-in ready feels like: fully updated, thoughtfully finished, and zero projects waiting. Just unpack and live.

104 Chambers St, Federalsburg

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$395,000
4 Beds ⋅ 3 Baths
Updated + Upgraded - Turn-key 4BR/2.5BA contemporary 2-story home on a culdesac lot backing to trees, near historic downtown Denton - a true gem of an Eastern Shore town, perched on the banks of the Choptank River - but tucked away on a residential court. New flooring + paint throughout, new granite counters, new kitchen appliances, new fixtures. Wide open floorplan boasts tall ceilings, spacious rooms throughout, and lots of great light. Great room with new LVP flooring offers living, dining, breakfast, and kitchen spaces. Bright + cheery kitchen - light gray cabinetry, new stainless steel appliances, gorgeous granite counters, new custom tile backsplash. Sliders out to the expansive deck overlooking your roomy yard. Separate flex room - perfect for a home office, study - whatever you like. A half bath completes the 1st floor. Upstairs, primary bedroom with vaulted ceiling, new carpet, walk-in closet, full, en-suite bath - new tile floors, step-in shower, double-sink vanity. 3 additional bedrooms - all with new carpet. 2nd full bath with tub/shower combo, tile flooring. Laundry room with new tile floors completes the home's interior. Attached 2-car garage with extra space for storage, concrete driveway, nice-sized storage shed. 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. This home is ready for its new owner to just move in and enjoy. Sizes, taxes, distances approximate.

502 Kathryn Ct, Denton

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$625,000
2 Beds ⋅ 2 Baths
Always dreamed of living in a tree house on a Lake? Here's your opportunity....lovely A-frame home on Lake Caroline with Lake views from Living, dining room and Loft/Bedroom! This charming, updated home has a large, stone fireplace and large deck off the living room; for cozy nights and morning coffee. Well equipped kitchen with stove, microwave, dishwasher, stove top and refrigerator; open to expansive dining area. Main floor bedroom with ample closet space and adjacent bath; that has been updated w/large walk-in shower. Upstairs you find an open, loft/bedroom with vaulted, beamed ceiling and attached, updated bath w/walk-in shower; along with a mini-split to control your room temp. Covered lower patio leads into the basement & crawl space which is climate controlled; perfect for storing your Kayaks and water toys. Follow the paved steps/walkway down to the large yard and dock. Dock has diving platform and steps for ease into the water. The large garage (26 feet long) has room for cars, as well as a shop! Newer Roof. Come enjoy all the amenities that lovely, Lake Caroline has to offer! Close to Highways, shopping, restaurants and the new Kalahari Resort (12/26); making this perfect for a week-end getaway or a primary home!

206 Lake Caroline Dr, Ruther Glen

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

$659,000
4 Beds ⋅ 3 Baths
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:

$769,000
3 Beds ⋅ 3 Baths
**Don't Miss This Rare Opportunity** Pride of ownership shines throughout this beautifully appointed home, featuring 3 bedrooms, a bonus room, 3 full bathrooms, a dedicated office space and much more- set on over 4 serene acres. This property includes approximately 2.5 wooded acres with private walking trails and an abundance of wildlife. Major 2025 home improvements including a brand new roof, siding and 10 Velux skylights, along with a new Bosch heat pump installed in 2024. This one-of-a-kind retreat is located just 10 minutes from Easton and only 2 miles from the Choptank Marina for easy boat access. Expanded in a major 2006 renovation which nearly doubled the living space, this bright and airy home is the definition of open-concept. It is clearly designed for both comfortable everyday living and effortless entertaining. At the heart of the home is the stunning 20' x 27' kitchen, complete with rich cherry cabinetry, quartz countertops and stainless steel appliances. The 12’ island makes preparing food a seamless experience while entertaining guests. A cozy wood-burning brick fireplace, featuring an efficient Jotul insert, adds warmth and character, creating the perfect gathering space for family and friends. An oversized walk-in pantry with white cabinetry and an additional sink provides even more counter space. The pantry is already wired for an additional oven and refrigerator, should you desire them. Flowing right off of the kitchen, the show-stopping, expansive 25' x 25' living room impresses with soaring cathedral ceilings, abundant natural light, and 6 brand-new skylights with built-in remote-controlled solar shades. A beautiful stone fireplace with gas logs anchors this inviting room, and creates an atmosphere ideal for relaxing or entertaining year-round. The 11 windows and 3 paneled glass doors allow expansive views of nature to flow into this breathtaking room. Along with the large kitchen and living room, this home offers a sunny 10’ x 20’ room which has previously been used as both a family room and a home office. With two spacious master suites on separate ends of the home, an additional bedroom, a bonus room, three full bathrooms, a dedicated mud-room, large pantry, and office, this layout truly offers incredible flexibility for multigenerational living, multiple guests, or work-from-home needs. When you are ready to step outside and enjoy the peaceful tranquility of this property, you will love the expansive deck overlooking the beautiful and secluded backyard. There is ample space for a large garden, or for any of your desired outdoor activities. Nature lovers will appreciate the property’s reputation as a bird lover’s paradise with 98 documented bird species seen on the property throughout the last 3 years. The numerous nesting boxes and feeders throughout the grounds, and even a deer stand for hunting enthusiasts, will convey. Your dogs will also enjoy roaming the property safely, as this property includes approximately 1.5 acres of invisible dog fencing. The two large pole barns, (30’x40’x10’ and 30’x40’x14’) which also received new roofs and skylights in 2025, can easily store multiple vehicles and large equipment. Besides vehicle storage, the spacious pole barns could easily be used to house your dream home gym, workshop and or hobby space! This exceptional property offers the rare combination of modern updates, natural beauty, functional open-concept space, and unmatched privacy—all meticulously maintained and ready for its next proud owner.

3547 Prchal Rd, Preston

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact: 4109724000
$375,000
3 Beds ⋅ 2 Baths
Nestled on the edge of town, 1010 S 2nd Street delivers the convenience of in-town living without in-town taxes. Situated on 1.06 beautifully landscaped acres with mature plantings, this 3-bedroom, 2-bath home offers a spacious feel inside and out. Interior features include hardwood, LVP, and tile flooring, along with a cozy pellet stove fireplace insert for efficient heating, complemented by hot water baseboard heat as backup. The full basement provides approximately 2,864 total square feet of living and storage potential, ideal for entertaining, hobbies, or additional flex space. Relax on the screened-in porch overlooking the private backyard and large detached garage/shop. Enjoy easy walking access to schools, shopping, restaurants, and parks, making this property a rare combination of space, convenience, and charm. Seller to find home of choice.

1010 S 2nd St, Denton

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

$399,000
3 Beds ⋅ 2 Baths
This very comfortable rancher has ramps at rear of home for accessibility for those not able to walk up steps very well. Roomy kitchen and open floor plan allows large gatherings to enjoy the roominess. Large counter seats 4 comfortably. Dining area for full-size table and chairs. Working stone wood-burning fireplace is great for use to heat home all winter or just on-call use when you want the ambiance.. Convenient mudroom off garage with washer and dryer; going on into the kitchen with the pantry next to mudroom for convenience. Full-size attic with flooring providing lots of storage area. Large 24' deep x 23' wide two-car garage with overhead door and remote controls complete with shelving for storage. Two large sheds (insulated and electric) for many uses including a craft shop, carving shop, etc.; one is complete with a pellet stove for cool/cold days or evenings. All of this and more comes with privacy and deeded rights to the dock/pier at the end of the lane. Perfect to just relax and enjoy the water or to crab/fish. Some types of "farm animals" are allowed as long as they do not go off the property onto some other property (refer to docs). All this comes with 3.23 private acres of "home" written all over. Schedule your appointment today!

7392 Todds Wharf Rd, Preston

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