Caroline County, VA 55+ Community Homes for Sale

Welcome to 1210 Market Street. Located just minutes from shopping and downtown. This charming bungalow is charming and has been well maintained. Adjoining bedrooms or bedroom and deidcated home office space. Wood accents through the home make it warm and welcoming. Efficient oil heat . All appliances convey. This is the perfect home for starting out, slowing down. More afforable than renting. This home has detached shed for storage and a wonderfully shaded rear yard. Recent termite inspection and seller maintenance add to peace of mind when buying.

1210 Market St, Denton

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

$580,000

6 Beds ⋅ 4 Baths

Welcome to 11592 Holly Road in Ridgely, MD! This spacious 6-bedroom, 3.5-bath home offers plenty of room inside and out, with a flexible layout to fit a variety of needs. Inside, you'll find a bright kitchen with premium appliances, a comfortable living room with a gas fireplace, and a primary suite featuring a separate sitting area and attached office. The home also includes an in-law suite, providing additional space for family or guests. Outside, enjoy a nice-sized yard with a paver patio, gazebo, and stone fire pit. An attached garage provides additional parking and storage. With plenty of living space and convenient access to local schools and amenities, 11592 Holly Road is ready for its next owner.

11592 Holly Rd, Ridgely

Listing courtesy of Samson Properties. Contact:

$299,900

Across from the boat ramp and water view of 3 ponds on the property! Outdoor enthusiasts, nature lovers, and adventure seekers — welcome to your dream retreat. This one‑of‑a‑kind property offers an extraordinary blend of privacy, recreation, and natural beauty that is nearly impossible to find elsewhere. Set on gently rolling terrain overlooking multiple deep‑water ponds, this property delivers exceptional fishing, peaceful kayaking, scenic hiking trails, and endless opportunities to observe local wildlife. Deer roam the back woods, birds frequent the water’s edge, and the entire landscape offers a sense of tranquility that feels worlds away — yet still close to everything you need. The property also includes a 2‑bedroom home (possibly a 3rd). Enjoy all the benefits of living near the water without the added taxes of owning water‑privileged property. Recent enhancements include a charming decorative three‑rail fence and a privacy fence accented with topiary evergreens, adding both character and curb appeal. With its natural setting and recreational features, this property is perfectly suited for those seeking adventure or considering investment potential such as cabin rentals or VRBO. The possibilities are wide open. Just a quarter mile away, you’ll find two boat ramps, a pavilion picnic park, an additional launch area, playground, splash pad, basketball courts, river trails, an electric vehicle charging station, and more — making this location even more desirable for outdoor enjoyment. Don’t miss this rare opportunity. Schedule your visit and experience firsthand the peace, beauty, and uniqueness of this exceptional property. It truly is a retreat like no other.

2766 Veterans Dr, Federalsburg

Listing courtesy of Benson & Mangold, LLC. Contact:

$750,000

This is your farmette dream come true! This beautiful 3 bed, 2 full bath home is situated on 6+ acres of partially fenced in land, has a barn with a tack room, a large screened-in back porch, a 2 car garage and an in-ground saltwater pool. The barn features 3 stalls, a hay loft with elevator, washroom, a tack room with a closet and shelves for storage. The water to the barn is sourced from a 290 foot well that also sources to the home. There is also a paddock area for riding and training for your equestrian dreams. The saltwater pool goes up to 6 feet deep. Solar panels were installed in the yard to heat the pool which extends the months of use. The home has a nice front porch perfect for enjoying your country living setting. As you enter the home, the living room has a stand alone Argon gas stove. You'll love cooking and entertaining in the large eat-in kitchen with stainless steel appliances. The second living room has a gas fireplace perfect for cozy evenings. The updated bathrooms have walk in showers. Other features include newer Anderson windows, newer siding, tankless water heater and a semi-floored attic. You don't want to miss the opportunity to enjoy country living at it's best! Schedule your showing today.

3769 Bradley Rd, Federalsburg

Listing courtesy of Coldwell Banker Realty. Contact:

$729,900

Enjoy the space, privacy, and convenience of country living on 9 beautiful acres in Caroline County! This brick-front rambler offers comfortable one-level living just minutes from Thornburg, I-95, and the area’s growing selection of shopping, dining, and everyday conveniences. Step inside to hardwood floors that flow throughout the main level and a bright, open floor plan designed for easy living and entertaining. The centrally located kitchen keeps you connected to the heart of the home, while the wood-burning brick fireplace adds warmth and character. A versatile bonus room gives you options for a private home office, guest space, workout room, hobby room, or more. The spacious primary suite is a retreat of its own, featuring a huge walk-in closet and a luxury bath with dual shower heads plus a separate tub and shower combination. Outside, relax on the deck overlooking the lush backyard and enjoy all the possibilities that come with 9 acres. Two storage sheds provide extra space for tools, equipment, and outdoor gear. Added peace of mind comes with a newer HVAC system and an encapsulated crawl space by JES. With acreage, one-level living, flexible space, and a location convenient to Thornburg’s continued growth, this home offers room to live, relax, and make it your own.

13080 Paige Rd, Woodford

Listing courtesy of Coldwell Banker Elite. Contact:

$325,000

4 Beds ⋅ 4 Baths

MOVE-IN READY & MOTIVATED SELLER ! THREE LEVEL TOWNHOME IN PENDLETON GOLF COMMUNITY! Back on the market through no fault of the seller! The seller has found a home of choice and is ready to move. This well-appointed three-level townhouse in Pendleton Golf Community in Ruther Glen offers 3 bedrooms, 2 full baths, 2 half baths, a one-car garage, and a new HVAC system installed in August 2026. The bright main level features an inviting living area and spacious kitchen with a center island, ideal for everyday living and entertaining. Step onto the rear deck for outdoor dining, grilling, or relaxing, and enjoy the privacy of the low-maintenance vinyl-fenced backyard. Upstairs, generously sized bedrooms include a comfortable primary suite with a private bath. The additional bedrooms offer flexibility for guests, a home office, hobbies, or other needs. The attached garage provides secure parking and storage, with additional driveway parking available. Conveniently located in Caroline County along the Fredericksburg–Richmond corridor, this home offers easy access to I-95, shopping, dining, entertainment, and everyday amenities. Enjoy established golf community living, flexible three-level space, private outdoor areas, and low-maintenance convenience. Schedule your private showing today!

18424 Congressional Cir, Ruther Glen

Listing courtesy of Real Broker, LLC. Contact:

$299,900

The Upgrades Are In. All That’s Missing Is You! Move In Ready- Beautifully designed new construction interior townhome located in an established community in the heart of Denton, Maryland! Offering 4 spacious bedrooms, 2.5 baths, and an oversized rear-load garage, this home combines modern style with everyday functionality. The open-concept floor plan is perfect for both entertaining and daily living, featuring a gourmet kitchen with quartz countertops, a large center island, and a dedicated coffee station that adds both charm and convenience. The seamless flow from the kitchen to the dining and living areas creates an inviting space filled with natural light. Upstairs, you'll find three bedrooms, including a spacious owner's suite with a private bath and walk-in closet. Thoughtfully designed finishes, energy-efficient construction, and quality craftsmanship make this home move-in ready. Located in an established neighborhood, you'll enjoy the convenience of nearby shopping, dining, schools, parks, and easy access to major commuter routes while experiencing the charm of small-town living. Don't miss this opportunity to own a brand-new home with today's most sought-after features in one of Denton's desirable communities! Ask about our Builder Incentives, Everything is Included: Fridge, Garage Door Opener, deck AND $ 5,000 closing cost help or rate buy down options with use of preferred lender.

243 Briarwood Cir, Denton

Listing courtesy of Island Realty, LLC. Contact:

$420,000

Welcome home to this practically new, beautifully maintained property offering the perfect blend of peaceful country living and everyday convenience. Situated on a spacious 1-acre lot along sought-after Macedonia Road, this charming residence features comfortable living spaces, abundant natural light, and a functional layout ideal for both relaxing and entertaining. The home offers generously sized bedrooms, inviting common areas, and a well-appointed kitchen with ample cabinet and counter space. Step outside to enjoy the expansive yard with plenty of room for outdoor activities, gardening, pets, or future improvements. Mature trees and scenic surroundings create a private, tranquil setting while still being just minutes from shopping, dining, commuter routes, and all that Fredericksburg has to offer. Whether you're looking for your first home, additional space, or a peaceful retreat with easy access to town, this property delivers exceptional value and opportunity. Don’t miss your chance to own a slice of countryside charm in a fantastic location!

7264 Macedonia Rd, Woodford

Listing courtesy of Ascendancy Realty LLC. Contact:

$739,000

NEW NEW LOWER PRICE__$739,000--Beautiful Waterfront Home -On Large Lot--Great Views --Nice Home Beautiful landscaped WATERFRONT Property--Large Lot (.75) with lots of water frontage and views-Main bedroom with a Fireplace and Great View of the Lake--Lots of closet space and two pantries -- Large deck overlooking the Lake ---Patio with wood fireplace--Two HVAC units---Two Hot water heaters (one electric one Gas)--"Four Season" Room with mini split--Floors are a combination of tile, carpet and pine wood--Kitchen has Granite countertops-Beautiful updated appliances---2 Car Garage and paved driveway--An awesome walk under crawl space with insulation for additional storage -- Attics with flooring----Nice Front Porch----Brochure in Documents section -this home you will not want to miss -- It has so much to offer--Sign on Property

520 Lake Caroline Dr, Ruther Glen

Listing courtesy of Samson Properties. Contact:

$414,499

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:

$395,000

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. Last but not least the possibility of a portable VA interest rate to qualified buyers. 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:

$100,000

3 Beds ⋅ 1 Baths

Discover the potential in this ranch-style home situated on a spacious lot in Caroline County. This property is ready for renovation and offers a great opportunity to update and customize to your vision. Major improvements have already been completed, including a newer roof and updated windows, providing a solid starting point for your renovation plans. The home is served by a private well and septic system and offers the charm of country living with convenient access to Preston and surrounding areas. Bring your ideas and restore this property to its full potential.

4471 Harmony Rd, Preston

Listing courtesy of XRealty.NET LLC. Contact:

$575,000

You'll love this custom home nestled on 2.13 private acres, offering over 2,854 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. It is heated and cooled and 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 offers 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:

$259,900

The joy of one level living!! This home is in Move-in ready condition. Nice size 2 Bedroom 1 Full Bath. Level lot with Patio for enetertaining. Conveniently located within town limits. Shop, parks, restuarants, Brewery. Public Boat ramp to the Choptank River less than a mile.

325 Carter Ave, Denton

Listing courtesy of Brenton Realty Group. 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.

6323 Sterling Way, Ruther Glen

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

$150,000

Discover a hidden gem in this charming 2-bedroom, 1-bathroom ranch-style home, built in 1950 and brimming with potential. Nestled on a generous 0.48-acre lot, this property offers ample space for expansion or outdoor enjoyment, making it an ideal investment opportunity for those looking to enhance their portfolio. The detached structure, constructed with durable block materials, presents a solid foundation for your vision. While the home is currently in below-average condition, this offers a unique chance for savvy investors to renovate and increase its value significantly. With a little creativity and effort, you can transform this space into a cozy retreat or a lucrative rental property. The expansive driveway accommodates up to six vehicles, providing convenience for tenants or guests. Located in a peaceful neighborhood, this property is poised for appreciation, especially as the demand for rental homes continues to rise. With the right updates, you can create a warm and inviting atmosphere that appeals to a broad range of tenants, ensuring a steady stream of rental income. Seize this opportunity to invest in a property with great potential and make it your own. The possibilities are endless-turn this house into a home that generates returns for years to come!

6132 Harmony Rd, Preston

Listing courtesy of Exit Community Realty. Contact:

$339,900

2 Beds ⋅ 2 Baths

Welcome to this Charming Home featuring two spacious bedrooms and 1.5 baths. Primary suite features French doors that lead to an extra-large deck. The layout extends to a versatile bonus room, complete with a closet and egress highlighted by a stunning arched window this room offers endless possibilities The airy family room offers natural light from two sky lights. Soaring cathedral ceilings elevate both spaces adding a dramatic sense of openness. Kitchen has a new refrigerator, stove, dishwasher and gleaming granite countertops. Accessible from the kitchen is a combined pantry and laundry room, equipped with shelves. Beautifully updated flooring throughout the home with laminate, carpeting and ceramic tile. Many new double -hung windows installed, 3 ceiling fans, new electrical sockets. The interior of the home has recently been professionally painted. Roof and skylights replaced approximately 6 years ago. The property also features a custom pole building and small garage both with electrical on concrete slabs. BONUS: An additional 1.11 acres is included at no extra cost! Whether you are looking to build your dream home, expand your acreage, or just keep it as an investment, this property offers incredible versatility. The extra land provides endless possibilities for your future plans.

17263 New Baltimore Rd, Milford

Listing courtesy of Ascendancy Realty LLC. Contact:

$289,900

Remarkable Move in Ready Townhome! Beautifully designed new construction interior townhome located in an established community in the heart of Denton, Maryland! Offering 4 spacious bedrooms, 2.5 baths, and an oversized rear-load garage, this home combines modern style with everyday functionality. The open-concept floor plan is perfect for both entertaining and daily living, featuring a gourmet kitchen with quartz countertops, a large center island, and a dedicated coffee station that adds both charm and convenience. The seamless flow from the kitchen to the dining and living areas creates an inviting space filled with natural light. Upstairs, you'll find three bedrooms, including a spacious owner's suite with a private bath and walk-in closet. Thoughtfully designed finishes, energy-efficient construction, and quality craftsmanship make this home move-in ready. Located in an established neighborhood, you'll enjoy the convenience of nearby shopping, dining, schools, parks, and easy access to major commuter routes while experiencing the charm of small-town living. Don't miss this opportunity to own a brand-new home with today's most sought-after features in one of Denton's desirable communities! Ask about our Builder Incentives, Everything is Included: Fridge, Garage Door Opener, deck AND $ 5,000 closing cost help or rate buy down options with use of preferred lender.

245 Briarwood Cir, Denton

Listing courtesy of Island Realty, LLC. Contact:

$546,740

Welcome to the 2818 sq ft Hanover model, offering a modern open-concept living space designed to meet your family’s needs. The main level features a combined family room and casual dining area, creating a spacious area perfect for entertaining and daily activities. The chef-inspired kitchen boasts a large center island, a walk-in pantry, and ample counter space, making it ideal for cooking and gathering. A formal dining room and office provide additional spaces for both work and relaxation, while a convenient powder room completes the main floor. Upstairs, an additional living space provides even more flexibility, whether you need a home office, play area, or entertainment room. The primary suite is a true retreat, featuring a large walk-in closet and a luxurious bathroom with separate vanities and a private water closet. The second floor also includes a laundry room, a full bathroom, and three additional spacious bedrooms, ensuring plenty of space for the whole family. Photos are from builder's library, actual selections and finishes may vary.

6235 Sterling Way, Ruther Glen

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

$269,000

4 Beds ⋅ 2 Baths

This charming cape cod home is waiting for your creative touches! Lots of room on three floors. The main floor boasts a large living room with new vinyl flooring. A separate dining room, large kitchen, full bath and mudroom with washer and dryer. The second floor has four spacious bedrooms and a charming vintage bath with claw foot tub! The basement is a perfect place for crafts, hobbies and plenty of storage. Outside you will find a huge intown lot with a newly built shed the size of a one care garage that makes a perfect workshop. Price to sell! Be sure to schedule your personal tour today!

108 N Academy St N, Greensboro

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

$310,000

3 Beds ⋅ 4 Baths

Welcome home to 17304 Camellia Dr, a corner townhome in the sought-after Ladysmith Village community of Ruther Glen. Thoughtfully laid out across three levels, this 3-bedroom, 3.5-bath home offers space and flexibility for today's buyer. The ground floor features a 2-car garage, kitchen with stainless steel appliances, dining area, half bath, and a living room with an electric fireplace (conveys as-is). Upstairs on the second floor, you'll find a full hallway bathroom, a primary bedroom with a full en-suite bath and walk-in closet, and a second bedroom with its own walkout balcony. A versatile walkthrough room with doors connects to the laundry room (washing machine conveys as is). The third floor offers a private retreat with a full bathroom, bedroom, and open area. Set on a corner lot in Ladysmith Village, this home offers added privacy and natural light along with convenient access to local amenities and an easy commute along the I-95 corridor. Ready to move in — schedule your tour on ShowingTime today and see why this property stands out.

17304 Camellia Dr, Ruther Glen

Listing courtesy of Samson Properties. Contact:

$295,000

Seller is offering a $4,500 credit for new carpet in all 3 bedrooms! Welcome home to this charming 3-bedroom, 2-bath rancher offering the perfect blend of comfort and convenience. Nestled on a quiet street within the city limits, this property provides a peaceful, country-like setting while remaining just minutes from Easton, Denton, Federalsburg, and Cambridge. Step inside to find luxury vinyl plank flooring throughout the main living areas, with cozy carpeted bedrooms creating a warm and inviting retreat. New flooring has been installed in the hall bathroom as well as a new washer and dryer! The spacious primary suite features a private bath complete with a walk-in shower for added comfort. Outside, you'll appreciate the generous back yard and large storage shed, already equipped with electricity, providing ample space amd function for tools, lawn equipment, hobbies, or additional storage. Whether you're looking for your first home, downsizing, or simply seeking low-maintenance one-level living in a tranquil setting, this property offers the best of both worlds—small-town convenience with a rural feel. Don't miss your opportunity to make this inviting rancher your next home!

212 Apple Ln, Preston

Listing courtesy of Keller Williams Realty. Contact:

$620,000

Privacy, space, and endless possibilities — this 5.06-acre retreat offers the lifestyle you've been looking for. Tucked into a partially wooded setting at the end of a quiet drive, 16881 Heritage Hills Ln provides the perfect blend of seclusion, functionality, and room to grow. Best of all, there's no HOA, giving you the freedom to truly enjoy your property. Built in 2005, the home offers 2,704 square feet of thoughtfully designed living space, plus an additional 300 square feet under heat, air, and electric that's ready to be finished or used as storage, a home gym, hobby room, or flex space—bringing the total conditioned space to approximately 3,000 square feet. Inside, you'll find four spacious bedrooms with the potential for a fifth bedroom or nursery connected to the primary suite, a dedicated office, two separate living areas, and a cozy family room just off the kitchen. The beautifully updated kitchen features granite countertops, stainless steel appliances (installed in 2024), and an ideal layout for entertaining. The primary suite is a true retreat with a renovated bathroom, walk-in closet, and adjoining flex space that can easily adapt to your needs. Nine-foot ceilings throughout the first floor create an open, airy feel. Step outside and you'll quickly see what makes this property special. Relax on the 16x13 screened porch with its brand-new roof, gather on the adjoining decks, or enjoy evenings around the fire pit on the paved patio. The property is already wired and ready for a hot tub, making it easy to create your own backyard oasis. A spacious outbuilding offers endless opportunities for storage, a workshop, or recreational equipment, while the attached two-car garage features a MyQ smart garage door opener with an integrated camera. With over five acres, the land offers incredible flexibility for those looking to embrace country living. Whether you envision horses, livestock, gardens, recreational trails, or simply enjoying the privacy, the possibilities are endless. Hunters will appreciate the secluded back field complete with an established food plot and tower stand already in place for the season. This home has also been meticulously maintained, with a new roof featuring a transferable warranty, new water heater (2026), new water softener (2026), and the septic system professionally serviced in 2026. Properties offering this much privacy, usable acreage, flexible living space, and modern updates are a rare find. Welcome home!

16881 Heritage Hills Ln, Henderson

Listing courtesy of Benson & Mangold, LLC. Contact:

$330,000

Discover the charm of this beautifully designed raised ranch in the desirable Lake Land Or community. With 1,000 sq. ft. of thoughtfully laid-out space, this home features three spacious bedrooms and two full baths, including a freshly updated primary bathroom for your convenience. The combination kitchen and dining area is perfect for entertaining, while the entry-level bedroom offers flexibility for guests or a home office. Enjoy modern living with essential appliances, including a stainless-steel refrigerator, oven, dishwasher, washer and dryer, ensuring efficiency and ease in your daily routine. Step outside to your private fenced backyard with a small deck, ideal for morning coffee or evening relaxation. The community pool invites you to unwind and socialize during warm months. With a gravel driveway accommodating up to four vehicles, parking is a breeze. This charming home combines comfort, functionality, and community amenities, making it a perfect choice for those seeking a vibrant lifestyle. With fresh paint throughout, updated primary ensuite bathroom, stained front and back porches, new carpets in all three bedrooms, brand-new custom granite countertops, and freshly lined driveway, you can comfortably move right in!

750 Canterbury Dr, Ruther Glen

Listing courtesy of Golston Real Estate Inc.. Contact:

$469,900

New Home- Ready Fall 2026 in Lake Land Or. Photos are from previously model and are virtually staged!

813 Moorefield Dr, Ruther Glen

Listing courtesy of Coldwell Banker Elite. Contact:

$375,000

Step into this beautifully crafted ranch-style home that blends classic craftsman charm with today’s modern touches. Featuring 3 bedrooms and 2 bathrooms, this thoughtfully laid-out home boasts an open-concept design perfect for both relaxing and entertaining. Enjoy a spacious living area, a stylish kitchen with premium quartz countertops, and a generous island ideal for gatherings. The primary suite is a private retreat with a walk-in closet and a luxurious en-suite bath complete with dual vanities and gorgeous tilework. Throughout the home, you’ll find high-end finishes including luxury vinyl plank flooring, stunning tile showers, and brand-new stainless-steel appliances. Located in the sought-after Caroline Pines community, residents can enjoy amenities such as swimming pools, a playground, basketball courts, and a scenic lake. Don’t miss your chance to call this incredible home yours!

12136 Monterey Rd, Ruther Glen

Listing courtesy of Spring Hill Real Estate, LLC.. Contact:

$72,000

HUGE PRICE REDUCTION. READY FOR A QUICK SALE. Excellent investment opportunity! Over 1/4 acre lot. Home needs TLC. Partial owner financing available. Call for more info. This deal will not last long. Grab it while you have the chance!

310 Central Ave, Federalsburg

Listing courtesy of R&R Executive Realty. Contact:

$399,000

Very rustic and private 3 bedroom, 1 and a 1/2 bath log cabin on 15 private wooded acres. There is a large building and a sun porch overlooking a stream running through the property. Excellent hunting property for whitetail deer and turkey!

21370 Skeleton Creek Rd, Preston

Listing courtesy of Meredith Fine Properties. 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. Photos are from builder's library, actual finishes and features may vary.

17456 Clark And York St, Ruther Glen

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

$199,000

2 Beds ⋅ 2 Baths

This charming farmhouse-style home, built in 1904 has undergone a major renovation in 2026. With 812 square feet of thoughtfully designed living space, this delightful residence features two cozy bedrooms and one and a half bathrooms, making it an ideal retreat for those seeking comfort and style. Step inside to discover a beautifully updated interior adorned with luxury vinyl plank flooring, providing both elegance and durability. The heart of the home is the well-appointed kitchen, equipped with essential appliances including a built-in microwave, range, dishwasher, and refrigerator, ensuring meal preparation is a breeze. A convenient stacked washer and dryer on the main floor adds to the home's practicality. Nestled on a generous 0.17-acre lot that backs to trees, this property offers a peaceful outdoor setting perfect for relaxation or entertaining. Parking is hassle-free with a driveway and on-street options available. Experience the charm and warmth of this inviting property, where every detail has been considered for your comfort and enjoyment. Don't miss the opportunity to make this house your home!

310 Park Ave, Federalsburg

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

$1,175,000

4 Beds ⋅ 4 Baths

Bayfront living with exceptional waterfront amenities! This home offers a rare opportunity to enjoy water views, a boat dock with slip, and a private beach area. The sunroom/sun porch provides the perfect space to relax, entertain, or simply take in the peaceful waterfront setting. The home features a desirable first-floor primary suite with its own private exterior entrance and generous closet space. A separate suite over the garage, also with its own private entry, adds wonderful flexibility for guests, extended living, a home office, studio, or private retreat. With a spacious and versatile layout, multiple private-entry living areas, and direct access to the water, this property is full of potential and ready for its next chapter.

30019 Goose Point Ct, Port Royal

Listing courtesy of 1st Choice Better Homes & Land, LC. Contact:

$799,900

Welcome to 322 Lake Caroline Drive, where every day feels like a vacation. Perfectly positioned on approximately 95 feet of protected shoreline with deep water, a rebuilt private dock complete with an expanded sun deck, and panoramic lake views, this exceptional waterfront home offers the lifestyle so many buyers dream about but rarely find. Located within the gated community of Lake Caroline, just minutes from I-95 and conveniently situated between Richmond and Washington, D.C., this beautifully maintained home combines peaceful waterfront living with an easy commute and outstanding community amenities. Completely reimagined in 2003, this home underwent an extensive renovation and expansion, transforming nearly every aspect of the property. Taken down to the studs, it was thoughtfully redesigned with a new floor plan, two additions, new drywall, insulation, electrical, plumbing, HVAC, and quality finishes throughout. The result is a home that offers the charm of an established waterfront setting with the features and functionality buyers expect today. Every improvement was thoughtfully designed to maximize natural light, capture stunning lake views, and create comfortable spaces for everyday living and entertaining. Rich hardwood floors, soaring ceilings, custom architectural columns, recessed lighting, and five skylights flood the home with natural light, creating a bright, open atmosphere that immediately welcomes you inside. Additional features include Andersen 400 Series windows and doors, a high-efficiency two-stage Trane HVAC system with an air cleaner installed in 2018, a new water heater in 2024, whole-house surge protection, surround sound throughout the home and rear deck, a separate laundry room, handicap accessibility, and a well-maintained crawlspace. Designed for both everyday living and entertaining, the custom kitchen is sure to impress. Featuring beautiful custom cabinetry, abundant countertop space, a center island with a prep sink, double ovens, a new cooktop, and thoughtful storage throughout, it's a space that will make even the most discerning home chef feel right at home. The spacious living room flows seamlessly to the screened porch, where you can enjoy your morning coffee while taking in peaceful lake views. The primary suite also offers direct access to the porch, allowing you to wake each morning to the beauty of the water. The primary bath features a relaxing soaking tub, separate walk-in shower, and generous space to unwind. Outdoor living is truly the centerpiece of this property. Spend evenings on the expansive rear deck overlooking the lake or head down on your golf cart to the private dock, completely rebuilt and expanded in 2012 to include a large sun deck. Whether you enjoy boating, fishing, kayaking, paddleboarding, swimming, or simply relaxing by the water, this property is ready to support every lakefront adventure. With approximately 95 feet of rip-rapped shoreline and deep water, you'll enjoy both beauty and peace of mind for years to come. Life at Lake Caroline extends well beyond your own backyard. Residents enjoy a 277-acre recreational lake, two sandy beaches, a swimming pool, a clubhouse, tennis, pickleball, and basketball courts, playgrounds, boating, fishing, and other water activities, and an active community with multiple events throughout the year. Whether you're searching for your forever home, a weekend escape, or the waterfront lifestyle you've always imagined, 322 Lake Caroline Drive offers a rare opportunity to own one of the community's finest lakefront properties. The setting is extraordinary. The lifestyle is waiting. Simply move in and start making memories on the lake.

322 Lake Caroline Dr, Ruther Glen

Listing courtesy of Coldwell Banker Elite. Contact:

$479,000

Custom Brick Rancher with 2500 sq ft of living space sitting on over half an acre just outside of downtown Federalsburg overlooking Chambers Park is waiting for you to come see to appreciate. Owners have done many improvements and upgrades to the property, but left some of it's timeless charm. New carpet has been installed on the porch, breakfast nook, and family room July 2026, new windows 2026, New refrigerator July 2026, new HVAC 2021, 3yr old whole house water treatment with R/O system, and a 40 breaker 4D electrical panel is new, too! With a mix of formal rooms and recreation areas all off the kitchen, but split from the generously sized Bedrooms, you will have no problem entertaining all year round. 2 Sheds, both with electric, one with garage door and workbenches help with all those indoor and outdoor projects. 3rd full bath is off the enclosed sunporch for ease of use from multiple areas and outside. In addition to Chambers Park the Federalsburg Park and Marina is just down the road for added recreation, along with shopping and restaurants in Federalsburg, Easton, Preston, or just over into Delaware not to mention multiple Beaches in both MD and DE that are close enough to spend the day and come back home. Don't miss your opportunity to see this one and call it yours!

104 Charlotte Ave, Federalsburg

Listing courtesy of Benson & Mangold, LLC. Contact:

$297,900

Sellers are offering $3,000 closing costs with an acceptable offer!!! A place that feels like home from the moment you pull in. Sitting on .72 acres with no HOA, this property gives you the space and freedom that's becoming harder to find. Enjoy evenings around the firepit, morning coffee on the back deck, and a partially fenced backyard with plenty of room to garden, play, or simply relax. Conveniently located just 20 minutes to Downtown Fredericksburg, 45 minutes to Short Pump, and 5–10 minutes to I-95 for an easy commute, and close to Kalahari resorts, Caroline County Park, Rt 639 Farmers Market, and amazing resturants. You'll have the best of both privacy and convenience. Inside, you'll find fresh paint throughout, updated LVP flooring, and an inviting layout that's both comfortable and functional. The living room welcomes you in with plenty of natural light, while the refreshed kitchen features thoughtful accent updates that make it a warm space to cook, gather, and entertain. Three spacious bedrooms provide room for family, guests, or a home office, while the updated full bathrooms offer a clean, modern feel. Whether you're buying your first home, downsizing, or simply looking for a move-in ready property with room to spread out, this home offers the perfect blend of character, comfort, and convenience.

13340 Countyline Church Rd, Woodford

Listing courtesy of Genalo & Associates, LLC.. Contact:

$220,000

Welcome to this beautifully maintained newer town home that has been virtually staged was built in late 2025, in the charming Riverwalk community of Federalsburg. Offering 3 bedrooms, 2.5 bathrooms, and modern construction, this home combines today's sought-after finishes with the warmth and small-town charm that make Maryland's Eastern Shore such a desirable place to call home. Close to Federalsburg Community Park & Marina, as well as walking Trails. Whether you're a first-time home buyer, looking to downsize, or searching for a newer home with minimal maintenance, this Riverwalk townhome offers exceptional value in a growing community. Experience modern construction, comfortable living, and the lifestyle that makes Federalsburg one of the Eastern Shore's best-kept secrets. Schedule your private tour today and discover why so many are choosing to call Riverwalk home.

122 Julie Ln, Federalsburg

Listing courtesy of Remax Vision. Contact:

$324,900

Welcome to this turn-key, eco-friendly rancher offering single-level living and a modern, open layout. Step inside to a fluid floor plan featuring striking dark wood-look laminate flooring throughout. The spacious living room features a designer green accent wall and flows seamlessly into the country kitchen and dining combination. The kitchen boasts sleek white cabinetry, stainless steel appliances, a center island, and a breakfast bar peninsula—ideal for casual dining or entertaining. The home includes three generous bedrooms, highlighted by a private primary suite with an en suite full bathroom. A dedicated laundry and utility room adds daily convenience. The rear exit leads to your own private outdoor oasis. The fully fenced backyard comes complete with an above-ground pool, a lush lawn, and a detached wooden storage shed. The wide gravel driveway offers ample multi-car parking. Best of all, say goodbye to high utility bills with the premium, fully paid-off, roof-mounted solar panel array providing massive, worry-free energy efficiency year-round.. Enjoy the quiet charm of a historic Eastern Shore crossroads community. This scenic location offers easy access to outdoor recreation, including kayaking and canoeing at nearby Tuckahoe Creek public landings, local municipal parks, and neighborhood general stores. Conveniently located near major commuter routes and the Delaware border for tax-free shopping and quick beach trips. Schedule your tour today!

504 Main St, Goldsboro

Listing courtesy of The Parker Group. Contact:

$299,800

Ready to own without the stress? This fully renovated home is one your friends will be drooling over. Move in and start your life, not your renovation. 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. Your 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. This is what move-in ready actually feels like: fully updated, thoughtfully finished, zero projects waiting. And a seller who's willing to work with you on the numbers. Just unpack and live.

104 Chambers St, Federalsburg

Listing courtesy of Benson & Mangold, LLC. Contact:

$399,999

Welcome to 13577 Countyline Church Road in Woodford, VA—a beautifully updated 3-bedroom, 2-bath home offering the perfect combination of modern upgrades and peaceful country living. Situated on 2.53 private acres, this move-in-ready property provides the space, comfort, and freedom you've been searching for. Inside, you'll find a bright, inviting floor plan featuring fresh paint, new flooring throughout, and an updated kitchen complete with modern cabinetry, countertops, and newer appliances. Both bathrooms have been tastefully renovated, creating stylish, functional spaces you'll enjoy every day. The spacious primary suite includes a private bath and plenty of closet space, while the additional bedrooms offer flexibility for family, guests, or a home office. Major system updates—including a newer roof and HVAC system—offer peace of mind and added value for years to come. while high-speed internet makes working from home or streaming your favorite shows a breeze. Step outside to enjoy the expansive property from the welcoming front porch or spacious back porch, ideal for morning coffee or evening sunsets. The yard provides space for pets and play. Whether you're dreaming of gardening, raising animals, or simply enjoying wide-open spaces, this property offers endless possibilities. Conveniently located between Fredericksburg and Richmond with easy access to major highways, you'll enjoy the tranquility of country living without sacrificing convenience to shopping, dining, schools, and commuter routes. If you've been looking for an updated home on acreage with no HOA, modern improvements, and room to live the lifestyle you want, this exceptional property is one you won't want to miss. Schedule your private showing today!

13577 Countyline Church Rd, Woodford

Listing courtesy of Next Home Elite Plus. Contact:

$449,999

4 Beds ⋅ 2 Baths

PRICE REDUCED!! Step into history when walking through the front entrance of this early 20th century home. This home still has the charm to bring you back in time with recent modern upgrades. Such as new oak hardwood floors installed downstairs in 2023, leaving the original wood upstairs underneath the recently professionally cleaned Berber carpet waiting to be revealed, new roof in 2021, stainless appliances, updated downstairs bathroom with walk-in shower and tankless water heaters for the entire house. Electrical was updated in the early 2000’s along with double hung windows and all plaster replaced with drywall. This home is nestled on 1.45 case and has the feel of country with the convenience of being situated between Fredericksburg and Richmond. You can enjoy your quiet evenings sitting on the wrap around porch or soaking in the hot tub listening to the birds sing throughout the many mature trees on the property. Bonus Spring house is ready to remodel to an in-law suite or She/he-shed.

11456 Chesterfield Rd, Ruther Glen

Listing courtesy of LJ Realty Company, Inc.. Contact:

$585,900

This is the one! Approx. 16.77 acres with an owner built 3 bedroom home. One acre with home plus additional acreage. Some acreage is wooded with wild life including, but not limited to, rabbit, deer, and turkey. This home has magnificent kitchen with custom cabinetry and SS appliances, including a 5 burner stove and double wall oven. Pellet stove is included for those cool evenings and damp days. Large parking area for several vehicles and a boat. Run in shed for your lawnmower and other boat. 16x32 pool with screened pavilion for your crab feast or just hanging out. (Pool unused at present) Additional well for irrigation. You really need to come walk through and around this one! No AI was used in the creation of this description. (Though it probably would have been better) Tax IDs 03002187 03002101

28402 Liden School Rd, Denton

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

$320,000

Charming updated Farmhouse style home with hardwood floors throughout and tiled bathrooms. The open kitchen features quartz countertops, a center island for extra prep space and casual dining, stainless steel appliances, and a tile backsplash. The first floor includes a full bath with a tiled walk-in stall shower, plus a separate laundry/mud room. Dual-zone heating and air for year-round comfort. Major updates completed in 2021: new windows, plumbing, electrical, and LED lighting, Sliding doors open to a large backyard with a patio and a new storage shed. Located less than a block from the park, offering a playground, skate park, walking trails, ball fields, and tennis and basketball courts.

306 Caroline Ave, Ridgely

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

$1,150,000

An exceptional offering, beautifully situated along the deep, protected waters of Tuckahoe Creek. This beautifully appointed waterfront residence has undergone an extensive renovation, blending timeless design, quality craftsmanship, and comfortable luxury. Professionally redesigned with Barclay Designs and interiors by Sanctuary Interiors, the home features thoughtfully selected finishes and custom details throughout. The stunning kitchen showcases blue marble countertops, handcrafted cabinetry, Wolf gas cooktop, Sub-Zero refrigerator, beverage refrigerators, and a spacious center island. Rich hardwood flooring, designer lighting, custom window treatments, and beautifully renovated bathrooms complement the interior. The primary suite offers heated bathroom floors and a private Juliet balcony. Designed for exceptional indoor and outdoor living, an expansive Balau hardwood deck overlooks the spacious rear yard and heated saltwater pool, surrounded by travertine, natural stone, and professionally designed landscaping. Additional outdoor amenities include a fully equipped kitchen, fire table, tranquil fountain, and enclosed four-season sunroom. A private pier provides access to deep, unobstructed, protected water, ideal for boating, waterskiing, wakeboarding, and enjoying the Eastern Shore lifestyle. Additional improvements include Everlast Advanced Composite Siding, updated HVAC (2023), modernized electrical, a custom bunk room, and numerous additional upgrades. Conveniently located just minutes from Talbot County and Easton, with easy access to Routes 50 and 404, Annapolis, and MD & DE beaches. Enjoy the privacy of a peaceful waterfront setting without sacrificing convenience. An added benefit, the property is located outside the designated floodplain.

23071 Tuckahoe Springs Dr, Denton

Listing courtesy of Sharon Real Estate P.C.. Contact:

$371,740

Welcome to the Delmar in Ladysmith Village! This thoughtfully designed 3-bedroom, 2.5-bath home offers 1,509 sq. ft. of modern living space with a 1-car garage and elegant exterior. The open-concept first floor features a bright living room, dining area, and a well-equipped kitchen with ample cabinetry, pantry, and counter space, plus a convenient powder room. Upstairs, enjoy a spacious primary suite with a walk-in closet and private bath with double vanity, along with two additional bedrooms and a full hall bath. Photos and renderings are from builder's library, actual selections and finishes may vary.

17399 Riverside Dr, Ruther Glen

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

$385,000

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:

$387,950