Caroline Homes for Sale

Caroline Homes for Sale

Welcome to Caroline County, a hidden gem nestled in the heart of Virginia. Known for its picturesque landscapes and rich history, this charming county offers a perfect blend of rural tranquility and modern convenience. With sprawling fields, serene lakes, and lush woodlands, Caroline County provides an idyllic backdrop for those seeking a peaceful lifestyle while remaining connected to urban amenities.

The county is steeped in history, with several historical landmarks and sites that tell the story of its vibrant past. From the quaint downtown areas of Bowling Green to the scenic vistas along the Mattaponi River, Caroline County boasts an array of outdoor activities, including hiking, fishing, and camping. The friendly community spirit and welcoming atmosphere make it an ideal place for families, retirees, and anyone looking to escape the hustle and bustle of city life.

For those considering a move, Caroline County has a variety of homes for sale that cater to diverse tastes and budgets. Whether you’re searching for a charming historic home, a modern family residence, or a cozy cottage, the real estate market here has something for everyone. With competitive prices and an array of options, you can find the perfect place to call home.

As you explore the homes for sale in Caroline County, you’ll discover not just a house, but a community where you can create lasting memories. Embrace the opportunity to live in this beautiful county, where nature, history, and a sense of belonging await you. Your dream home in Caroline County is just a visit away!

Newest Caroline Homes for Sale

4 Beds ⋅ 2 Baths

Opportunity awaits on this peaceful 1.46± acre wooded parcel in Preston. Tucked among mature trees, this property offers a private country setting with endless potential for its next chapter. The existing ranch-style home is being conveyed as part of an estate and is being sold AS-IS, including all remaining personal property and contents. Buyers should plan to complete their own due diligence regarding the condition of the home. Whether you're searching for your next renovation project or envisioning the possibilities this beautiful homesite has to offer, this property provides a rare chance to invest in a quiet, rural setting. No Inside Photos

21579 Tanyard Rd, Preston

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

4 Beds ⋅ 3 Baths

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

22733 Squire Ln, Queen Anne

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

2 Beds ⋅ 1 Baths

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: 4104794663

3 Beds ⋅ 2 Baths

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

23118 Tuckahoe Springs Dr, Denton

Listing courtesy of Brenton Realty Group. Contact: 4104794663

4 Beds ⋅ 2 Baths

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

17122 New Baltimore Rd, Milford

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

3 Beds ⋅ 2 Baths

MOVE IN READY!! HOME SWEET HOME! Don't miss your chance to see this adorable home that is part of a beautiful, gated community in Lake Land'Or. The neighborhood itself has tons of amenities-community center, swimming pool, recreation center, playgrounds, lakes & beachy area...and so much more! Convenient to I-95, restaurants, and shopping! ***The sellers have already paid the entire HOA dues for the year and have been so generous enough to "pay it forward". This wonderful 3 bedroom, 2 bath home has just recently been updated with brand new LVP flooring as well as fresh paint throughout the entire home. New light fixtures, ceiling fans, and almost brand new washer & dryer that conveys. Appliances are stainless steel & HVAC recently replaced with regular annual service. Make your way out back where you can enjoy nature while sitting on the deck or relax by a cozy fire in the back yard! Large shed out back is in great condition and already has electricity to it! The sellers have done a wonderful job maintaining this home & now all it needs is a new buyer to call it "home!" Don't miss your opportunity to see this one before it's gone!

432 Cornwall Dr, Ruther Glen

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 5406258100

3 Beds ⋅ 2 Baths

Welcome to 11139 Central Avenue, where the tranquility of country living meets the convenience of a prime Caroline County location. Nestled on one acre outside Ridgely, this updated 3 bed 2 bath rancher offers space, functionality, and modern updates. The open concept layout is great for entertaining, while the 30 x 50 shop shines for those who need serious workspace, storage, or just a big toybox;) Commuters will appreciate easy access to Denton, Easton, Annapolis, and beyond. Move-in ready, well maintained, and perfectly positioned for both quiet country living and convenient commutes. Call for a showing today!

11139 Central Ave, Ridgely

Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011

3 Beds ⋅ 2 Baths

Charming rambler on large, private lot. Freshly painted, new flooring, new appliances, new roof, and so much more. Home features a huge backyard with endless potential and large deck, ideal for entertaining and outdoor living. Inside is a large kitchen, 3 large bedrooms with ample closet space, and large laundry area. This home is a must see!

13364 Julien St, Woodford

Listing courtesy of M.O. Wilson Properties. Contact: 7038780000

3 Beds ⋅ 2 Baths

Here is your opportunity to own a family compound spanning approximately 6.5 acres over 2 parcels with 2 separate homes! The larger home has an additional guest suite on the main level! The larger home on acreage offers a rare and versatile main-level guest suite or entertainment wing at the rear of the home, complete with its own laundry, kitchenette, living spaces, and two full bathrooms. This flexible layout provides exceptional options for a variety of needs and lifestyles. Step inside from the spacious front porch to 9-foot ceilings and wood floors throughout most of the main level, creating an open and welcoming feel from the moment you enter. Recent updates add to the home’s appeal, including a water filtration system in 2025, quartz kitchen counters, kitchen backsplash, and refrigerator in 2024, wood floors in 2023, garage landing in 2022, paved driveway in 2021, original home HVAC in 2018, original home roof in 2017, and well pump in 2017. Step outside and enjoy plenty of room to run, relax, or explore the walking trails created through the wooded portion of the acreage. This smaller home is subject to a lease through November 2026 and will not be sold separately. The home is well kept and shows very well!

22623 & 22617 Telegraph Rd, Ruther Glen

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

5 Beds ⋅ 5 Baths

This home on acreage was renovated in 2010 to include a 2,600 square foot addition. It features a rare and versatile main-level guest suite (with it's own laundry, kitchenette, living spaces and 2 full bathrooms) or entertainment wing at the rear of the home, providing exceptional flexibility for a variety of needs. Step inside from the spacious front porch to 9-foot ceilings and wood floors throughout most of the main level, creating an open and welcoming feel from the moment you enter. Recent updates add to the home’s appeal, including a water filtration system in 2025, quartz kitchen counters, kitchen backsplash, and refrigerator in 2024, wood floors in 2023, garage landing in 2022, paved driveway in 2021, HVAC in 2018, partial roof replacement in 2017, and well pump in 2017. With its thoughtful layout, flexible living spaces, and meaningful updates, this home is designed to adapt to a variety of needs and lifestyles. Step outside and enjoy plenty of room to run, relax, or explore the walking trails created through the wooded portion of the acreage.

22617 Telegraph Rd, Ruther Glen

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

4 Beds ⋅ 3 Baths

The Sidney offers over 1,841+ square feet of thoughtfully designed living space with 4 bedrooms and 2.5 bathrooms, blending comfort and functionality for modern living. The first floor welcomes you with a spacious open-concept layout featuring a large family room and dining area—perfect for entertaining or everyday gatherings. The kitchen is designed for both style and convenience, with a peninsula that overlooks the dining space and a generous walk-in pantry for ample storage. Just off the rear-load garage, a practical laundry and mudroom creates the perfect drop zone and flows directly into the kitchen. A convenient powder room completes the main level. Upstairs, the expansive primary suite provides a relaxing retreat, highlighted by an oversized walk-in closet and a private en-suite bath with double vanities and a walk-in shower. Three additional bedrooms and a full bathroom with tub provide comfortable accommodations for family members or guests. With its open main living areas, smart storage solutions, and spacious bedrooms, the Sidney is designed to make everyday living easy and enjoyable. Renderings are from builder's library, actual finishes and features may vary.

17484 Clark And York Blvd, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

4 Beds ⋅ 4 Baths

The Irwin floorplan offers a thoughtfully designed two-story layout with 2,298 square feet of living space, making it perfect for families who appreciate both style and functionality. This home features 4 bedrooms and 3.5 bathrooms, providing plenty of space for privacy and convenience. The primary bedroom, located on the second floor, is a spacious retreat with a large walk-in closet and an en-suite bathroom, complete with luxurious fixtures and a modern design. The open-concept kitchen serves as the heart of the home, featuring sleek quartz countertops that are both durable and visually striking. The kitchen flows seamlessly into the dining and living room areas, creating an ideal space for family gatherings and entertaining. With top-of-the-line appliances, abundant cabinet space, and ample counter space, the kitchen is both practical and beautiful. You’ll find two additional bedrooms upstairs and one downstairs, each generously sized, along with two full bathrooms to accommodate family and guests. A half-bathroom on the first floor adds convenience for all. The 2-car garage offers additional storage and easy access to the home. Photos and renderings are from builder's library, finishes and features might vary.

17480 Clark And York Blvd, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

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