Caroline County Homes under $250,000

Caroline County Homes under $250,000

Welcome to Caroline County, a hidden gem nestled in the heart of Virginia! Known for its picturesque landscapes, rich history, and vibrant community, Caroline County offers a unique blend of rural charm and modern convenience. With its lush greenery, tranquil rivers, and welcoming neighborhoods, it's no wonder that families and individuals alike are drawn to this idyllic region.

One of the standout features of Caroline County is its affordability in the housing market. If you're on the hunt for a cozy home without breaking the bank, you're in luck! The county boasts a variety of charming homes priced under $250,000, making it an attractive option for first-time buyers, investors, or anyone looking to downsize. These homes often feature classic architecture, spacious yards, and a sense of community that is hard to find in larger cities.

Imagine settling down in a quaint cottage surrounded by nature, or a modern townhouse just a stone’s throw from local amenities. With options ranging from historic homes to contemporary builds, there’s something for everyone. The county is also conveniently located near major highways, providing easy access to nearby cities while still allowing you to enjoy the peace and quiet of rural living.

In Caroline County, you’ll not only find affordable housing but also a supportive community that celebrates local events, outdoor activities, and a slower pace of life. Come discover the charm and affordability of Caroline County – your dream home awaits!

Newest Caroline County Homes under $250,000

21269 Dover Bridge Rd Unit LOT 15, Preston
$60,000
3 Beds ⋅ 2 Baths
Nestled in Dover Bridge Mobile Home Park—formerly Prettyman Manor.This large double-wide manufactured home offers plenty of space and potential. While it could use a bit of attention, it’s a wonderful opportunity to make this home your own in a quiet, welcoming setting. Conveniently located between Easton and Preston.

21269 Dover Bridge Rd Unit LOT 15, Preston

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

200 Maple Ave, Greensborough
$205,000
3 Beds ⋅ 2 Baths
Charming 3-bedroom, 2-bath home in the heart of Greensboro.This is an incredible opportunity to build instant equity. Enjoy outdoor living with a generous backyard perfect for entertaining and relax on the porch. Conveniently located near local shops, schools, and parks, this home combines small-town charm with everyday convenience—ideal for families or first-time buyers.

200 Maple Ave, Greensborough

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

215 N Main St, Federalsburg
$225,000
3 Beds ⋅ 2 Baths
Welcome to this charming 3BR/2BA classic Craftsman. Pull into the driveway and make your way to the covered front porch and the door to your forever home. Step inside to discover a home filled with original character, including beautiful original hardwood floors throughout. The main level showcases the traditional layout and timeless charm of a Craftsman, featuring a spacious living room that flows seamlessly into the dining room and kitchen. Just off the dining area is a cozy cabin-style room, offering incredible versatility as a family room, home office, or guest bedroom. This space also provides convenient access to a full bathroom featuring a walk-in shower. Upstairs, you'll find two spacious secondary bedrooms and a large primary bedroom filled with abundant natural light. The bedrooms share a full bathroom. The unfinished lower level offers laundry, ample storage, and plenty of room to create additional living space. Outside, the expansive lot provides abundant green space and endless possibilities, making this classic Craftsman a wonderful place to call home. Within the past six years, the home has benefited from several updates, including a new roof and multiple split HVAC units. The main unit can expand the system to accommodate up to three additional units, providing flexibility for future needs. This home also includes a Rinnai tankless hot water heater (2018). From the main floor, step outside onto a large wood deck that leads down to the expansive lot, offering abundant green space and so many possibilities. This home is ideal for any new homeowner and is located in a beautiful neighborhood with convenient access to shopping, restaurants, and commuter routes.

215 N Main St, Federalsburg

Listing courtesy of LPT Realty, LLC. Contact:

216 S 3rd St, Denton
$250,000
3 Beds ⋅ 2 Baths
Why rent when you can own and start building equity and an asset of your own? Priced at just $250,000, this charming home in the heart of downtown Denton offers an affordable opportunity to put your personal touches into a home and make it your own. The main level features a spacious living room with updated flooring, kitchen with separate dining area, office/flex space, mudroom, and a full bathroom, while upstairs you'll find three bedrooms and another full bathroom. An unfinished basement provides additional storage space & laundry and the inviting front porch with swing is the perfect spot to relax and enjoy the charm of this walkable downtown location. Conveniently located near the Choptank River, shops, dining, and everything downtown Denton has to offer. This home offers plenty of space, character, and potential for someone looking for an opportunity to own rather than rent. Seller will need a short 1 week rent back & subject to finding a home of choice. Don't delay and schedule your showing on this adorable bungalow today!

216 S 3rd St, Denton

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

215 Hamilton Dr, Ruther Glen
$200,000
3 Beds ⋅ 2 Baths
Bring your contractor, your vision, and your imagination—215 Hamilton Dr is ready for a complete transformation. This property needs a full renovation from top to bottom and is priced accordingly, offering an opportunity for an investor, experienced renovator, or buyer looking for a serious project. This is not a little paint-and-flooring makeover. The home needs substantial work, but the asking price reflects the condition and is positioned well below comparable renovated homes. For the right buyer, the value is in what this property can become. Renovate for resale, create a rental investment, or completely reimagine it for yourself. If you've been waiting for a true fixer-upper where you aren't paying for someone else's updates, this may be the one. Bring your ideas and take a look at the possibilities!

215 Hamilton Dr, Ruther Glen

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

105 Park Ave, Ridgely
$239,000
3 Beds ⋅ 2 Baths
Welcome to this charming Colonial home located in the heart of Ridgely! With a little TLC, this property has the potential to become your very own “Home Sweet Home.” Enjoy a convenient location close to Tuckahoe State Park and the local town park, which offers tennis courts, pickleball courts, and a playground for outdoor recreation and family fun. Firehouse, local shops, and medical centers are also nearby for added convenience. The home features a nice fenced backyard, perfect for enjoying outdoor activities, gardening, or relaxing. Bring your vision and make this home your own! Home is being Sold "AS IS" but well worth the price. Seller motivated.

105 Park Ave, Ridgely

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

6149 Bethlehem Rd, Preston
$225,000
2 Beds ⋅ 1 Baths
Charming and full of potential, this 2-bedroom, 1-bath home offers an excellent opportunity in Preston! Set on approximately 0.55 acres, this 891-square-foot single-level home features a spacious deck and a practical layout ready for its next chapter. Whether you're searching for an affordable primary residence, a weekend getaway, or an investment opportunity, this property is worth a look. Enjoy the space and privacy of an unincorporated setting while being conveniently located in the Preston area. Don't miss the opportunity to make 6149 Bethlehem Road your own!

6149 Bethlehem Rd, Preston

Listing courtesy of Keller Williams Realty. Contact:

1115 Market St, Denton
$229,900
2 Beds ⋅ 1 Baths
REDUCED $10,000!! Nestled in the charming Town of Denton, this Adorable Cottage exudes warmth and character! Lots of Upgrades and Updates are all sure to please! This beautiful home features 2 Bedrooms and an updated Full Bathroom. The inviting living space is enhanced by luxury vinyl plank flooring, seamlessly blending comfort and style. Set on a generous sized lot, the property offers room for expansion, along with ample outdoor space for gardening, playing, and relaxing in the sun! The private driveway accommodates up to three vehicles, ensuring convenience for you and your guests. A handy shed provides extra storage for your outdoor tools and hobbies. The Denton Area is known for its friendly community vibe, with local parks, shops, waterfront restaurant and eateries just a stone's throw away. Enjoy leisurely strolls through tree-lined streets or explore nearby recreational opportunities. Embrace the charm and make this cute cottage your own!

1115 Market St, Denton

Listing courtesy of RE/MAX Executive. Contact:

104 University Ave S, Federalsburg
$249,000
3 Beds ⋅ 1 Baths
Completely transformed from top to bottom, 104 S University Ave is the definition of move-in ready! This beautifully updated home features luxury vinyl plank flooring throughout, custom built-ins in the living room, and countless upgrades that allow you to move in with confidence. Step outside to enjoy the large fenced backyard, a newly sealed driveway, and a detached one-car garage with a finished bonus room that's perfect for a home office, gym, hobby space, or extra storage. With major mechanical updates already completed and every detail thoughtfully refreshed, all that's left to do is unpack and make yourself at home!

104 University Ave S, Federalsburg

Listing courtesy of Keller Williams Realty. Contact:

305 Caroline Ave, Ridgely
$224,000
2 Beds ⋅ 1 Baths
Affordable 2-Bedroom Home in the Heart of Ridgely. Welcome to 305 Caroline Avenue, a charming and budget-friendly two bedroom, one bath that's conveniently located. It's a livable home that's ready for your updates, giving you a great opportunity to build equity. Enjoy small town living with easy drives to Denton, Easton, and Annapolis via major roadways. Located within a community known for its strong schools, this home offers potential, flexibility, and value. Call today!

305 Caroline Ave, Ridgely

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

21182 Marsh Creek Road E-10 Rd, Preston
$74,900
3 Beds ⋅ 2 Baths
The home is located in between Easton and Preston, very close to Easton major shopping centers. This home offers 3 bedroom 2 full baths, and a large living room, Very private setting. For an application go to tenantrelationships@rentstackhouse.com, For question call 855-548-3642. You will get an AI recepticent , ask for Cecelia for billing questions and Brandis for application questions

21182 Marsh Creek Road E-10 Rd, Preston

Listing courtesy of Benson & Mangold, LLC. Contact:

12246 Bunya Ln, Ruther Glen
$190,000
3 Beds ⋅ 1 Baths
Investor Special or Make It Your Own! This Ruther Glen home is priced for a buyer ready to put in some work and is being sold strictly as-is. Currently livable but in need of repairs and updates throughout, this property offers an opportunity for an investor looking to build equity or a homeowner ready to renovate and make it their own. Seller has disclosed that a floor joist beneath the kitchen is damaged/broken and that there is visible sagging/depression in the kitchen floor. Seller and Listing Broker make no representation regarding the extent of the condition. Buyer is advised to conduct any inspections deemed necessary. Conveniently located in Caroline County, this home is ready for a fresh start. Bring your vision, your crew, or your Pinterest board and see the possibilities. Seller will make no repairs. Inspections are welcome for buyer's informational purposes only. Cash or hard money financing preferred, though buyers should confirm financing options and property eligibility directly with their lender based on the property's current condition.

12246 Bunya Ln, Ruther Glen

Listing courtesy of Samson Properties. Contact:

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