Caroline County Real Estate

Caroline County Real Estate

Welcome to Caroline County, a hidden gem nestled in the heart of Virginia, where the charm of small-town living meets the allure of natural beauty. This picturesque county, rich in history and community spirit, is the perfect place for those seeking a serene lifestyle without sacrificing modern conveniences.

Caroline County is renowned for its lush landscapes, featuring rolling hills, sprawling fields, and tranquil waterways. Outdoor enthusiasts will find plenty to love, from hiking along scenic trails to fishing in the pristine waters of the Mattaponi and Pamunkey Rivers. With numerous parks and recreational areas, there’s no shortage of opportunities to embrace the great outdoors.

History buffs will delight in Caroline’s storied past. The county is home to several historic sites, including the charming town of Bowling Green, which serves as the county seat. Here, visitors can explore beautifully preserved architecture and learn about the area’s rich heritage. Additionally, Caroline County hosts various community events and festivals throughout the year, fostering a strong sense of belonging among residents.

Families will appreciate the county's top-notch schools and friendly neighborhoods, making it an ideal place to raise children. With a close-knit community atmosphere, Caroline County offers a welcoming environment where neighbors become friends and lifelong memories are made.

Whether you’re looking to buy your first home, retire in peace, or invest in a property that holds promise for the future, Caroline County stands ready to welcome you with open arms. Discover the perfect blend of tranquility and opportunity in this enchanting Virginia locale. Your dream home awaits!

Newest Listings in Caroline County

$299,900
4 Beds ⋅ 3 Baths
Welcome home to this beautifully designed new construction interior townhome, ideally situated in an established community in the heart of Denton, Maryland. Offering 4 spacious bedrooms, 2.5 baths, and an oversized rear-load garage, this thoughtfully designed home delivers the perfect combination of modern finishes, comfortable living, and everyday functionality. Step inside to a bright and inviting open-concept floor plan designed for both entertaining and daily life. The gourmet kitchen serves as the heart of the home, featuring quartz countertops, a large center island, and a dedicated coffee station for added style and convenience. The kitchen flows seamlessly into the dining and living areas, creating an open, welcoming space filled with natural light. Upstairs, you'll find three bedrooms, including a spacious owner's suite complete with a private bath and walk-in closet. Quality craftsmanship, thoughtfully selected finishes, and energy-efficient construction are incorporated throughout the home, providing the benefits and peace of mind that come with owning brand-new construction. Enjoy the charm of small-town Denton living while remaining close to shopping, dining, schools, parks, and major commuter routes. This established neighborhood offers a convenient location paired with the comfort and style of a brand-new home. And there's even more to love — ask about our Builder Incentives! A FREE DECK is already installed, giving you additional outdoor living space that's ready for relaxing, grilling, and entertaining family and friends. Homes will be ready in less than 60 days, so now is the perfect time to make your move and enjoy a brand-new home featuring today's most sought-after amenities. Pictures are for illustrative purposes only.

247 Briarwood Cir, Denton

Listing courtesy of Island Realty, LLC. Contact:

$449,900
3 Beds ⋅ 2 Baths
Professional photos and remarks coming soon

421 W Sunset Ave, Greensboro

Listing courtesy of Coldwell Banker Realty. Contact: 3025391777
$585,000
5 Beds ⋅ 4 Baths
Welcome home to 18015 Jackson Dr! Tucked on a corner lot, this is one of the neighborhood's original and best-loved homes. This stunning 5 bedroom, 3.5 bath colonial offers the space, quality, and lifestyle that most dream of, all less than 5 minutes from historic downtown Bowling Green. Grab a coffee at The Mix House and browse local shops on Main Street, or enjoy the small town charm that makes this location so special, all just minutes from your front door. From the moment you step onto the inviting front porch, you'll feel the pride of ownership that's gone into this home. Inside; abundance of natural light and cathedral ceilings set the tone for a home that's as beautiful as it is functional. This home has been beautifully crafted with comfort in mind. The main level offers a formal living room , a formal dining space, and a large family room centered around a cozy gas fireplace with beautiful bay windows. The gourmet eat in kitchen is the true showstopper; featuring granite countertops, a large center island, a cooktop, spacious pantry, plenty of counter space for cooking and hosting. The kitchen flows into a stunning sunroom/ eat in space with loads of natural light from windows all around, perfect for gathering with family and friends. Upstairs, retreat to a luxurious primary suite complete with a huge walk-in closet, a private sitting area, and a spa-like bathroom with a soaking tub, separate shower, and linen closet. Three additional bedrooms, a full bath, and a convenient laundry room complete the upper level. The walkout basement adds incredible versatility, with a recreation area, kitchenette, and spacious bedroom with a full bath. Basement also offers incredible storage and gym area; this basment is perfect for multigenerational living, guests, or even a home business. Outside, enjoy a fenced-in yard, a sparkling pool, a Trex deck, and a patio. all the space you need for summer fun and outdoor entertaining. Home also offers a 2 car garage and solar! Come checkout this beautiful home!!

18015 Jackson Dr, Bowling Green

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 5403715220
$249,000
2 Beds ⋅ 1 Baths
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: 4102218000
$600,000
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: 7033788810
$380,000
3 Beds ⋅ 2 Baths
Welcome to 737 Glen Cove Drive, a 3-bedroom, 2-bath home located in the desirable Lake Land’Or community. This spacious split-foyer offers a functional layout with comfortable living areas and plenty of potential. The upper level features a bright living room, an eat-in kitchen, two bedrooms, and a full bath. New carpet adds a fresh touch and enhances the home's move-in appeal. The lower level provides additional living space with a family room, laundry area, and a private primary suite complete with a walk-in closet and en-suite bath. Enjoy the convenience of an attached two-car garage and the outdoor space this property provides, perfect for relaxing or entertaining. Located in the Lake Land’Or community with access to recreational amenities, this home offers an opportunity to enjoy a convenient location, community amenities, and make the space your own. Schedule your showing today!

737 Glen Cove Dr, Ruther Glen

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$99,500
2 Beds ⋅ 1 Baths
This cottage is being sold in "As Is" condition and can be renovated into a beautiful home. Bring your ideas of how you can renovated it and make an offer.

4669 Gadow Road Unit #`, Preston

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

$330,000
3 Beds ⋅ 2 Baths
Welcome to 20121 Sparta Rd — a cozy split foyer home offering 3 bedrooms and 1.5 baths. Enjoy the peace of country living just minutes from the quaint town of Bowling Green. This move-in ready home has been thoughtfully updated with a newer roof, hot water heater, appliances, windows, and HVAC system, giving you peace of mind for years to come. Being sold as-is, the sellers are offering a $10,000 credit toward paint and doors — giving you the chance to personalize the home to your own style and taste. Don't miss this opportunity to own this home with major updates already in place, in a peaceful setting close to town amenities.

20121 Sparta Rd, Milford

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com
$309,000
2 Beds ⋅ 1 Baths
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: (410) 745-0415
$554,000
4 Beds ⋅ 3 Baths
Welcome to 22677 Camryn’s Way, where timeless Colonial charm, thoughtful updates, and a peaceful setting come together on more than one spacious, private acre. Built in 2010 and meticulously maintained, this four-bedroom, two-and-a-half-bath home is truly move-in ready. Beautifully refinished hardwood floors have been extended throughout the main level, stair treads, and upper landing, creating a polished and seamless look. Natural light fills the home, highlighting its warm and inviting living spaces. The completely updated kitchen is sure to impress with timeless Shaker-style cabinetry, solid-surface countertops, and a fresh, modern design. Upstairs, four generously sized bedrooms provide plenty of room, including an expansive primary suite with a walk-in closet and private bath featuring a double vanity and separate shower. A two-car garage offers ample parking and storage. With its exceptional condition, stylish improvements, and private country setting, this Queen Anne home offers the space and comfort you’ve been waiting for.

22677 Camryns Way, Queen Anne

Listing courtesy of Taylor Properties. Contact:

$175,000
USE 18330 POND RD RUTHER GLEN FOR GPS - WILL TAKE YOU RIGHT TO THE PARCEL B Incredible opportunity to build on this beautiful piece of land! Years before seller purchased, this parcel had a functioning well and septic. Purchaser will be responsible to get a perk test - soil study etc. The property has electricity in place (power pole). Please schedule your showing so the seller can make sure she is present to help understand the location of the corners. The property has “Do Not Enter” signs intended to discourage unauthorized recreational access, including dirt-bike riding and fishing. These signs do not prevent scheduled property showings. Please do not enter or explore the property without an appointment. Contact the listing agent for pricing, additional information, and access instructions.

Pond Rd, Ruther Glen

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$755,000
3 Beds ⋅ 2 Baths
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: 4105434545
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