Caroline County Public Schools Homes for Sale

Caroline County Public Schools Homes for Sale

Welcome to Caroline County, Virginia, where a vibrant community and exceptional educational opportunities await you! Nestled in the heart of the picturesque countryside, Caroline County Public Schools provides a nurturing environment for students to thrive academically and socially. With a commitment to excellence, the school district boasts a range of programs designed to meet the diverse needs of its students, from innovative STEM initiatives to robust arts programs. Parents can rest assured knowing their children are receiving a high-quality education that prepares them for future success.

Caroline County is not just about education; it’s a place where families can build lasting memories and enjoy a serene lifestyle. The real estate market here offers a variety of homes for sale that cater to different preferences and budgets. Whether you’re seeking a charming cottage with a white picket fence or a spacious family home with modern amenities, you’ll find plenty of options to choose from. Many of these homes are situated in friendly neighborhoods, fostering a sense of community and belonging.

Living in Caroline County means you can enjoy the best of both worlds: the tranquility of rural living with easy access to urban conveniences. Explore the beautiful parks, scenic trails, and local events that bring residents together. With a focus on community and education, Caroline County is an ideal place to plant your roots. Discover your dream home today and become part of a thriving community that values both learning and living!

Newest Caroline County Public Schools Homes for Sale

$429,000
3 Beds ⋅ 3 Baths
Coming soon. More to follow. Professional photo's taken on Tuesday 9/29.

24882 Riverview Way, Ridgely

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$299,900
4 Beds ⋅ 2 Baths
Step into the timeless charm of this beautifully maintained circa-1880 home, where historic elegance meets thoughtful modern updates. Offering over 2,774 square feet of living space, this exceptional residence features 4 spacious bedrooms, 2 full bathrooms, and an abundance of original architectural character that has been lovingly preserved while incorporating today's modern conveniences. From the moment you arrive, you'll be captivated by the home's classic curb appeal and inviting front porch. Inside, soaring ceilings, oversized rooms, abundant natural light, and rare original heart-of-pine hardwood floors create a warm and welcoming atmosphere. Rich in history and craftsmanship, the home showcases beautiful millwork, original trim, and timeless architectural details rarely found in newer construction. The spacious country kitchen features custom cabinetry, generous counter space, and plenty of room for gathering with family and friends. A bright, sun-filled laundry room adds convenience, while multiple living spaces provide flexibility for entertaining, working from home, hobbies, or everyday living. Thoughtful updates throughout the home offer modern comfort while preserving its historic charm. In 2026, the front living room and full bathroom were beautifully renovated, and new plumbing lines were installed. Additional improvements include energy-efficient mini-split HVAC systems with smart controls, a new furnace (2025), updated electrical service, numerous replacement windows, remodeled bathrooms, built-in cabinetry, a replacement roof, refinished exterior, front porch enhancements, and many other upgrades that reflect exceptional pride of ownership. Step outside to enjoy your own private backyard retreat. A newer 6-foot privacy fence surrounds the outdoor space, where a brick patio, mature landscaping, and towering shade trees create the perfect setting for relaxing, entertaining, gardening, or enjoying a quiet morning coffee. The peaceful backyard offers privacy and plenty of room to enjoy every season. Located in the charming town of Greensboro, this home offers the best of Eastern Shore living. Enjoy a peaceful small-town setting just minutes from the scenic Choptank River, local parks, schools, restaurants, and everyday conveniences. Outdoor enthusiasts will appreciate nearby boating, fishing, kayaking, and recreational opportunities. The Delaware state line is only a short drive away, making tax-free shopping, beaches, dining, and entertainment easily accessible. High-speed internet is available, making remote work or streaming effortless, while the spacious floor plan easily accommodates growing families, multigenerational living, or anyone seeking additional room to spread out. The seamless blend of historic charm, quality craftsmanship, and modern updates creates a home that is both functional and full of character. Homes of this caliber and history rarely become available. Meticulously maintained and thoughtfully updated, this one-of-a-kind property preserves the timeless beauty and craftsmanship of the past while offering the comfort, efficiency, and conveniences today's buyers expect. Whether you're searching for your forever home or a distinctive property with unmatched character, this remarkable residence is ready for its next chapter. Don't miss this rare opportunity to own a beautifully preserved piece of history. Mortgage savings may be available for buyers of this listing.

111 Maple Ave, Greensboro

Listing courtesy of Redfin Corp. Contact: 3016586186
$434,500
3 Beds ⋅ 2 Baths
Welcome to S Quail Ct in Greensboro! The model home is located across the street and can be toured 13926 S Quail Ct. This to-be-built home offers just over 1,800 square feet of thoughtfully designed living space on more than an acre, backing to mature trees for added privacy. Tucked away on a dead-end street with no through traffic, the setting offers plenty of space and privacy while still providing the convenience of a beautiful new home. From the moment you arrive, you'll notice the attention to detail, including an inviting covered front porch, large driveway, oversized two-car garage, and exterior soffit lighting surrounding the home for an impressive look after dark. Step inside to a bright, open floor plan filled with upgraded finishes. The spacious kitchen is designed to be the heart of the home and features a large center island, stainless steel appliances, upgraded lighting, and plenty of room for gathering and entertaining. Pella windows and doors, high-end LVP flooring, recessed lighting throughout, upgraded trim, and carefully selected fixtures give the home a clean, custom feel. The bathrooms continue the upgraded finishes with stylish vanities and tile, including a beautiful walk-in shower. Ceiling fans are installed in all bedrooms, and the separate laundry room includes both a utility sink and washer and dryer. Out back, enjoy the low-maintenance deck overlooking the spacious yard and mature trees — a great setting for relaxing, grilling, or entertaining. The oversized two-car garage is fully finished and painted with plenty of lighting, making it as functional as it is clean. With over an acre of land, more than 1,800 square feet of living space, quality finishes throughout, an oversized finished garage, private backyard setting, and a 2-year home warranty, this new construction home offers much more than just "brand new." Come see the craftsmanship, upgrades, and attention to detail for yourself!

S Quail Ct, Greensboro

Listing courtesy of CR Realty. Contact: 4104900460
$375,000
3 Beds ⋅ 2 Baths
One-level living with no HOA! Set on 0.45 acres, this inviting home offers spacious bedrooms, comfortable living areas, and outdoor space to garden, play, or unwind in the peaceful country setting. Hardwood floors and chair rail add a welcoming touch throughout. A two-car garage and a 12-by-24-foot shed with a 4-by-8-foot bump-out offer plenty of room for parking, storage, and hobbies. Only 5 minutes from I-95 !!

8311 Stonewall Ln, Woodford

Listing courtesy of Samson Properties. Contact: (703) 378-8810
$554,740
4 Beds ⋅ 3 Baths
Welcome to the 2818 sq ft Hanover floor plan, 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. Incentives with use of preferred lender. Photos and renderings are from builder's library, actual selections and finishes may vary.

17370 Pirogue Ln, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139
$528,740
5 Beds ⋅ 3 Baths
Welcome to the 2511 sq ft Hayden model, offering a modern open-concept living space designed for both comfort and flexibility. The main level features a welcoming living room, a spacious dining room, and a well-appointed kitchen with walk-in pantry, perfect for family gatherings and entertaining. The main floor also includes a full bedroom, a bathroom, and a versatile flex room, allowing you to create the ideal space for your family’s needs. Upstairs, an additional living space offers even more flexibility for a home office, playroom, or entertainment area. The large primary suite is a true retreat, featuring 2 large walk-in closets 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 room for everyone. The Hayden model is the perfect live-play-work home, offering flexible living spaces and modern amenities for today’s family, providing everything you need to live, work, and play in comfort. Photos are from builder's library, actual selections and finishes may vary.

17376 Pirogue Ln, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139
$600,000
4 Beds ⋅ 4 Baths
Welcome Home! This stunning 2023 Colonial in the desirable Pendleton golf course community offers approximately 3,008 square feet of beautifully finished living space with all of the builder’s available options and upgrades. Situated on a desirable corner lot, this home features 4 bedrooms, 3.5 baths, a fully finished walkout basement, attached garage, and fenced backyard. The open-concept main level showcases beautiful LVP flooring, abundant natural light, an electric fireplace, and a gourmet kitchen with stainless steel appliances, cooktop, double wall ovens, built-in microwave, dishwasher, and more. The spacious primary suite provides a relaxing retreat, while the finished basement offers flexible space for a home theater, gym, recreation room, or additional living area. Enjoy outdoor living in the fenced backyard, along with the exceptional amenities Pendleton has to offer, including a clubhouse, pool, pickleball courts, walking/jogging paths, dog park, and access to the community’s beautiful golf course. Best of all, this home comes with a home warranty for added peace of mind. With its premium builder selections, desirable corner-lot location, finished basement, and resort-style community amenities, this home is ready to welcome you home!

7092 Iron Gall Ln, Ruther Glen

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 5407359176
$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: 8773662213
$554,740
4 Beds ⋅ 3 Baths
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.

17382 Pirogue Ln, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139
$574,900
4 Beds ⋅ 3 Baths
Beautifully Maintained Home with Private In-Law Suite, Pool & Exceptional Workshop Space This well-maintained property offers outstanding flexibility with a spacious private in-law suite connected to the main home by a bright sunroom with direct access to the deck and backyard. Perfect for multi-generational living, guests, or potential rental income. The main home features an updated kitchen with maple cabinetry, granite countertops, pantry, hardwood flooring, recessed lighting, and premium Jenn-Air, Viking, and LG Café stainless steel appliances. The living room showcases a stone wood-burning fireplace and opens to the dining area. The primary suite includes an updated walk-in shower, while two additional bedrooms and a bonus room provide flexible living space. A full-length composite front porch adds charm and curb appeal. The sunroom, with slate flooring and abundant natural light, leads to the deck, hot tub, and fully fenced backyard. Outdoor amenities include a saltwater in-ground pool and screened pool house with a ceiling fan and changing room, creating an ideal setting for entertaining and relaxation. The private in-law suite offers a living room, eat-in kitchen, spacious bedroom with ensuite bath, half bath, dedicated laundry room, and attached one-car garage with handicap-accessible ramp. Additional features include ceiling fans throughout the home, suite, workshop, and screened porch; a stone driveway with ample parking; a 12' x 20' shed; a 12' x 30' workshop with electric; an 18' x 30' RV/boat carport; and an insulated 24' x 30' garage/workshop with electricity, gas heat, built-in shelving, and custom workbench. Recent improvements include new concrete patios, walkways, and fire pit (2026), upgraded septic system, encapsulated crawl space with dehumidifiers, encapsulated attic, LeafFilter gutter protection, and a new hot water heater in the in-law suite (2026). The beautifully landscaped grounds feature excellent drainage, established gardens, and a secluded sitting area to enjoy nature and local wildlife. Surrounded by Lynch Preserve, the community offers miles of scenic walking trails. Combining comfortable living, versatile space, and resort-style outdoor amenities, this unique property truly has something for everyone. Within minutes to Neighborhood Ramp for all your boatig and fishing needs on the Choptank River. Less than 1 hour to the Bay Bridge. Easy commute to Easton, Delaware or Salisbury. Schedule your private tour today.

24308 Marlyn Dr, Preston

Listing courtesy of Brenton Realty Group. Contact: 4104794663
$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:

$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: (540) 786-0088
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