Caroline County Public Schools Real Estate

Caroline County Public Schools Real Estate

Welcome to the heart of Caroline County, where education meets opportunity in the esteemed Caroline County Public Schools district. Nestled in the picturesque landscapes of Virginia, this vibrant community is dedicated to fostering a nurturing and innovative learning environment for students from all walks of life.

Caroline County Public Schools is renowned for its commitment to academic excellence, providing a well-rounded education that prepares students for future success. With a focus on personalized learning, the district offers a variety of programs tailored to meet the diverse needs of its students. From advanced placement courses to vocational training, Caroline County ensures that every child has the tools and resources necessary to thrive.

Parents will appreciate the small class sizes and dedicated educators who are passionate about their students' growth. The district prides itself on fostering strong relationships between teachers, parents, and the community, creating a supportive network that enhances the educational experience. Extracurricular activities abound, allowing students to explore their interests in sports, arts, and community service, further enriching their school experience.

Safety and well-being are paramount in Caroline County Public Schools, where modern facilities and resources are designed to provide a safe and engaging learning environment. The district's commitment to technology integration ensures that students are not only prepared for today's challenges but also equipped with the skills needed for tomorrow's opportunities.

Choosing to live in Caroline County means investing in a bright future for your family. With its strong educational foundation, this community is not just a place to call home, but a place where dreams take flight. Discover the charm and potential of Caroline County Public Schools today!

Newest Listings in Caroline County Public Schools

$345,000
3 Beds ⋅ 3 Baths

7220 Senate Way, Ruther Glen

Listing courtesy of Lee Sherbeyn Real Estate Services & Referrals. Contact: 5408783068
$465,000
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
$374,900
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
$524,500
4 Beds ⋅ 3 Baths
Welcome to your own private retreat! Situated on 4 peaceful acres, this well-maintained 4-bedroom, 2.5-bath home offers the perfect combination of comfort, privacy, and functionality. Inside, you'll find a spacious and inviting floor plan with generous living areas, an updated kitchen, and plenty of room for family and guests. Step outside to the enormous rear deck, an ideal space for entertaining, grilling, or simply relaxing while enjoying the peaceful surroundings. One of the property's standout features is the incredible heated and air-conditioned pole barn. This impressive building includes a finished second floor and half bath, making it perfect for a home-based business, workshop, hobby space, gym, recreational area, additional storage, or countless other possibilities. Located just minutes from Tuckahoe State Park, you'll enjoy easy access to miles of hiking and horseback riding trails, kayaking, fishing, camping, and some of the Eastern Shore's best outdoor recreation while still being conveniently close to shopping, dining, and major commuter routes. Whether you're looking for room to spread out, a place to store equipment and toys, or simply a private country setting with exceptional amenities, this property delivers. Don't miss this rare opportunity to own a versatile property that truly has it all. Schedule your private showing today!

22845 Peaviner Rd, Ridgely

Listing courtesy of CR Realty. Contact: 4104900460
$300,000
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
$399,000
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
$309,000
3 Beds ⋅ 2 Baths

13364 Julien St, Woodford

Listing courtesy of M.O. Wilson Properties. Contact: 7038780000
$994,000
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
$649,000
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
$455,740
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
$505,740
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
$2,500,000
Exceptional opportunity for forward-thinking developers! This nearly 92-acre tract of undeveloped land is ideally located just 2 miles from the I-95/Lady Smith interchange and offers approximately 1,255 feet of commercial frontage along busy US-1. Set in a natural, wooded landscape abutting Lake Caroline and neighboring residential communities, the property presents a rare canvas in a high-demand growth corridor. With easy access to Washington, D.C. via I-95 and only minutes from Lady Smith Road, the location is primed for a luxury active 55+ community or mixed-use development. The area has seen a surge in residential and commercial expansion, and this parcel sits just outside the bustle—offering outstanding visibility, accessibility, and long-term potential. Whether you're envisioning a thoughtfully designed 55+ residential enclave or a larger scale commercial project that captures the area's upward trajectory, this site is the perfect investment for those ready to shape the next phase of Caroline County’s growth.

Us Route 1, Ruther Glen

Listing courtesy of RE/MAX Supercenter. Contact:

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