Windsor Real Estate

Windsor Real Estate

Welcome to Windsor, Pennsylvania—a charming gem nestled in the heart of York County. With its picturesque landscapes and friendly community, Windsor offers a delightful blend of small-town charm and modern convenience. This quaint borough is perfectly situated, providing easy access to major highways, making it a convenient hub for commuters heading to nearby cities like York and Lancaster.

Windsor boasts a rich history, reflected in its well-preserved architecture and local landmarks. The town is a tapestry of vibrant neighborhoods, where tree-lined streets and welcoming front porches invite you to explore. Residents enjoy a slower pace of life while still having access to essential amenities, including local shops, restaurants, and parks. The nearby Susquehanna River offers scenic views and recreational opportunities, perfect for outdoor enthusiasts looking to hike, fish, or simply enjoy nature.

Families will appreciate the strong sense of community and the highly-rated schools that serve the area. Windsor is known for its family-friendly atmosphere, where children can play safely in the parks and neighbors become lifelong friends.

As you consider your next home, Windsor presents an inviting option with a variety of housing styles, from charming historic homes to modern developments. Whether you're a first-time buyer or looking to settle down, Windsor is a place where you can truly feel at home. Discover the warmth and beauty of Windsor, PA—your perfect slice of Americana awaits!

Newest Listings in Windsor

$995,000
7 Beds 7 Baths
Nearly 6,000 square feet • 7 bedrooms • 5.5 baths • Five-stall renovated barn • Three fenced pastures • Heated in-ground pool • Separate apartment • Agricultural zoning! ONE OF THE LARGEST HOMES IN THE AREA with acreage, this exceptional property offers the perfect blend of historic charm, modern updates, and endless possibilities. Featuring nearly 6,000 square feet of in home living space, a beautifully renovated five-stall/ two-story barn, three fenced pastures, a heated in-ground salt water pool, basketball court, and year-round creek, this one-of-a-kind property is ready to make your dreams a reality. Originally built in 1886, this seven-bedroom, five-and-a-half-bath home has been thoughtfully expanded and recently renovated while preserving its timeless FARMHOUSE CHARACTER. The stunning eat-in kitchen showcases ORIGINAL WOOD BEAMS, abundant custom cabinetry, granite countertops, and an impressive 10' x 12' walk-in pantry. The expansive 27' x 16' gathering/living room (currently used as the formal dining room) easily accommodates seating for 20+ guests, making it ideal for holidays and entertaining. Take the entertainment also to the huge deck overlooking the pastures and pool area! Designed with flexibility in mind, the home offers THREE SEPARATE LIVING AREAS, making it an excellent option for multigenerational living, guest accommodations, or shared living arrangements. The MAIN LEVEL features a spacious primary suite with a walk-in closet and full bath, a warm and inviting family room, a library with built-in bookshelves, a dedicated office, first-floor laundry, and an additional full bath. A staircase from the family room leads to a SECOND FLOOR loft-style living area with four generously sized bedrooms connected by two Jack-and-Jill bathrooms. A second staircase accesses another private wing featuring two additional bedrooms, a full bath, and abundant closet space. The LOWER LEVEL offers a fully equipped apartment with its own private entrance, while also remaining accessible from the main house. Complete with a kitchen, dining area, living room, bedroom, laundry area, and one-and-a-half baths, this space is ideal for extended family, guests, or potential rental income (buyer to verify permitted uses). OUTSIDE, the opportunities continue. Agriculturally zoned, the property is well suited for horses, livestock, homesteading, hobby farming, or a farm-based business. The newly renovated five-stall barn includes water, a tack room, feed room, and an expansive second floor that offers incredible flexibility for storage, recreation, workshops, or entertaining. Three fenced pastures, TWO WELLS, and a picturesque YEAR ROUND CREEK further enhance the property's functionality and charm. Spend summer days enjoying the fenced, heated in-ground pool with a heating system that is only three years old, or challenge friends and family on the BASKETBALL COURT. Whether you're looking for a private country estate, an equestrian property, a working homestead, or a home that offers room for everyone, this extraordinary property delivers a rare combination of space, versatility, and lifestyle.

1025 Gebhart Rd, Windsor

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: 8003833535

$449,900
4 Beds 3 Baths
Welcome home to the highly sought-after Chatham Creek community, where opportunities like 325 Thomas Armor Dr are few and far between. Lovingly maintained by its original owner, this residence reflects true pride of ownership at every turn. From the moment you arrive, the curb appeal stands out with mature, thoughtfully designed landscaping that brings color, shade, and charm throughout the seasons. A large 2-car garage adds both convenience and functionality, complementing the home’s impressive exterior. The fully fenced rear yard creates a private outdoor retreat—ideal for entertaining, pets, or everyday relaxation. Enjoy seamless indoor-outdoor living with a spacious deck overlooking the yard, along with a walk-out lower-level patio that extends your living space even further. Peace of mind comes with major recent updates, including a brand-new roof (2026), replacement windows, and a new HVAC system installed in 2024—offering both comfort and efficiency for years to come. Inside, the home opens to a warm, inviting layout designed for both everyday living and entertaining. A formal dining room sets the stage for gatherings, while the spacious kitchen with a center island flows effortlessly into the comfortable family room. Just beyond, a stunning four-season sunroom—fully heated and air conditioned—offers a light-filled sanctuary perfect for morning coffee, reading, or unwinding year-round. The upper level features four generously sized bedrooms, including a serene primary suite complete with a private en-suite bath. A conveniently located upper-level laundry adds everyday ease and functionality. The fully finished lower level dramatically expands the living space, offering a large recreation area perfect for a media room or home theater setup, a dedicated bonus room currently used as a home gym, and an additional storage/mechanical area with walk-out access to the backyard. This level is designed to flex with your lifestyle. This home blends comfort, space, and thoughtful updates in one of Windsor’s most desirable neighborhoods. A rare opportunity—don’t miss your chance to make it yours. Interior photos are not publicly available. Please contact the listing agent or your Realtor to schedule a private showing.

325 Thomas Armor Dr, Windsor

Listing courtesy of Cavalry Realty LLC. Contact: (717) 932-2599

$426,990
4 Beds 3 Baths
Discover the Landon Heritage, a 4-bedroom, 2.5-bath single-family home for sale in York, PA. Step inside through the front door to find a private study on your left, perfect for a home office or quiet retreat. Continue down the hall past the stairs to the heart of the home, where an open-concept layout seamlessly connects the Kitchen, Family Room, and Dining Area. Just off the Kitchen, you’ll find a convenient entry space with a half bath and access to the 2-car garage. Upstairs, the Owner’s Suite offers a generously sized walk-in closet and a private ensuite featuring a double-bowl vanity. The second floor also includes a Laundry Room for added convenience, 3 additional bedrooms, and a family bath. An unfinished basement adds 981 square feet of flexible space, ready for future living, storage, or recreation. Welcome to Walnut Creek, a vibrant and thriving community of brand-new construction homes nestled in the picturesque landscape of York County, Pennsylvania. Walnut Creek beckons with the promise of a wonderful suburban lifestyle with 148 homesites ranging in size from 1/5 to 1/4 acre, ensuring that you find the perfect space to call your own in Windsor, York, PA. Our quality homes are backed with an industry-leading 20-year warranty structural warranty. Learn more about how Keystone Custom Homes are 80% more efficient than used homes and 50% more efficient than other new homes.

307 Boxwood Dr, Windsor

Listing courtesy of Patriot Realty, LLC. Contact: (717) 963-2903

$424,990
4 Beds 3 Baths
Discover the Landon Traditional, a 4-bedroom, 2.5-bath single-family home for sale in York, PA. Step inside through the front door to find a private study on your left, perfect for a home office or quiet retreat. Continue down the hall past the stairs to the heart of the home, where an open-concept layout seamlessly connects the Kitchen, Family Room, and Dining Area. Just off the Kitchen, you’ll find a convenient entry space with a half bath and access to the 2-car garage. Upstairs, the Owner’s Suite offers a generously sized walk-in closet and a private ensuite featuring a double-bowl vanity. The second floor also includes a Laundry Room for added convenience, 3 additional bedrooms, and a family bath. An unfinished basement adds 981 square feet of flexible space, ready for future living, storage, or recreation. Welcome to Walnut Creek, a vibrant and thriving community of brand-new construction homes nestled in the picturesque landscape of York County, Pennsylvania. Walnut Creek beckons with the promise of a wonderful suburban lifestyle with 148 homesites ranging in size from 1/5 to 1/4 acre, ensuring that you find the perfect space to call your own in Windsor, York, PA. Our quality homes are backed with an industry-leading 20-year warranty structural warranty. Learn more about how Keystone Custom Homes are 80% more efficient than used homes and 50% more efficient than other new homes.

309 Boxwood Dr, Windsor

Listing courtesy of Patriot Realty, LLC. Contact: (717) 963-2903

$430,990
4 Beds 3 Baths
Discover the Landon Farmhouse, a 4-bedroom, 2.5-bath single-family home for sale in York, PA. Step inside through the front door to find a private study on your left, perfect for a home office or quiet retreat. Continue down the hall past the stairs to the heart of the home, where an open-concept layout seamlessly connects the Kitchen, Family Room, and Dining Area. Just off the Kitchen, you’ll find a convenient entry space with a half bath and access to the 2-car garage. Upstairs, the Owner’s Suite offers a generously sized walk-in closet and a private ensuite featuring a double-bowl vanity. The second floor also includes a Laundry Room for added convenience, 3 additional bedrooms, and a family bath. An unfinished basement adds 981 square feet of flexible space, ready for future living, storage, or recreation. Welcome to Walnut Creek, a vibrant and thriving community of brand-new construction homes nestled in the picturesque landscape of York County, Pennsylvania. Walnut Creek beckons with the promise of a wonderful suburban lifestyle with 148 homesites ranging in size from 1/5 to 1/4 acre, ensuring that you find the perfect space to call your own in Windsor, York, PA. Our quality homes are backed with an industry-leading 20-year warranty structural warranty. Learn more about how Keystone Custom Homes are 80% more efficient than used homes and 50% more efficient than other new homes.

311 Boxwood Dr, Windsor

Listing courtesy of Patriot Realty, LLC. Contact: (717) 963-2903

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