Windsor Real Estate

Windsor Real Estate

Welcome to Windsor, Pennsylvania – a charming borough nestled in the heart of York County, where small-town allure meets vibrant community spirit. With a rich history dating back to the 18th century, Windsor offers a delightful blend of heritage and modern living, making it an ideal place to call home.

Situated just a short drive from the bustling city of York, Windsor boasts a peaceful rural atmosphere while maintaining easy access to urban conveniences. The area is characterized by its picturesque landscapes, including rolling hills and serene farmland, providing residents with a tranquil escape from the hustle and bustle of city life. Outdoor enthusiasts will relish the nearby parks and recreational areas, perfect for hiking, biking, or simply enjoying a picnic with family and friends.

Windsor is known for its tight-knit community, where neighbors become friends and local events foster a sense of belonging. The borough hosts various community gatherings throughout the year, from seasonal festivals to farmers' markets, celebrating the region's rich agricultural heritage and local artisans.

Education is a priority in Windsor, with access to quality schools that nurture young minds and prepare them for future success. Families will appreciate the safe, welcoming environment that makes raising children a joy.

Whether you're seeking a cozy starter home or a spacious family residence, Windsor offers a variety of real estate options to suit your needs. Experience the charm of Windsor, PA – a place where community, nature, and history come together to create a truly special living experience. Come and discover your dream home in this enchanting borough!

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
$167,500
3 Beds ⋅ 2 Baths
Beautiful Brand-New 3 Bedroom, 2 Bath Home on a Large Corner Lot! Located in the Deerfield Oaks 55+ Community This stunning, brand-new home sits on a premium, spacious corner lot, offering extra privacy and plenty of outdoor space. Inside, you'll find a thoughtfully designed, low-maintenance, open floor plan with plenty of modern extras, including: Modern Kitchen: Complete with sleek stainless steel appliances. Primary Suite: Featuring a spacious, easily accessible walk-in shower. Storage & Space: Ample closet space throughout. ☀️ Premium Outdoor Living: Step outside onto your large deck, complete with an awning for perfect shade—ideal for entertaining, relaxing, or taking in the peaceful country views right from your expansive corner backyard (which also includes a handy outdoor storage shed). Perfectly situated in a highly desirable location within a quiet, welcoming 55+ community, this home is the perfect place to settle down. Don't miss the chance to call this brand-new, beautiful home yours!

100 Fawn Circle Dr, Windsor

Listing courtesy of Iron Valley Real Estate of Lancaster. Contact: (717) 740-2221
$885,000
4 Beds ⋅ 3 Baths
Nestled on nearly 8 picturesque acres, this exceptional property offers the perfect blend of peaceful country living and unmatched versatility. This well-maintained home features multiple living spaces, a functional floor plan, a spacious primary suite with a soaking tub and separate shower, three additional bedrooms, and a walkout basement ready for storage or future finishing. Step outside to enjoy the privacy, open views, and expansive grounds complete with a classic red barn, fenced pasture, and plenty of room to garden, entertain, or simply enjoy the outdoors. Adding to the property’s incredible value is an established commercial kennel facility featuring 44 total dog runs, a dedicated cat boarding building, grooming area, office, reception/retail space, food preparation area, bathing station, exercise yards, and multiple support buildings. Whether you’re looking to operate an animal-related business, pursue an agricultural venture, or simply enjoy the flexibility these improvements provide, the possibilities are endless. Properties that combine a beautiful country home, nearly 8 acres, and this level of infrastructure are exceptionally rare. Whether you’re searching for privacy, space to grow, or the opportunity to live and work in one location, 333 Newcomer Road offers a lifestyle that’s difficult to duplicate.

333 Newcomer Rd, Windsor

Listing courtesy of Iron Valley Real Estate of York County. Contact: (717) 316-8777
$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
$109,900
3 Beds ⋅ 2 Baths
With a tree line to the rear, this 1 story living home sets in a 55+ neighborhood. In the living room, there is a pass thru window to the Eat-in-Kitchen, the Laundry area is here with a door to a small deck, the Owners Bedroom Suite has a step in shower and a walk in closet, the main bath offers a tub shower, additions include: a ramp, grab bars, new Hot Water Heater, Refrigerator and Dryer.

123 White Tail Ln, Windsor

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: (800) 383-3535
$265,000
Unique investment opportunity! This single-story duplex offers two separate units, providing excellent income potential or multi-generational living options. Situated on a spacious lot in Windsor, each unit features its own private entrance and functional layout. Each unit offers two bedrooms and 1 full bath. New septic was installed in 2020. Conveniently located with easy access to local amenities, major routes, and nearby conveniences. Whether you're looking to expand your investment portfolio or occupy one unit while renting the other, this property offers flexibility and value.

2312 Craley Rd, Windsor

Listing courtesy of EXP Realty, LLC. Contact: 8885434829
$139,900
Lovely 6+ acre wooded lot on a cul-de-sac close to shopping, schools and yet secluded and rural. Spring fed stream. Includes 2 Parcels Tax ID# 67350001400310000000 & 67350001400320000000.

30-34 Abby Rd, Windsor

Listing courtesy of Keller Williams Keystone Realty. Contact: 7177555599
$79,900
Build your dream home on this stunning lot in Windsor, PA. Selling 2.0 acres of this 3.51 acre lot. There are two options for subdivision depending on where buyer would prefer to access new property. Sellers will consider selling 1 to 2 acres. Electric available. Perc and probe were successfully done on the portion that is not for sale. Sand mound system was NOT required. Survey has been done. The whole property was approved for up to 3 residential lots. Take advantage of this rare opportunity to collaborate on the property lines before the subdivision is done. Plan to subdivide at settlement. New Tax ID issued then. Please do your own due diligence and confirm statements with Windsor Township.

1155 Gebhart Rd Unit #LOT B, Windsor

Listing courtesy of Coldwell Banker Realty. Contact: (717) 757-2717
$416,990
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
$414,990
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
$420,990
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
$165,000
Located along Main St in Windsor is this circa 1940's block building which had been a garage, then a variety store, beauty shop, consignment store etc. This building has 44' x 66' exterior dimensions with access from rear by way of a concrete bridge which flows level in to the ground floor of the building by way of two large doors. Room to park six plus cars in rear. Lower level is concreted with high ceilings and may accommodate up to eight to ten vehicles. East side of main floor has numerous small rooms next to a large open area. West side was a beauty shop for many years and has three large rooms. New roof 2024 on building. Modern oil fired boiler provides heat. Contact Windsor Boro for possible uses. May require flood insurance for financing. Property sold as-is to settle estate.

144 W Main St, Windsor

Listing courtesy of Century 21 Dale Realty Co.. Contact: (717) 244-4574
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