Windsor Real Estate

Welcome to Windsor, Pennsylvania – a charming gem nestled in York County that beautifully blends small-town charm with modern convenience. This picturesque community is known for its friendly atmosphere, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle.

Windsor boasts a rich history, with roots that trace back to the 18th century. The town is characterized by its quaint streets lined with historic homes, offering a glimpse into the past while providing all the comforts of contemporary living. Residents enjoy a close-knit community feel, where neighbors become friends and local events bring everyone together.

Nature enthusiasts will find plenty to love about Windsor, as it is surrounded by scenic landscapes and recreational opportunities. The nearby Susquehanna River invites outdoor activities such as fishing, kayaking, and hiking. Parks and green spaces dot the area, providing perfect spots for picnics, sports, and family gatherings.

Windsor’s location is another of its many advantages. Situated just a short drive from larger cities like York and Lancaster, residents enjoy easy access to shopping, dining, and entertainment options while still relishing the tranquility of suburban life. The local school district is highly regarded, making it a great choice for families looking to provide their children with quality education.

Whether you’re looking to buy your first home, settle down, or invest in a rental property, Windsor offers a variety of real estate options that cater to diverse tastes and budgets. Explore the charm of Windsor, PA, and discover why it’s the perfect place to call home!

Newest Listings in Windsor

$299,900

4 Beds ⋅ 2 Baths ⋅ PAYK2113674 MLS

SPECIAL BUYER INCENTIVE! Qualified buyers may be eligible for 5.99% financing, potentially reducing monthly principal & interest payments by 10%+, OR choose up to $10,000 in seller assistance. Ask agent for details. Welcome home to this inviting 4-bedroom, 2-full-bathroom home nestled in a peaceful neighborhood just a short walk from Windsor Elementary School and only minutes from downtown York, PA! With thoughtful updates, a functional layout, and comfortable living spaces, this home offers the perfect blend of convenience and charm. Step inside to a welcoming living room featuring luxury vinyl plank (LVP) flooring that flows throughout the space. Just off the living room, a hallway leads to a convenient main-level bedroom with plush new carpet and a full bathroom complete with a shower/tub combination, vanity, and new fixtures. The kitchen is sure to impress with its bright white cabinetry, upgraded granite countertops, new appliances, and a refrigerator in like-new condition. The seamless connection between the kitchen and dining area creates a comfortable space for everyday meals and entertaining. Upstairs, you'll find three additional bedrooms all with plush new carpeting and a second full bathroom featuring a shower/tub combination. The third bedroom offers extra space, creating the potential for a spacious primary bedroom retreat or a flexible space to suit your needs. The unfinished basement provides even more storage more. Outside, enjoy the partially fenced backyard, complete with a paver patio that's perfect for relaxing, hosting gatherings, or enjoying the outdoors. With four bedrooms, two full bathrooms, desirable updates, and a convenient location close to schools and downtown amenities, this home is ready for its next owner to make it their own!

2164 Windsor Rd, Windsor

$279,000

3 Beds ⋅ 2 Baths ⋅ PAYK2113738 MLS

This property offers privacy and seclusion on nearly two acres of land. Enjoy morning coffee outside on cover front deck and rear deck with a view. Enjoy quiet undisturbed peaceful evenings watching deer and other wildlife, without traffic noise on this secluded property. The three-bedroom two full bath home with a professionally installed whole house generator adds backup-power capability, and a Generac 10,000 starting/8,000 running-watt portable generator is included. Also has a 1 car garage and storage building, to keep your tools , mowers etc. Plenty of room for your children and pets to play.

22 Brownell Ln, Windsor

$465,000

3 Beds ⋅ 2 Baths ⋅ PAYK2113586 MLS

Absolutely immaculate 2100 sq ft rancher on 1.99 acres adjacent to open farmland back a long private lane. Huge kitchen with center island and all appliances. Very large dining room to accommodate almost any size table. Living room has corner propane fireplace. Three nice size bedrooms with generous closets. First floor laundry open to an oversize two car garage with built in cabinetry and propane heat. Very clean and in move in condition. NOTE: This property was just sub-divided from a larger tract and has not yet been assessed so taxes are unknown! This is a flag lot. The pond is not on this parcel. See associated docs.

850 Gebhart Rd, Windsor

$332,800

3 Beds ⋅ 3 Baths ⋅ PAYK2113310 MLS

Great opportunity to own this two-story home offering three bedrooms, with two and a half baths. Interior features include a spacious kitchen with ample storage and workspace plus a cozy fireplace in the living area. Oversized deck, great for relaxing and entertaining. Put this one on your list to see.

365 Stabley Ln, Windsor

$190,000

3 Beds ⋅ 2 Baths ⋅ PAYK2112990 MLS

Nestled in the charming community of Windsor Boro, this delightful Colonial home, built around 1900, exudes timeless character and warmth. With three spacious bedrooms and two full bathrooms, this residence offers a perfect blend of classic charm and modern comfort, making it an ideal retreat for those seeking a cozy haven. Step inside to discover an interior that invites you to create lasting memories. For the ultimate convenience, there is a full bath and laundry on the main floor. The full basement provides ample storage space or the potential for a personalized workshop. The off-street parking accommodates up to three vehicles, ensuring convenience for you and your guests. The 0.11-acre lot offers a manageable outdoor space, perfect for gardening or enjoying a quiet afternoon in the sun. Imagine sipping your morning coffee on the deep front porch, surrounded by the serene ambiance of this friendly neighborhood. This home is not just a place to live; it's a canvas for your dreams. Whether you envision hosting gatherings in the inviting living spaces or enjoying peaceful evenings in your private sanctuary, this property is ready to welcome you home. With its rich history and solid construction, this Colonial gem is waiting for you to add your personal touch. Don't miss the opportunity to make this charming residence your own and experience the comfort and joy of living in Windsor Boro. Schedule your private tour today!

55 E Main St, Windsor

$205,770

PAYK2112678 MLS

Situated on an approximately 0.25-acre (10,890± SF) site, this distinctive four-unit residential property is improved with two separate buildings containing a total of 13 bedrooms and 4 bathrooms. The property contains approximately 5,811 SF of above-grade building area, plus approximately 2,730 SF of basement/lower-level area, with over 109 feet of frontage on West Main Street. Zoned Village Center, the property is served by public water and sewer, natural gas, electric and cable/internet. The architecturally distinctive circa-1928 front “Mansion” is a two-story brick residence with basement configured as two dwelling units and highlighted by a large wraparound covered porch, turret, multiple gables, tall windows and period architectural detailing. The accessible interior features impressive original character, including substantial wood trim, paneled doors, hardwood flooring, tall ceilings, decorative millwork and a prominent wood staircase and balustrade. A separate 2½-story rear building contains two additional dwelling units with more conventional apartment-style layouts, spacious living areas, kitchens, multiple bedrooms and full bathrooms. The property combines the historic character and architectural presence of the Mansion with the practical income-producing potential of four residential units on a single parcel. Additional improvements and features include porches, walkways, yard/open areas between the buildings, a central boiler providing baseboard heat to all four units, and individual domestic hot-water heaters for each unit. The combination of two separate residential buildings, 13 bedrooms, substantial building area, distinctive historic features and renovation/value-add potential make this an appealing opportunity for residential investors, renovators and owner/users. This property will be offered at auction on Wednesday, October 28, 2026, at 10:00AM. Auction will be conducted at the Four Points Sheraton Hotel, 1650 Toronita Street, York, PA 17402. PUBLIC AUCTION – BID YOUR PRICE! The List Price shown is the property's current tax-assessed value and is used solely to satisfy MLS listing requirements. It is NOT an asking price, opening bid, reserve price, minimum bid, or representation of fair market value. Property will be sold by competitive bidding at Live & Online Public Auction, subject to the published Terms and Conditions of Sale and required governmental approval. Five separate properties will be offered as part of this auction. 22 W Main St, Windsor, PA, Single Family Home. 35 W Main St Windsor, PA, Four Plex. 100 Henrietta St, Red Lion, PA, Single Family Home. 106 S Main St, Yoe, PA, Duplex. 3424-2426 N George St, Emigsville, PA, Duplex.

35 W Main St, Windsor

$96,680

3 Beds ⋅ 1 Baths ⋅ PAYK2112676 MLS

Single-Family Home in quaint Windsor, PA with approximately 37 feet of frontage on W. Main Street. Lap siding, shingle roof with brick exterior basement. Colonial style with forced-air heating, hardwood floors in living and dining room and tiled bathroom. Three bedrooms and one bathroom total. This property will be offered at auction on Wednesday, October 28, 2026, at 10:00AM. Auction will be conducted at the Four Points Sheraton Hotel, 1650 Toronita Street, York, PA 17402. PUBLIC AUCTION – BID YOUR PRICE! The List Price shown is the property's current tax-assessed value and is used solely to satisfy MLS listing requirements. It is NOT an asking price, opening bid, reserve price, minimum bid, or representation of fair market value. Property will be sold by competitive bidding at Live & Online Public Auction, subject to the published Terms and Conditions of Sale and required governmental approval. Five separate properties will be offered as part of this auction. 22 W Main St, Windsor, PA, Single Family Home. 35 W Main St Windsor, PA, Four Plex. 100 Henrietta St, Red Lion, PA, Single Family Home. 106 S Main St, Yoe, PA, Duplex. 3424-2426 N George St, Emigsville, PA, Duplex.

22 W Main St, Windsor

$180,000

3 Beds ⋅ 1 Baths ⋅ PAYK2112508 MLS

This property will be offered at Public Auction on Thursday, 11/19 at 6:00 PM. The listing price is the opening bid only and in no way reflects the final sale price. 10% down due at auction, 2% transfer tax to be paid by the purchaser. Real estate taxes will be prorated. An exceptional real estate opportunity awaits you in York County with this upcoming public auction featuring a single-family home located at 41 West High Street, Windsor, PA 17366. This live public auction will take place on November 19 at 6pm. Bid online or in person the night of the sale. Positioned prominently for buyers looking in the Central Pennsylvania real estate market, this sturdy 1953 property offers incredible potential for first-time home buyers, car enthusiasts, tradespeople, and savvy investors looking for a prime property in a fantastic local neighborhood. This comfortable residence spans 864 square feet of total interior livable area and features 3 bedrooms and 1 bathroom. The home is equipped with central cooling to keep you comfortable during the summer months and features an efficient heating system. A major standout feature of this property is the large oversized 3 car heated detached workshop/garage, providing an incredible dedicated space for vehicle storage, mechanical work, hobbies, or extra business storage.Situated on a 7,632 square foot lot, the property offers a manageable outdoor space while maximizing utility with its impressive detached garage structure. Bidders will enjoy effortless access to the local Windsor and Red Lion area communities, nearby shopping, dining, and major transport routes connecting you seamlessly to York, Lancaster, and the wider Central Pennsylvania region. Do not miss your chance to bid on this unique property with its premium workshop space.

41 W High St, Windsor

$289,000

4 Beds ⋅ 2 Baths ⋅ PAYK2109328 MLS

Step foot into this beautiful, recently remodeled, 4 bedroom, 2 bath home, in Eastern school districts. This property boasts a large, first floor primary suite with a beautifully remodeled primary bathroom, a detached, 2 story garage, perfect for a woodshop or hobby room, new appliances throughout, new windows, new electrical service, and a new large walkout deck and balcony overlooking the back yard and creek. Ship-lap and granite countertops in the kitchen and fresh paint and new flooring throughout. Plenty of space with the finished basement and separate laundry room. Large, unfinished, attic space could be used for storage or another bedroom. Whether its from the 2nd story balcony, main level deck, or the breezeway between home and garage, you'll be sure to appreciate the butterfly garden, the expansive backyard with vegetable gardens, and the stream flowing through it. Don't miss this little slice of paradise. Schedule your showing today!

1883 Craley Rd, Windsor

$429,000

4 Beds ⋅ 4 Baths ⋅ PAYK2111326 MLS

Welcome to 215 Azalea Drive in the beautiful Laurel Vistas neighborhood of Windsor, PA — where space, comfort, and luxury come together seamlessly. Over 4,000 finished sq. ft - you have to see it in person to experience how spacious it is! BONUS - buy with confidence! Recent home/property & termite inspections done with no major issues! This stunning home offers 4 spacious bedrooms, 3.5 bathrooms, and thoughtfully designed living areas perfect for both everyday life and entertaining. The gourmet kitchen is the heart of the home, featuring a large center island, abundant cabinetry, and plenty of space to gather. Additional rooms on the main floor include the beautiful family room, just off of the kitchen, featuring a gas fireplace and abundant natural lighting, as well as a formal sitting room or additional family room, plus an office! The fully finished walk-out basement expands your living space even further with a private movie theater, two versatile flex rooms ideal for a home office, gym, or guest space, and a full bathroom — creating the perfect setup for multigenerational living or hosting. Step outside to relax in your hot tub tucked under the deck for year-round enjoyment, offering privacy and comfort in your own backyard retreat. The Laurel Vistas community offers a walking trail & park for the kiddos, too! This home offers the space you need and the lifestyle you’ve been waiting for! Schedule your showing to see if it's the perfect home for you! Contingent upon seller closing on new home. Buyer to verify square footage. Seller reserves the right to accept offer at any time!

215 Azalea Dr, Windsor

$89,999

3 Beds ⋅ 2 Baths ⋅ PAYK2110492 MLS

Welcome to Shalako MHP. This nicely maintained Champion has 3 bedrooms and 2 bathrooms with over 1300 square feet! The property feels very spacious roomy and bright with the open floor plan. You will see there is tons of storage throughout the kitchen and bedrooms. All appliances, dishwasher, refrigerator, stove, washer and dryer are included in the sale. All you need to do is move in and enjoy this beautifully maintained home with very a spacious deck outside. All buyers must be park approved and adhere to the rules and pet regulations. Current lot rent is $530 a month and includes sewer and trash. Make sure you come and see all this beautifully maintained property has to offer!

56 Cherokee Dr, Windsor

$995,000

7 Beds ⋅ 7 Baths ⋅ PAYK2107748 MLS

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

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INFORMATION DEEMED RELIABLE, BUT NOT GUARANTEED. Listings courtesy of WEST PENN MULTILIST, INC.

Listings courtesy of Pike Wayne Association of Realtors as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Windsor Real Estate

Newest Listings in Windsor

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