Windsor Homes under $250,000

Windsor Homes under $250,000

Welcome to Windsor, Pennsylvania – a charming town nestled in the heart of York County. Known for its friendly community and picturesque landscapes, Windsor offers a delightful blend of small-town charm and modern convenience. With its rich history and a variety of local amenities, this town is an ideal place for families, retirees, and first-time homebuyers alike.

Windsor boasts a range of homes under $250,000, making it an attractive option for those looking to invest in real estate without breaking the bank. Whether you’re searching for a cozy bungalow, a well-maintained ranch-style home, or a quaint cottage, Windsor has something to suit every taste and budget. These affordable properties often feature spacious yards, inviting interiors, and easy access to local parks and recreational activities, providing the perfect backdrop for creating lasting memories.

The community spirit in Windsor is palpable, with friendly neighbors and a strong sense of belonging. Residents enjoy the convenience of nearby shopping, dining, and entertainment options, while also benefiting from the serene countryside that surrounds the area. Families will appreciate the quality schools and safe neighborhoods, making Windsor an excellent choice for raising children.

With its affordable housing market, welcoming atmosphere, and beautiful surroundings, Windsor, PA, is more than just a place to live – it’s a place to call home. Discover the charm of Windsor and explore the wonderful homes available under $250,000, where your dream of homeownership can become a reality!

Newest Windsor Homes under $250,000

55 E Main St, Windsor
$190,000
3 Beds ⋅ 2 Baths
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

Listing courtesy of Coldwell Banker Realty. Contact:

35 W Main St, Windsor
$205,770
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. This property will be offered in a multi-parcel auction, giving buyers the flexibility to purchase Lot 1, Lot 2, Lot 3, Lot 4, Lot 5, any combination of Lots, or all of the properties. Lot 1: 22 W Main St, Windsor, PA, Single Family Home. Lot 2: 35 W Main St Windsor, PA, Four Plex. Lot 3: 100 Henrietta St, Red Lion, PA, Single Family Home. Lot 4: 106 S Main St, Yoe, PA, Duplex. Lot 5: 3424-2426 N George St, Emigsville, PA, Duplex.

35 W Main St, Windsor

Listing courtesy of Hurley Real Estate & Auctions. Contact:

22 W Main St, Windsor
$96,680
3 Beds ⋅ 1 Baths
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. This property will be offered in a multi-parcel auction, giving buyers the flexibility to purchase Lot 1, Lot 2, Lot 3, Lot 4, Lot 5, any combination of Lots, or all of the properties. Lot 1: 22 W Main St, Windsor, PA, Single Family Home. Lot 2: 35 W Main St Windsor, PA, Four Plex. Lot 3: 100 Henrietta St, Red Lion, PA, Single Family Home. Lot 4: 106 S Main St, Yoe, PA, Duplex. Lot 5: 3424-2426 N George St, Emigsville, PA, Duplex.

22 W Main St, Windsor

Listing courtesy of Hurley Real Estate & Auctions. Contact:

41 W High St, Windsor
$180,000
3 Beds ⋅ 1 Baths
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

Listing courtesy of Cavalry Realty LLC. Contact:

128 W Gay St, Windsor
$195,000
2 Beds ⋅ 1 Baths
Welcome to this charming 2-bedroom, 1-bath detached home in Windsor, PA! This home offers a comfortable layout with several recent updates, making it move-in ready for its next owner. The windows have been replaced, providing a fresh, updated look throughout the home. The kitchen features freshly painted walls and new flooring, giving the space a clean and refreshed feel. A recently added laundry room provides added convenience and functionality. With its detached-home layout, practical updates, and convenient Windsor location, this property is a great opportunity for a first-time buyer, downsizer, or investor. Come take a look and see what this home has to offer!

128 W Gay St, Windsor

Listing courtesy of Coldwell Banker Realty. Contact:

56 Cherokee Dr, Windsor
$99,999
3 Beds ⋅ 2 Baths
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

Listing courtesy of Iron Valley Real Estate of Lancaster. Contact:

100 Fawn Circle Dr, Windsor
$155,000
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:

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