Windsor Homes under $500,000

Windsor Homes under $500,000

Welcome to Windsor, Pennsylvania—a charming small town nestled in the heart of York County. Known for its picturesque landscapes and friendly community, Windsor offers a delightful blend of rural tranquility and modern convenience. With its rich history and close-knit atmosphere, it’s no wonder that families and individuals alike are seeking to call this lovely town home.

Windsor boasts a variety of amenities that cater to a diverse lifestyle. Enjoy leisurely afternoons at local parks, explore the scenic beauty of nearby hiking trails, or indulge in the delightful offerings of local eateries and shops. The town is also conveniently located near major highways, making commuting to larger cities like York and Lancaster a breeze.

For those looking to invest in their dream home without breaking the bank, Windsor presents an enticing real estate market with homes available for under $500,000. Whether you’re a first-time buyer or looking to downsize, you’ll find a range of options that suit your needs. From charming single-family homes with spacious yards to modern townhouses with contemporary finishes, there’s something for everyone here.

With a strong sense of community and a welcoming atmosphere, Windsor is not just a place to live; it’s a place to thrive. Discover the perfect home in this idyllic town, where your dreams of comfortable living can come true—all at an affordable price. Come explore Windsor, PA, and see why so many are choosing to make this hidden gem their home!

Newest Windsor Homes under $500,000

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:

1883 Craley Rd, Windsor
$295,000
4 Beds ⋅ 2 Baths
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

Listing courtesy of RE/MAX SmartHub Realty. Contact:

40 2nd St, Windsor
$274,900
4 Beds ⋅ 1 Baths
Charming Home in quaint town of Windsor is just what you're looking for: spacious, open rooms with plenty of natural light, easy care laminate floors, and a kitchen you will love. Unwind in the cozy family room in the basement or spend summer days in the fenced yard. New HVAC 2025. There's so much to enjoy here! Do not miss this one!

40 2nd St, Windsor

Listing courtesy of Iron Valley Real Estate of Central PA. Contact:

215 Azalea Dr, Windsor
$429,000
4 Beds ⋅ 4 Baths
Back on market - no fault of sellers! 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 finding & securing their next home. Buyer to verify square footage. Seller reserves the right to accept offer at any time!

215 Azalea Dr, Windsor

Listing courtesy of The Exchange Real Estate Company LLC. 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:

325 Thomas Armor Dr, Windsor
$449,990
4 Beds ⋅ 3 Baths
Rare opportunity in the highly sought-after Chatham Creek community! Lovingly maintained by its original owner, this beautiful 4-bedroom home offers exceptional curb appeal, mature landscaping, a 2-car garage, and a fully fenced backyard with a spacious deck and walk-out patio. Major updates include a new roof (2026), new HVAC (2024), and replacement windows, providing years of worry-free ownership. Inside, you'll find a formal dining room, a spacious kitchen with a center island open to the family room, and a heated and air-conditioned four-season sunroom perfect for year-round enjoyment. Upstairs features four generously sized bedrooms, including a private primary suite, plus convenient upper-level laundry. The finished walk-out lower level offers a large recreation room, bonus room, and plenty of storage. 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:

307 Boxwood Dr, Windsor
$404,990
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:

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