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93 Belaski Rd, Windsor
$565,000
3 Beds ⋅ 3 Baths ⋅ 5090593 MLS
Exceptional Cape in Historic Windsor: Pool, Views & In-Law Suite Welcome home to this impeccably maintained Cape-style residence, where timeless charm meets modern elegance. Set against breathtaking protected views of Mt. Ascutney, this stunning 3-bedroom, 3-bath property is a rare find in one of Vermont's most storied communities. The heart of the home is a beautifully appointed, ultra-modern kitchen featuring rich maple cabinetry and a striking granite-topped island, perfect for both everyday living and entertaining. Gleaming oak hardwood floors flow seamlessly through the kitchen, formal dining room, primary and second bedrooms, and the spacious den/office. The sun-filled living room commands attention with its soaring cathedral ceiling and cozy propane fireplace, creating an inviting space for all seasons. The walkout basement offers exceptional versatility with a generous family room, utility room, 3/4 bath, and abundant storage ready to adapt to your lifestyle. Step outside and be captivated by professionally curated flower gardens and lush, artful landscaping that elevates the entire property to resort-like status. Cool off and unwind at the sparkling in-ground salt water pool with 4 filter system, complete with a private cabana. A standout bonus: a partially finished two-room apartment with a bedroom balcony sits above the detached two-car garage ideal as an accessory dwelling. All of this is within easy walking distance to schools, churches, and recreation areas. Historic Windsor itself offers an array of amenities including acclaimed restaurants, an Amtrak station, a country club, and a local high school, with effortless access to the Upper Valley and Claremont. Commuters will appreciate the quick drive to I-91 Exits 8 and 9. This is a home that truly has it all-you will not be disappointed.

93 Belaski Rd, Windsor

64 State St, Windsor
$425,000
5079828 MLS
Windsor’s income-producing potential meets turnkey ease in this updated five-unit multifamily, perfectly positioned in Vermont’s historic “Birthplace of Vermont” along the Connecticut River and at the base of Mount Ascutney. With four one-bedroom units and one two-bedroom, the property offers a flexible mix of traditional tenancy and high-demand furnished rentals in a market supported by year-round outdoor recreation, nearby employment, and a vibrant local downtown. Currently, one unit is leased and the remaining apartments are operating as furnished short-term and mid-term rentals through platforms like Airbnb and Furnished Finder, giving new owners an immediate, plug-and-play investment with established rental use and the option to adjust strategy over time. Most furnishings are included, allowing you to step into an already curated, move-in-ready building—ideal for relocating professionals, travel nurses, or weekend adventurers who come for Windsor’s trails, lakes, and four-season recreation.

64 State St, Windsor

6 Pine St, Windsor
$418,000
3 Beds ⋅ 2 Baths ⋅ 5100530 MLS
Shown by Appointment Only! Single Family or Duplex! Live in it as a spacious 3 bedroom, 2 bath single family home, or take advantage of the current setup as two separate 1 bedroom units, each with its own utilities. That kind of flexibility is hard to find, whether you're thinking multigenerational living, rental income, or just extra breathing room. And then there's the view. Gorgeous lake views greet you from inside this home, the kind that make you stop and appreciate where you live every single day. This is a true Victorian, full of the character and detail that newer homes just can't replicate. The full basement includes a bonus room, perfect for a home office, workshop, or extra storage. A detached garage adds even more convenience for parking and yard equipment. Tucked into charming Windsor, you're close to 91 and just minutes from local shops and restaurants downtown. Homes with this much versatility and this kind of view don't come along often.

6 Pine St, Windsor

273 Rte 5 N, Windsor
$399,000
4 Beds ⋅ 3 Baths ⋅ 5080622 MLS
Motivated Seller - Price Improved! Own a remarkable piece of Vermont history in the heart of Windsor. Built circa 1790, this beautifully preserved brick-and-frame Colonial blends timeless New England character with the modern updates today's buyers appreciate. Rich in craftsmanship and architectural detail, this one-of-a-kind home offers the perfect balance of historic charm, everyday comfort, and exciting future potential. Inside, you'll find wide-plank hardwood and softwood floors, abundant natural light from updated windows, fresh interior paint, and thoughtfully updated electrical and heating systems. A classic standing seam roof enhances both the home's historic appeal and long-term durability. At the heart of the home is a truly unforgettable kitchen, where carefully repurposed materials create a warm, inviting space full of personality and Vermont character. The attached one-car garage features a dedicated workshop and storage area, while the expansive attic—accessible from both levels—offers incredible flexibility for a studio, workshop, additional storage, or future finished living space. Located just moments from Artisans Park, downtown Windsor, and Interstate 91 (Exit 9), this property provides convenient access to the Upper Valley, DHMC, Dartmouth College, and nearby NH communities. Whether you're commuting, working remotely, or looking for a centrally located Vermont home, you'll appreciate the convenience without sacrificing small-town charm. With commercial zoning potential, this property presents a rare opportunity for entrepreneurs, professionals, investors, or anyone seeking a live-work lifestyle. Imagine a boutique office, gallery, creative studio, or small business operating from one of Windsor's historic homes while enjoying all the comforts of a private residence. Whether you're searching for a historic Vermont home, a unique investment property, or a place where your home and business can thrive, stop scrolling and come see.

273 Rte 5 N, Windsor

143 Ascutney St, Windsor
$354,000
2 Beds ⋅ 2 Baths ⋅ 5103773 MLS
Welcome to 143 Ascutney Street, a well-maintained 2-bedroom, 1.5-bath home offering 1,092 square feet of comfortable living space. Thoughtfully cared for over the years, this home features a functional layout with bright living areas, an eat-in kitchen, and the convenience of a first-floor half bath. Outside, enjoy a manageable yard that's easy to maintain while still providing space for gardening, pets, or relaxing. A detached garage offers additional storage or workshop potential. Conveniently located just minutes from downtown Windsor, local restaurants, shopping, and recreation, this property is also within walking distance of Kennedy Pond, making it easy to enjoy fishing, kayaking, or an evening stroll. Whether you're searching for your first home, looking to downsize,this move-in ready property is one you won't want to miss.

143 Ascutney St, Windsor

5 Clough Ave, Windsor
$339,000
3 Beds ⋅ 1 Baths ⋅ 5104866 MLS
Move-in ready 3-bedroom, 1-bath bungalow, fully renovated and waiting for you! Too many renovations to list (needed a separate list)!! Even with the extensive renovations, the original charm was thoughtfully maintained: 1920s woodwork, pocket doors, hardwood floors, etc.! Bright, updated interior features fresh flooring, a refreshed kitchen and bath. Three cozy bedrooms offer flexible space for a growing family, guest room, or home office. Low-maintenance yard is perfect for first-time owners. Enjoy the covered porch and three season porch with original casement windows! Minutes to downtown Windsor's shops and restaurants, the Connecticut River, and easy access to Rt. 5 and I-91. Skip the fixer-upper! This one's done! A perfect opportunity to stop renting and start building equity.

5 Clough Ave, Windsor

74 Union St, Windsor
$319,000
4 Beds ⋅ 2 Baths ⋅ 5082070 MLS
Discover space, flexibility, and everyday convenience in this charming 4-bedroom, 2-bath home in the heart of Windsor. Thoughtfully designed with a spacious floor plan, the main living area features warm hardwood floors and abundant natural light, creating a bright and welcoming atmosphere throughout. The formal dining area flows seamlessly into the living room, perfect for both everyday living and entertaining. A main-level bedroom and full bath, along with convenient first-floor laundry, offer ideal single-level living options or guest accommodations. Upstairs, you’ll find three generously sized bedrooms, providing plenty of space for family, guests, or a home office setup. Set on a quarter-acre lot, the property offers ample parking and a detached one-car garage, perfect for storage, hobbies, or a workshop. Centrally located and easy access to town, grab your morning coffee just a short walk away or head to the nearby pond for a relaxing swim. A wonderful opportunity to own a well-located home with space, charm, and versatility in Windsor!

74 Union St, Windsor

319 Back Mountain Rd, Windsor
$307,000
2 Beds ⋅ 1 Baths ⋅ 5106677 MLS
Welcome to 319 Back Mountain Road in Windsor, Vermont, a comfortable 2-bedroom ranch situated on approximately one acre in a peaceful country setting. The home features an updated kitchen and a spacious living and dining area with plenty of natural light, creating a warm and inviting space for everyday living and entertaining. A metal roof and updated heating system add to the home's practicality and ease of ownership. A one-car garage provides convenient parking along with additional storage space. Outside, the level yard with mature trees offers plenty of room for gardening, recreation, or simply enjoying the Vermont surroundings. Located along the eastern slopes of Mount Ascutney, with its hiking trails and recreational activities. This property offers a wonderful balance of rural living and convenience, with easy access to downtown Windsor, I-91, and the area's abundant recreational opportunities. Whether you're looking for a primary residence, Vermont getaway, or a home to make your own, 319 Back Mountain Road offers an appealing opportunity in a desirable Upper Valley location.

319 Back Mountain Rd, Windsor

2799 County Rd, Windsor
$304,000
2 Beds ⋅ 1 Baths ⋅ 5110782 MLS
Nestled on 6.62 private acres in the heart of Windsor, Vermont, this striking contemporary home offers a unique blend of rustic charm and modern updates. Built in 1983, the home features 17’ ceilings, creating an airy and inviting atmosphere. With 2 bedrooms and 1 bathroom, it’s a perfect fit for those seeking a peaceful retreat or efficient year-round living. Thoughtful updates include a newer furnace, roof, and windows that provide comfort, energy efficiency, and peace of mind. The surrounding land offers a mix of woods and open space, ideal for gardening, recreation, or simply enjoying the quiet beauty of nature. Located just minutes from Windsor village amenities, Mt. Ascutney trails, and the Connecticut River, this property is both a private escape and a convenient home base.

2799 County Rd, Windsor

15 Rt 5 N, Windsor
$302,000
2 Beds ⋅ 1 Baths ⋅ 5103442 MLS
Completely rebuilt in 2014 (except for the storage room) and set on 2.51 acres spanning both Windsor and Hartland, this 2-bedroom, 1-bath ranch offers comfortable one-level living with plenty of potential. The open-concept living, dining, and kitchen area creates a functional layout, while the attached direct-entry garage and unfinished attached space provide excellent storage or future expansion possibilities. Outside, the property features a circular driveway, a partially level yard, a small, fenced area off the garage, a larger split-rail fenced paddock with a run-in, a storage shed, and a dedicated chicken coop area, offering flexibility for gardening, hobbies, small animals, or outdoor enjoyment. Conveniently located with easy access to area amenities, this property presents a wonderful opportunity to make it your own. Easy access to I-91, 23 min to DHMC, 15 min from West Lebanon, 22 min to Woodstock, 40 min to Okemo. Open house Saturday, August 8th, 10am-12pm

15 Rt 5 N, Windsor

3 Cherry St, Windsor
$259,000
3 Beds ⋅ 1 Baths ⋅ 5079791 MLS
Classic Vermont character meets everyday convenience in this sweet in-town New Englander. Set in the heart of Windsor, this three-bedroom, one-bath home puts you steps from local shops, dining, and all the charm of one of Vermont's most historic villages. Inside, a fireplace anchors the living space, offering the kind of warmth that makes a New England winter something to look forward to. The thoughtful layout makes the most of every square foot, with comfortable bedrooms and a functional flow throughout. Outside, a detached garage provides coveted covered parking and additional storage — a true Vermont essential. The in-town location means walkability without sacrificing the quiet, neighborly feel that defines life in the Upper Valley. Whether you're a first-time buyer, looking to downsize, or searching for a Vermont retreat, this is a home that delivers on all the right things: location, character, and comfort.

3 Cherry St, Windsor

84 Cubb Ct, Windsor
$98,995
3 Beds ⋅ 2 Baths ⋅ 5050700 MLS
Welcome to 84 Cubb Court, , Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-66 model manufactured home offers 3 bedrooms, 2 bathrooms, and 880 sq. ft. (13'4"x66) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient construction, modern appliances, and low-maintenance materials, making it perfect for easy living. Located in a peaceful and well-maintained community, this home is ideal for those looking for a move-in-ready option in a convenient location. Don’t miss out on this opportunity! Contact us today for more details or to schedule a tour. The interior is approximately 90% complete. Interior showings will be available beginning August 15th. This property participates in the MHIP and is open exclusively to current residents of Vermont. The park owner is offering up $4,000 in closing costs and a waiver of the first 2 months of lot rent.

84 Cubb Ct, Windsor

517 Back Mountain Rd, Windsor
$96,232
2 Beds ⋅ 2 Baths ⋅ 5050699 MLS
Welcome to 517 Back Mountain Rd., Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient construction, modern appliances, and low-maintenance materials, making it perfect for easy living. Located in a peaceful and well-maintained community, this home is ideal for those looking for a move-in-ready option in a convenient location. Don’t miss out on this opportunity! Contact us today for more details or to schedule a tour. The interior is 100% complete. Home is available for showing. This property participates in the Mobile Home Infill Program (MHIP) and is open to anyone who works or lives in Vermont.

517 Back Mountain Rd, Windsor

11 Cubb Ct, Windsor
$96,232
2 Beds ⋅ 2 Baths ⋅ 5050703 MLS
Welcome to 11 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient construction, modern appliances, and low-maintenance materials, making it perfect for easy living. Located in a peaceful and well-maintained community, this home is ideal for those looking for a move-in-ready option in a convenient location. Don’t miss out on this opportunity! Contact us today for more details or to schedule a tour. The interior is 100% complete. Home is available for showing. This property participates in the Mobile Home Infill Program (MHIP) and is open to anyone who works or lives in Vermont. The park owner is offering up $4,000 in closing costs and a waiver of the first 2 months of lot rent.

11 Cubb Ct, Windsor

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