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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.

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

$530,000

This lovely home has plenty of sunny light filled space. Home features a large kitchen/eating area, with a formal-sized dining room, and spacious living room. First floor primary bedroom, and three more bedrooms upstairs. Main level laundry and lots of storage space in the basement.Two car garage with electric car charger.Recent improvements include paved driveway,mini splits and lifetime guttering. Located in a quiet Vermont neighborhood with convenient access to I 91 and I 89 also close enough to shopping needs in West Lebanon, lots of your boxes are checked. Easy commute to Ski areas, local hospitals or Dartmouth College.

4 Beds ⋅ 3 Baths ⋅ 5072087 MLS

This lovely home has plenty of sunny light filled space. Home features a large kitchen/eating area, with a formal-sized dining room, and spacious living room. First floor primary bedroom, and three more bedrooms upstairs. Main level laundry and lots of storage space in the basement.Two car garage with electric car charger.Recent improvements include paved driveway,mini splits and lifetime guttering. Located in a quiet Vermont neighborhood with convenient access to I 91 and I 89 also close enough to shopping needs in West Lebanon, lots of your boxes are checked. Easy commute to Ski areas, local hospitals or Dartmouth College.

223 Taylor Dr, Windsor

$500,000

Enjoy privacy and lovely views from this well executed contemporary home overlooking copious gardens and mature plantings to a spectacular pond with an arched footbridge (spotlights highlight the bridge after dark) to access your own little island. Beautiful updates throughout the home include new maintenance-free manufactured cedar-tone shingles on the entire house and workshop shed. The kitchen features custom oak cabinetry, granite counters and updated appliances. The living room has sweeping cathedral ceilings, hardwood walls, oversized windows, and a wood burning fireplace. There is a primary Bedroom ensuite, and a guest powder room off of the foyer mudroom complete with slate floors. Step out to a private iron balcony with Trex decking and spiral stairway accessing a stone terrace below complete with fire pit, water feature and screened gazebo. Upper level has a spacious loft area, and a second bedroom. The walk out lower level includes a third bedroom, studio/rec room (could accommodate overflow guests) and laundry, plus a wine or root cellar. Oversized two car garage with plenty of storage above. Located just minutes from I 91. Easy access to Upper Valley, DHMC, Woodstock, skiing and all recreation.

3 Beds ⋅ 3 Baths ⋅ 5046799 MLS

Enjoy privacy and lovely views from this well executed contemporary home overlooking copious gardens and mature plantings to a spectacular pond with an arched footbridge (spotlights highlight the bridge after dark) to access your own little island. Beautiful updates throughout the home include new maintenance-free manufactured cedar-tone shingles on the entire house and workshop shed. The kitchen features custom oak cabinetry, granite counters and updated appliances. The living room has sweeping cathedral ceilings, hardwood walls, oversized windows, and a wood burning fireplace. There is a primary Bedroom ensuite, and a guest powder room off of the foyer mudroom complete with slate floors. Step out to a private iron balcony with Trex decking and spiral stairway accessing a stone terrace below complete with fire pit, water feature and screened gazebo. Upper level has a spacious loft area, and a second bedroom. The walk out lower level includes a third bedroom, studio/rec room (could accommodate overflow guests) and laundry, plus a wine or root cellar. Oversized two car garage with plenty of storage above. Located just minutes from I 91. Easy access to Upper Valley, DHMC, Woodstock, skiing and all recreation.

3361 County Rd, Windsor

$426,000

Conveniently located from Interstate 91 and Route 5 in the Taylor Drive neighborhood sits a tidy cape home ready for its new owners. Many choices for bedrooms including a downstairs primary suite currently used as a den and 3 bedrooms upstairs for use as such or perhaps office and music space. The kitchen has been thoughtfully updated and the open concept between kitchen, living and dining invites entertainment opportunities and gatherings. The basement provides additional living space opportunity with high ceilings and no water issues. Great overflow play space for the littles or teens. The lot consists of an upper area where the home, 1 car finished garage and fenced in area are placed The lower area, currently wooded, would make for excellent play or camping spot when you need to get away but can't. Is this your place to call home? Come see! Individual appointment requests honored or come to the open house on Saturday, December 6 from 10 - 12pm.

4 Beds ⋅ 3 Baths ⋅ 5071233 MLS

Conveniently located from Interstate 91 and Route 5 in the Taylor Drive neighborhood sits a tidy cape home ready for its new owners. Many choices for bedrooms including a downstairs primary suite currently used as a den and 3 bedrooms upstairs for use as such or perhaps office and music space. The kitchen has been thoughtfully updated and the open concept between kitchen, living and dining invites entertainment opportunities and gatherings. The basement provides additional living space opportunity with high ceilings and no water issues. Great overflow play space for the littles or teens. The lot consists of an upper area where the home, 1 car finished garage and fenced in area are placed The lower area, currently wooded, would make for excellent play or camping spot when you need to get away but can't. Is this your place to call home? Come see! Individual appointment requests honored or come to the open house on Saturday, December 6 from 10 - 12pm.

473 Taylor Dr, Windsor

$425,000

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.

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

$418,000

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.

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

$400,000

OWNERS SAY SELL before Winter. Check out the new PRICE! Nestled on 1.34 picturesque acres in historic Windsor, this classic 4-bedroom Colonial blends timeless charm with comfortable living. Set back from the road, the home offers privacy and space to enjoy Vermont’s natural beauty while being just minutes from town amenities, schools, and I-91. Inside, you'll find a traditional floor plan with spacious living and dining areas, a well-appointed kitchen, and plenty of natural light throughout. With this flexible layout, you can configure bedrooms on 1 or both levels. The basement is dry, and has ample finished space for an extra playroom or family room, including 1/2 bathroom. The expansive yard is ideal for gardening, play, or simply taking in the peaceful surroundings. With room to grow, work from home, or create the lifestyle you've been dreaming of, this Windsor gem is ready to welcome its next chapter.

4 Beds ⋅ 3 Baths ⋅ 5054676 MLS

OWNERS SAY SELL before Winter. Check out the new PRICE! Nestled on 1.34 picturesque acres in historic Windsor, this classic 4-bedroom Colonial blends timeless charm with comfortable living. Set back from the road, the home offers privacy and space to enjoy Vermont’s natural beauty while being just minutes from town amenities, schools, and I-91. Inside, you'll find a traditional floor plan with spacious living and dining areas, a well-appointed kitchen, and plenty of natural light throughout. With this flexible layout, you can configure bedrooms on 1 or both levels. The basement is dry, and has ample finished space for an extra playroom or family room, including 1/2 bathroom. The expansive yard is ideal for gardening, play, or simply taking in the peaceful surroundings. With room to grow, work from home, or create the lifestyle you've been dreaming of, this Windsor gem is ready to welcome its next chapter.

96 Dairy Ln, Windsor

$399,000

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.

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

$395,900

Welcome to this well-kept ranch home in the heart of Windsor, VT. Offering 3 bedrooms and 1.5 baths, this home provides a comfortable layout, perfect for everyday living. The spacious living room is bright and inviting, opening easily into the eat-in kitchen where there’s plenty of room for family and friends to gather. This is what a true turnkey home looks like; new roof, windows, siding, decking, electrical, flooring, whole house generator, and beautiful new baths and kitchen complete with granite countertops. Boiler was replaced just before these owners purchased in 2016. Even the basement has potential to be fully finished if you need more living space or to have a workshop or home studio. Enjoy the convenience of a 2-car garage and a level lot that’s ideal for gardening, pets, or outdoor entertaining. Single-level living makes this property easy to maintain, while the location offers quick access to Windsor’s shops, restaurants, and local amenities. Whether you’re looking for your first home, a place to downsize, or a Vermont getaway, this ranch is full of potential and ready for its next chapter.

3 Beds ⋅ 2 Baths ⋅ 5062273 MLS

Welcome to this well-kept ranch home in the heart of Windsor, VT. Offering 3 bedrooms and 1.5 baths, this home provides a comfortable layout, perfect for everyday living. The spacious living room is bright and inviting, opening easily into the eat-in kitchen where there’s plenty of room for family and friends to gather. This is what a true turnkey home looks like; new roof, windows, siding, decking, electrical, flooring, whole house generator, and beautiful new baths and kitchen complete with granite countertops. Boiler was replaced just before these owners purchased in 2016. Even the basement has potential to be fully finished if you need more living space or to have a workshop or home studio. Enjoy the convenience of a 2-car garage and a level lot that’s ideal for gardening, pets, or outdoor entertaining. Single-level living makes this property easy to maintain, while the location offers quick access to Windsor’s shops, restaurants, and local amenities. Whether you’re looking for your first home, a place to downsize, or a Vermont getaway, this ranch is full of potential and ready for its next chapter.

58 Morningside Dr, Windsor

$354,000

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.

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

$339,000

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.

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

$319,000

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!

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

$315,000

Open House 10/4/1025 11Am-1Pm. This lovingly maintained Cape-style home, perfectly set on a 0.18-acre corner lot. With 2 bedrooms, 1.5 bathrooms, a welcoming covered porch, and spacious basement, this home blends classic Vermont character with everyday comfort. The home has a standing seam roof and a brand new boiler, with timeless features such as built-in cabinetry, hardwood floors, and ample closet space. Bonus rooms on each floor add to its charm and flexibility. The two-car garage with attic storage offers plenty of room for vehicles, tools, and more. Inside, the traditional layout provides a functional, warm, and inviting flow but leaves room for adding your own personal touches. Enjoy the convenience of being within walking distance to local amenities like Kennedy’s Pond and the Windsor Fairgrounds all while savoring the peace and space of your corner lot, ideal for gardening, play, or quiet relaxation.

2 Beds ⋅ 2 Baths ⋅ 5063490 MLS

Open House 10/4/1025 11Am-1Pm. This lovingly maintained Cape-style home, perfectly set on a 0.18-acre corner lot. With 2 bedrooms, 1.5 bathrooms, a welcoming covered porch, and spacious basement, this home blends classic Vermont character with everyday comfort. The home has a standing seam roof and a brand new boiler, with timeless features such as built-in cabinetry, hardwood floors, and ample closet space. Bonus rooms on each floor add to its charm and flexibility. The two-car garage with attic storage offers plenty of room for vehicles, tools, and more. Inside, the traditional layout provides a functional, warm, and inviting flow but leaves room for adding your own personal touches. Enjoy the convenience of being within walking distance to local amenities like Kennedy’s Pond and the Windsor Fairgrounds all while savoring the peace and space of your corner lot, ideal for gardening, play, or quiet relaxation.

1 Dorrance St, Windsor

$312,000

Offering 3 bedrooms and 1 full bath. Bright living spaces flow easily to a deck, plus a versatile enclosed porch for year-round enjoyment. Set in a convenient Windsor location close to shops, schools, and the scenic Connecticut River Valley.

3 Beds ⋅ 1 Baths ⋅ 5110505 MLS

Offering 3 bedrooms and 1 full bath. Bright living spaces flow easily to a deck, plus a versatile enclosed porch for year-round enjoyment. Set in a convenient Windsor location close to shops, schools, and the scenic Connecticut River Valley.

173 Orchard Ln, Windsor

$304,000

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.

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

$302,000

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

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

$273,000

3 Beds ⋅ 1 Baths ⋅ 5104328 MLS

61 Kennedy Dr, Windsor

$271,000

Step into the timeless appeal of this beautifully maintained 1920s home, ideally situated in the heart of Olde Windsor. The inviting front patio welcomes you into a charming entryway that opens to a cozy living room, perfect for relaxing evenings or entertaining guests. Gleaming hardwood floors flow through the entry and dining areas, adding warmth and character throughout. The spacious dining room connects seamlessly to a well-appointed kitchen, offering both functionality and charm. A conveniently located half bath on the main floor includes an integrated washer and dryer for added ease. From the dining area, step out to the back patio and take in serene views of the expansive backyard, ideal for outdoor gatherings, gardening, or summer barbecues. Upstairs, you’ll find three comfortable bedrooms and a full bath, providing plenty of space for family or guests. Perfectly positioned between Mill Pond, Lake Runnenede, and the Connecticut River, this home offers a unique blend of tranquility and convenience. Enjoy a leisurely 15-minute walk to Main Street, where local shops and restaurants create a vibrant small-town atmosphere. Combining vintage charm with thoughtful updates, this Olde Windsor gem is ready to welcome its next chapter.

3 Beds ⋅ 2 Baths ⋅ 5064694 MLS

Step into the timeless appeal of this beautifully maintained 1920s home, ideally situated in the heart of Olde Windsor. The inviting front patio welcomes you into a charming entryway that opens to a cozy living room, perfect for relaxing evenings or entertaining guests. Gleaming hardwood floors flow through the entry and dining areas, adding warmth and character throughout. The spacious dining room connects seamlessly to a well-appointed kitchen, offering both functionality and charm. A conveniently located half bath on the main floor includes an integrated washer and dryer for added ease. From the dining area, step out to the back patio and take in serene views of the expansive backyard, ideal for outdoor gatherings, gardening, or summer barbecues. Upstairs, you’ll find three comfortable bedrooms and a full bath, providing plenty of space for family or guests. Perfectly positioned between Mill Pond, Lake Runnenede, and the Connecticut River, this home offers a unique blend of tranquility and convenience. Enjoy a leisurely 15-minute walk to Main Street, where local shops and restaurants create a vibrant small-town atmosphere. Combining vintage charm with thoughtful updates, this Olde Windsor gem is ready to welcome its next chapter.

10 Mckenzie Dr, Windsor

$259,000

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 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

$256,500

Located near the end of a dead end street and also near Mill Pond, this home is convenient to where you need to go! There's a nice covered front porch as well as a detached 1 car garage. The interior features 3 bedrooms, formal dining room, a nicely sized living room and character and charm throughout. This property is definitely worth checking out!

3 Beds ⋅ 1 Baths ⋅ 5062472 MLS

Located near the end of a dead end street and also near Mill Pond, this home is convenient to where you need to go! There's a nice covered front porch as well as a detached 1 car garage. The interior features 3 bedrooms, formal dining room, a nicely sized living room and character and charm throughout. This property is definitely worth checking out!

21 Bavier Ave, Windsor

$235,000

Looking for an affordable way into homeownership? This ranch features 3 bedrooms and 1 full bath, this single-level home is perfect for first-time buyers or downsizers. Cozy up in the living room next to the fireplace or relax on the covered porch with your morning coffee. The easy, one-floor layout means low-maintenance living at a price that's hard to beat. Located just minutes from downtown Windsor's shops, restaurants, K-12 school, and Kennedys Pond, this home offers small-town charm with everyday convenience. Priced to sell at $225,000: Schedule your showing today.

3 Beds ⋅ 1 Baths ⋅ 5098856 MLS

Looking for an affordable way into homeownership? This ranch features 3 bedrooms and 1 full bath, this single-level home is perfect for first-time buyers or downsizers. Cozy up in the living room next to the fireplace or relax on the covered porch with your morning coffee. The easy, one-floor layout means low-maintenance living at a price that's hard to beat. Located just minutes from downtown Windsor's shops, restaurants, K-12 school, and Kennedys Pond, this home offers small-town charm with everyday convenience. Priced to sell at $225,000: Schedule your showing today.

24 Cherry St, Windsor

$230,000

Welcome to 2545 County Road in Windsor, Vermont! This inviting 3-bedroom, 2-bath raised ranch offers over 2,200 square feet of comfortable living space on a picturesque one-acre lot. The home features an open and bright floor plan with a spacious kitchen and dining area that flows seamlessly into the living room, perfect for gatherings or quiet evenings at home. Enjoy mornings with coffee on the large back deck overlooking the peaceful yard and surrounding countryside. The main level includes three well-sized bedrooms and a full bath, while the finished lower level offers flexible living options ideal for a family room, home office, or guest suite. With a detached shed, plenty of parking, and easy access to Windsor’s charming downtown, local schools, and I-91, this home combines rural tranquility with everyday convenience. Whether you’re looking for your first home or a quiet Vermont retreat, 2545 County Road offers the perfect blend of space, privacy, and potential.

3 Beds ⋅ 2 Baths ⋅ 5068382 MLS

Welcome to 2545 County Road in Windsor, Vermont! This inviting 3-bedroom, 2-bath raised ranch offers over 2,200 square feet of comfortable living space on a picturesque one-acre lot. The home features an open and bright floor plan with a spacious kitchen and dining area that flows seamlessly into the living room, perfect for gatherings or quiet evenings at home. Enjoy mornings with coffee on the large back deck overlooking the peaceful yard and surrounding countryside. The main level includes three well-sized bedrooms and a full bath, while the finished lower level offers flexible living options ideal for a family room, home office, or guest suite. With a detached shed, plenty of parking, and easy access to Windsor’s charming downtown, local schools, and I-91, this home combines rural tranquility with everyday convenience. Whether you’re looking for your first home or a quiet Vermont retreat, 2545 County Road offers the perfect blend of space, privacy, and potential.

2545 County Rd, Windsor

$226,000

3 Beds ⋅ 1 Baths ⋅ 5104329 MLS

4 Bavier Ave, Windsor

$175,000

Single-Level Home in the Heart of Windsor! Welcome to this inviting 3-bedroom, 2-bath home nestled on a quiet street in historic Windsor, Vermont. This well-maintained, single-level property offers the perfect blend of comfort, convenience, and New England charm. Step inside to discover a bright and open living space with warm hardwood floors, plenty of natural light, and a cozy atmosphere that makes you feel right at home. The kitchen features ample cabinet space and a functional layout, ideal for everyday living or entertaining. Each of the three bedrooms is generously sized with closet space and pleasant views of the surrounding neighborhood. A full basement offers extra storage or the potential for a workshop or hobby area. The Fairgrounds is right across the street, complete with dog park, skate park, basketball courts, tennis courts, ball fields, and a playground, and let's not forget the trail system. Located just minutes from local shops, schools, parks, and the picturesque Connecticut River, this home offers small-town charm with easy access to I-91 for commuting. Whether you're a first-time buyer, looking to downsize, or searching for a peaceful retreat, this property is a must-see.

3 Beds ⋅ 2 Baths ⋅ 5040643 MLS

Single-Level Home in the Heart of Windsor! Welcome to this inviting 3-bedroom, 2-bath home nestled on a quiet street in historic Windsor, Vermont. This well-maintained, single-level property offers the perfect blend of comfort, convenience, and New England charm. Step inside to discover a bright and open living space with warm hardwood floors, plenty of natural light, and a cozy atmosphere that makes you feel right at home. The kitchen features ample cabinet space and a functional layout, ideal for everyday living or entertaining. Each of the three bedrooms is generously sized with closet space and pleasant views of the surrounding neighborhood. A full basement offers extra storage or the potential for a workshop or hobby area. The Fairgrounds is right across the street, complete with dog park, skate park, basketball courts, tennis courts, ball fields, and a playground, and let's not forget the trail system. Located just minutes from local shops, schools, parks, and the picturesque Connecticut River, this home offers small-town charm with easy access to I-91 for commuting. Whether you're a first-time buyer, looking to downsize, or searching for a peaceful retreat, this property is a must-see.

44 Rte 44, Windsor

$165,000

68 Jarvis Street — a freshly painted, move-in ready 3-bedroom, 1-bath home on a double lot in downtown Windsor, Vermont. This well-kept property offers just the right amount of space, with a practical layout and room to grow both inside and out. Inside, you'll find a bright and spacious living area, three comfortable bedrooms, and a clean, functional kitchen. The basement provides extra storage or potential workshop space. Everything is in place for you to move right in and make it your own. Step outside and enjoy a large yard with plenty of space for parking, gardening, or relaxing. You're just a short walk to downtown Windsor's shops, restaurants, schools, and the Amtrak station — perfect for commuters or anyone looking for convenience. Plus, you're near the Connecticut River and close to local parks and trails. This home is ideal for first-time buyers, downsizers, or investors looking for a solid property in a growing area.

3 Beds ⋅ 1 Baths ⋅ 5067807 MLS

68 Jarvis Street — a freshly painted, move-in ready 3-bedroom, 1-bath home on a double lot in downtown Windsor, Vermont. This well-kept property offers just the right amount of space, with a practical layout and room to grow both inside and out. Inside, you'll find a bright and spacious living area, three comfortable bedrooms, and a clean, functional kitchen. The basement provides extra storage or potential workshop space. Everything is in place for you to move right in and make it your own. Step outside and enjoy a large yard with plenty of space for parking, gardening, or relaxing. You're just a short walk to downtown Windsor's shops, restaurants, schools, and the Amtrak station — perfect for commuters or anyone looking for convenience. Plus, you're near the Connecticut River and close to local parks and trails. This home is ideal for first-time buyers, downsizers, or investors looking for a solid property in a growing area.

68 Jarvis St, Windsor

$139,000

In the heart of Windsor, this charming opportunity was fully rebuilt in 2018. During the renovation, the foundation was raised to sit securely out of the flood zone, giving you peace of mind. Inside, the home features a large, over-sized entryway that leads into a comfortable open living space. The open loft adds a lot of character and extra charm to the layout. Enjoy the covered porch and the strip of opportunity to tend to some raised garden beds or entertain company. Within walking distance to the Amtrak station and downtown, and just a short drive to the hospital. Whether you want a low-maintenance home for yourself or a solid rental property near major employers, this updated home is a great choice.

1 Beds ⋅ 1 Baths ⋅ 5085360 MLS

In the heart of Windsor, this charming opportunity was fully rebuilt in 2018. During the renovation, the foundation was raised to sit securely out of the flood zone, giving you peace of mind. Inside, the home features a large, over-sized entryway that leads into a comfortable open living space. The open loft adds a lot of character and extra charm to the layout. Enjoy the covered porch and the strip of opportunity to tend to some raised garden beds or entertain company. Within walking distance to the Amtrak station and downtown, and just a short drive to the hospital. Whether you want a low-maintenance home for yourself or a solid rental property near major employers, this updated home is a great choice.

38 Jarvis St, Windsor

$115,000

The Stephen Jacob House is an extremely important historic residence in a town known for its historic architecture. Built in 1784 in the Georgian/Federal style, the residence was sited on the rise of State Street from the Village of Windsor. It's commanding presence was embellished with cornice dentil detailing and possibly a Palladian window. Having been used for many purposes over the years, the house was purchased by Historic Windsor, Inc. in 2008. Recognizing its historic significance along with much original fabric intact, Historic Windsor, Inc. engaged in a massive cleanup, extensive documentation and a complete paint job with some sections reroofed with standing seam. The residence is now ready for the next phase of its life as a single family residence, up to 4 residential apartments, owner occupied business or a cultural center. All of the necessary as built architectural plans, documentation of existing materials and fabric and proposed Feasibility Plans are available. The project will require all new systems and rehab working with the extensive original fabric including interior shutters, period flooring and window and door detailing. Many original doors. The residences rich history with Stephen Jacob and its architectural significance will regain its prominence in Historic Windsor upon completion.

5 Beds ⋅ 4 Baths ⋅ 4953869 MLS

The Stephen Jacob House is an extremely important historic residence in a town known for its historic architecture. Built in 1784 in the Georgian/Federal style, the residence was sited on the rise of State Street from the Village of Windsor. It's commanding presence was embellished with cornice dentil detailing and possibly a Palladian window. Having been used for many purposes over the years, the house was purchased by Historic Windsor, Inc. in 2008. Recognizing its historic significance along with much original fabric intact, Historic Windsor, Inc. engaged in a massive cleanup, extensive documentation and a complete paint job with some sections reroofed with standing seam. The residence is now ready for the next phase of its life as a single family residence, up to 4 residential apartments, owner occupied business or a cultural center. All of the necessary as built architectural plans, documentation of existing materials and fabric and proposed Feasibility Plans are available. The project will require all new systems and rehab working with the extensive original fabric including interior shutters, period flooring and window and door detailing. Many original doors. The residences rich history with Stephen Jacob and its architectural significance will regain its prominence in Historic Windsor upon completion.

70-74 State St, Windsor

$98,995

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.

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

$96,232

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.

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

$96,232

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.

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