Windsor, VT Homes

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  /38

  $435,000

  • 4 Beds
  • 2.5 Baths
  • 2,272 Sq Ft

  96 Dairy Ln, Windsor, VT 05089

  Before the leaves have fallen, the PRICE on this one has! 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

  Katie Ladue Gilbert KW Vermont Woodstock

  96 Dairy Ln, Windsor, VT 05089
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  Explore Windsor

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  /3

  $1,975 - $2,300 per month

  12 Lowell St

  1 - 2 Beds

  12 Lowell St, Windsor, VT 05089

  12 Lowell St, Windsor, VT 05089
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  /21

  $310,000 Sold Sep 05, 2025

  • 1,391 Sq Ft
  • $223/SF
  • 43 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1964

  205 Channing Dr, Windsor, VT 05089

  Welcome to this inviting 2-bedroom, 1.5-bath ranch-style home located just a short distance from Main Street in Windsor, VT. Set on a manageable and sunny .29-acre lot, this home offers convenient single-level living with a bright, open-concept kitchen and living area—perfect for relaxing or entertaining. A spacious back enclosed porch extends your living space, ideal for enjoying Vermont’s

  Katie Ladue Gilbert KW Vermont Woodstock

  205 Channing Dr, Windsor, VT 05089
• 

  

  

  /20

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,509 Sq Ft

  51 River St, Windsor, VT 05089

  51 River St, Windsor, VT 05089
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  /39

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 1,452 Sq Ft

  3361 County Rd, Windsor, VT 05089

  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

  Danny Kogut Williamson Group Sothebys Intl. Realty

  3361 County Rd, Windsor, VT 05089
• 

  

  /18

  $219,000 Sold Sep 02, 2025

  • 1,743 Sq Ft
  • $126/SF
  • 56 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1856

  66 Union St, Windsor, VT 05089

  PRICE JUST IMPROVED!Welcome to this beautifully maintained New Englander nestled in the historic town of Windsor — Vermont's first capital and a gem of the Upper Valley. This classic 3-bedroom, 2-bath home blends timeless charm with thoughtful updates, offering a perfect retreat in a vibrant, small-town setting.Located within walking distance to Windsor’s shops, restaurants, schools,

  Katie Ladue Gilbert KW Vermont Woodstock

  66 Union St, Windsor, VT 05089
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  /35

  Est $433,316 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,832 Sq Ft

  473 Taylor Dr, Windsor, VT 05089

  473 Taylor Dr, Windsor, VT 05089
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  /36

  $325,000

  • 4 Beds
  • 2 Baths
  • 2,452 Sq Ft

  358 Us Route 5 S, Windsor, VT 05089

  Charming Duplex in the Heart of Windsor – Ideal for Owner-Occupants or Investors! Discover a fantastic opportunity to own a versatile, income-producing duplex in the vibrant and historic town of Windsor. Perfectly suited for an owner-occupant looking to offset their mortgage with rental income—or a savvy investor seeking solid returns—this well-maintained property offers both comfort and cash

  Daniel Preston KW Vermont Woodstock

  358 Us Route 5 S, Windsor, VT 05089
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  /20

  $350,000 Sold Aug 29, 2025

  • 1,196 Sq Ft
  • $293/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 1996

  255 Channing Dr, Windsor, VT 05089

  Extremely well maintained 3 bedroom / 2 bath ranch style home located in the Juniper Terrace neighborhood. The home offers a Buderus boiler, radiant floors, open floor plan with natural wood trim, wood floors in the main living area and a 2 flue chimney for woodstove hookup. Cooks will love the kitchen with its cherry cabinets, granite counters, stainless steel appliances, pantry and 5 burner

  Lisa Baldwin Coldwell Banker LIFESTYLES - Hanover

  255 Channing Dr, Windsor, VT 05089
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  /40

  Est $358,674 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft

  157 Jewett Rd, Windsor, VT 05089

  157 Jewett Rd, Windsor, VT 05089
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  /30

  $299,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,332 Sq Ft

  2505 County Rd, Windsor, VT 05089

  Here's a hidden gem for you in the heart of Vermont's magical, tranquil and picturesque countryside. Situated on 22 acres of forest and field sits a modest ranch home that is simplistic in style but overflowing with warmth and contentment. Loved for 40k+ years, it will be hard to turn over to its next denizen. The home is a time capsule of 70's charm and with some updating, can be enhanced

  Leila Tarantelli KW Coastal and Lakes & Mountains Realty/Hanover

  2505 County Rd, Windsor, VT 05089
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  /29

  $200,001 Sold Aug 28, 2025

  • 2,310 Sq Ft
  • $87/SF
  • 17 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1890

  9 Main St, Windsor, VT 05089

  A Grand Old Home Full of Character and PotentialWhat a beauty this home once was—and can be again! Brimming with historic charm, this spacious residence is just waiting for someone to restore it to its full glory. From the high ceilings and rich pecan woodwork to the elegant crown moldings and soapstone countertops, the original details create a timeless backdrop for your

  Linda Benoit Highland Realty

  9 Main St, Windsor, VT 05089
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  /27

  Est $241,885 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,080 Sq Ft

  18 Fairview Terrace, Windsor, VT 05089

  18 Fairview Terrace, Windsor, VT 05089
• 

  

  /27

  $292,500 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,560 Sq Ft

  2085 Us Route 5 S, Windsor, VT 05089

  Brimming with character and thoughtful upgrades, this lovingly maintained turnkey Colonial offers the perfect balance of rural New England charm and everyday convenience. Enjoy serene pastoral views from cozy living spaces, and a functional kitchen enhanced with tasteful improvements. Expansive yard spaces provide endless possibilities—garden, play, or host memorable gatherings with friends and

  Josh Gray Real Broker LLC

  2085 Us Route 5 S, Windsor, VT 05089
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  /22

  $292,500 Sold Aug 28, 2025

  • 1,606 Sq Ft
  • $182/SF
  • 2 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1920

  32 Clough Ave, Windsor, VT 05089

  Welcome to this rejuvenated home with one car garage with recent updates including fresh paint and flooring, new kitchen counter tops and cabinets and light fixtures. There’s good interior space with a living room, dining room, family room, second floor laundry and 3 bedrooms upstairs as well as an enclosed front porch for evening relaxing. This is a great opportunity and should be on your short

  Susan Bellville Bellville Realty

  32 Clough Ave, Windsor, VT 05089
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  /14

  Est $144,595 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  17 Fairview Terrace, Windsor, VT 05089

  17 Fairview Terrace, Windsor, VT 05089
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  /36

  $139,000

  • 1 Bed
  • 1 Bath
  • 240 Sq Ft

  505 Back Mountain Rd Unit 14, Windsor, VT 05089

  This beautifully crafted 2024 “Incredible Tiny Home,” built by Amish artisans, is ready for its next owner. Thoughtfully designed for efficiency and comfort, the home features a convenient kitchen, a spacious bathroom, and a loft sleeping area with stairs for easy access. A mini-split system provides both heating and cooling, ensuring year-round comfort.Step outside to enjoy the well-built

  Jenna Luce RE/MAX Upper Valley

  505 Back Mountain Rd Unit 14, Windsor, VT 05089
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  /25

  $290,000 Sold Aug 25, 2025

  • 2,196 Sq Ft
  • $132/SF
  • 14 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1975

  1471 County Rd, Windsor, VT 05089

  Nestled in a peaceful rural setting, this roomy 4-bedroom, 3-bathroom home offers incredible potential for those looking to create their dream country home. While the property is in need of some work, it features a generous layout and sits on a little over an acre, which allows for plenty of space to enjoy the beautiful setting. The home features hardwood floors, vinyl windows, a pellet stove, as

  Jenn Boyer Coldwell Banker Homes Unlimited

  1471 County Rd, Windsor, VT 05089
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  /23

  Est $271,069 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,270 Sq Ft

  15 Fairview Terrace, Windsor, VT 05089

  15 Fairview Terrace, Windsor, VT 05089
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  /55

  $598,000

  • 3 Beds
  • 3.5 Baths
  • 2,391 Sq Ft

  3440 Route 44, West Windsor, VT 05037

  Views of Mt. Ascutney from this well cared for contemporary home that has only been used as a second home for the original owners. The house takes advantage of the southwest exposure to be able to bring the outside in with the use of large palladium windows and multiple French doors. Some of the interior features include 3 woodburning fireplaces ,wide pine floors ,vaulted ceilings ,and skylights.

  Carol Wood Williamson Group Sothebys Intl. Realty

  3440 Route 44, West Windsor, VT 05037
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  /15

  $210,000 Sold Aug 06, 2025

  • 1,056 Sq Ft
  • $199/SF
  • 7 Days On Market

  • 1 Bed
  • 1.5 Baths
  • Built 1920

  14 Central St, Windsor, VT 05089

  Discover this incredibly efficient, modern home in downtown Windsor, fully updated in 2018. This turn-key property offers comfort, convenience, and contemporary living.Step inside to find all main living areas thoughtfully located on the second floor. The primary bedroom boasts an oversized, ensuite bathroom with a spacious walk-in shower, providing a private oasis. The kitchen is a

  David White OwnerEntry.com

  14 Central St, Windsor, VT 05089
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  /38

  Est $288,550 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 955 Sq Ft

  87 Kennedy Dr, Windsor, VT 05089

  87 Kennedy Dr, Windsor, VT 05089
• 

  

  /36

  $325,000

  • 2,452 Sq Ft

  358 Us Route 5 S, Windsor, VT 05089

  Charming Duplex in the Heart of Windsor – Ideal for Owner-Occupants or Investors! Discover a fantastic opportunity to own a versatile, income-producing duplex in the vibrant and historic town of Windsor. Perfectly suited for an owner-occupant looking to offset their mortgage with rental income—or a savvy investor seeking solid returns—this well-maintained property offers both comfort and cash

  Daniel Preston KW Vermont Woodstock

  358 Us Route 5 S, Windsor, VT 05089
• 

  

  /11

  $240,000 Sold Jul 21, 2025

  • 2,504 Sq Ft
  • $96/SF
  • 7 Days On Market

  • 6 Beds
  • 2 Baths
  • Built 1840

  338 Us Route 5 S, Windsor, VT 05089

  Imagine waking to the soft glow of dawn filtering through the windows of your charming three-story farmhouse, nestled in the heart of Vermont’s historic birthplace. As you sip coffee in the sunlit kitchen, the Connecticut River glimmers across the street, promising a day of serenity. This -bedroom, 2-bath home, brimming with character, becomes your sanctuary.Upstairs, the tranquil bedrooms

  Kevin Holmes Blue Slate Realty

  338 Us Route 5 S, Windsor, VT 05089
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  /17

  Est $218,788 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,064 Sq Ft

  93 Weston Heights, Windsor, VT 05089

  93 Weston Heights, Windsor, VT 05089
• 

  

  /16

  $390,000

  • 3 Beds
  • 1 Bath
  • 1,620 Sq Ft

  181 Banister Rd, Windsor, VT 05089

  Over 10 acres of beautiful fields and pasture with long range views and stone walls lining the property. Mature trees dot the perimeter and a lovely stream runs along the roadside. There is a multilevel functioning barn with water and electricity and a small gated paddock off to the side. Located in the heart of Horse Country, this would be and ideal equestrian property or a great place to raise

  Dan Noble Snyder Donegan Real Estate Group

  181 Banister Rd, Windsor, VT 05089
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  /25

  $145,000 Sold Jul 18, 2025

  • 1,742 Sq Ft
  • $83/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2004

  7 Stardust Cir, Windsor, VT 05089

  Welcome to this spacious and well-maintained double-wide home located in a desirable age-restricted community in Weathersfield, Vermont. Offering 3 comfortable bedrooms and 2 bathrooms, this home provides an ideal blend of functionality and ease of living. The open-concept living and dining area is perfect for entertaining or relaxing, while the primary suite offers a private bath and

  Katie Ladue Gilbert KW Vermont Woodstock

  7 Stardust Cir, Windsor, VT 05089
• 

  

  /13

  Est $210,654 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,373 Sq Ft

  128 Weston Heights, Windsor, VT 05089

  128 Weston Heights, Windsor, VT 05089
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  /4

  $195,000

  • 5 Beds
  • 3.5 Baths
  • 4,011 Sq Ft

  70-74 State St, Windsor, VT 05089

  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

  Wade Treadway Wade I Treadway Real Estate

  70-74 State St, Windsor, VT 05089
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  /16

  $235,000 Sold Jul 11, 2025

  • 2,662 Sq Ft
  • $88/SF
  • 5 Days On Market

  • Built 1917

  3 Foster Ave, Windsor, VT 05089

  Welcome to 3-5 Foster Avenue – A Rare Opportunity with Generational CharmLovingly cared for by the same owner for over 77 years, this classic duplex is full of warmth, character, and potential. Nestled on a quiet dead-end street, each unit offers 3 spacious bedrooms, inviting covered porches, and generous living space perfect for relaxing or entertaining. The fenced-in backyard is ideal for

  Raelene Robinson-Garrow Real Broker LLC

  3 Foster Ave, Windsor, VT 05089
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  /26

  Est $184,611 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,452 Sq Ft

  1092 Weeden Hill Rd, Windsor, VT 05089

  1092 Weeden Hill Rd, Windsor, VT 05089
• 

  

  /16

  $96,232 New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  11 Cubb Ct, Windsor, VT 05089

  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

  Kate Barry EXP Realty

  11 Cubb Ct, Windsor, VT 05089
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  /23

  $255,000 Sold Jul 01, 2025

  • 1,008 Sq Ft
  • $253/SF
  • 90 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1942

  59 Weston Heights, Windsor, VT 05089

  Great Location! Well-Maintained! 4BR's Cape Full Basement with work bench, Many recent updates in the last three years, Rear deck, Garden area and Private backyard.

  Don Chabot Town and Country Realty

  59 Weston Heights, Windsor, VT 05089
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  /29

  Est $281,313 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,142 Sq Ft

  74 Union St, Windsor, VT 05089

  74 Union St, Windsor, VT 05089
• 

  

  /11

  $87,826 New Construction

  • 1 Bed
  • 1 Bath
  • 643 Sq Ft

  23 Cubb Ct, Windsor, VT 05089

  Welcome to 23 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 1 bedroom, 1 bathroom, and 643 sq. ft. (13'4"x48) 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

  Kate Barry EXP Realty

  23 Cubb Ct, Windsor, VT 05089
• 

  

  /18

  $229,000 Sold Jun 25, 2025

  • 1,665 Sq Ft
  • $138/SF
  • 20 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1940

  3 Fitch Ct, Windsor, VT 05089

  Ready for the next generation is this lovingly cared for New Englander.Nestled on a quiet side street in the heart of Windsor, VT, this classic 2-bedroom, 2-bath home offers both character and warmth. The inviting front porch welcomes you into a sunlit living space featuring hardwood floors, original woodwork, and large windows that let in plenty of natural light.The spacious

  Katie Ladue Gilbert KW Vermont Woodstock

  3 Fitch Ct, Windsor, VT 05089
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  /40

  Est $267,019 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,728 Sq Ft

  2 Terrace St, Windsor, VT 05089

  2 Terrace St, Windsor, VT 05089
• 

  

  /16

  $96,232 New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  517 Back Mountain Rd, Windsor, VT 05089

  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

  Kate Barry EXP Realty

  517 Back Mountain Rd, Windsor, VT 05089
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  /60

  $579,000 Sold Jun 19, 2025

  • 3,006 Sq Ft
  • $193/SF
  • 39 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1800

  2 Walker Cemetery Trail, Windsor, VT 05089

  Tucked into a peaceful Vermont country setting, this c.1800 Antique Cape blends historic charm with modern comforts on a scenic 2.57-acre corner lot and a lovely spring-fed pond. The recently installed, and fully paid for, solar array gives extensive financial and green benefits - offsetting around $100/mnth in electricity costs (or $20,000 worth of mortgage value). The 3-4 bedroom, 4-bath home

  John Bassette Bassette Real Estate Group

  2 Walker Cemetery Trail, Windsor, VT 05089
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  /40

  Est $367,110 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,074 Sq Ft

  172 State St, Windsor, VT 05089

  172 State St, Windsor, VT 05089

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