Windsor, VT Homes

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  /37

  $459,000

  • 4 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  96 Dairy Ln, Windsor, VT 05089

  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

  Katie Ladue Gilbert KW Vermont Woodstock

  96 Dairy Ln, Windsor, VT 05089
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  Explore Windsor

• 

  

  

  /18

  $1,050 - $1,575 per month

  63 Main Street

  1 - 2 Beds

  55 Depot Ave, Windsor, VT 05089

  55 Depot Ave, 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
• 

  

  

  /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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  /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
• 

  

  /3

  $1,275 per month

  Apartment for Rent

  1 Bed

  9 Central St, Windsor, VT 05089

  Private porch entrance to this spacious second-floor, one-bedroom apartment, just a short walk from downtown Windsor.This unit features a generous eat-in kitchen equipped with a stove, refrigerator, and dishwasher. Enjoy two large living areas, a comfortably sized bedroom, and a bathroom with a tub/shower combination.Heating fuel, parking-one car, trash removal, snow plowing are

  9 Central St, Windsor, VT 05089
• 

  

  /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
• 

  

  /35

  Est $427,381 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
• 

  

  /21

  $350,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,391 Sq Ft

  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
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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 KW Vermont Woodstock

  3 Foster Ave, Windsor, VT 05089
• 

  

  /40

  Est $324,867 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,588 Sq Ft

  157 Jewett Rd, Windsor, VT 05089

  157 Jewett Rd, Windsor, VT 05089
• 

  

  /20

  $349,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft

  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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  /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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  /27

  Est $207,923 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
• 

  

  /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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  /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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  /14

  Est $138,967 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  17 Fairview Terrace, Windsor, VT 05089

  17 Fairview Terrace, Windsor, VT 05089
• 

  

  /22

  $292,500 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,606 Sq Ft

  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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  /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
• 

  

  /23

  Est $260,115 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,270 Sq Ft

  15 Fairview Terrace, Windsor, VT 05089

  15 Fairview Terrace, Windsor, VT 05089
• 

  

  /25

  $289,900 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,196 Sq Ft

  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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  /20

  $180,000 Sold Jun 13, 2025

  • 1,182 Sq Ft
  • $152/SF
  • 204 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1958

  1807 Route 44, Windsor, VT 05089

  This home is ideal for a builder, investor or new homeowner who can qualify for a conventional or construction loan. Sale price includes a variety of building materials. The home appears structurally sound with a 3 zone hot water heating system, drilled well and public sewer. This property features an attached 1 car garage or a heated workshop, 3 BR's, 1.5 baths, office, fireplaced LR /with

  Don Chabot Town and Country Realty

  1807 Route 44, Windsor, VT 05089
• 

  

  /38

  Est $293,265 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,215 Sq Ft

  87 Kennedy Dr, Windsor, VT 05089

  87 Kennedy Dr, Windsor, VT 05089
• 

  

  /36

  $250,000

  • 3 Beds
  • 1.5 Baths
  • 1,900 Sq Ft

  31 Maple St, Windsor, VT 05089

  Discover classic Vermont charm in this 3-bedroom, 1.5-bathroom home located on a quiet, tree-lined street just steps from downtown Windsor. This home is perfect for those who appreciate historic charm and are ready to make it their own. Inside, you’ll find a welcoming layout and abundant natural light. The first floor features a full bathroom, laundry, spacious living and dining areas, and an

  Tara Reeves Vermont Real Estate Company

  31 Maple St, Windsor, VT 05089
• 

  

  /17

  $275,000 Sold Jun 09, 2025

  • 1,264 Sq Ft
  • $218/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1934

  42 Elm St, Windsor, VT 05089

  OFFER DEADLINE: 3/27/2025 at 2pm.Nestled in the heart of Windsor, VT, this delightful 3-bedroom, 2-bathroom home offers classic New England charm with many recent renovations. Situated in a desirable in-town location, this two-story home boasts a welcoming front porch, perfect for relaxing with your morning coffee.Inside, you'll find a warm and inviting layout. The entry way provides a place for

  Katie Ladue Gilbert KW Vermont Woodstock

  42 Elm St, Windsor, VT 05089
• 

  

  /17

  Est $235,039 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,064 Sq Ft

  93 Weston Heights, Windsor, VT 05089

  93 Weston Heights, Windsor, VT 05089
• 

  

  /55

  $598,000

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

  3440 Route 44, West Windsor, VT 05037

  This well cared for contemporary home 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. The floor plan has an easy

  Carol Wood Williamson Group Sothebys Intl. Realty

  3440 Route 44, West Windsor, VT 05037
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  /28

  $245,000 Sold Jun 02, 2025

  • 1,654 Sq Ft
  • $148/SF
  • 39 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1940

  2125 U S 5, Windsor, VT 05089

  With fabulous curb appeal and a welcoming covered porch, this turn-key circa 1940 New England home beautifully blends timeless design with modern comfort. The open-concept kitchen and dining area flow seamlessly into spacious living areas, creating a warm and inviting atmosphere. Elegant features such as French doors, a fireplace with a classic brick hearth, and bay windows add character and

  Katie Ladue Gilbert KW Vermont Woodstock

  2125 U S 5, Windsor, VT 05089
• 

  

  /13

  Est $229,081 Not Listed For Sale

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

  128 Weston Heights, Windsor, VT 05089

  128 Weston Heights, Windsor, VT 05089
• 

  

  /39

  $635,000

  • 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
• 

  

  /30

  $335,000 Sold Jun 02, 2025

  • 5,088 Sq Ft
  • $66/SF
  • 126 Days On Market

  • 8 Beds
  • 4 Baths
  • Built 1860

  77 Taylor Dr, Windsor, VT 05089

  A stellar combination and flexible to your needs. This 3 unit building situated on a large lot includes workshops, storage for tenants, and /or covered parking. Included is a single family manufactured home for additional income or a great spot to build a 2 bedroom cottage / tiny home. Great property for rental income or make this a family compound. Just north of town there is ample lawn for

  Katie Ladue Gilbert KW Vermont Woodstock

  77 Taylor Dr, Windsor, VT 05089
• 

  

  /26

  Est $205,350 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
• 

  

  /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
• 

  

  /23

  $210,000 Sold May 30, 2025

  • 1,352 Sq Ft
  • $155/SF
  • 44 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1938

  28 Bishops Loop, Windsor, VT 05089

  OFFER DEADLINE: MONDAY 4/21/25 6pmReady to start your real estate investment journey? This 3-bedroom home is the perfect opportunity for someone eager to build equity and willing to add their own personal touch. Upstairs, you’ll find three spacious bedrooms and a convenient half bath—ideal for families or future tenants.The eat-in kitchen is ready for your updates, offering a blank canvas to

  Katie Ladue Gilbert KW Vermont Woodstock

  28 Bishops Loop, Windsor, VT 05089
• 

  

  /29

  Est $268,049 Not Listed For Sale

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

  74 Union St, Windsor, VT 05089

  74 Union St, Windsor, VT 05089
• 

  

  /27

  $57,000

  • Land
  • 0.67 Acre
  • $85,075 per Acre

  00 Snow Ln, Windsor, VT 05089

  Lovely residential neighborhood with easy access to I-91. This easy access building lot (Parcel #3) sits on a short private roadway with convenient hookups to town water and sewer. Power and internet is also at the street and easily available. Property is located on the school bus route and is a great location for families. Land is relatively flat and should be easy building. Good expansion

  John Bassette Bassette Real Estate Group

  00 Snow Ln, Windsor, VT 05089
• 

  

  /32

  $350,000 Sold May 30, 2025

  • 3,990 Sq Ft
  • $88/SF
  • 232 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1900

  30 Union St, Windsor, VT 05089

  Step into timeless elegance with this grand Victorian home, beautifully situated on a charming in-town lot. This stately residence showcases stunning hardwood floors throughout, preserving its classic heritage while offering modern comforts. The spacious first-floor bedroom features an en suite bath, providing both luxury and convenience. A cozy fireplace adds warmth and character to the main

  Katie Ladue Gilbert KW Vermont Woodstock

  30 Union St, Windsor, VT 05089
• 

  

  /40

  Est $247,735 Not Listed For Sale

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

  2 Terrace St, Windsor, VT 05089

  2 Terrace St, Windsor, VT 05089
• 

  

  /29

  $55,000

  • Land
  • 0.56 Acre
  • $98,214 per Acre

  00 Snow Ln, Windsor, VT 05089

  Lovely residential neighborhood with easy access to I-91. This perfect building lot (Parcel #2) sits on a short private roadway with convenient access to town water and sewer. Power and internet is at the street and easily available. Property is located on the school bus route and is a great location for families. The land is relatively flat and should be an easy building location. Good expansion

  John Bassette Bassette Real Estate Group

  00 Snow Ln, Windsor, VT 05089
• 

  

  /36

  $270,000 Sold May 12, 2025

  • 2,052 Sq Ft
  • $132/SF
  • 294 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1989

  4 Old Mill Pond Rd, Windsor, VT 05089

  Old Mill Pond Condominiums offer an idyllic haven in the heart of Windsor. Imagine enjoying mountain views, pond access, and amenities such as an in-ground pool and tennis courts.This unit features vaulted ceilings and unique architectural elements often missing in typical condominiums. Guests can relax by the cozy fireplace or on the spacious deck with mountain views, depending on the

  Julie Davis KW Vermont Woodstock

  4 Old Mill Pond Rd, Windsor, VT 05089

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