Windsor, VT Homes

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  /18

  $229,000

  • 2 Beds
  • 2 Baths
  • 1,665 Sq Ft

  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
• 

  

  

  /13

  $1,650 per month

  63 Main Street

  2 Beds

  55 Depot Ave, Windsor, VT 05089

  55 Depot Ave, Windsor, VT 05089
• 

  

  

  /56

  $119,000 Sold Mar 17, 2025

  • 1,523 Sq Ft
  • $78/SF
  • 139 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1935

  17 Dewey Ave, Windsor, VT 05089

  Nicely located just walking distance to the school and town amenities. Nice level lot with home just waiting for you to make it your own. Three bedrooms and spacious main level.

  Dorothy Griswold The Clerkin Agency, P.C.

  17 Dewey Ave, Windsor, VT 05089
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  /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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  /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
• 

  /2

  $1,875 per month

  8 Union St.

  3 Beds

  8 Union St, Windsor, VT 05089

  8 Union St, Windsor, VT 05089
• 

  

  /39

  $325,000 Sold Feb 12, 2025

  • 1,400 Sq Ft
  • $232/SF
  • 36 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1890

  18 County Rd, Windsor, VT 05089

  Enjoy all the conveniences of Village life, with a tranquil view of rolling green horse pastures right from your window. This absolutely-charming antique New Englander has one of the best locations in town. Just outside your back door you'll enter the 200 AC Paradise Park nature trail network, complete with ponds, waterfalls, vernal pools and wildlife. The house is tidy, efficient, and lovingly

  Danny Kogut Williamson Group Sothebys Intl. Realty

  18 County Rd, Windsor, VT 05089
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  /9

  Est $183,544 Not Listed For Sale

  324 Old Mill Pond Rd, Windsor, VT 05089

  324 Old Mill Pond Rd, 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
• 

  

  /12

  $1,250 per month

  Apartment for Rent

  2 Beds

  5 Acme St, Windsor, VT 05089

  5 Acme St, Windsor, VT 05089
• 

  

  /28

  $281,500 Sold Jan 30, 2025

  • 1,271 Sq Ft
  • $221/SF
  • 3 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1976

  57 Victory Cir, Windsor, VT 05089

  Nestled in the heart of Vermont’s outdoor adventure region, this charming 2-bedroom, 1-bathroom cabin-style home in Windsor offers a perfect blend of rustic charm and modern comfort. Situated on 2 acres with stunning mountain views from the back deck and second floor, it’s an outdoor enthusiast’s dream. Inside, warm wood detailing creates a cozy ambiance throughout. The spacious living room

  Chelsea Bevis KW Vermont Woodstock

  57 Victory Cir, Windsor, VT 05089
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  /35

  Est $428,735 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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  /41

  $98,000

  • Land
  • 1.23 Acres
  • $79,675 per Acre

  00 Snow Ln, Windsor, VT 05089

  Lovely residential neighborhood with easy access to I91. These two separate and contiguous building lots sit on a small private road and have town water and sewer access on the edge of the property. Power is also on-site. This listing is for 1.23 acres that are divided into two separate buildable lots of Parcel #2 which is .56 acres (MLS #5036196), and Parcel #3 which is .67 acres (MLS #5036198).

  John Bassette Bassette Real Estate Group

  00 Snow Ln, Windsor, VT 05089
• 

  

  /20

  $1,725 per month

  77 Union St

  2 Beds

  77 Union St, Windsor, VT 05089

  77 Union St, Windsor, VT 05089
• 

  

  /19

  $262,000 Sold Dec 18, 2024

  • 1,710 Sq Ft
  • $153/SF
  • 5 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1971

  242 Huntington Dr, Windsor, VT 05089

  Welcome home to this inviting 3-bedroom, 1-bath ranch-style gem nestled in one of Windsor’s most sought-after neighborhoods. Step inside to find a cozy living room with a beautiful fireplace, perfect for New England winters. The kitchen opens into the dining room, and could be your chance at a fun remodel. Each bedroom provides comfort and plenty of natural light, making it a warm retreat for

  Katie Ladue Gilbert KW Vermont Woodstock

  242 Huntington Dr, Windsor, VT 05089
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  /29

  Est $353,610 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,517 Sq Ft

  3 Old Mill Pond Rd, Windsor, VT 05089

  3 Old Mill Pond Rd, Windsor, VT 05089
• 

  

  /23

  $255,000

  • 4 Beds
  • 1 Bath
  • 1,008 Sq Ft

  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
• 

  

  /23

  $2,450 per month

  • 2-3 Beds
  • 1 Bath
  • 1,275 Sq Ft
  • Condo for Rent

  2460 Us Route 5 N, Windsor, VT 05089

  3 bed/1 bath, fully furnished, all utilities included. Possibility of pets. Has been used as short term rental, will consider long term rental. Unit is fully furnished including linens, dishes, cleaning supplies, etc. High speed internet, trash, electric, heat, water/sewer, washer/dryer included. Up to two parking spots. Town of Windsor, stores, restaurants, laundromat, post office, rec center,

  2460 Us Route 5 N, Windsor, VT 05089
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  /40

  $425,000 Sold Dec 17, 2024

  • 3,146 Sq Ft
  • $135/SF
  • 151 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1796

  25 Main St, Windsor, VT 05089

  Built in 1796, the historic Trask House is located on beautiful Main St. in the heart of downtown Windsor. The center hall Federal sits on just under 1/2 acre and has an attached barn/garage in the back with plenty of storage. There is a private brick patio surrounded by a white picket fence and lovely landscaping. Inside, you are greeted by large open rooms with hardwood floors, high ceilings,

  Dan Noble Snyder Donegan Real Estate Group

  25 Main St, Windsor, VT 05089
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  /40

  Est $340,048 Not Listed For Sale

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

  157 Jewett Rd, Windsor, VT 05089

  157 Jewett Rd, Windsor, VT 05089
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  /16

  $435,000

  • 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
• 

  

  /23

  $2,650 per month

  • 2-3 Beds
  • 1 Bath
  • 1,275 Sq Ft
  • Condo for Rent

  2460 Us Route 5 N, Windsor, VT 05089

  3 bed/1 bath, fully furnished, all utilities included. Possibility of pets. Has been used as short term rental, will consider long term rental. Unit is fully furnished including linens, dishes, cleaning supplies, etc. High speed internet, trash, electric, heat, water/sewer, washer/dryer included. Up to two parking spots. Town of Windsor, stores, restaurants, laundromat, post office, rec center,

  2460 Us Route 5 N, Windsor, VT 05089
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  /26

  $306,000 Sold Dec 16, 2024

  • 2,289 Sq Ft
  • $134/SF
  • 24 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1890

  2446 Us Route 5 N, Windsor, VT 05089

  This beautifully updated 4-bedroom, 2-bath New England Colonial, nestled in a friendly neighborhood, combines classic charm with modern convenience. Step inside to discover a warm and inviting oversized mudroom, seamlessly flowing into a bright kitchen featuring a custom island and an abundance of cabinetry for all your storage needs. Just off the kitchen, the graciously sized dining room is

  2446 Us Route 5 N, Windsor, VT 05089
• 

  

  /27

  Est $244,067 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
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  /3

  $590,000

  • 17 Beds
  • 2,768 Sq Ft

  1185 U S 5 S, Windsor, VT 05089

  Introducing a prime investment opportunity nestled on 1.44 acres of picturesque countryside just moments away from the convenience of town living. Whether you're a seasoned investor seeking a lucrative addition to your portfolio or a newcomer to the world of real estate investment, this 8-unit property presents an attractive proposition. With its idyllic location, modern updates, and reliable

  Katie Ladue Gilbert KW Vermont Woodstock

  1185 U S 5 S, Windsor, VT 05089
• 

  

  /21

  $253,000 Sold Nov 27, 2024

  • 1,300 Sq Ft
  • $195/SF
  • 10 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1957

  54 Hillside Dr, Windsor, VT 05089

  Nestled just off the main road, this charming split-level home offers the perfect blend of privacy and convenience. Located just moments from town, you'll enjoy the peaceful setting without sacrificing easy access to local amenities. The inviting living room features a large picture window, filling the space with natural light. The adjacent kitchen includes a cozy dining area, ideal for family

  Katie Ladue Gilbert KW Vermont Woodstock

  54 Hillside Dr, Windsor, VT 05089
• 

  

  /14

  Est $147,938 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  17 Fairview Terrace, Windsor, VT 05089

  17 Fairview Terrace, Windsor, VT 05089
• 

  

  /20

  $168,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,182 Sq Ft

  1807 Rte 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 Rte 44, Windsor, VT 05089
• 

  

  /30

  $325,000 Sold Nov 27, 2024

  • 1,700 Sq Ft
  • $191/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  918 Us Route 5 N, Windsor, VT 05089

  Discover your dream home in this beautifully renovated 3-bedroom, 2-bath split-level residence, nestled in the serene landscapes of Windsor. This move-in-ready gem boasts a host of modern updates, making it the perfect blend of comfort and style. Step inside to a welcoming heated mudroom that leads you into the spacious living area, adorned with stunning hardwood floors and vaulted ceilings that

  918 Us Route 5 N, Windsor, VT 05089
• 

  

  /23

  Est $276,547 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,270 Sq Ft

  15 Fairview Terrace, Windsor, VT 05089

  15 Fairview Terrace, Windsor, VT 05089
• 

  

  /36

  $329,000 Pending

  • 3 Beds
  • 4 Baths
  • 2,052 Sq Ft

  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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  /27

  $460,000 Sold Nov 21, 2024

  • 2,044 Sq Ft
  • $225/SF
  • 6 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1965

  152 Rice Rd, Windsor, VT 05089

  This charming four-bedroom home is set on seven acres in a rural location. Tucked away on a quiet dirt road, the property offers lovely views of the surrounding hills and serves as an ideal escape from the hustle and bustle, while still being a quick commute to the amenities of Hanover and Lebanon. At the heart of the home is the beautifully appointed kitchen, featuring soapstone countertops and

  Susan Zak Four Seasons Sotheby's Int'l Realty

  152 Rice Rd, Windsor, VT 05089
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  /38

  Est $321,767 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
• 

  

  /30

  $264,900 Pending

  • 4 Beds
  • 1.5 Baths
  • 2,116 Sq Ft

  43 River St, Windsor, VT 05089

  Charming & spacious home with timeless character. Step into a home where classic charm meets modern convenience! From the moment you enter, you'll be captivated by the warmth of the hardwood floors, wide trim, built-ins, and soaring ceilings that create an inviting and spacious atmosphere. The generously sized rooms effortlessly accommodate daily life, while the enclosed three-season porch

  Katie Ladue Gilbert KW Vermont Woodstock

  43 River St, Windsor, VT 05089
• 

  

  /39

  $275,000 Sold Nov 15, 2024

  • 1,242 Sq Ft
  • $221/SF
  • 30 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  69 Morningside Dr, Windsor, VT 05089

  Don’t scroll past this listing without flipping through all the pictures! This turn-key 1988 ranch with a full concrete basement and attached garage in a quiet cul-de-sac neighborhood located in Windsor, Vermont is calling your name! Move right in with ease as the property is available now. Live comfortably on the main level with three bedrooms and two full bathrooms, plus the downstairs has

  Krista Harness Heney Realtors - Element Real Estate (Montpelier)

  69 Morningside Dr, Windsor, VT 05089
• 

  

  /17

  Est $255,498 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,064 Sq Ft

  93 Weston Heights, Windsor, VT 05089

  93 Weston Heights, Windsor, VT 05089
• 

  

  /17

  $275,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,264 Sq Ft

  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

  Katie Ladue Gilbert KW Vermont Woodstock

  42 Elm St, Windsor, VT 05089
• 

  

  /20

  $161,710 Sold Nov 15, 2024

  • 1,439 Sq Ft
  • $112/SF
  • 9 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1941

  146 Ascutney St, Windsor, VT 05089

  Come check out this very cute diamond in the rough! This home offers 2 good sized bedrooms with huge closets and a primary with a deck off the bedroom, as well as potential for a en suite bathroom....Several possibilities for the downstairs as well....Along with a 2 car garage with possible furnace hook up and its own electrical panel. This property is convenient to in town amenities and all that

  Jenn Boyer Coldwell Banker Homes Unlimited

  146 Ascutney St, Windsor, VT 05089
• 

  

  /15

  Est $270,106 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,532 Sq Ft

  19 Weston Heights, Windsor, VT 05089

  19 Weston Heights, Windsor, VT 05089
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  /42

  $490,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,340 Sq Ft

  71 Brian Jones Rd, Windsor, VT 05089

  Price reduction, motivated sellers! Great opportunity to make rental income, or have a secluded in-law apartment! Two well-maintained properties being sold together on a total of 13.6 +/- acres! Located on a country road in beautiful Ascutney VT with easy access to I-91. The main property, #71, is a cape-style house built in 1938 that was updated and renovated (including new insulation and

  Chelsea Richardson Barrett and Valley Associates Inc.

  71 Brian Jones Rd, Windsor, VT 05089

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