Windsor, VT Homes

• 

  

  

  /19

  $165,000 Under Contract

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

  44 Route 44, Windsor, VT 05089

  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

  Katie Ladue Gilbert KW Vermont Woodstock

  44 Route 44, Windsor, VT 05089
• 

  

  

  /23

  $244,900 Sold Oct 31, 2024

  • 1,196 Sq Ft
  • $205/SF
  • 11 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1932

  2156 U S 5, Windsor, VT 05089

  Step into this beautifully taken care of vintage charmer, where classic Vermont character meets modern comfort. The home's original features are intact, including stunning maple hardwood floors and a striking tiger eye maple staircase that captures the essence of timeless elegance. The kitchen is a perfect blank canvas to add in your own personal touches. Enjoy the serenity of the seasons on

  Katie Ladue Gilbert KW Vermont Woodstock

  2156 U S 5, Windsor, VT 05089
• 

  

  

  /27

  Est $277,424 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,154 Sq Ft

  159 Estey Ln, Windsor, VT 05089

  159 Estey Ln, Windsor, VT 05089
• 

  

  

  /29

  $199,900

  • 4 Beds
  • 1.5 Baths
  • 2,310 Sq Ft

  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
• 

  

  

  /39

  $350,000 Sold Oct 21, 2024

  • 2,160 Sq Ft
  • $162/SF
  • 74 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1967

  39 Huntington Dr, Windsor, VT 05089

  Price Just Improved!...... Welcome to this well-maintained ranch located in the highly sought-after Juniper Terrace neighborhood. This delightful home features 3 cozy bedrooms and 1 full bath, perfect for comfortable living. The inviting living area is complemented by a pellet stove, providing warmth and ambiance during the cooler months. The highlight of this home is the finished basement,

  Katie Ladue Gilbert KW Vermont Woodstock

  39 Huntington Dr, Windsor, VT 05089
• 

  

  /29

  Est $237,235 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  28 Enright Ave, Windsor, VT 05089

  28 Enright Ave, Windsor, VT 05089
• 

  /2

  $379,000

  • 7 Beds
  • 4 Baths
  • 3,894 Sq Ft

  102-104 State St, Windsor, VT 05089

  INVESTMENT PROPERTY. 4 UNITS, 1 1-bedroom unit & 3 2-bedroom units. Separate basement for each unit. Recent improvement includes, new roof, replaced plywood, foam board and membrane, at a cost of $70,600.00. Heat is separate pellet stoves for each unit, also an oil-fired steam system if needed for backup. Electric is separate, tenants pay electric. Landlord pays heat. Minimum of 48-hour required

  Don Chabot Town and Country Realty

  102-104 State St, Windsor, VT 05089
• 

  

  /37

  $540,000 Sold Oct 16, 2024

  • 3,026 Sq Ft
  • $178/SF
  • 53 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2005

  207 Garden Way, Windsor, VT 05089

  MOTIVATED SELLERS! This 4 bedroom, 3 bath turnkey cape has been lovingly cared for by its owners. This home is situated on a large level lot on a private road right over the Connecticut River from Claremont, NH. Less than a mile from Exit 8 off I-91, <30 mins to Lebanon/Hanover. Situated within a school choice district and walking distance from highly rated Weathersfield School. Open concept main

  Jeffrey Brown American Dream Real Estate Associates, L

  207 Garden Way, Windsor, VT 05089
• 

  

  /28

  Est $188,270 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  9 Dewey Ave, Windsor, VT 05089

  9 Dewey Ave, Windsor, VT 05089
• 

  

  /38

  $380,000 Sold Oct 11, 2024

  • 2,656 Sq Ft
  • $143/SF
  • 14 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1909

  1124 U S 5, Windsor, VT 05089

  This property is the perfect fit if you are new to home ownership and would like to have a portion of your mortgage paid monthly. The main home is 3 bedrooms, 3 bathrooms, new deck, spacious yard, and updated appliances. The 1 bedroom unit has a nice enclosed porch, adding seasonal living space, and has been renovated. There is also storage space above that could be added to this unit. In the

  Katie Ladue Gilbert KW Vermont Woodstock

  1124 U S 5, Windsor, VT 05089
• 

  

  /40

  Est $320,520 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,296 Sq Ft

  39 Dairy Ln, Windsor, VT 05089

  39 Dairy Ln, Windsor, VT 05089
• 

  

  /39

  $821,500 Sold Oct 02, 2024

  • 2,238 Sq Ft
  • $367/SF
  • 38 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1801

  3223 County Rd, Windsor, VT 05089

  Welcome to this exquisite four-bedroom, two-bathroom Colonial home, built in 1801, nestled on a sprawling 10.4-acre lot in Windsor, Vermont. This charming residence boasts maple and bamboo floors as well as original wide pine flooring, spacious bedrooms, and tiled bathrooms. The property includes a two-bedroom, one-bathroom ADU, perfect for generating rental income or accommodating guests. Enjoy

  Kate Cassidy Four Seasons Sotheby's Int'l Realty

  3223 County Rd, Windsor, VT 05089
• 

  

  /37

  Est $353,580 Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 3,176 Sq Ft

  40 Village Green, Windsor, VT 05089

  40 Village Green, Windsor, VT 05089
• 

  

  /33

  $305,000 Sold Sep 26, 2024

  • 1,800 Sq Ft
  • $169/SF
  • 9 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1852

  6 Buena Vista Ct, Windsor, VT 05089

  Charming Cape with a spacious L addition and attached barn with storage above. Features include 3 bedrooms and a full bath upstairs, and a bedroom with a half bath on the first floor (just needs a door). Enjoy a 22x12 front living room with beautiful old wood floors, a remodeled kitchen with newer stainless appliances and a walk-in pantry, and a sunny dining room with built-ins. The private,

  Deb Roberts RE/MAX Upper Valley

  6 Buena Vista Ct, Windsor, VT 05089
• 

  

  /15

  Est $154,423 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 384 Sq Ft

  807 County Rd, Windsor, VT 05089

  807 County Rd, Windsor, VT 05089
• 

  

  /32

  $1,350,000 Sold Sep 19, 2024

  • 2,736 Sq Ft
  • $493/SF
  • 21 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2006

  2768 Hunt Rd, Windsor, VT 05089

  Fox Penny Farm, an established horse farm on 62 acres of open fields, trails, and woods on the Windsor/West Windsor line with westerly views of Mt Ascutney, is now offered for sale. Offering an expansive 3-bedroom 2.5 baths colonial with light-filled spaces, hardwood floors, spacious kitchen, dining room & propane fireplaced living room. Upstairs provides three large bedrooms with a primary

  Scott Monahan Williamson Group Sothebys Intl. Realty

  2768 Hunt Rd, Windsor, VT 05089
• 

  

  /13

  Est $258,091 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  96 Cole Hill Rd, Windsor, VT 05089

  96 Cole Hill Rd, Windsor, VT 05089
• 

  

  /34

  $405,000 Sold Aug 29, 2024

  • 1,638 Sq Ft
  • $247/SF
  • 33 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1986

  37 Morningside Dr, Windsor, VT 05089

  Price Just Improved! Discover your dream home nestled in a serene neighborhood! This charming 3-bedroom Cape Cod-style house sits on a spacious 1.15-acre lot adorned with delightful perennial gardens. Step inside to experience a cozy, yet spacious interior that seamlessly blends classic charm with modern comfort. The home features a thoughtfully designed layout, ideal for both relaxation and

  Katie Ladue Gilbert KW Vermont Woodstock

  37 Morningside Dr, Windsor, VT 05089
• 

  

  /20

  Est $256,018 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,266 Sq Ft

  17 Clough Ave, Windsor, VT 05089

  17 Clough Ave, Windsor, VT 05089
• 

  

  /21

  $277,000 Sold Aug 26, 2024

  • 2,554 Sq Ft
  • $108/SF
  • 8 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1950

  119 Ascutney St, Windsor, VT 05089

  OPEN HOUSE Saturday, June 15th 10-12 PM! Nestled on the edge of Windsor Village, this charming cape-style home has a well-maintained allure and picturesque appeal, inviting new homeowners to make it their own. A cobblestone chimney accents the exterior and a welcoming split rail fence adds to its quaint charm. Many new upgrades and features include a circular driveway, all new vinyl siding, new

  Tyler Hall BHHS Verani Upper Valley

  119 Ascutney St, Windsor, VT 05089
• 

  

  /39

  Est $223,961 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,354 Sq Ft

  21 Cherry St, Windsor, VT 05089

  21 Cherry St, Windsor, VT 05089
• 

  /2

  $365,000 Sold May 15, 2025

  • 1,998 Sq Ft
  • $183/SF
  • 0 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1919

  32 Ascutney St, Windsor, VT 05089

  This inviting 4-bedroom, 3-bath colonial home offers the perfect blend of traditional charm and modern convenience. Located on a 0.33-acre lot, this property is just a short distance from town, providing easy access to shops, restaurants, and more while maintaining a peaceful residential feel.

  Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

  32 Ascutney St, Windsor, VT 05089
• 

  

  /17

  Est $308,094 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,550 Sq Ft

  109 Morningside Dr, Windsor, VT 05089

  109 Morningside Dr, Windsor, VT 05089
• 

  /2

  $240,000 Sold Apr 21, 2025

  • 2,662 Sq Ft
  • $90/SF
  • 0 Days On Market

  • Built 1917

  36 River St, Windsor, VT 05089

  Allison Griep KW Vermont Woodstock

  36 River St, Windsor, VT 05089
• 

  

  /21

  Est $270,026 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,734 Sq Ft

  72 Harris Rd, Windsor, VT 05089

  72 Harris Rd, Windsor, VT 05089
• 

  

  /30

  Est $279,020 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,008 Sq Ft

  333 Brook Rd, Windsor, VT 05089

  333 Brook Rd, Windsor, VT 05089
• 

  

  /40

  Est $340,223 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,161 Sq Ft

  49 Valley View Trace, Windsor, VT 05089

  49 Valley View Trace, Windsor, VT 05089
• 

  

  /24

  Est $259,600 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft

  161 Birch Heights, Windsor, VT 05089

  161 Birch Heights, Windsor, VT 05089
• 

  

  /11

  Est $168,995 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,196 Sq Ft

  2 Bavier Ave, Windsor, VT 05089

  2 Bavier Ave, Windsor, VT 05089
• 

  

  /13

  Est $190,547 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 696 Sq Ft

  141 Ascutney St, Windsor, VT 05089

  141 Ascutney St, Windsor, VT 05089
• 

  

  /14

  Not Listed For Sale

  • 8 Beds
  • 6 Baths
  • 3,560 Sq Ft

  54 Ascutney St, Windsor, VT 05089

  54 Ascutney St, Windsor, VT 05089
• 

  

  /36

  Est $471,869 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,048 Sq Ft

  38 Ascutney St, Windsor, VT 05089

  38 Ascutney St, Windsor, VT 05089
• 

  

  /31

  Est $283,392 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,364 Sq Ft

  2 Ascutney St, Windsor, VT 05089

  2 Ascutney St, Windsor, VT 05089
• 

  

  /17

  Est $407,058 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,212 Sq Ft

  142 Old Bridge Rd, Windsor, VT 05089

  142 Old Bridge Rd, Windsor, VT 05089
• 

  

  /37

  Est $277,549 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,813 Sq Ft

  126 Thrasher Rd, Windsor, VT 05089

  126 Thrasher Rd, Windsor, VT 05089
• 

  

  /40

  Est $406,123 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,668 Sq Ft

  1520 Thrasher Rd, Windsor, VT 05089

  1520 Thrasher Rd, Windsor, VT 05089
• 

  

  /40

  Est $331,252 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,932 Sq Ft

  20 Rice Rd, Windsor, VT 05089

  20 Rice Rd, Windsor, VT 05089
• 

  

  /31

  Est $441,751 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,632 Sq Ft

  5 42nd St, Windsor, VT 05089

  5 42nd St, Windsor, VT 05089
• 

  

  /3

  Est $62,572 Not Listed For Sale

  81 Paradise Dr, Windsor, VT 05089

  81 Paradise Dr, Windsor, VT 05089
• 

  

  /26

  Est $248,369 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,546 Sq Ft

  69 Belknap Ln, Windsor, VT 05089

  69 Belknap Ln, Windsor, VT 05089

Showing Results 81 - 120, Page 3 of 18