Windsor, VT Homes

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  /20

  $248,000 Sold Nov 04, 2024

  • 1,400 Sq Ft
  • $177/SF
  • 26 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1938

  4 Kiniry St, Windsor, VT 05089

  Back on the market. Did you miss this one in the first round? Completely Remodeled! This stunning home has undergone a total makeover, emerging as a beautiful, clean, and charming retreat in a lovely neighborhood. With nothing left to do but move in and enjoy, this 3+ bedroom residence boasts a brand-new kitchen, updated bathroom, and a newly restored mudroom entry and deck with laundry and 1/2

  Katie Ladue Gilbert KW Vermont Woodstock

  4 Kiniry St, Windsor, VT 05089
• 

  

  

  /20

  Est $281,000 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,164 Sq Ft

  210 Weston Heights, Windsor, VT 05089

  210 Weston Heights, Windsor, VT 05089
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  /28

  $240,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,654 Sq Ft

  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
• 

  

  

  /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
• 

  

  

  /13

  Est $237,771 Not Listed For Sale

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

  128 Weston Heights, Windsor, VT 05089

  128 Weston Heights, Windsor, VT 05089
• 

  

  /23

  $199,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,352 Sq Ft

  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

  Katie Ladue Gilbert KW Vermont Woodstock

  28 Bishops Loop, 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
• 

  

  /26

  Est $221,739 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
• 

  

  /30

  $359,000 Under Contract

  • 8 Beds
  • 4 Baths
  • 5,088 Sq Ft

  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
• 

  

  /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
• 

  

  /29

  Est $327,530 Not Listed For Sale

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

  74 Union St, Windsor, VT 05089

  74 Union St, Windsor, VT 05089
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  /32

  $399,900 Under Contract

  • 4 Beds
  • 4.5 Baths
  • 3,990 Sq Ft

  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
• 

  

  /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 $272,796 Not Listed For Sale

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

  2 Terrace St, Windsor, VT 05089

  2 Terrace St, 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
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  /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
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  /40

  Est $401,356 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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  /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
• 

  

  /18

  Est $234,618 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,514 Sq Ft

  159 State St, Windsor, VT 05089

  159 State St, Windsor, VT 05089
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  /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
• 

  

  /25

  Est $251,037 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  153 State St, Windsor, VT 05089

  153 State St, Windsor, VT 05089
• 

  

  /40

  $100,000 Sold Sep 18, 2024

  • 2,504 Sq Ft
  • $40/SF
  • 105 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1840

  338 Us Route 5 S, Windsor, VT 05089

  Spacious and affordable 3-story dwelling in Windsor. Buy it as a starter home, or take the opportunity for renovation and rental or resale. Pleasant stone landscaping in the yard. A kitchenette is found in the 3rd floor apartment (perhaps a rental unit or an in-law suite?) There's proximity to shopping (including a fine glass store, brewery, distillery, and jam shop), Amtrak, Mount Ascutney

  Zachary Zupan EXP Realty

  338 Us Route 5 S, Windsor, VT 05089
• 

  

  /21

  Est $362,664 Not Listed For Sale

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

  9 Old Mill Pond Rd, Windsor, VT 05089

  9 Old Mill Pond 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
• 

  

  /3

  Est $271,562 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,288 Sq Ft

  92 Back Mountain Rd, Windsor, VT 05089

  92 Back Mountain Rd, 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
• 

  

  /13

  Est $195,658 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,800 Sq Ft

  14 Mccarty Ave, Windsor, VT 05089

  14 Mccarty Ave, Windsor, VT 05089
• 

  

  /3

  $175,000 Sold Aug 02, 2024

  • 3,500 Sq Ft
  • $50/SF
  • 55 Days On Market

  • Studio
  • Built 1900

  9 Durkee St, Windsor, VT 05089

  Let this rooming house be your next great investment. 10 rooms, and a 2 bedroom apartment. Some long term renters. Rooms still available, and new boiler just installed.

  Katie Ladue Gilbert KW Vermont Woodstock

  9 Durkee St, Windsor, VT 05089
• 

  

  /39

  Est $399,200 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,156 Sq Ft

  1670 Marton Rd, Windsor, VT 05089

  1670 Marton Rd, Windsor, VT 05089
• 

  

  /38

  $930,000 Sold Jul 31, 2024

  • 1,282 Sq Ft
  • $725/SF
  • 15 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2020

  5 Maple Heights, Windsor, VT 05089

  5 MAPLE HEIGHTS- Simply stunning newer construction home with long range easterly views. This Scandinavian-inspired design built by Ambrose Custom Builders sits on a private hilltop in an ideal private setting with 8+ acres. The finish quality of the home is premium across the board. A large central great room has dramatic cathedral ceilings featuring Baltic Birch paneling, oversized windows to

  David Donegan Snyder Donegan Real Estate Group

  5 Maple Heights, Windsor, VT 05089
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  /4

  Est $208,671 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft

  17 Maple St, Windsor, VT 05089

  17 Maple St, Windsor, VT 05089
• 

  

  /13

  $224,900 Sold Jul 26, 2024

  • 696 Sq Ft
  • $323/SF
  • 8 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1941

  141 Ascutney St, Windsor, VT 05089

  RECENT UPDATES INCLUDE NEW WIRING, STANDING SEAM ROOF, PLUMBING, HOT WATER HEATER, KITCHEN CABINETS & COUNTERTOPS AND FLOORING, LANDSCAPED GROUNDS WITH A HUGE ARRAY OF FLOWERS PLUS BLUEBERRIES, RASPBERRIES AND PLUM TREE. WALK TO TOWN, TENNIS, BASKETBALL COURTS AND KENNEDY'S POND.

  Don Chabot Town and Country Realty

  141 Ascutney St, Windsor, VT 05089
• 

  

  /40

  Est $514,317 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,024 Sq Ft

  29 Main St, Windsor, VT 05089

  29 Main St, Windsor, VT 05089
• 

  

  /23

  $110,000 Sold Jun 26, 2024

  • 2,009 Sq Ft
  • $55/SF
  • 82 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1795

  149 Main St, Windsor, VT 05089

  Behind the gated picket fence, is a 1795 dwelling waiting to be restored to its former beauty. Beautiful wooden beams and wood floors. Upon entering the dwelling, there is a good sized living room on the left, and bedroom to the right. There are rooms in the back of the first floor [including a ½ bath] which potentially could be converted a den or into a large kitchen with a dining area which

  Amy Messina Town and Country Realty

  149 Main St, Windsor, VT 05089
• 

  

  /36

  Est $842,121 Not Listed For Sale

  • 9 Beds
  • 8.5 Baths
  • 6,232 Sq Ft

  26 Main St, Windsor, VT 05089

  26 Main St, Windsor, VT 05089
• 

  

  /40

  $386,000 Sold Jun 21, 2024

  • 1,668 Sq Ft
  • $231/SF
  • 2 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1970

  1520 Thrasher Rd, Windsor, VT 05089

  Such pretty setting for this one level three-bedroom home nestled on a quiet country road. One of the best features of the home is its grand living room where a focal point is a beautiful field stone fireplace. Perfect setting for entertaining. The kitchen has plenty of cabinets and ample counter space, spacious dining area has a large picture window with a view of the front yard. There is plenty

  Karolina Burtt EXP Realty

  1520 Thrasher Rd, Windsor, VT 05089
• 

  

  /31

  Est $332,950 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,354 Sq Ft

  369 Juniper Hill Rd, Windsor, VT 05089

  369 Juniper Hill Rd, Windsor, VT 05089
• 

  

  /31

  $270,000 Sold Jun 14, 2024

  • 1,364 Sq Ft
  • $198/SF
  • 2 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1905

  2 Ascutney St, Windsor, VT 05089

  Absolutely charming Windsor Village home with authentic period detail. With a dining area that has a built-in China Cabinet, beautiful wood floors, natural woodwork and banister, you will immediately fall in love. Although this property sports old world character, the updates are what you are truly looking for; newer windows, vinyl siding, standing seam roof, newly lined septic line, newer

  Jennifer Snyder Fogg Black House Real Estate

  2 Ascutney St, Windsor, VT 05089
• 

  

  /37

  Est $428,242 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  148 Hewett Rd, Windsor, VT 05089

  148 Hewett Rd, Windsor, VT 05089
• 

  

  /27

  $242,000 Sold May 17, 2024

  • 1,154 Sq Ft
  • $210/SF
  • 6 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1957

  159 Estey Ln, Windsor, VT 05089

  Discover the potential of this charming 2-bedroom, 2-bathroom ranch property set on 1.10 acres of picturesque land in Windsor, VT. This home offers a canvas for your imagination and personal touch. Inside, you'll find updated stainless steel appliances in the kitchen, alongside custom built-in storage for added convenience. Cozy up by the wood fireplace with a brick mantle in the living area, or

  159 Estey Ln, Windsor, VT 05089

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