Windsor, VT Homes

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  /11

  $98,995 New Construction

  • 3 Beds
  • 2 Baths
  • 880 Sq Ft

  84 Cubb Ct, Windsor, VT 05089

  Welcome to 84 Cubb Court, , Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-66 model manufactured home offers 3 bedrooms, 2 bathrooms, and 880 sq. ft. (13'4"x66) 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

  84 Cubb Ct, 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
• 

  

  

  /18

  Est $224,587 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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  /41

  $98,000 Pending

  • 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
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  /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
• 

  

  /25

  Est $233,742 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
• 

  

  /27

  $57,000 Pending

  • 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
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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
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  /32

  Est $348,760 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,721 Sq Ft

  18 Pine St, Windsor, VT 05089

  18 Pine St, Windsor, VT 05089
• 

  

  /29

  $55,000 Pending

  • 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
• 

  

  /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
• 

  

  /13

  Est $184,871 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,800 Sq Ft

  14 Mccarty Ave, Windsor, VT 05089

  14 Mccarty Ave, Windsor, VT 05089
• 

  

  /17

  $38,500 Pending

  • 2 Beds
  • 1 Bath
  • 434 Sq Ft

  138 Ascutney St, Windsor, VT 05089

  Cash Sale - Being Sold in "As Is - As Seen" Condition. This Trailer (+) addition(s) is on it's own land (Not in a Park). Is is located just a short walk form Kennedy Pond and Downtown Windsor VT. This home will NOT qualify for lender financing in its current condition. What started out as a trailer has had a couple of different additions over the years. Currently, you'll find a Kitchen/Dining

  DJ Chabot Town and Country Realty

  138 Ascutney St, 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
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  /39

  Est $370,893 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  1670 Marton Rd, Windsor, VT 05089

  1670 Marton Rd, Windsor, VT 05089
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  /36

  $235,000 Under Contract

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

  31 Maple St, Windsor, VT 05089

  PRICE REDUCTION! 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

  Tara Reeves Vermont Real Estate Company

  31 Maple St, Windsor, VT 05089
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  /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
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  /4

  Est $213,604 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft

  17 Maple St, Windsor, VT 05089

  17 Maple St, Windsor, VT 05089
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  /15

  $96,232 Under Contract

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  132 Cubb Ct, Windsor, VT 05089

  Welcome to 132 Cubb Court, 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

  132 Cubb Ct, Windsor, VT 05089
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  /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
• 

  

  /23

  Est $175,792 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,165 Sq Ft

  149 Main St, Windsor, VT 05089

  149 Main St, Windsor, VT 05089
• 

  

  /26

  $94,900 Under Contract

  • 2 Beds
  • 1 Bath
  • 660 Sq Ft

  16 Day St, Windsor, VT 05089

  "Highest & Best Offer" deadline for submission is 10am EDT, Friday 5/23.This property is eligible under the Freddie Mac First Look Initiative through 06/15/2025.This property is offered 'as is'. Seller has not occupied property therefore there are no 'disclosures' offered.Interior ceiling damage(s) caused by roof 'failure' but half of roof was covered with corrugated metal

  Robert Balewicz Evergreen Realty of Vermont

  16 Day St, Windsor, VT 05089
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  /30

  $274,000 Sold May 09, 2025

  • 2,116 Sq Ft
  • $129/SF
  • 34 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1850

  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
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  /40

  Est $496,202 Not Listed For Sale

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

  29 Main St, Windsor, VT 05089

  29 Main St, Windsor, VT 05089
• 

  

  /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
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  /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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  /36

  Est $872,712 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
• 

  /2

  $379,000 Pending

  • 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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  /2

  $490,000 Sold Mar 14, 2025

  • 2,340 Sq Ft
  • $209/SF
  • 203 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1936

  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
• 

  

  /34

  Est $409,341 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,638 Sq Ft

  37 Morningside Dr, Windsor, VT 05089

  37 Morningside Dr, 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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  /37

  Est $439,937 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
• 

  

  /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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  /27

  Est $462,399 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,044 Sq Ft

  267 Taylor Dr Unit DRL, Windsor, VT 05089

  267 Taylor Dr Unit DRL, Windsor, VT 05089
• 

  

  /19

  $262,000 Sold Dec 18, 2024

  • 1,110 Sq Ft
  • $236/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
• 

  

  /34

  Est $508,492 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,468 Sq Ft

  223 Taylor Dr, Windsor, VT 05089

  223 Taylor Dr, Windsor, VT 05089
• 

  

  /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
• 

  

  /27

  Est $233,333 Not Listed For Sale

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

  159 Estey Ln, Windsor, VT 05089

  159 Estey Ln, Windsor, VT 05089
• 

  

  /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

  Livian Vermont KW Vermont

  2446 Us Route 5 N, 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

Showing Results 41 - 80, Page 2 of 18