Windsor, VT Homes

• 

  

  

  /40

  Est $380,176 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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /18

  Est $198,885 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,514 Sq Ft

  159 State St, Windsor, VT 05089

  159 State St, Windsor, VT 05089
• 

  

  

  /16

  $410,000

  • 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
• 

  

  /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
• 

  

  /25

  Est $237,359 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
• 

  

  /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
• 

  

  /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
• 

  

  /32

  Est $376,881 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,273 Sq Ft

  18 Pine St, Windsor, VT 05089

  18 Pine St, Windsor, VT 05089
• 

  

  /4

  $195,000

  • 5 Beds
  • 3.5 Baths
  • 4,011 Sq Ft

  70-74 State St, Windsor, VT 05089

  The Stephen Jacob House is an extremely important historic residence in a town known for its historic architecture. Built in 1784 in the Georgian/Federal style, the residence was sited on the rise of State Street from the Village of Windsor. It's commanding presence was embellished with cornice dentil detailing and possibly a Palladian window. Having been used for many purposes over the

  Wade Treadway Wade I Treadway Real Estate

  70-74 State 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
• 

  

  /13

  Est $189,299 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,800 Sq Ft

  14 Mccarty Ave, Windsor, VT 05089

  14 Mccarty Ave, Windsor, VT 05089
• 

  

  /16

  $96,232 New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  11 Cubb Ct, Windsor, VT 05089

  Welcome to 11 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 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 energy-efficient

  Kate Barry EXP Realty

  11 Cubb Ct, 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
• 

  

  /39

  Est $390,118 Not Listed For Sale

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

  1670 Marton Rd, Windsor, VT 05089

  1670 Marton Rd, Windsor, VT 05089
• 

  

  /11

  $87,826 New Construction

  • 1 Bed
  • 1 Bath
  • 643 Sq Ft

  23 Cubb Ct, Windsor, VT 05089

  Welcome to 23 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 1 bedroom, 1 bathroom, and 643 sq. ft. (13'4"x48) 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 energy-efficient

  Kate Barry EXP Realty

  23 Cubb Ct, 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
• 

  

  /4

  Est $195,483 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft

  17 Maple St, Windsor, VT 05089

  17 Maple St, Windsor, VT 05089
• 

  

  /16

  $96,232 New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  517 Back Mountain Rd, Windsor, VT 05089

  Welcome to 517 Back Mountain Rd., 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

  517 Back Mountain Rd, 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
• 

  

  /23

  Est $131,894 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,009 Sq Ft

  149 Main St, Windsor, VT 05089

  149 Main St, Windsor, VT 05089
• 

  

  /15

  $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
• 

  

  /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
• 

  

  /40

  Est $482,814 Not Listed For Sale

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

  29 Main St, Windsor, VT 05089

  29 Main St, Windsor, VT 05089
• 

  

  /15

  $209,000 Pending

  • 1 Bed
  • 1.5 Baths
  • 1,056 Sq Ft

  14 Central St, Windsor, VT 05089

  Discover this incredibly efficient, modern home in downtown Windsor, fully updated in 2018. This turn-key property offers comfort, convenience, and contemporary living.Step inside to find all main living areas thoughtfully located on the second floor. The primary bedroom boasts an oversized, ensuite bathroom with a spacious walk-in shower, providing a private oasis. The kitchen is a

  David White OwnerEntry.com

  14 Central St, 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

  Livian Vermont KW Vermont

  918 Us Route 5 N, Windsor, VT 05089
• 

  

  /36

  Est $829,096 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
• 

  

  /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
• 

  

  /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
• 

  

  /37

  Est $390,575 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
• 

  

  /11

  $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
• 

  

  /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
• 

  

  /27

  Est $467,552 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,212 Sq Ft

  267 Taylor Dr Unit DRL, Windsor, VT 05089

  267 Taylor Dr Unit DRL, Windsor, VT 05089
• 

  

  /18

  $239,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft

  66 Union St, Windsor, VT 05089

  PRICE JUST IMPROVED!Welcome to this beautifully maintained New Englander nestled in the historic town of Windsor — Vermont's first capital and a gem of the Upper Valley. This classic 3-bedroom, 2-bath home blends timeless charm with thoughtful updates, offering a perfect retreat in a vibrant, small-town setting.Located within walking distance to Windsor’s shops, restaurants, schools,

  Katie Ladue Gilbert KW Vermont Woodstock

  66 Union 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
• 

  

  /34

  Est $493,577 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
• 

  

  /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
• 

  

  /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
• 

  

  /24

  Est $217,996 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,608 Sq Ft

  6 Hall St, Windsor, VT 05089

  6 Hall St, Windsor, VT 05089

Showing Results 41 - 80, Page 2 of 18