Windsor VT Real Estate & Homes for Sale

18 Properties Found

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Beds:
4
Baths:
4.00
Sq.Ft.:
3,720
Status:
NEW LISTING
MLS#:
5095057
Type:
Single Family
Lot size:
4.96 Acres
Year built:
1900
Courtesy: Snyder Donegan Real Estate Group
View additional info

ADDITIONAL INFORMATION

"The Plateau", originally part of the Kennedy Biscuit Co. (Nabisco) family estate, is nestled on a plateau at the end of a private road which greets you with open fields, mature trees, beautiful gardens, and a protected front-and-center view of Mt. Ascutney to the West and the Connecticut River to the East. This private peaceful setting includes an inground pool for those hot summer days, and two porches: one open air and one screened-in, with views into the New Hampshire hillsides. Inside, the house is open and bright with a wonderful flow throughout. The large living room features a wood-burning fireplace and plenty of windows streaming in lots of natural light. The formal dining room, with built-in cabinets and a second wood burning fireplace, connects to the kitchen which is open to the family room. A beautiful spindle staircase with oversized steps leads you upstairs to the four bedrooms, including the primary with an ensuite bath and an attached office. The main guest/children's bedroom features a magnificent turret style sunroom taking in views of the Connecticut River, and a second set of stairs leads back down to the mudroom. The full basement offers plenty of storage and all the utilities. The large 2 story garage offers room for 4 vehicles and plenty of storage on the 2nd floor. This unique property presents a rare opportunity to own a special homestead in the Windsor area, just minutes from downtown shopping and restaurants.

Open House:

Saturday, 6/20 11:00-2:00PM

More Open House Info >

Beds:
3
Baths:
1.00
Sq.Ft.:
1,012
Status:
NEW LISTING
MLS#:
5094873
Type:
Single Family
Lot size:
0.64 Acres
Year built:
1958
Courtesy: Willow Brook Realty
View additional info

ADDITIONAL INFORMATION

Open House Saturday 6/20 11 AM to 2 PM - 56 Jenness Road, Ascutney, Vermont - Lovingly cared for by the same family since 1958, this cherished Vermont home is ready to welcome its next chapter. Nestled in the shadow of Mount Ascutney and conveniently located across from the Weathersfield School, with easy access to I-91 and nearby New Hampshire, the property offers a wonderful balance of community, convenience, and country living, all on one level. Imagine warm summer afternoons spent beneath the shade of a mature maple tree, sipping lemonade while butterflies dance among the perennial gardens. Garden enthusiasts will delight in the raised bed vegetable gardens, colorful pollinator gardens, and open yard that invites both relaxation and recreation. A spacious deck provides the perfect setting for morning coffee, family gatherings, or simply enjoying the peaceful surroundings. Inside, the home offers comfortable living with a wood-burning fireplace, creating a cozy gathering place during Vermontâ??s changing seasons. A generous mudroom welcomes muddy boots and snowy coats, while the one-car garage serves double duty as a home gym. The full basement provides ample space for hobbies, projects, and workshop needs. Recent improvements add peace of mind, including a new hot water heater and a brand-new three-bedroom septic system scheduled for installation this summer. A durable standing seam metal roof crowns the home, reflecting the thoughtful stewardship it has enjoyed since welcoming its first family in 1958. More than just a house, 56 Jenness Road is a place where gardens flourish, memories are made, and the simple joys of Vermont living can be savored every day.

Open House:

Sunday, 6/21 11:30-1:00PM

More Open House Info >

Beds:
2
Baths:
2.00
Sq.Ft.:
1,817
Status:
Active
MLS#:
5092971
Type:
Single Family
Lot size:
5.4 Acres
Year built:
2025
Courtesy: Williamson Group Sothebys Intl. Realty
View additional info

ADDITIONAL INFORMATION

Constructed in 2025, and located in the desirable Rush Meadow region of West Windsor, this impeccably orchestrated Yankee Barn Post and Beam home features superb materials, old world craftsmanship and detailed fit and finish. Custom milled cabinetry and built-ins throughout. The rooms are filled with natural light with stunning bucolic views from every window. The home is centered by a dramatic floating staircase leading to the loft area. Red oak flooring runs throughout. The open concept kitchen is suited with top quality appliances, and a center island with a rich walnut edged yellow birch countertop. The first level Primary ensuite has a dressing room with laundry, and bathroom with a walk in shower and soaking tub. Up the stairs, there's a spacious area for TV Room, or office and a guest bedroom. The walk-out lower basement level is spacious with high ceilings- perfect opportunity for future expansion. The home connects seamlessly to exterior spaces with a stone terrace and a screened porch, both situated to highlight the lovely pastoral views to Mt Ascutney, and beyond. State of the art mechanicals with central AC. Convenient to trail network, all recreation, Woodstock, Hanover NH and Interstate.

Beds:
6
Baths:
4.00
Sq.Ft.:
4,933
Status:
Active
MLS#:
5089288
Type:
Single Family
Lot size:
0.48 Acres
Year built:
1855
Courtesy: Bellville Realty
View additional info

ADDITIONAL INFORMATION

Come see and appreciate this recently rejuvenated and extraordinary home that includes 6 bedrooms and 4 bathrooms as well as a 2 car garage! Located just off the downtown village area, this unique property features historical charm and character with vintage woodwork, custom wood floors, high ceilings, spacious rooms and the nooks and crannies a classic home has to offer! Relax on the rear porch or enjoy the private yard and great family room that overlook the nearby pond providing a peaceful retreat at the end of a long day!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,820
Status:
Active
MLS#:
5086806
Type:
Single Family
Lot size:
10.26 Acres
Year built:
2007
Courtesy: Williamson Group Sothebys Intl. Realty
View additional info

ADDITIONAL INFORMATION

This impeccably orchestrated cottage style contemporary home was crafted by Ennis Builders in 2006 with an eye to meticulous detail. The sweeping cherry spiral staircase, beautiful stonework and superior fit and finish imbue a quality of workmanship that reflects throughout the home. The main level features an open-concept kitchen with maple butcher block counters, and quality stainless steel appliances, a dining area with a bank of Pella windows providing plenty of natural light throughout the day. The living room is anchored by a fieldstone fireplace designed and built by master stonemason, Hector Santos flanked by custom cabinetry. There is a guest bedroom/office, and ¾ bathroom. Moving upstairs, the generous primary suite has a walk in closet and luxury spa bathroom. Watch sunsets from the west facing Juliet balcony. The basement level has laundry/utility room with excellent quality Veissmann boiler, and heated two car garage. Central vacuum, radiant and baseboard heat. Mini split to cool those hot summer days. Bamboo floors run throughout main floor, and cherry on second level. Tranquil, private end of road location with sweeping westerly views over an expansive open field. Close proximity to State Forest for hiking, 35 miles of biking trails on Mt Ascutney. Easy access to Interstate, Woodstock, and Hanover NH, and all recreation.

Beds:
4
Baths:
4.00
Sq.Ft.:
5,173
Status:
Active
MLS#:
5086498
Type:
Single Family
Lot size:
10.07 Acres
Year built:
2006
Courtesy: Williamson Group Sothebys Intl. Realty
View additional info

ADDITIONAL INFORMATION

Prominently and privately sited overlooking the desirable Bible Hill region of West Windsor, this exceptional, meticulous Davis Timber Frame contemporary home has a panoramic view of Mt Ascutney, and sweeping views of the New Hampshire hillside and down the CT River Valley. Masterfully crafted with superior fit and finish, the home is anchored by a 36â?? cathedral ceiling with floor to ceiling windows, and a commanding fieldstone fireplace. Gourmet chefâ??s kitchen with excellent quality appliances, custom Alder Wood cabinetry, soapstone counters and hammered copper farm sink. Luxury primary suite on main level with renovated bathroom, and walk in closet. Three additional bedrooms on the second level. The finished walk out lower level featuring a billiards room, media room with pellet stove, a wet bar, steps out to a stone terrace with hot tub, tea room, outdoor shower. Entertain and wow your guests in your very own heated, covered pizza pavilion. The well-appointed post and beam barn has two stalls with direct turn-out and a 3 bay utility garage. Saddle up, or hop on your bike, and ride into the extensive dirt road and trail systems of West Windsor. Easy access to Interstate, Woodstock and Hanover NH. Extensive list of details and features under documents tab. By appointment only-no drive-ups please.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,554
Status:
Active
MLS#:
5085969
Type:
Single Family
Lot size:
26.72 Acres
Year built:
1842
Courtesy: LandVest, Inc/Woodstock
View additional info

ADDITIONAL INFORMATION

Farm at Gaelic Crossing is an equestrian property set on 26.72± acres, has dramatic views of Mount Ascutney and, after summer showers, the frequent and magical appearance of rainbowsâ??often even double rainbowsâ??across the wide, open sky. This updated c.1842 New England Cape offers 2,554 square feet of finished living space, including four bedroomsâ??two conveniently located on the first floor. Wide pine and maple floors run throughout, adding classic farmhouse character. The equestrian amenities are outstanding: a 3,024-square-foot stable with seven spacious stalls, a heated tack room, wash stall, bathroom, and laundry area. The 100' x 200' riding arena features a state-of-the-art, eco-friendly footing made from recycled sneakers, offering outstanding drainage, low dust, and excellent footing. Outdoor facilities also included are a round pen, four grass paddocks, and one dirt paddock. Quiet gravel roads invite walking and riding, with access to the Green Mountain Horse Association trail system. A stream winds along the property's West border, while apple and pear trees provide seasonal bounty. High-speed internet ensures fast connectivity. Ascutney Outdoors, with 40 miles of trails for horseback riding, mountain biking, skiing, and hiking, is nearby, and the popular Brownsville Butcher and Pantry is less than two miles away. (Horses not included)

Beds:
2
Baths:
1.00
Sq.Ft.:
1,008
Status:
Active
MLS#:
5085358
Type:
Single Family
Lot size:
0.08 Acres
Year built:
2025
Courtesy: KW Vermont Woodstock
View additional info

ADDITIONAL INFORMATION

Take a look at this rare chance to own a BRAND NEW home in the heart of Windsor. Built for efficiency, the house features a raised foundation to keep it out of the flood zone for extra peace of mind. The layout is practical and spacious, offering an open-concept first floor and large bedrooms upstairs. You are within walking distance to the Amtrak station and downtown, and our local Moover public transit service is ready to help. The community hospital is just a shore drive as well. Whether you want a low-maintenance home for yourself or a solid rental property near major employers, this new construction is a great choice.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,008
Status:
Active
MLS#:
5085357
Type:
Single Family
Lot size:
0.05 Acres
Year built:
2025
Courtesy: KW Vermont Woodstock
View additional info

ADDITIONAL INFORMATION

Experience the rare opportunity to own a BRAND NEW home, located in the heart of Windsor. This home seamlessly blends efficiency with style, featuring a thoughtfully elevated foundation designed to sit securely out of the flood zone for total peace of mind. The interior offers open living on the first level, and generous sized bedrooms upstairs, maximizing all the available space. The exterior offers a charming covered porch perfect for relaxing. Enjoy the convenience of being just steps away from the Amtrak station, short drive to the local hospital, access to public transportation, and sidewalks that lead you right up into town. Whether you are looking for a low-maintenance primary residence or a high-demand rental asset, this propertyâ??s brand-new construction and proximity to major employers is a win-win.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,142
Status:
Active
MLS#:
5082070
Type:
Single Family
Lot size:
0.25 Acres
Year built:
1890
Courtesy: KW Vermont Woodstock
View additional info

ADDITIONAL INFORMATION

Discover space, flexibility, and everyday convenience in this charming 4-bedroom, 2-bath home in the heart of Windsor. Thoughtfully designed with a spacious floor plan, the main living area features warm hardwood floors and abundant natural light, creating a bright and welcoming atmosphere throughout. The formal dining area flows seamlessly into the living room, perfect for both everyday living and entertaining. A main-level bedroom and full bath, along with convenient first-floor laundry, offer ideal single-level living options or guest accommodations. Upstairs, youâ??ll find three generously sized bedrooms, providing plenty of space for family, guests, or a home office setup. Set on a quarter-acre lot, the property offers ample parking and a detached one-car garage, perfect for storage, hobbies, or a workshop. Centrally located and easy access to town, grab your morning coffee just a short walk away or head to the nearby pond for a relaxing swim. A wonderful opportunity to own a well-located home with space, charm, and versatility in Windsor!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,888
Status:
Active
MLS#:
5080622
Type:
Single Family
Lot size:
1.22 Acres
Year built:
1790
Courtesy: BHHS Verani Upper Valley
View additional info

ADDITIONAL INFORMATION

Motivated seller! Price drop! A rare piece of Vermont history, thoughtfully preserved for modern living. Dating to 1790, this distinguished brick and frame Colonial stands as a testament to early New England craftsmanship â?? and it's ready for its next chapter. Meticulously maintained over the centuries and updated where it counts, this two-story home offers the warmth of wide-plank hardwood and softwood floors, the peace of mind of updated electrical and heating systems, and the curb appeal of a classic standing seam roof and fresh paint throughout. Recent windows flood the interior with natural light while preserving the home's timeless character. Whether you're drawn by the historic details or the practical updates, this property is move-in ready from day one. The kitchen is showstopping with a seamless blend repurposed materials. It exudes character and charm. The attached 1 car garage â?? complete with a dedicated storage room/workshop area and a massive open attic accessible from both levels â?? offers flexible space for a workshop, studio, or expansion. A property of this age rarely offers this much functional square footage. Positioned conveniently off Exit 9, commuting to the Upper Valley and beyond is effortless. The commercial zoning potential makes this an exceptional opportunity for buyers seeking a live-work arrangement, professional office space, or a savvy investment in one of Vermont's most storied small towns. Historic character. Modern comfort. Extraordinary potential.

Beds:
3
Baths:
3.00
Sq.Ft.:
3,392
Status:
Active
MLS#:
5079803
Type:
Single Family
Lot size:
3.03 Acres
Year built:
2002
Courtesy: BHHS Verani Upper Valley
View additional info

ADDITIONAL INFORMATION

Experience Vermont living at its finest in this custom-built home, thoughtfully designed by the builder for exceptional energy efficiency and year-round comfort. Perfect as a relaxing getaway, this property offers expansive sleeping spaces ideal for hosting family and friends. Spend your days exploring the nearby VAST Trail system or Ascutney Mountain, and your evenings unwinding by the fireplace, taking in sweeping views of the surrounding landscape. With its blend of modern craftsmanship, outdoor adventure, and serene retreat-like atmosphere, this home is an inviting escape in every season. A 2 car garage adds convenience and extra storage. Situated in a sought-after Vermont community known for its natural beauty and year-round recreation, this home is ready to be your full-time residence or relaxing getaway.

Beds:
1
Baths:
1.00
Sq.Ft.:
240
Status:
Active
MLS#:
5079488
Type:
Single Family
Year built:
2024
Courtesy: RE/MAX Upper Valley
View additional info

ADDITIONAL INFORMATION

This beautifully crafted 2024 "Incredible Tiny Home" built by Amish Artisans, is ready for its next owner. Thoughtfully designed for efficiency and comfort, the home features a convenient kitchen, a spacious bathroom, and a loft sleeping area with stairs for easy access. A mini-split system provides both heating and cooling, ensuring year-round comfort. Step outside to enjoy the well-built deck--perfect for converting in to a sunroom--as well as a screened gazebo and a storage shed included in the sale. Located in a small, quiet park just 4 miles from I-19, this property offers both charm and convenience. If you've ever dreamed of owning a Tiny Home, this is your opportunity!

Beds:
2
Baths:
1.00
Sq.Ft.:
720
Status:
Active
MLS#:
5062560
Type:
Single Family
Lot size:
0.84 Acres
Year built:
1968
Courtesy: Century 21 Highview Realty
View additional info

ADDITIONAL INFORMATION

Here's a chance to own your own property in West Windsor. This 3/4 +/- acre of land abuts one side up to Beaver Brook and you get views of Mt. Ascutney on the other side. This older mobile home with basement, offers the perfect opportunity for an investor. Restore the homes vintage charm or you could modernize the site with a new mobile unit. This was constructed as a 2-bedroom 1 bath home. One bedroom is now the laundry room. Bring your ideas and possibly build a new home. Just about 4 minutes away from Mt. Ascutney. Property is being sold in as is condition. Seller has not occupied home in 5 years. Currently a tenant resides here. 24-to-48-hour notice requested for showings.

Beds:
2
Baths:
2.00
Sq.Ft.:
777
Status:
Active
MLS#:
5050703
Type:
Mobile Home
Year built:
2025
Courtesy: EXP Realty
View additional info

ADDITIONAL INFORMATION

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 construction, modern appliances, and low-maintenance materials, making it perfect for easy living. Located in a peaceful and well-maintained community, this home is ideal for those looking for a move-in-ready option in a convenient location. Donâ??t miss out on this opportunity! Contact us today for more details or to schedule a tour. The interior is 100% complete. Home is available for showing. This property participates in the Mobile Home Infill Program (MHIP) and is open to anyone who works or lives in Vermont. The park owner is offering up $4,000 in closing costs and a waiver of the first 2 months of lot rent.

Beds:
1
Baths:
1.00
Sq.Ft.:
643
Status:
Active
MLS#:
5050702
Type:
Mobile Home
Year built:
2025
Courtesy: EXP Realty
View additional info

ADDITIONAL INFORMATION

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 construction, modern appliances, and low-maintenance materials, making it perfect for easy living. Located in a peaceful and well-maintained community, this home is ideal for those looking for a move-in-ready option in a convenient location. Donâ??t miss out on this opportunity! Contact us today for more details or to schedule a tour. The interior is approximately 90% complete. Interior showings will be available beginning August 15th. This property participates in the MHIP and is open exclusively to current residents of Vermont. The park owner is offering up $4,000 in closing costs and a waiver of the first 2 months of lot rent.

Beds:
2
Baths:
2.00
Sq.Ft.:
777
Status:
Active
MLS#:
5050701
Type:
Mobile Home
Year built:
2025
Courtesy: EXP Realty
View additional info

ADDITIONAL INFORMATION

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 energy-efficient construction, modern appliances, and low-maintenance materials, making it perfect for easy living. Located in a peaceful and well-maintained community, this home is ideal for those looking for a move-in-ready option in a convenient location. Donâ??t miss out on this opportunity! Contact us today for more details or to schedule a tour. The interior is 100% complete. Home is available for showing. This property participates in the Mobile Home Infill Program (MHIP) and is open to anyone who works or lives in Vermont. The park owner is offering up $4,000 in closing costs and a waiver of the first 2 months of lot rent.

Beds:
2
Baths:
2.00
Sq.Ft.:
777
Status:
Active
MLS#:
5050699
Type:
Mobile Home
Year built:
2025
Courtesy: EXP Realty
View additional info

ADDITIONAL INFORMATION

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 energy-efficient construction, modern appliances, and low-maintenance materials, making it perfect for easy living. Located in a peaceful and well-maintained community, this home is ideal for those looking for a move-in-ready option in a convenient location. Donâ??t miss out on this opportunity! Contact us today for more details or to schedule a tour. The interior is 100% complete. Home is available for showing. This property participates in the Mobile Home Infill Program (MHIP) and is open to anyone who works or lives in Vermont.

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Andrea D. Conner, License 71221, Xome Inc., License 68390, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Ste 100, Lewisville, TX 75067


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Windsor 05089 Real Estate

Windsor is located in Vermont. Windsor, Vermont 05089has a population of 3,561. Windsor 05089 is less family-centric than the surrounding county with 18.28% of the households containing married families with children. The county average for households married with children is 26.01%.

The median household income in Windsor, Vermont 05089 is $44,761. The median household income for the surrounding county is $63,787 compared to the national median of $69,021. The median age of people living in Windsor 05089 is 43 years.

Windsor Weather

The average high temperature in July is 80.5 degrees, with an average low temperature in January of 7 degrees. The average rainfall is approximately 44.1 inches per year, with 75.3 inches of snow per year.

Windsor Map

Windsor Real Estate Market Conditions

  • Median sales price

    $142,500
    19.1%
    change since last quarter
  • # Active listings

    18
    30-day change

Windsor Schools and Demographics

Education near Windsor, VT

City County
High School Graduates 88.21 94.16
College Degree - 2 year 8.42 8.49
College Degree - 4 year 26.24 40.21
Graduate Degree 9.22 12.49
Expenditures per Student 26,463 26,463
Students per Teacher 12.3 12.3

Elementary Schools near Windsor, VT

Grades Students P/T Ratio ZIP
Albert Bridge School (West Windsor) PK - 06 80 7.3 05037
Hartland Elementary School PK - 08 316 14.4 05048
Reading Elementary School PK - 06 57 9.4 05062
Weathersfield School PK - 08 215 12.8 05030
Windsor State Street School PK - 06 274 16.3 05089

High Schools near Windsor, VT

Grades Students P/T Ratio ZIP
Windsor High School 07 - 12 294 12.2 05089

Demographics near Windsor, VT 05089

Zip Code City
Neighborhood Type Small town
Population 3,561 57,593
Population Density 183 59
Median Age 43 47.8
People per Household 2.1 2.3
Median Household Income 44,761 63,787
Average Income per Capita 31,922 39,377

Real estate near Windsor