Windsor VT Real Estate

Windsor  - A small town that is filled to the brim with American history. Windsor’s forefathers played key roles in the foundation of the country, the establishment of the VT constitution, and their industrious nature and determination clearly live on in this tight-knit locality. If you seek community living near the Upper Valley and immersed in a rich past, a home in Windsor, VT, may be right for you.

Windsor VT is a community that offers everything you need to keep your family happy, including the Windsor School District and the award-winning Mt. Ascutney Hospital. Real Estate in Windsor is surrounded by the allure of this historically significant town. Come find out why Windsor has great real estate values and discover the convenience of living here for yourself. Learn more about Windsor.

Windsor VT Homes for Sale

Questions about a property? Give us a call at 802.457.2244!

1528 Route 5 South Windsor VT 05089

Windsor, VT1528 Route 5 South

Price$1,650,000

Est. Mortgage: $/month

MLS Number 4830038

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 6
  • Square Feet 9,352

Extraordinary opportunity to own one of the 'finest homes in the Upper Valley' formerly known as 'Gilnocky Farm' located in Windsor, the 'Birthplace of Vermont' is private yet convenient to I-91. This home built in 1810 has a wonderfully understated Federal exterior; the interior which was later renovated in the Georgian Revival style, offers 9352 sq ft of living space. Character abounds in large rooms, accented by beautiful 'wavy glass' windows complete with Indian shutters & 'pumpkin pine' floors original to the house. The subtle detail of fine craftsmanship is evident throughout. 10' ceilings, natural light, a lovely foyer, 6 fireplaces, 6 bedrooms, 7 baths, a south facing porticoed porch overlooks the 217.82 acres offering an in-ground pool, 6 car garage, stables w/ 9 stalls, 3 bay closed equipment shed, tennis court, perennials, lawns & pastures, woods and 4-5 miles of equestrian trails. Property is served by town water & sewer, enrolled in the VT current use program and conserved with Upper Valley Land Trust.

Listed by Dana Waters and Paula Waters, Dark Horse Realty

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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153 Pembroke Road Windsor VT 05089

Windsor, VT153 Pembroke Road

Price$1,195,000

Est. Mortgage: $/month

MLS Number 4819544

  • Residential Single Family
  • Construction Existing
  • Bathroom 21
  • Bedrooms 17
  • Square Feet 14,000

The Windsor Mansion, sits high on Juniper Hill within the town limits of the historic hamlet of Windsor, Vermont. Built in 1902 by prominent New York lawyer Maxwell Evarts and listed on the National Register of Historic Places, it has welcomed countless distinguished guests in its storied past including Presidents Theodore Roosevelt, Woodrow Wilson, and Calvin Coolidge. The stately 17-bedroom Colonial Revival home is perched on 14 private acres replete with breathtaking views of Lake Runnemede, the Cornish Hills, and Mount Ascutney. A recent million dollar+ restoration and renovation project, though large in scale, beautifully preserved the elegant historic integrity of the original design while complementing with state-of-the-art modern amenities. Sprawling lawns with impeccably manicured gardens and an expansive deck and patio overlooking the Connecticut River Valley make it the perfect setting for entertaining friends and family. Currently the property is operating as an Inn but could also make a spectacular large family home. Only 19 miles to Hanover, NH/Dartmouth College and 16 miles to Woodstock, Vermont, Windsor Mansion is centrally located to all the best that the Upper Valley and New England have to offer.

Listed by David Donegan, Snyder Donegan Real Estate Group

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$
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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1672 Hunt Road Windsor VT 05089

Windsor, VT1672 Hunt Road

Price$905,000

Est. Mortgage: $/month

MLS Number 4791655

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 5,265

Kimball Brook Farm, C. 1789, has a storied history. It was once the residence of author and music critic Marcia Davenport, and is featured in her 1967 autobiography, “Too Strong for Fantasy”. Residents of Windsor report that Katherine Hepburn, a long-time friend of Ms. Davenport's was a visitor to the farm. This spectacular home embodies rambling country elegance and provides generous amounts of room for entertaining, family gatherings and/or events. Kimball Brook is comprised of 8 bedrooms and 5 baths - a total of 5,300 sq feet. There are both large formal areas and cozy spaces, which along with its 5 working fireplaces, highlight the farm's classic Vermont country character. The systems and structure, including heat, water, roofing, siding, foundation, and security have all been intelligently updated with state-of-the-art systems and materials. The large antique barn is a remarkable entity, providing space for projects, animals, vehicles, or celebrations. The property is nestled in a quiet valley amidst the rolling hills of historic Windsor on 32 ac of mixed open and wooded land, overlooking a pond with views into New Hampshire. It is a very short walk (or snowshoe, or bike ride) to an 900+ acre State Wildlife Management Area that provides the many year-round, outdoor activities enjoyed by all Vermonters. Despite its privacy and tranquility, the farm remains easily accessible to local attractions, including Hanover, NH and Woodstock, VT, both within 20 minutes.

Listed by Seth Warren, Seth Warren Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1747 Hunt Road Windsor VT 05089

Windsor, VT1747 Hunt Road

Price$450,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4830372

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,530

Cider Hill Farm is one of Windsor's favorite hidden gems. Located just minutes from the West Windsor town line, and Windsor Village, this tranquil, secluded farm property features a three bedroom post and beam cape, filled with warmth, comfort, and creative, inspiring elements. The living room has cathedral ceilings anchored by a fireplace, and sliders that step out to a private deck. The spacious, open country kitchen is the perfect place to gather and entertain friends and family. There are two cozy bedrooms on the main level, and a painter's studio that could serve as a great family room, or bedroom. There is one bedroom upstairs, with two oversized loft spaces (an easy conversion to sleeping quarters). The finished lower level could transition to a master suite, office or playroom. There is a lot of multi-functional space within a very efficient footprint. The grounds are lovely, with copious, established perennial gardens, and footpaths lacing through an everchanging palette of specialized woodland plantings. There is a separate studio/office cottage, garden and equipment sheds, apple orchards, an old cider house / barn, and a pond. It's a bird sanctuary by day, with owls to serenade you at night. This is a true working farm, with countless options and directions that one could take - retreat, artist colony, airbnb, events venue, farm to table, on and on. Come see for yourself, and experience the magic of Cider Hill Farm. This property is offered for sale "As Is".

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3528 44 Route Windsor VT 05089

Windsor, VT3528 44 Route

Price$424,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4830857

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,578

Echo Farm on Firefly Hill, new to the market! Classic Vermont farmhouse near the base of Mt Ascutney. This pretty traditional cape sits on almost 20 acres of picturesque rolling fields and surrounding woods. Convenient to all Upper Valley amenities. A short 1.2 miles to the Brownsville Butcher and Pantry Store and close to downtown Windsor. Located on a state road, so you won't be snowed in! The charming home is warm and inviting. A one car garage and carport connects to the main cape via a spacious eat in kitchen with wood beams, a pellet stove and loads of character. The large deck opens to amazing views to your fields and the hills of West Windsor. The barn is from approx. 1860. Currently working as a great stop for local antique shoppers and pickers alike, this grand old structure has lots of potential and could possibly be brought back to work for your small animals, maybe even horses. The home has space for everyone. The oversized kitchen serves as a wonderful gathering place. The main level also includes a formal dining, full bath and a large living room. The second floor has a nice sized master, two additional bedrooms, a full bath and a very large bonus space for a studio, extra sleep quarters or hobbies. There are endless possibilities. Perfectly comfortably, as is! This wonderful old farm property is solid, has tons of charm and awaits its new owners. Do not wait!

Listed by Mark Roden, BH&G - The Masiello Group

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2469 US RT. 5 North Route Windsor VT 05089

MLS Number 4825065

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,766

Sitting just North of the village of Windsor, this 1805 Greek Revival is sure to entice your sense of prestige and distinction. This home boasts a beautiful kitchen, front and back parlors, endless bedroom options, office space, expansive yard for gardening or playing with the kiddos, and garage/barn space that lends itself to working nicely for a business entity. With endless historic notations, including the National Historic Registry, you will feel the character and charm of years gone by, with simple touches being added by each owner. Bring your own ideas, and make this one HOME.

Listed by Katie Ladue Gilbert, RE/MAX Upper Valley

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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418 Moonrise Hill Windsor VT 05089

Windsor, VT418 Moonrise Hill

Price$289,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4822255

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,740

Beautiful southerly views of Mt Ascutney, nice lot and location, privately sited but convenient to town and the upper valley. Spacious rooms, master suite with bath and walk-in closet. Lovely screen porch off the kitchen overlooking the open land and view. Full walk-out basement. Outdoor wood boiler can provide supplemental heat if desired. Solar array.

Listed by Seth Warren, Seth Warren Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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46 Union Street Windsor VT 05089-1511

Windsor, VT46 Union Street

Price$249,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4828360

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 1,808

Completely renovated Antique home that is just about ready for new residents! Fabulous ceiling height, beautiful wood floors, all new appliances and utilities. There is a front garden area, close to schools and walking distance to the Village of Windsor.

Listed by Daphne Lowe and Carol Wood, Williamson Group Sothebys Intl. Realty

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$
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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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9 Old Mill Pond Road Windsor VT 05089

Windsor, VT9 Old Mill Pond Road

Price$225,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4829857

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 1,765

This townhouse style condominium is a sought after end unit. Enjoy gorgeous views of Mt. Ascutney and Kennedy Pond right from your deck. 3 master suites adorn this layout, including one on the main living level. A wood fireplace, finished basement space, a one car garage, hardwood Maple flooring, cathedral ceilings all in a private quiet setting. Excellent amenities: in-ground pool, basketball and tennis courts are all great places to spend hours and hours making memories. This home has everything you could want within walking distance to town and minutes from I91.

Listed by Katie Ladue Gilbert, RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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69 Belknap Lane Windsor VT 05089

Windsor, VT69 Belknap Lane

Price$179,900

Est. Mortgage: $/month

MLS Number 4834623

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,546

Fall is here, and this cozy home could be perfect for you. Open feel, open concept and open to new homeowners is the best description for this quaint 2 bedroom home on the fringe of town. Current owners have taken this Contemporary from house to home with warm, inviting spaces including a gourmet kitchen . You can have your own private oasis with garden space, a garage and plenty of room for your pets. Close to all town amenities including the pond, tennis courts, ball fields, and dog park! Showings to begin Sunday, October 18, 2020.

Listed by Katie Ladue Gilbert, RE/MAX Upper Valley

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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10 Clough Avenue Windsor VT 05089

Windsor, VT10 Clough Avenue

Price$179,900

Est. Mortgage: $/month

MLS Number 4799715

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1,744

This spacious, low maintenance home in the Village of Windsor offers comfort and convenience. It has an updated kitchen, baths, appliances, hot water heater, oil tank, a new pellet stove and deck, as well as a full unfinished basement perfect for a workshop. The tri level floor plan offers a space for everyone including plenty of room for an office for remote working and a home gym or studio. The home offers a fenced in back yard for the family pet or play area for young children. Various mature berry bushes add to the appeal of this home. All this is walking distance to schools, the recreation center and downtown restaurants and shopping. A must see!

Listed by Diana Cushing, Montshire Properties

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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16 Enright Avenue Windsor VT 05089

Windsor, VT16 Enright Avenue

Price$174,900

Est. Mortgage: $/month

MLS Number 4835056

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,440

This could be exactly what you have been waiting for! Three bedroom home located just outside of town, in a desirable neighborhood. Walking, you are just minutes from the town Fairgrounds and beautiful Kennedy Pond. Safely walk to school. The covered three season porch welcomes you as you enter the home, and the flow of the first floor makes it functional for all. Three bedrooms upstairs with a full bath. Great size lot with endless possibilities. Add a one car garage to the mix and we have the whole package ready for new owners!

Listed by Katie Ladue Gilbert, RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2020 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated October 24, 2020.