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Windsor VT Real Estate

Windsor, Vermont real estate provides owners with access to a rich history, outdoor recreational opportunities, and unique shops. Popular activities include hiking, biking, fishing, paddling, and snowshoeing. Browse current Windsor, Vermont real estate listings below, including single family homes, multi family homes, and land. You may also be interested in viewing real estate listings in other Vermont towns.

Homes for Sale in Windsor

Contact LindeMac Real Estate at 603-643-4900 if you have questions or would like to schedule a tour. Register to save your favorite listings and get email notifications when similar properties become available.

807 County Road Windsor VT 05089

Windsor, VT807 County Road

Price$159,000

Est. Mortgage: $/month

MLS Number 4978024

  • Residential Single Family
  • Construction Existing
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 384

The original tiny living! Enjoy this rustic camp just minutes to town. Home features an open living room and kitchen area with a seperate bedroom. Cozy propane space heater heats the whole place. Screen porch for extra space in the warmer months. Mt. Ascutney Hospital is just down the road. Drilled well and public sewer!

Listed by Dorothy Griswold of The Clerkin Agency,P.C.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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21 Cherry Street Windsor VT 05089

Windsor, VT21 Cherry Street

Price$198,000

Est. Mortgage: $/month

Pending

MLS Number 4976750

  • Multifamily
  • Bathroom 2
  • Units 2
  • Area In Town
  • Acreage 0.19

This Sears home has stood the test of time of that bygone era where quality home building was the pride of America. One of the first pioneers in the prefab world, Sears homes were built with quality materials as the bones of this home so proudly show. The roof line is straight, the floors are level, the basement is dry and the little details such as stain glass windows and wood staircases still function as they did in the early 1900's. Converted into a two unit home several years back, this home has been a steady income producer for the owner over the last several years. As life changes so do needs thus this home is ready for its new stewards. The first floor apartment is vacant in the event an owner would like to occupy it and offset their mortgage with the income produced from the 2nd floor tenant. Rentals being in high demand, the first floor unit will have no problem finding an occupant should the owner desire. Walking distance from beautiful Mill Pond with a public beach for your use, the location can't be beat!

Listed by Leila Tarantelli of KW Coastal and Lakes & Mountains Realty/Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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25.5 Union Street Windsor VT 05089

Windsor, VT25.5 Union Street

Price$147,900

Est. Mortgage: $/month

MLS Number 4976062

  • Residential Single Family
  • Bathroom 1
  • Construction Existing
  • Bedrooms 2
  • Square Feet 1,115

Take advantage of this convenient home that places you right in the heart of downtown Windsor, Vermont. Walking distance to the amenities you need. With emergency response in eye view you will need to worry less about your home and more about filling your day with all of the festivities Vermont has to offer. Find affordable shelter out of the cold with an October 2020 new furnace and a new water heater as of 2021. Comes with new kitchen appliances installed in 2021. There's a shed to store all of your outdoor tools and toys. In addition, there's a slab beside the home and ready for your ideas! The bathroom has been recently remodeled. This home is happily expecting its new owner. Schedule a showing now!

Listed by Taylor Medeiros-Batey of KW Coastal and Lakes & Mountains Realty/Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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17 Fairview Terrace Windsor VT 05089

Windsor, VT17 Fairview Terrace

Price$129,000

Est. Mortgage: $/month

Pending

MLS Number 4976048

  • Residential Single Family
  • Bathroom 1
  • Construction Existing
  • Square Feet 768
  • Bedrooms 2

What a convenient location - this two bedroom home offers one level living with many upgrades including newer bathroom, flooring and roof to name a few; it is just waiting for a new owner to take it to the next level and make it HOME. Windsor, steeped in history, and often called the birthplace of Vermont, has much to offer and many recreational opportunities abound including swimming at Kennedy's Pond with a public beach, parks and close to Ascutney Mountain for hiking and other activities. Easy access to I91 and all amenities in the Upper Valley.

Listed by Berna Rexford of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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109 Morningside Drive Windsor VT 05089

Windsor, VT109 Morningside Drive

Price$244,000

Est. Mortgage: $/month

Pending

MLS Number 4974792

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,550

This charming ranch-style home offers a perfect blend of comfort and convenience, with its spacious deck and meticulously landscaped yard providing an inviting outdoor oasis. The heart of the home is the living room, with a fireplace, creating a warm and welcoming atmosphere. The adjoining dining area is perfect for entertaining and family gatherings. Located in a sought-after neighborhood, this property is not only a comfortable and inviting home but also an excellent investment in quality living. Don't miss the opportunity to make this ranch-style retreat with a deck and landscaped yard your own. It's a place where indoor and outdoor living harmoniously come together to create your ideal haven. Open House Sunday, October 22, 2023 10-12n

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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357 Route 5 Windsor VT 05089

Windsor, VT357 Route 5

Price$37,900

Est. Mortgage: $/month

MLS Number 4973374

  • Land
  • Acreage 0.39
  • Utilities None
  • PricePerSqFt 97179.49
  • Water View

Potential build site on the Connecticut River. Public water and power nearby.

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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2 Pine Street Windsor VT 05089

Windsor, VT2 Pine Street

Price$499,000

Est. Mortgage: $/month

MLS Number 4972807

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 4,933

Beautiful views of Lake Runnemede! Overlooking Runnemede with convenient trail systems to take to town or around the lake. Conveniently located in town but also very private! This is truly a majestic house that is in need of some rehab to bring it back to its former glory. Features a large kitchen space, a formal dining room and two main floor living rooms and a first floor bedroom with bath. All with high ceilings and fireplaced living rooms. Upstairs you will find 5 more bedrooms, a laundry room and bathrooms. Historical inlayed hardwood floors that have amazing potential! This property is ready to become a lovely family home! Delayed showings until 10/9/2023

Listed by Jenna Luce and Deb Roberts of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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473 Taylor Drive Windsor VT 05089

Windsor, VT473 Taylor Drive

Price$399,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4971987

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 3
  • Construction Existing
  • Square Feet 1,832

Welcome to this well maintained Cape Cod home, built in 2003, which combines the enduring charm of Cape Cod style with contemporary amenities. Just 18 minutes to Lebanon, NH and in a lovely private neighborhood, this 4-bedroom, 3-bathroom residence offers a modern open concept design. The living room flows seamlessly into the dining area and kitchen, creating a welcoming environment perfect for entertaining. A standout feature of this home is the first-floor bedroom, accompanied by an adjacent 3/4 bathroom, this design offers flexibility making it ideal for guests, a home office, or convenient single-level living. Upstairs are 3 bedrooms and a full bathroom. Hardwood floors throughout the home add warmth and character to the space. Outside, the fully fenced backyard is a secure and peaceful space for outdoor activities, and pets. With a paved driveway, the one-car garage provides parking convenience and additional storage. This home offers comfort, convenience, and classic style in a highly desirable neighborhood. SHOWINGS START on Friday 9/29. OPEN HOUSE on 9/30 from 10:00-12:30.

Listed by Marco Day of BHHS Verani Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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51-53 River Street Windsor VT 05089

Windsor, VT51-53 River Street

Price$249,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4971110

  • Multifamily
  • Units 3
  • Acreage 0.37
  • Square Feet 2,509
  • Utilities Internet - Cable

This is a great investment for income, or live in the main dwelling and rent the two apartments with good rental history. Plenty of space, large fenced-in backyard with raised beds, fire pit and room for a pool. Deck off game room with pool table and bar, heated workshop, multiple sheds and outbuildings for storage. Close to town and the upper valley is 1 exit up I91.

Listed by Ara Cardew of BHG Masiello Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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108 Main Street Windsor VT 05089

Windsor, VT108 Main Street

Price$340,000

Est. Mortgage: $/month

MLS Number 4955144

  • Multifamily
  • Units 4
  • Bathroom 4
  • Acreage 0.11
  • Square Feet 4,096

This charming piece of VT history was originally built as an apothecary in 1804. Now it's a charming, fully occupied, four unit multi-family building consisting of three one-bedroom units and one two-bedroom. Original features and high ceilings. Small yard requires little maintenance. One parking space per unit. Convenient location in a commercial zone. Close to restaurants, schools and hospital.

Listed by Rachel Brandli of Fidelity Real Estate Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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70-74 State Street Windsor VT 05089

Windsor, VT70-74 State Street

Price$195,000

Est. Mortgage: $/month

MLS Number 4953869

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,011

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 years, the house was purchased by Historic Windsor, Inc. in 2008. Recognizing its historic significance along with much original fabric intact, Historic Windsor, Inc. engaged in a massive cleanup, extensive documentation and a complete paint job with some sections reroofed with standing seam. The residence is now ready for the next phase of its life as a single family residence, up to 4 residential apartments, owner occupied business or a cultural center. All of the necessary as built architectural plans, documentation of existing materials and fabric and proposed Feasibility Plans are available. The project will require all new systems and rehab working with the extensive original fabric including interior shutters, period flooring and window and door detailing. Many original doors. The residences rich history with Stephen Jacob and its architectural significance will regain its prominence in Historic Windsor upon completion.

Listed by Wade Treadway of Wade I Treadway Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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1528 Route 5 South Windsor VT 05089

Windsor, VT1528 Route 5 South

Price$1,950,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4949295

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 7
  • 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 of Dark Horse Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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 2023 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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 November 28, 2023 7:23 AM EST