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Windham VT Real Estate

Located in the Windham County of southern Vermont, Windham is a quaint, rural town. The mountainous terrain of Windham offers a secluded, private lifestyle for those who reside there. Chartered in the early 1770s, Windham’s village center is designated as the Windham Village Historic District. Windham is home to a tight-knit community that embraces the countryside living that the town has to offer. 

Search the latest real estate in Windham, Vermont with Maple Sweet Real Estate. Find the right property for you from a variety of listings. ‚ÄčRegister to save your favorite listings and you can get email notifications when similar properties are posted. Have an account? Log in here.

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2181 White Road Windham VT 05143

Windham, VT2181 White Road

Price$999,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4998938

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 2,916

Nestled along a serene country road, this enchanting home exudes rustic charm and timeless elegance. The “Twin Brooks” that flank the property and private pond round out the much desired water features. Hand hewn beamed ceilings welcome you into a cozy haven where every detail tells a story. Adorned with captivating features, the interior boasts a marble-faced fireplace, a soapstone stove radiating warmth and comfort, wood flooring, transitional lighting and a hand painted mural. Delightful granite countertops adorn the kitchen, complemented by a Viking range and solid antique butcher block. The primary bedroom offers a tranquil retreat with its own fireplace and displaying a whimsical contrasting of crystal chandeliers poised below the rusty touched metal ceiling. The antique barnwood too evokes a sense of the history embedded in this mid 19th century homestead. Many outdoor living spaces including a hot tub oasis and a patio with a fire pit are perfect for gatherings under the stars. Deep fieldstone walls by Dan Field frame the home and meadows while old pines and maple trees line the landscape. A three-car garage, workshop and sheds provide ample space for projects. All of this is surrounded by lush perennials and breathtaking hill vistas! The field of sunflowers, a chicken coop, raised beds and greenhouse give homage to the farm. This home is a sanctuary where modern comfort meets rustic allure, offering a peaceful retreat for those who cherish the beauty of nature.

Listed by Lavinia Lee Brown and Nancy Jensen of Four Seasons Sotheby's Int'l Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.77% last updated on 2024-07-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

7406 Windham Hill Road Windham VT 05359

Windham, VT7406 Windham Hill Road

Price$795,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5001885

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • Bedrooms 3
  • Bathroom 4

Designed with an open layout, this contemporary farmhouse is awash with natural light. The chef's kitchen features local Danby Marble countertops and ample built-in storage. The soft patina of Ash wood floors are a highlight throughout the entire home. Built in 2008, with a custom interior completed in 2016, it includes two spacious en-suite bedrooms and a third bedroom with a dedicated bath and private sitting area. Additionally, there's a gym space for your fitness needs. The living room boasts nine-foot ceilings and a highly efficient fireplace that warms the entire home. The heated two-car garage, with elegant wood paneling, has hosted dinners for up to 40 guests. Above the garage is a versatile heated space, ideal for an office or studio. Whole house A/C. The fenced backyard, surrounded by hydrangeas, features a large deck and fire pit, perfect for gatherings and romping children and dogs. A dedicated storage barn offers space for gear, with a direct connection to the VAST trails, allowing snowmobile access to local dining spots such as the Townshend Dam Diner. At the base of Timber Ridge Mountain, this turn-key property is close to skiing, farmers markets, and local summer theater. Enjoy Friday pizza nights at the West Townshend Country Store, farm-to-table dining at SoLo or the Grafton Inn, and excursions to the Southern Vermont Arts Center. 5-7 miles from Magic Mt. and Viking Nordic Center and 14-18 miles to Bromley and Stratton. 2:45 hrs to Boston. 4:15 hrs to NY

Listed by Dia Jenks and T Story Jenks of LandVest,Inc/Woodstock

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.77% last updated on 2024-07-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2253 White Road Windham VT 05359

Windham, VT2253 White Road

Price$725,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5002967

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2

Stunning acreage surrounds this charming home in Windham, Vermont. A quintessential get-away with a large screened-in porch overlooking the waterfall and pond. Follow the bridge across the pond to the meadow and trails. The extensive trail network is well maintained, meandering throughout the 110 acres. Enjoy all seasons of exploring! The bungalow style house was completely redone in 2001. The light colored wood floors enhance the light, open layout which includes 2 bedrooms and 2 bathrooms. A soapstone wood stove in the sitting area gives promise of cozy winter days. The basement has high ceilings and a garage door, most recently housing the John Deere that was used around the property. Find extra storage in the small barn. The acreage has been maintained with great care. There is a park-like wooded area just across the road, making the view from the front porch very tranquil. With skiing at Okemo, Bromley, Magic, Stratton and Mount Snow only 20 minutes away, dining in Grafton, Weston and Chester in minutes and theater near-by, find year-round entertainment on this very special property.

Listed by Alison Cummings of Cummings & Co

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.77% last updated on 2024-07-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2105 White Road Windham VT 05359

Windham, VT2105 White Road

Price$595,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4982519

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,466

There is a lot more to this sweet house than meets the eye… come see it for yourself and prepare to be enchanted! What was once one of Windham's quaint schoolhouses is now the quintessential Vermont escape, blending classic architectural charm and design with the convenience and efficiency of a modern home. The schoolhouse was moved to its current location and placed on a new concrete foundation and renovated with two sizeable additions to add a Great Room and 1st floor primary suite. Offered mostly-furnished, this house will be a turn-key purchase for you and ready to enjoy throughout all of Vermont's beautiful seasons. During the winter months, you will appreciate sunlit living areas, cozy spaces, and 2 woodstoves… while you dream about warmer months when you will enjoy time outside on the beautiful stone patio, lovely lawn and central A/C. Plenty of storage for vehicles, toys and tools in the large woodshed and an over-sized one-car garage with workspace. There are 10.8 acres of your own private woods to explore and enjoy and you can walk, hike, bike, or snowshoe from your front door. The house is almost equidistant to the picturesque villages of Grafton, Chester, Londonderry, and Weston with VAST access is nearby, and skiing at Magic Mountain just a few minutes-drive away and Bromley, Stratton and Okemo are 20-30 minute further. Lowell Lake State Park is also nearby, offering trails, kayaking and abundant wildlife viewing. Make this your southern Vermont home!

Listed by Claudia Harris of Mary Mitchell Miller Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.77% last updated on 2024-07-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

599 Hitchcock Hill Road Windham VT 05359

Windham, VT599 Hitchcock Hill Road

Price$589,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5002926

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

Sunlight pours in to this charming log home in Windham. It is exceptionally well sited to take advantage of the landscape, exposure and view. Many large south facing windows allow for ample light inside and the large deck that surrounds the home extends the living space to outside. Discover the space in between, a large sun room just off the living area, perfect for enjoying the sunset year round. Enter through the mudroom and into an open concept kitchen and dining area. Take in the cozy atmosphere with soaring ceilings and warm wood tones throughout. In the living room enjoy a fire in the wood burning fireplace. This thoughtful layout includes 3 bedrooms, one on each level. The ensuite on the top floor opens to a loft area for extra sleeping or an office. The nicely sized main floor bedroom has an adjacent bath. This great home on 14+ acres has direct trail access to VAST trails. The land is filled with wild berry bushes and a hidden stream complete with a waterfall. All of this is within a short distance to year round recreation including farmers markets, summer theater, 5 local ski areas and so much more of what Vermont offers. Call for a showing today!

Listed by Alison Cummings of Cummings & Co

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.77% last updated on 2024-07-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Windham Hill Road Windham VT 05359

Windham, VTWindham Hill Road

Price$329,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4978543

  • Land
  • Acreage 58.7
  • Utilities None
  • PricePerSqFt 5604.77
  • Zoning Residential

58.7 Acres in Windham VT. This Parcel is a combination of 2 lots…17 acres off Scott Pet Rd and 41.3 off Windham Hill Rd (Rt. 121). Stunning views from the top look west towards Bromley Mt or look east toward Chester VT. These 58+/- acres have been partially logged and cleared for potential building sites. Access from either Scott Pet Rd or Windham Hill Rd and walk through the clearings and enjoy the views. Great potential to build your VT Dream Home or build out for several home sites.

Listed by Dan McKenna of Cummings & Co

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.77% last updated on 2024-07-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

121 Windham Springs Road Windham VT 05359

Windham, VT121 Windham Springs Road

Price$289,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4994046

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 2
  • Square Feet 1,748

What a location! This great get-away has been loved by one family for a very long time and they are now ready to pass it on to the next owners! Large windows bring in the light and make you feel like you are in a treehouse! Slate floors and warm woodwork give this home a rustic, comfortable feel. The open concept floor plan on the main level allows for a variety of options in how the living space is laid out. There are 4 bedrooms and 1 bath on the second floor with 2 smaller bedrooms on the 3rd floor. Windham is centrally located and is in close proximity to Magic Mountain, Bromley, Stratton, Mount Snow and Okemo for winter recreation as well as a short drive to Weston, Grafton and Chester. Don't miss this one!

Listed by Alison Cummings of Cummings & Co

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.77% last updated on 2024-07-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

173 Horsenail Road Windham VT 05359

Windham, VT173 Horsenail Road

Price$195,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4990434

  • Land
  • Acreage 36.25
  • Utilities Cable - At Site
  • PricePerSqFt 5379.31

Over 35 acres with more than 2,500 feet of PRIME ROAD FRONTAGE on Vermont Route 11, a major east west corridor from Springfiled to Manchester. This open level lot is a perfect spot for your business starting from the ground up. With great exposure and easy access to Route 91 and Vermont Route 7 this ultimate location is waiting for you and your ideas.

Listed by Frank Provance of Diamond Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.77% last updated on 2024-07-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

3128 Windham Hill Road Windham VT 05359

Windham, VT3128 Windham Hill Road

Price$150,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5005075

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2

Historic mid 19th century cape in the south hamlet of Windham being sold as is. Current owner has begun renovating, but there is still plenty left to do. There is a brand new boiler in the basement, but is presently not connected. This is a lovely location at the south end of town with ready access to local ski areas including Magic, Stratton, Bromley and Okemo, and close proximity to Jamaica State Park, West Townshend General Store, Londonderry Farmers Market and local shopping.

Listed by Christopher Cummings of Cummings & Co

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.77% last updated on 2024-07-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

176 Harrington Road Windham VT 05359

Windham, VT176 Harrington Road

Rental Price$3,000The price has recently decreased

For Rent

MLS Number 4998584

  • Rentals
  • Bedrooms 2
  • Bathroom 2
  • Lease Term Monthly
  • Utilities None

SUMMER SEASONAL RENTAL!! Charming well kept log home tucked away in a country setting in Windham. Centrally located between Chester, Grafton and Londonderry. A great getaway to enjoy all of what VT has to offer (summer activities, wildlife and hiking trails to name a few). Fully furnished and all inclusive for $3,000.00 per month. Available July 2024 thru October 2024. Application required.

Listed by Team BVA Rentals of Barrett and Valley Associates Inc.

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.77% last updated on 2024-07-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

6802 Popple Dungeon Road Windham VT 05359

MLS Number 4982148

  • CommercialLease
  • Lease 1500

Great for storgage.

Listed by Frank Provance of Diamond Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.77% last updated on 2024-07-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity 

Copyright 2024 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 July 24, 2024 7:38 AM EDT

 

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