Previous Previous ImageNext Next Image
Slideshow Divider

Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

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.

For more information, any questions you may have & to schedule a show, please feel free to give us a call or contact us online.

6802 Popple Dungeon Road Windham VT 05359

Windham, VT6802 Popple Dungeon Road

Price$2,995,000The price has recently decreased

MLS Number 4889528

  • Commercial
  • Acreage 639.3

Turn onto Popple Dungeon Road once you hit the property line you'll be welcomed with stone walls and mature maples. What was once a thriving golf course can now be transformed into whatever your your heart desires. (within the law) This 639+ acre parcel would be ideal as an equestrian farm, hunting preserve, farm, wellness retreat etc. With acres of woods, meadows, ponds and vista views, the setting is idyllic. The current Club House needs total restoration but could be a beautiful residence, gather place for members or guests. All you need is a vision the blank canvas is there!

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:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

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

2226 West Windham Road Windham VT 05359

Windham, VT2226 West Windham Road

Price$1,790,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4912508

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 5
  • Square Feet 4,800

Looking for your Vermont Legacy Property? Cobb Brook Farm has been in the same family for three generations and it is now time for new owners! Nestled in the West Windham Valley, this authentic farmhouse has been lovingly crafted into a welcoming escape from life's hustle and bustle. Traditional lines and accents are preserved within an updated home meant for the Vermont lifestyle! Spend time in the woods and meadows, exploring Cobb Brook, swimming in the pond, or enjoying the lovely stone terraces accentuated by extensive perennial gardens. The original 1790's farmhouse was expanded in 2005 by a locally crafted post & beam addition, a creative blend of old and new. Natural light flows in from the large windows throughout. Local Danby marble graces the chefs kitchen providing a cheerful efficient workspace. Spend the evenings in front of the cozy woodstoves after a day snowshoeing or skiing at one of the 5 ski areas within 30 minutes of Cobb Brook Farm. Seven bedrooms provide room for larger groups. Ample living spaces both indoors and out allow for time to relax and enjoy. There is even a home office with a private entrance. Set on the back side of Glebe Mountain, this charming farm has endless possibilities. Suitable as a horse property, an event venue, artist and yoga retreat or as your homestead, this is a special piece of Vermont, and an unusual offering. Sellers are licensed Real Estate Agents.

Listed by Alison Cummings and 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:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

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

1245 Burbee Pond Road Windham VT 05359

Windham, VT1245 Burbee Pond Road

Price$499,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4922198

  • Residential Single Family
  • Construction Existing
  • Square Feet 1,800
  • Bedrooms 4
  • Bathroom 2

This well maintained home borders Burbee Pond in a serene country setting with wildlife and beautiful views. A great spot to relax in the Vermont outdoors with a heated outdoor pool, large deck with a hot tub, sprawling lawn, beautiful gardens, blueberry bushes, apple trees and a greenhouse for growing and equipped with electric and water. New upgrades to the four bedroom home include heat pumps, renovated bathrooms, new flooring and appliances, new pressure tank and insulated attic and basement. The two car garage is fully insulated and heated. 7.2 miles from Magic Mtn and Lowell Lake. This home is a must see!

Listed by Jessica Citera 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: 6.29% last updated on 2022-09-22

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

7271 Windham Hill Road Windham VT 05359

Windham, VT7271 Windham Hill Road

Price$274,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4929888

  • Residential Single Family
  • Bathroom 3
  • Construction Existing
  • Bedrooms 3
  • Square Feet 1,266

This sweet A-Frame has plenty to offer! Located on the beautiful Windham Hill Road, within 30 minutes to Magic Mountain, Bromley Mountain, and Stratton Mountain, this would make an excellent vacation home or primary home for anyone that loves nature or hitting the slopes. Surrounded by conserved land, woods, wetlands, and pastures, this is the bird watchers dream location. The house has been very well maintained by the current owners, who replaced the shingle roof only 3 months ago. They have also installed a dog fence which they're happy to keep up for the dog lover, or take down if desired. After a long day, this is a perfect spot to get cozy by the fireplace while enjoying the rustic ambiance. Come see for yourself!

Listed by Chelsea Cary of Barrett & Valley Associates,Inc/Sprin

{$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:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

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

3709 Windham Hill Road Windham VT 05359

Windham, VT3709 Windham Hill Road

Price$195,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4922505

  • Residential Single Family
  • Construction Existing
  • Bedrooms 1
  • Square Feet 420
  • Acreage 20

Off the grid 3 season 30x14 Tiny House located on 20 acres overlooking a spring fed pond and on a Vermont country road. House features solar panels and a generator. There is a drilled well (not connected to the house), a 10x14 shed, 10x10 horse barn with coral, 12x12 pig pen, herb garden, raspberry & blueberry bushes and a stream. You could build your dream home as there is an approved 3 bedroom septic design with wastewater permit (WW-2-2380) and electric on site (not connected to the house). This is a nature lovers dream location with fish, deer, fox and bear! This special property is waiting just for you. Cannot live there full time unless you put in the septic system.

Listed by Jennifer Densmore of Deerfield Valley Real Estate

{$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:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

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

Lot 8 Glebe Mountain Road Windham VT 05359

Windham, VTLot 8 Glebe Mountain Road

Price$42,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4907875

  • Land
  • Acreage 2.29
  • Utilities None
  • Zoning Rural Residential

This 2+ acre wooded corner is one of the larger lots in the Timber Ridge Association and is easily accessible. Walk to mountain trails to hike or snowmobile. Just 4.2 miles from Magic Mountain. Easy drive to Londonderry (6 miles) and Chester (11.9 miles).

Listed by Jessica Citera 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: 6.29% last updated on 2022-09-22

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

3091 Rt 121 Windham VT 05143

Windham, VT3091 Rt 121

Rental Price$15,000The price has recently decreased

For Rent

MLS Number 4930450

  • Rentals
  • Bathroom 2
  • Lease Term Seasonal
  • Bedrooms 4

If you are looking for a cozy retreat to weather the cold and snow look no further. Beautifully furnished farmhouse centrally located to Chester, Grafton and Londonderry. Close to recreational sites. 20 miles or less to the ski mountains (Stratton, Bromley, Okemo and Magic). Available for January-April 2023 season. $15,000.00 all inclusive.

Listed by Jessica Landers 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: 6.29% last updated on 2022-09-22

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

Broker Reciprocity

Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. 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 September 29, 2022 3:24 AM EDT.

 

Pomfret Dream

6 BR, 57.55 +/- AC $1,285,000 Details

Newbury, Huge Views+Pond

Post+Beam, 27 AC $849,900 Details

 

Stratton Trail Views, 45 Ac

Frank Lloyd Wright Design  $3,950,000 Details