Flat Fee Real Estate logo

and narrow your search. If you have fewer than 200 results, you can save your search.

Windsor County Real Estate

Windsor County is located along Vermont's eastern border with New Hampshire. It like many of its fellow counties has so much for avid outdoor enthusiasts. From skiing at Okemo Mountain and Suicide Six to flyfishing on the Connecticut River or golfing at the Quechee Club, there is something to do every season in Windsor County. Windsor County also contains many quintessential New England village squares. For instance, the  Village of Woodstock features a retail block, a town square, and the historic Woodstock Inn. Not be outdone though, the County also has other villages, such as Weston that has its own village square and features the famous Vermont Country Store. The largest towns in Windsor County are Hartford, Springfield, and Woodstock. Browse available Windsor County real estate below. 

Windsor County VT Homes for Sale

Tip - Create an account (it’s free) to save your favorite Vermont real estate listings and get notified when similar properties are posted.

Questions? Call Flat Fee Real Estate at 802-318-0833 or contact us online!

338 VT Rt 12 Route Pomfret VT 05091

Pomfret, VT338 VT Rt 12 Route

Price$539,000

Est. Mortgage: $/month

MLS Number 4875258

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,400

Fantastic location and views, this exquisite perfectly-small-house is sited on a knoll above rural VT Rt 12 - looking across at the barn, pastures and hills of a permanently conserved historic Vermont dairy farm. Located in desirable Pomfret Vermont, just 7 mins to Woodstock village - it offers easy access to everything. Offered with all furniture and furnishings - literally move in ready right down to the brand new coffee maker and mugs, linens, kitchen knives. The current owner (second owner) - over the past 12 years - has meticulously renovated this house 100% from the studs up. New heating/central air systems, full back up generator, new insulation, standing seam roof, new windows and doors, new cedar siding, all new kitchen with Bosch appliances, new bathrooms, new hardwood floors, very substantial landscaping - the list goes on. Wonderful bonfire/campsite in the hill above the house has the same fantastic views over the old Lewis farm and hills beyond. This is one of the most exquisite, move-in-ready small homes to hit the market in 2021. Showings will start Sunday morning Aug 1. Cash offers strongly preferred.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

860 Murphy Road Hartford VT 05059

MLS Number 4875243

  • Condo
  • New Contruction Existing
  • Village Quechee
  • Complex Windsor Village
  • Year Built 1982

Fabulous 2BR, 1.5BA end unit townhouse located within walking distance to Lake Pinneo and all of the wonderful amenities Quechee has to offer! Tired of renting---this affordable townhouse style condo features: Recently renovated kitchen with all new appliances, a gas fireplace, open living space, upper balcony, and a walk-out garden patio. Newly installed heat pump system, blown in insulation, and window inserts make this condo energy efficient. Conveniently located close to all amenities that Quechee has to offer. Sale is contingent upon Owner finding suitable housing.

Listed by Herb Hart of Quechee Lakes Real Estate Center

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

693 Lovers Lane Road Chester VT 05143

Chester, VT693 Lovers Lane Road

Price$425,000

Est. Mortgage: $/month

MLS Number 4875140

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,613

On one of the best locations in town you will find this well cared for 3 Bedroom saltbox home on 5.5 private acres just 1 mile from the village. The home is full of charm and many highlights. You'll find a large country kitchen with a ton of counter and cabinet space with an eat in breakfast area that opens up to the side yard deck. The kitchen has a pass through opening to the dining room which has a slider door to a private 10X20 deck ideal for relaxing. The first floor also boasts a good sized living room with woodburning stove, big den that has multiple uses, 1/2 bath and laundry/pantry/coat room off kitchen. The second floor gives you 3 good sized bedrooms including an owners bedroom with private bath and an office perfect for working at home with fiber optic internet available. Hardwood floors are found throughout the first 2 floors. The basement features a huge rec room with a walkout to the backyard. The property itself is exceptional. 5.5 acres, much of it open featuring a side yard along the road hidden by a privacy fence. The other side of the house features the deck where you can sit and listen to the bordering Lover Lane Brook. The backyard slopes down to the firepit and an open field that will make you feel like you are away from it all even though your only a mile from town. The location is perfect!. Just a 20 minute drive to Okemo and close proximity to the VAST trials. The Chester Town Recreation center is just down the street. A must see!

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

603 Mountains Edge Road West Windsor VT 05037

MLS Number 4875136

  • Condo
  • New Contruction Existing
  • Year Built 1984
  • Construction Wood Frame
  • Square Feet 1,800

Spacious condo in coveted Brownsville area on Mt. Ascutney! 3 bedrooms and 3 baths plus a bonus room in this unit. A separate interior entry on the main level provides flexibility for rental, airBnb, in-law quarters - whatever you may need. Master suite on the upper level with large dining/living area with a wide array of configurations for your furnishings. Newer butcher block counters, hardwood floors, fireplace - what a cozy low maintenance place to live. Amenities include snow removal and exterior maintenance as part of the HOA fees. Short walk or drive down to the Climb Fitness club, Ascutney Outdoors' ski/ mountain trails, great Brownsville Butcher and Pantry eatery in town. Wonderful quiet village, easy commute to schools, Upper Valley and other ski /recreational / park areas. A must see in a great condo complex. Schedule your showing today!

Listed by Kevin Channell of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

264 Grasshopper Lane Reading VT 05153

Reading, VT264 Grasshopper Lane

Price$249,900

Est. Mortgage: $/month

MLS Number 4875186

  • Land
  • Acreage 62.45
  • Utilities None
  • Zoning RR10

A tree-lined country lane leads to this 62-acre private parcel of woodlands and open meadow bordered by stone walls, complete with camp and outbuilding. Views of Mt Ascutney. Prime location for hiking, biking, skiing, & miles of trails and dirt roads for horseback riding. Proximity to Okemo Mountain Resort, Echo Lake, Ascutney Outdoors, Green Mountain Horse Association and Woodstock for dining & shopping. Easy access to I-91.

Listed by Scott Monahan of Dark Horse Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

111 Kettlebrook Road Ludlow VT 05149

MLS Number 4875181

  • Condo
  • New Contruction Existing
  • Complex Kettlebrook
  • Year Built 1984
  • Construction Wood Frame

Private and pretty two bedroom, two bath condo in the slopeside Kettlebrook community. On 2 levels, this neat and clean property has sliders to a deck that looks out to the Kettlebrook trail. Upgraded kitchen, flooring, decor and heating system make this a move-in ready condo. In a private, picture perfect setting, the main level has the mudroom, kitchen, dining and living area with sliders to the deck, fireplace and a bedroom and full bath. The lower level walk out has a bedroom and a full bath. There are also outdoor tennis courts for the summer season!

Listed by Suzanne Garvey and Elissa Scully of Mary W. Davis Realtor & Assoc., Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Dean Brook Road Chester VT 05143

Chester, VTDean Brook Road

Price$22,000

Est. Mortgage: $/month

MLS Number 4875070

  • Land
  • Acreage 2
  • Area Rural
  • Utilities None
  • Zoning Res

This wooded and idyllic parcel will make a great recreational campsite for anyone looking to get away from it all. With some light clearing there is a great spot already marked out that might easily accommodate a camper, tent or teepee. With easy access to the road frontage it won't take long to set up camp. Drive-bys are welcome. The boundaries are marked with cable and tape and the proposed area for a driveway is marked in the middle of the road frontage. You will love the sound of the babbling Great Brook right across the street! Come see this lovely site, it's just waiting for your imagination.

Listed by Daire Gibney of Barrett and Valley Associates, Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

2551 Pleasant Street Bethel VT 05032

Bethel, VT2551 Pleasant Street

Price$409,000

Est. Mortgage: $/month

MLS Number 4875088

  • Multifamily Multi-Family
  • Square Feet 2,578
  • Units 2
  • Acreage 2

This farmhouse was renovated and converted into a two unit dwelling. Conveniently located between Bethel village and Randolph, close to I89 in both directions. The upstairs unit offers two bedrooms and bath, kitchen, living room and bonus room. The downstairs unit offers a lovely kitchen and dining room separated by the decorative brick chimney. Beautiful built in shelving, spacious kitchen, as well as a beautiful sunroom, this unit has so much to offer! Come take a look at this great income property!

Listed by Danae LaBounty and Sherri McPhetres of Vermont Heritage Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

574 Willard Road Hartford VT 05059

MLS Number 4875077

  • Condo
  • New Contruction Existing
  • Village Quechee
  • Complex Quechee Hollow
  • Year Built 1978

Updated from top to bottom and everything is included in the sale! Without a doubt this is the prettiest Quechee Hollow condo and is one of the only ones with a washer and dryer in the unit. Located in an idyllic setting in the heart of Quechee Lakes this fully updated 2 bedroom condo makes the perfect home base for all that Quechee Life has to offer. Golf, tennis, skiing - downhill and cross country, fabulous dining and so much more. Showings begin 8/2.

Listed by Kasia Butterfield of Coldwell Banker LIFESTYLES - Quechee

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

108 North View Drive Rochester VT 05767

Rochester, VT108 North View Drive

Price$560,000

Est. Mortgage: $/month

MLS Number 4875234

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,532

You will know you have arrived in the sought after North Hollow area of central Vermont when you step into this property. Surrounded by mountains, farms, trails and a pond right at your door, you will not need to travel to recreate. This 4 bedroom 3 bath home custom built by its owner is well off the roadway for privacy and safety of children and pets. Lots of space for gardening, horse or farm animals complete with a barn for your application as a workshop, animal stalls. storage or garage. Many new updates including a front porch that extends the living area of the home and a hot tub on the side deck for evening sunset viewing. Owners are subdividing the property and will build a smaller home for summer visits on another portion of the land, out of view of this main home. Spacious, bright and airy with open concept living area and walk right out to your attached two car garage to keep it out of the elements year round.

Listed by Patricia Harvey of Xsell Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Broker Reciprocity

Copyright 2021 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 August 1, 2021.