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, in the  Village of Woodstock features a retail block, 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. 

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

Questions? Give us a call at 802-318-0833 or contact us online!

362 UPPER ROAD Bridgewater VT 05035

Price$835,000

Est. Mortgage: $/month

MLS Number 4741360

  • Residential Single Family
  • Listing Agent Name Laird Bradley
  • Construction Existing
  • Bathroom 11
  • Bedrooms 13

Word of mouth remains the Gold Standard in advertising...it has to be earned.The October Country Inn deservedly enjoys the finest reputation for warm, professional service in the tradition of New England's friendly hospitality. The original antique cape-style farmhouse dates from the founding of the township and is the centerpiece of the gracious, sunlit Inn. The in is expansive, but efficient with common rooms encouraging gatherings fireside and around expansive dining tables. The 10 rental rooms, all with private bathrooms, are cozy and well-appointed. The owners provide a hearty Vermont breakfast and serve evening meals for groups by prior reservation. The grounds are beautifully landscaped and a recently refurbished swimming pool overlooking the River Valley is a popular gathering spot on hot summer days. A private 3 bedroom owners quarters is connected to the main building. This arrangement allows the owners to interact with guests, but enables them to maintain a personal life. Offered 'turn-key' as a profitable business with many years of goodwill conveying too!

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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 A VisitAsk A QuestionMore Details

31 Elm St Woodstock VT 05091

Price$1,200,000

Est. Mortgage: $/month

MLS Number 4741335

  • Residential Single Family
  • Listing Agent Name Jennifer Falvey
  • Village Woodstock
  • Construction Existing
  • Bathroom 6

Lovely in-town classic, historical colonial, just steps from the center of Woodstock. Excellent condition. Entire house completely renovated in 2002. Large gourmet kitchen, with island, DCS range stove and Bosch dishwasher. Beautiful master bedroom suite with sitting room and must-see marble master bath. Traditional study/den and dining room with custom built ins. Original hand-hewn exposed beams can be seen in many of the rooms. Third floor dorm sleeps 8, and seconds as playroom with ensuite bath and double showers. Absolute must see. Broker owned.

Listed by Jennifer Falvey of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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 A VisitAsk A QuestionMore Details

262044 Trebo Chester VT 05143

Price$85,000

Est. Mortgage: $/month

MLS Number 4741127

  • Land
  • Listing Agent Name Jessica Citera
  • Acreage 11.4
  • Zoning Residential

Vermont land with a view! These two 11.4 acre parcels are in a desirable location in Chester tucked away on a dirt road yet still close to town. Cleared area perfect to build and back half offering both soft and hardwood trees. With a little clearing you can enjoy amazing view of Ascutney Mountain and surrounding ridge lines. Get your piece of Vermont!

Listed by Jessica Citera of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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 A VisitAsk A QuestionMore Details

492 North Main Street Bethel VT 05032

Price$224,000

Est. Mortgage: $/month

MLS Number 4741248

  • Residential Single Family
  • Listing Agent Name Susan Wylie
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3

This home is a 3 bedroom, 2 bath house on 1.2 acres in a neighborhood with an easy walk to the village. It has an extra large living room for hosting with a Vermont Castings wood stove for ambiance and emergency heat. There is a large kitchen with an eat-in dinning area. There is a pantry/laundry room with a chest freezer and tons of shelving. Den/office or possible ground floor 4th bedroom. Large master bedroom with 2 closets. Other bedrooms have large closets as well. 3 season, south facing sun porch. Full, unfinished basement. Deck and patio for outdoor entertaining. Wrap around driveway with plenty of parking and detached garage with storage. Up sloping backyard with established apple and pear trees, blueberry bushes and plenty of space and sun for a garden.

Listed by Susan Wylie of Vermont Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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 A VisitAsk A QuestionMore Details

Folding Hills Woodstock VT 05091

Price$139,000

Est. Mortgage: $/month

MLS Number 4741252

  • Land
  • Listing Agent Name Matthew Spittle
  • Acreage 17.2
  • Zoning RR5

Great views in South Woodstock! Privacy on the trail system. Two miles to Green Mountain Horse Association. 30 minutes to skiing at Killington. 3 miles to the Woodstock Country Club. Four bedroom septic design approved. Also septic designs for a second house that is out of sight of the primary house site. The property has state approval for a two lot subdivision.

Listed by Matthew Spittle of Vermont Horse Country Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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 A VisitAsk A QuestionMore Details

22 Norford Lake Road Norwich VT 05055

Price$549,000

Est. Mortgage: $/month

MLS Number 4741239

  • Residential Single Family
  • Listing Agent Name Jennifer Snyder
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3

Ideally located just 5 miles from downtown Norwich, this wonderful Cape is waiting for you! This home has a unique floor plan with an exuberant color/decorating scheme. This is truly a blank slate with great bones. A traditional Cape style that opens up into spacious rooms, light and bright sitting areas, open concept, high ceilings and a Master Bedroom Suite on the first floor, or on the second! There are hardwood floors, slate entryways, ample mudroom space and an attached 2 car garage. The living areas have a warm, cozy feel with a wonderful fireplace in the formal living room. There are views from every window overlooking the open fields. And don't forget access to the privately shared pond. Ready to enjoy all that this house has to offer? Don't wait, this is the one. With spring just around the corner, you will be mesmerized by the beauty that surrounds you when sitting out on the stone patio. This is home.

Listed by Jennifer Snyder of Coldwell Banker LIFESTYLES - Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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 A VisitAsk A QuestionMore Details

Birch Ludlow VT 05149

Price$80,000

Est. Mortgage: $/month

MLS Number 4741366

  • Land
  • Listing Agent Name Roger Danyew
  • Acreage 1.76
  • Zoning res

One of the last undeveloped lots in an established community only minutes to Okemo Mountain. This nearly (2) acre wooded parcel is ready to be developed with power and municipal septic at the edge of the property. The topography is relatively level though it is slightly elevated off the road. It offers very access to Route 103 being less than a mile.

Listed by Roger Danyew of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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 A VisitAsk A QuestionMore Details

289 Grafton Street Chester VT 05143

Price$125,000

Est. Mortgage: $/month

MLS Number 4741264

  • Residential Single Family
  • Listing Agent Name Amanda Stearns
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4

Handyman special! This property was once a historic gem and had many upgrades when it was operated as a bed and breakfast. Through the years it has had some deferred maintenance and could use a good polish to bring it back to life. The main entry welcomes you into a massive country kitchen with custom cabinetry, warm softwood floors and an expansive deck that overlooks the rear yard. The front sitting room and formal dining room offer an open concept and enjoy a large wood stove that is a focal point. The other two rooms could be converted into private quarters for guest or used as a first-floor master bedroom. Travel up the original grand staircase and find four more rooms with 2 full baths. The home is heated with a forced air furnace but also is equipped with a large pellet furnace if you choose to heat fuel free. This property has frontage on two roads and is walking distance to the picturesque village of Chester, VT.

Listed by Amanda Stearns and Joan Morey of Barrett and Valley Associates, Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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 A VisitAsk A QuestionMore Details

24 Pine Street Springfield VT 05156

Price$32,000

Est. Mortgage: $/month

MLS Number 4740991

  • Residential Single Family
  • Listing Agent Name Dick Thackston
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4

Property is HUD Owned. FHA Case# 531-024933. Room for everyone! Spacious four bedroom home close to schools and amenities! Paved driveway with a carport and public utilities! LBP. Finance Terms: Cash, 203K.

Listed by Dick Thackston of R.H. Thackston & Company

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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 A VisitAsk A QuestionMore Details

172 Sugar Hill Hartford VT 05059

MLS Number 4740980

  • Condo
  • Listing Agent Name Herb Hart
  • Village Quechee
  • Complex Sugar Hill
  • Year Built 1981

Spacious and lovingly cared for townhouse located in the Sugar Hill Condo Association. Three bedrooms and 2.5 bathrooms with a bonus room, family room and laundry room in the finished basement.

Listed by Herb Hart of Brick & Barn Real Estate Group/ Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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 A VisitAsk A QuestionMore Details

Broker Reciprocity

Copyright 2019 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 March 21, 2019.