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!

177 Trebo Road Chester VT 05143

Price$215,000

Est. Mortgage: $/month

MLS Number 4766166

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1,458

If your dream is to live in the quaint town of Chester here is your opportunity. This well cared for ranch offers one level living and has some delightful features that will make you smile. Located on a lovely 1.8+/- acre lot, drive into the circular driveway and delight in the lovely planting and flowers. As you step into the entry foyer you will enjoy the slate tile floor as you head to the large fire-placed living room. The newly updated kitchen has interesting features to enjoy while the adjacent dining room makes family meals easy. But wait there is more, the light filled family room provides hours of enjoyment to watch the deer and wildlife. If you prefer, step out on the deck to enjoy an evening beverage and watch the fireflies. After a busy day, retreat to the oversized master suite with warm wood floors and a beautiful stone fireplace fueled with propane. Two more bedrooms, a full basement, detached 2 car garage and a shed complete this lovely home.

Listed by Carol Cole of Muse and Associates Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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

2 Route 100 Andover VT 05143

Price$49,900

Est. Mortgage: $/month

MLS Number 4766254

  • Land
  • Acreage 11
  • Zoning RES

Located half-way between Ludlow and Weston, this 11-acre parcel is ready for you! Engineering shows a three-bedroom home can be built. Close proximity to skiing, dining and shops in Ludlow (5 minutes away) or theater, shops and summer recreation in Weston (also 5 minutes away).

Listed by Claudia Harris of Mary Mitchell Miller Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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

9393 VT Route 12 Road Barnard VT 05031

Price$159,000

Est. Mortgage: $/month

MLS Number 4766286

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Bedrooms 1
  • Square Feet 958

LOCUST CREEK SCHOOLHOUSE. This sweet dwelling started out life as a one-room schoolhouse in the Locust Creek area of Barnard. Enter into the cloak room which provides a convenient mudroom area. To the left is a private room that would make a perfect office/library/craft room. The surprise comes from the expansive main room where you'll find new wood flooring and an upgraded kitchen with new cabinets and a new gas range, dining area and living area with wood stove. Off to the side is a bedroom space adjacent to a full bathroom with newer upgrades, and a walk-in closet. The house is full of light from all directions courtesy of the over-sized windows. The vibe is historic landmark/modern studio. Outside is a generous-sized shed for your garden tools, sporting gear and other storage. A level lawn is dotted with trees and shrubs and there is room for vegetable beds. A split-rail fence lines the road, and some plantings obscure the road for privacy. The property is conveniently located just 8 minutes to Silver Lake, 20 minutes to Woodstock, 25 minutes to Killington ski area, 25 minutes to VT Law School, and 15 minutes to Exit 3 of Route 89! This would be a great starter home or investment property with short-term rental opportunities. Come and check it out!

Listed by Susan Hickey of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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

324 Tall Timber Hartford VT 05001

Price$26,900

Est. Mortgage: $/month

MLS Number 4766336

  • Mobile
  • Year Built 1986
  • Bedrooms 2
  • Square Feet 1,064
  • AVM

1986 Commodore/Parkhill model, 2-bedroom, 2-bath, 14' x 76' single-wide in desirable Tall Timbers residential park! Amenities include in-ground swimming pool and community clubhouse. Water and sewer included in monthly fee.

Listed by Steven Usle of Prudent Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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

Rose Hill Woodstock VT 05091

Price$269,000

Est. Mortgage: $/month

MLS Number 4766133

  • Land
  • Village Woodstock
  • Acreage 4.17
  • Zoning Res

Woodstock Village Land! Rare opportunity to own 4+ buildable acres in the Village of Woodstock. This property, tucked in off of Rose Hill Rd. is an ideal spot to build your dream house and is perfect for a primary or second home. Short distance to town, shopping and restaurants. Easy access to Mt. Tom, and close to Suicide 6 Ski Area, Woodstock Inn Country Club and the Sports Center. Town sewer line already in place onto the property as well as underground conduit for all utilities. Driveway cleared and roughed in up to the building site in the middle of the property. Potential views with clearing of trees. Wonderful opportunity!

Listed by Dan Noble of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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

15 Windy Meadow Road Hartland VT 05048

Price$295,000

Est. Mortgage: $/month

MLS Number 4766118

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,663

Fabulous energy efficient, well maintained split level home in quiet rural neighborhood. Great location - convenient to Woodstock and Upper Valley, but in a town that still offers school choice for high school. New standing seam roof, new hot water system, and new garage doors (installed soon!). Modern kitchen with plenty of cupboards for storage and counter space for food prep. Lovely dining area for intimate family gatherings or spread out on to the deck for large groups of friends and family. First floor master bedroom with private full bath and walk-in closet. Three additional spacious bedrooms offer loads of opportunity for a growing family or hosting guests. Septic designed for 3 bedroom house. Relax and enjoy the warm summer days around the deck and above ground pool. Flat level lawn is perfect for playing outdoor games or hosting a neighborhood block party. Back yard outdoor fireplace is great for toasting marshmallows, telling stories, or enjoying the starlit skies. Develop your green thumb in the established gardens or expand them for greater enjoyment and beauty around this lovely 2.79 acre lot.Two car detached garage with attached equipment shed could easily be turned into a workshop or small home business. Located on the Hartland Winter Trails X-Country Ski trails for summer time hiking or winter time skiing. Tremendous location and value! Won't last long - come take a look today.

Listed by John Bassette of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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

2220 Vt Route 103 South Highway Chester VT 05143

MLS Number 4766090

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 2
  • Square Feet 2,688

Retail Opportunity! Awesome 2 story property featuring large retail space with large 2 bedroom apartment on 2.22 +/- acres. Great for either owner occupied business or investment property. Act 250 vetted for retail and/or deli, the property offers great exposure on Route 103 South in Chester and has been approved for 10 parking spaces. There is an additional 3/4 bath on the first floor for the business space. Other features include, full basement, new furnace, baseboard heat, flexible floor plan with high ceilings, hardwired smoke and co2 detectors. Whether you are looking for an investment or owner occupied business this property has much potential!

Listed by Geralyn Donohue of Barrett and Valley Associates, Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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

2026 Faybrook Road Sharon VT 05065

Price$280,000

Est. Mortgage: $/month

MLS Number 4766023

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,625

Located less than 2.5 miles from I89 this home offers easy access to all the Upper Valley has to offer and the perfect VT country setting with rolling fields, apple trees, meadows a babbling brook and a view of the mountains. The open spaces in this 3 bedroom home make for a home that is very easy to live in and enjoy.

Listed by Bonnie Bergeron of Martha E. Diebold Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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

505 Fairbanks Turn Hartford VT 05059

Price$385,000

Est. Mortgage: $/month

MLS Number 4766094

  • Residential Single Family
  • Village Quechee
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4

Spacious 4-bedroom home with single level master living with the classic mountain and valley views that brought you to Vermont. Sited on highly desirable private Section 1 view lot with quick access to QLLA Club House by car or golf cart. Cathedral ceiling in living room and top floor bedrooms. Open concept main living space and brick wall fireplace adds to the ambiance of this bright and fun contemporary home. Flooded with natural light from a wall of Southern exposure glass that opens from every room on to the wraparound deck. Extras include air conditioning, wood stove, 5th bedroom potential, 2nd family/kids play room, and two car garage.

Listed by Derek Cosentino of BHG Masiello Group/Quechee

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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

32 Colburn Road Chester VT 05143

Price$345,000

Est. Mortgage: $/month

MLS Number 4765868

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,728

So much to appreciate in this almost-new home. Built with green technology and the ability to be off grid. Custom designed one level living with additional square footage above and below if expansion is desired. Preparing a meal for your guests is a breeze in the open kitchen: double ovens, soapstone counters and bamboo cabinetry made in the US. Hardwood maple flooring throughout the residence. If you need to work from home, the oversized master suite has separate office space. Solar system installed in 2014 generates enough energy so you may not get an electric bill. Quality mechanicals include air exchange heat system, R-39 insulation, auto propane generator, central air conditioning and a whole-house humidifier. Fish on the bordering Williams River, roam around your own 13 acres or the abutting 30 acres of conserved town land with ponds and trails, grow your own vegetables in the raised beds and ski and golf at nearby Okemo Mountain Resort. A wonderful location for year-round or part-time residents.

Listed by Teresa DiNapoli of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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 July 22, 2019.