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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 to be outdone though, the County also has other villages, such as Weston which 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

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2646 Curtis Hollow Road Woodstock VT 05071

MLS Number 4954660

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,352

Delano Birches Farm , built in 1834, has been lovingly cared for by the present owners for 36 years. The approach is down a country lane bordered by stone walls and mature trees. The owners added a bright open family /dining room and large primary bedroom with bath. This classic country home is filled with charm . There are two stone fireplaces as well as original wood floors. The grounds include a lovely year round pond , gardens as well as a brick patio for entertaining. Only minutes from Killington for skiing and historic Woodstock village for shops and restaurants. The area offers sports and entertainment for all seasons .

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 2023
* 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.

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157 Murdock Road Chester VT 05143

Chester, VT157 Murdock Road

Price$675,000

Est. Mortgage: $/month

MLS Number 4954753

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,051
  • Construction New Construction

A mix of artistry and environmental features are the strong points. This 3 bedroom house on 30+/- acres is only 8 miles to Okemo. This dream home was started with only the best materials and construction techniques. The dream is 95% finished and due to health factors the owner must sadly find the right owner who will bring this project to completion. Originally an off the grid fully sustainable home, it's now hooked up to the grid with backup Kohler generator and solar panels. Cedar siding with natural insect fighting abilities adorns the exterior and is protected by a high end standing seam roof. This house is ready for the elements! Inside the details continue, enter the garage and find a spacious mudroom space. The kitchen offers environmental quartz countertops of seashells and sea glass, equipped with an Italian LaNordica wood cook stove and stainless appliances with plenty of space to entertain. The beautiful oak floors and trim were cut from the homesite and milled locally. The main level is open concept and also includes a bedroom, office with French doors, full bath and laundry. Upstairs are the second and third bedrooms with a half bath. On the lower level walkout there is a Morso wood stove and to be finished rooms. The property comes with a cottage with a kitchen, wood stove, solar panels and a loft. This cottage is still off grid. Priced so you can finish this masterpiece! Taxes are based on current town assessment. Showings begin June 3rd at 11am.

Listed by Katherine Burns and Joseph Karl of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 2023
* 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.

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220 Spring Street Stockbridge VT 05762

Stockbridge, VT220 Spring Street

Price$169,900

Est. Mortgage: $/month

MLS Number 4954843

  • Residential Single Family
  • Bedrooms 6
  • Square Feet 4,548
  • Bathroom 6
  • Construction Existing

A lot to consider with this property - do I renovate, do I tear it down and start from scratch.... A great private location with a drilled well, community septic, power etc.. Close to all four-season recreation opportunities. Come take a look and see which direction you want to take it. Property is best suited for cash sale. All information deemed correct - Buyers and buyer's agents should do their due diligence - owner has never lived on the property. No interior access available at this time. Property is being sold "As Is"

Listed by Linda Benoit of Highland Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 2023
* 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.

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1157 Blackmer Road Pomfret VT 05067

Pomfret, VT1157 Blackmer Road

Price$1,160,000

Est. Mortgage: $/month

MLS Number 4954526

  • Residential Single Family
  • Square Feet 3,302
  • Bathroom 3
  • Bedrooms 6
  • Construction Existing

“MISTY VALE” - One of the most charming country RETREAT properties that our company has ever listed. Located in desirable Pomfret Vermont, just 20 mins to Woodstock and 30 mins to Hanover/Dartmouth, Misty Vale enjoys complete end of road privacy, sited on +/- 57 acres with TWO wonderful swimming ponds, gardens and landscaping, open meadows, woods and trails, a fantastic screen porch overlooking the 2nd pond, and one of the most charming great room/gathering room (c. 1810) with old beams, ceilings and floors, and a fabulous stone-faced wood-burning fireplace. This family compound property sleeps 14 people in two separate houses (the "main house" and the "barn house"), each with their own kitchen, living/dining/great room spaces, bedrooms and baths. A detached shed-garage and a charming gardening/studio shed (with glass doors) are nearby. Misty Vale has also been successfully rented. It is not enrolled in a current use conservation plan. Right of first refusal is in place. Each building has a full automatic propane backup generator, drilled well and modern septic system. A pre-listing inspection report was completed by Dave Desimone/River Valley Home Inspections. MISTY VALE is a picturesque photographic haven for all seasons. A property like this rarely becomes available.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 2023
* 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.

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7429 US Route 4 Bridgewater VT 05034

Bridgewater, VT7429 US Route 4

Price$469,500

Est. Mortgage: $/month

MLS Number 4954530

  • Residential Single Family
  • Bedrooms 3
  • Construction Existing
  • Square Feet 1,700
  • Bathroom 2

THE SUGAR HOUSE - Gorgeously renovated in 2007, this sunny home is proudly situated in the heart of historic Bridgewater, Vermont - a mere ten minutes from the village of Woodstock. With three bedrooms, two bathrooms, an open kitchen, and fully updated systems, this home enjoys walking distance to swimming holes, biking, horseback riding, local hiking trails, Ramunto's Pizza, and the Bridgewater Mill. The VAST trail is located about forty meters behind the house - excellent for winter recreation or for a quiet summer hike in the Green Mountains. The two-car garage has a spacious second-floor workshop, and the chicken coop is ready for your brood - or for simply enjoying a brew in the evening. Area ski resorts - including Okemo, Killington, Pico and Saskadena Six - are all easily accessible along well-maintained Route 4. While the home lives beautifully as a primary or vacation residence, it also boasts an excellent short-term rental history. With terrific school options and move-in ready condition, this property is a wonderful opportunity to have a home in the Upper Valley.

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 2023
* 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.

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1140 Murphy's Road Hartford VT 05059

Hartford, VT1140 Murphy's Road

Price$679,000

Est. Mortgage: $/month

MLS Number 4954544

  • Condo
  • Square Feet 2,439
  • Bedrooms 3
  • New Contruction Existing
  • Village Quechee

Outstanding end unit located in Deere Run Condominium Village. Overlooking the Lakeland Golf course and Lake Pineo. Bike, Walk and Golf cart distance to the Lake Pineo beach and cross the Ottauquechee river to the Quechee Lakes campus and club facility. This 3+ bedroom townhouse is in excellent condition with many wonderful upgrades and improvements. Three full baths and sauna compliment all the bedrooms and the near 2,400 square feet of finished space allows for comfort throughout. Beautiful renovated kitchen with upgraded appliances and new counter tops and fixtures . Lovely wrap around deck with BBQ right off the kitchen and dining area. Beautiful hard wood flooring along with ceramic tile add to the quality throughout. Direct Vent propane heat and two mini splits A/C with electric back up allow for comfort year round. Lower level family room with 3rd bedroom and bath and an extra full size room gives you additional options to consider. Master Bedroom is extremely spacious with renovated master bath and slider leading to a westerly facing balcony . Nice office space loft area directly adjacent to bedroom with storage area. This townhouse is being offered completely furnished and ready for immediate occupancy to enjoy the entire Quechee summer !

Listed by Charles Bacon of Quechee Lakes Real Estate Center

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 2023
* 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.

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244 Main Street Chester VT 05143

Chester, VT244 Main Street

Price$599,999

Est. Mortgage: $/month

MLS Number 4954502

  • Residential Single Family
  • Construction Existing
  • Square Feet 4,475
  • Bathroom 8
  • Bedrooms 7

You can sometimes search a lifetime for a property like this, a home that has a story, a town that is known to be quintessential VT living, and one that you can operate as an Inn or Bed & Breakfast, or have a wonderful family compound. Seek no further than this 1800's historical Victorian. The main house has 6 bedrooms on the second floor each with it's own private bathroom. On the first floor you'll find a kitchen prime for your renovation ideas, a formal dining room, front living room and a den that's ideal for a home office with fiber optic internet. You will also find gorgeous hardwood floors, original interior oak trim and a grand stairway leading up to the second floor. There is also a 1 bedroom apartment upstairs above the barn area. The porch overlooks a gorgeous green and town setting with shopping and restaurants alike. Complete this package with a guest cottage that was just fully renovated. Being sold mostly furnished, this will not last through the Summer.

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 2023
* 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.

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10024 Vermont Rte 12 Bethel VT 05032

Bethel, VT10024 Vermont Rte 12

Price$750,000

Est. Mortgage: $/month

MLS Number 4954501

  • Land
  • Acreage 65.26
  • Zoning RURAL

Beautiful acreage with fertile hay fields, hillside trails, mountain views, a meandering river, all in a sun-filled valley. Well, septic, and power on site. There is an old farmhouse that can be rehabilitated or disassembled to salvage the historic post and beams. Close to Silver Lake, Barnard, White River, Woodstock, Killington, the Upper Valley, and all points that the Green Mountain State has to offer. Mixed-use for farming and developing your homestead. The town maintains the bridge that accesses the land.

Listed by Derek Greene of Derek Greene

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 2023
* 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.

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808 Jericho Road Hartford VT 05001

Hartford, VT808 Jericho Road

Price$399,000

Est. Mortgage: $/month

MLS Number 4954471

  • Residential Single Family
  • Bedrooms 6
  • Construction Existing
  • Bathroom 1
  • Square Feet 1,494

Amazing opportunity to recreate this outstanding antique home from years past while bringing the house up to today's standards. The house has been occupied by the seller until recently, although the living space has decrease to only a few rooms on the lower level. Many original features of this glorious home are still present, including the slate roof, wide pine floors, plaster walls, stair bannister, and original trim molding throughout. The furnace, and water heater are in good working condition, and the full bathroom was updated. The original front entrance door is still in place and is outfitted with granite steps, and the stone/brick foundation is dressed with 5” granite veneer. The mica schist stone wall behind the house was built by Pete Clifford, a well-known mason in the area. The stones were harvested from a local quarry, and remain intact to date. The property abuts a small brook and has an open field above the house. This charming home has great potential but being sold “AS IS”.

Listed by Terry Davis of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 2023
* 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.

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1299 Quechee Main Street Hartford VT 05059

MLS Number 4954432

  • Condo
  • Bedrooms 2
  • Square Feet 1,063
  • New Contruction Existing
  • Complex Mill Run

Open and airy townhouse end-unit with water views! Kitchen features granite countertops, stainless steel appliances, tile backsplash and vaulted ceilings with beams. Living room/dining area with wood stove. Primary suite features a sliding glass door with walk-in closet and washer/dryer. Large deck overlooking the Ottaquechee River. Walking trails, Quechee Gorge, and shops and restaurants are all within walking distance. Year round fun with golf, skiing, swimming and so much more just minutes away. Agents: please see non public remarks.

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 2023
* 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

Broker Reciprocity 

Copyright 2023 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 May 31, 2023 11:11 AM EDT