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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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842 Bowen Hill Road Springfield VT 05156

Springfield, VT842 Bowen Hill Road

Price$419,000

Est. Mortgage: $/month

MLS Number 5026471

  • Residential Single Family
  • Full Bath 1
  • Address 842 Bowen Hill Road
  • Construction Existing
  • Bedrooms 3

Up the hill and through the woods, you will find a rustic retreat on 9.6 acres of private land, of which approximately 3 acres have been cleared. Upon arrival you will be greeted by a detached, heated, 36' X 36' garage with the capacity and storage space to handle any type of project your heart desires. Inside the home you will find the upper level has 3 bedrooms with brand new carpeting, adequate storage space, and a bathroom off the master. The main level has new wood flooring that includes a cozy living room with a beautiful stone fireplace, and a dining area off the kitchen. A new back door opens onto the newly built back deck, perfect for summer evenings. Off the back deck is a picturesque country setting with bench swings surrounding a brick firepit. The lower level of the home is a versatile space with entry and exit points through the attached garage, and another to the back yard. It includes a half bath, laundry and a large closet. This space could easily be a den, in law suite, or office. This property has been renovated with all the amenities a house in Vermont needs, such as a new electrical panel, whole house generator, all new vinyl siding and window framing, a lifetime steel roof, a brand-new furnace, water heater, refrigerator, washer and dryer. All of this is tucked away in a private, country setting, yet still close to restaurants, stores, and I-91. Come take advantage of these renovations by making this property your own!

Listed by Don Chabot of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* 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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339 Fox Lane Ludlow VT 05149

Ludlow, VT339 Fox Lane, Unit A1

Price$589,000

Est. Mortgage: $/month

MLS Number 5026407

  • Condo
  • Square Feet 2,584
  • Bedrooms 4
  • New Contruction Existing
  • Complex Fox Run

Welcome to Unit A-1, at Fox Run a natural light filled, end unit, with additional windows to let the sunshine in. Fox Run a unique complex of townhomes consisting of four bedroom four bath units situated over looking the Fox Run Golf Course with views of Okemo Mountain through the majestic white pines. Convenient front door parking at this four bedroom four bath townhome that is in turn key condition with a great rental history. In the kitchen enjoy wood cabinetry, and propane range that will have the chef of the family cooking with gas. You'll love the open concept of the main floor, kitchen, dining, living space with exposed wood beams, wood burning fireplace, and oversized sliders to the expansive deck with an expansive sky view. Get cozy in the well appointed living room and take in the Okemo view. Every bedroom has it's own bath for ultimate privacy. This four bedroom unit has so much to offer, walking distance to the Fox Run Golf Course Vermont's only 5 STAR golf course, with championship play on the Heathland Links course that has exceptional views from every hole. Year round activities from golf, bocce, horseshoes, and great hiking through the woods to cross country skiing, snowmobiling and Calcutta's Restaurant with live music on the patio. Just minutes to skiing at Okemo, downtown Ludlow, the lakes region for more recreation, and on the VAST trail for the snowmobile enthusiasts. This is an incredible townhome in an incredible location, a must see to appreciate!

Listed by Frank Provance of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* 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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33 Andover Street Ludlow VT 05149

Ludlow, VT33 Andover Street

Price$335,000

Est. Mortgage: $/month

MLS Number 5026403

  • Condo
  • Square Feet 1,426
  • Bedrooms 4
  • New Contruction Existing
  • Complex Trestle House

Perfect village townhome on the Okemo shuttle- with stunning slope views! This charming property offers the perfect blend of comfort and convenience for your mountain escape. Located on the free Okemo shuttle route, you'll enjoy effortless access to the slopes, and the heart of Ludlow is just a short stroll away. With no Uber in town, being able to walk to the local favorites like Goodman's, Dunkin', The Hatchery, DJs, Main & Mountain and Killarney's for dining and drinks makes this location unbeatable. After a fun night out, enjoy the luxury of walking home with ease. Ideal for families and groups, with a smart family-friendly layout. Quiet sleeping quarters are spread across three levels, ensuring restful nights for everyone. This home is fully furnished featuring 4 bedrooms, with two queen bedrooms, one full bedroom and four twins in the upper bedroom. You'll also enjoy modern amenities including fully equipped and recently remodeled kitchen, cozy living room with plenty of seating for everyone, in-unit laundry and a full basement with storage space for all your ski gear with external access. Loading and unloading is hassle free with parking available for four cars! Don't wait to look at this neat, clean and ready for family made memories in your year round Vermont living retreat.

Listed by Lisa Kelley of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* 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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1130 Safford Road Hartford VT 05059

Hartford, VT1130 Safford Road

Price$849,000

Est. Mortgage: $/month

MLS Number 5026377

  • Residential Single Family
  • Full Bath 2
  • Village Quechee
  • Address 1130 Safford Road
  • Construction Existing

Rarely does such a solidly built, meticulously maintained 5 BR, 5 BA house come on the market in Quechee! The expansive layout of this home can easily accommodate a large family or many visitors. The story of 1130 Safford Road begins with the one-of-a-kind, lush front garden that blooms with dozens and dozens of fragrant, colorful plants and flowers from spring through autumn. You may choose to enter the house through a large, perfectly functional mudroom. Or, you can enter through the more formal front entryway, where your eyes will immediately be drawn to stunning views through large picture windows that comprise the entire back wall. It's a sight to behold. This is a quintessential Vermont property located in a private, quiet country setting that is steps away from the trailhead to the beautiful Section 5 hiking trail network. Gorgeously curated perennial gardens and statuesque trees provide a special ambiance. The large backyard, a rare find in Quechee, is perfect for kids' play or for fruit bearing bushes and trees. The living room features a working fireplace enhanced by five large picture windows, adding warmth and a cozy feel to beautiful Vermont winters. In fact, large picture windows adorn all three floors and overlook striking views of gardens, the backyard and a lovely mountain view. A large, elegant outdoor bluestone patio off of the lower level and a large deck off of the main level provide perfect spots to dine and to view the scenery.

Listed by Herb Hart of Quechee Lakes Real Estate Center

$
$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* 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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18 Timber Creek Road Ludlow VT 05149

Ludlow, VT18 Timber Creek Road

Price$2,300,000

Est. Mortgage: $/month

MLS Number 5026376

  • Residential Single Family
  • Full Bath 3
  • Address 18 Timber Creek Road
  • Construction Existing
  • Bedrooms 4

Timber Creek on Okemo - A Mountain Retreat Like No Other. Discover the perfect blend of privacy and convenience with this stunning Timber Creek home, nestled on 3.31 serene acres at SouthFace Village on Okemo Mountain. Just steps from the Sunshine Quad, you'll enjoy unparalleled mountain access alongside exclusive amenities. This 4-bedroom, 5-bathroom, 3-level timber frame home offers an inviting open floor plan, ideal for hosting family and friends. Soaring cathedral ceilings showcase the craftsmanship of the timber frame design, while the crackling wood-burning fireplace serves as the centerpiece of the cozy living area making this the perfect mountain retreat. The chef's kitchen, featuring a large island, encourages lively gatherings, conveniently open to the dining room perfect for shared meals and many memories. The main level boasts an en suite bedroom, while upstairs you'll find three additional bedrooms, two with private baths making for great guest quarters. The lower level is designed for fun, with a spacious family room perfect for movie or game nights. With a two-car garage, mudroom for all your gear, and access to SouthFace Village amenities-including easy access to the Sunshine Quad located within Southface Village offering you great mountain access, a recently constructed clubhouse, heated outdoor pool and spa, fitness center, locker, and private parking-you'll have everything you need for a luxurious mountain lifestyle!

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* 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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18 Plumley Avenue Ludlow VT 05149

Ludlow, VT18 Plumley Avenue

Price$900,000

Est. Mortgage: $/month

MLS Number 5026367

  • Residential Single Family
  • Full Bath 1
  • Address 18 Plumley Avenue
  • Construction Existing
  • Bedrooms 3

This newly constructed home on the outskirts of Ludlow Village offers modern, efficient living with western views of Okemo Mountain. Constructed by a well-respected Montpelier-based builder, features include: 3 bedrooms (including 2 bedroom suites - one on main level, one on upper level), 2 offices with flexible space that can be converted to additional bedrooms with proper permitting, an open concept living, dining and kitchen area, a wrap around deck and handicap accessibility. Exceptionally energy efficient with triple-pane Marvin windows, R26 insulated walls, and heat pump systems for effective heating and cooling. There is an attached two-car garage on the lower level with additional unfinished space. All brand new and ready for occupancy - a perfect blend of comfort, modern technology with easy access to everything Ludlow.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* 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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95 Meetinghouse Road Norwich VT 05055

Norwich, VT95 Meetinghouse Road

Price$1,369,900

Est. Mortgage: $/month

MLS Number 5026285

  • Residential Single Family
  • Full Bath 2
  • Address 95 Meetinghouse Road
  • Construction Existing
  • Bedrooms 4

This classic center-entrance colonial home offers a serene retreat nestled in the heart of Norwich. Surrounded by trees and tranquility, it offers the perfect blend of updated functionality and traditional colonial appeal. The current owners have made significant investments that enhance the quality of life in the home, ensuring your comfort and ease of living. These include a solar array which takes full advantage of the home's SW orientation, a Tesla Energy Storage unit providing whole home back-up power, and central HVAC systems. Other enhancements, such as newly refurbished chimneys, a new wood burning insert in the Rear Living Room, and a new woodburning firebox in the Front Living Room further add to the inviting appeal of this classic home. Enjoy cheerful gatherings around the newly rebuilt backyard fireplace patio. The expansive deck and screened porch extend the home's living area and are perfect for relaxing or entertaining. This offering presents an opportunity to own a wonderful home with updated amenities and classic charm. Don't miss your chance to make this special property your own.

Listed by Alan DiStasio of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* 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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Lot 51 Partridge Road Ludlow VT 05149

Ludlow, VTLot 51 Partridge Road

Price$175,000

Est. Mortgage: $/month

MLS Number 5026282

  • Land
  • Acreage 1.02
  • Area VT-Windsor
  • PricePerSqFt 171568.63
  • Zoning Residential

1.02+/- acres. Lot 51. Ready to build. Prestigious neighborhood, some lots with views of Okemo Slopes with clearing. Very convenient to the village and Okemo Mountain Resort. This property is owned by a Vermont licensed real estate agent.

Listed by Boris Lavanovich of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* 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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Lot 48 Partridge Road Ludlow VT 05149

Ludlow, VTLot 48 Partridge Road

Price$195,000

Est. Mortgage: $/month

MLS Number 5026281

  • Land
  • Acreage 1
  • Area VT-Windsor
  • PricePerSqFt 195000
  • Zoning Residential

1.01+/- acres. Lot 48. Ready to build. Prestigious neighborhood, some lots with views of Okemo Slopes with clearing. Very convenient to the village and Okemo Mountain Resort. This property is owned by a Vermont licensed real estate agent.

Listed by Boris Lavanovich of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* 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

5534 Route 100 Plymouth VT 05056

Plymouth, VT5534 Route 100

Price$475,000

Est. Mortgage: $/month

MLS Number 5026224

  • Residential Single Family
  • Full Bath 2
  • Address 5534 Route 100
  • Construction Existing
  • Bedrooms 3

Attention Skiers and Snowmobilers! This newly updated, open concept 3 bedroom plus den, 2 full bathroom vacation retreat is minutes to Killington, Okemo or Woodstock. Conveniently located off of scenic Vermont Route 100 on 7.9 +/- acres with direct access to VAST Snowmobile Trails from the property. The property is situated across the street from Chloe's Market/ Plymouth Country Store to walk and enjoy gourmet coffee, treats, deli sandwiches, pre-made meals, and more. Wonderful open concept floor plan ideal for entertaining with loads of light and wood floors throughout. New front entry mudroom flows into a new renovated kitchen and brand-new pantry with stainless appliances and counters. After a day of outdoor play, kick back in the open great room and dining area. Cozy up next to the double-sided floor to ceiling fieldstone fireplace hearth with woodstove insert. Family and friends will love the recreation den room with a wall of sliding glass doors that lead you out to a cool deck to enjoy a drink on a summer evening. Close to world class skiing and golf, endless hiking/mountain biking trails, and pristine lakes. The property has an outdoor toy/snowmobile shed plus a one car detached garage. Strong rental potential here! Excellent short term investment opportunity in the heart of ski and snowmobile country. Zoned Residential and Commercial. Come check this one out!

Listed by Marni Rieger of KW Vermont-Killington

$
$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* 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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Broker Reciprocity 

Copyright 2025 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 January 14, 2025 12:23 AM EST