Pending Listings in Windsor County, VT

152 homes

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ABOUT THIS HOME
Pending Listing in Windsor County, VT:
Exquisite Vermont Estate with Okemo and Reservoir views! Discover refined four season Vermont living in this multi-level residence. Blending rustic elegance with modern comfort, the light-filled home showcases rich wood flooring, striking log beam accents, and a dramatic stone- backed gas fireplace as the centerpiece of its open living spaces. French doors connect the kitchen, dining and living areas to the wraparound deck, creating seamless indoor, outdoor flow. A private upper-level primary suite includes a loft office and an outdoor balcony, while 2 additional bedrooms and a full bath complete the main level. The lower level offers a guest bedroom, three quarter bath, spacious den and ge

$1,450,000

4 beds4 baths5,838 sq ft

44 John Deere Dr, Ludlow, VT 05149

Loft office • Recreation room • Reservoir views

CONTINGENT

ABOUT THIS HOME
Pending Listing in Windsor County, VT:
EXCELLENT INVESTMENT PROPERTY CONSISTS OF 2 COMMERCIAL GROUND FLOOR LEVEL SPACES & 7 APARTMENTS. WELL MAINTAINED WITH A GOOD RENTAL HISTORY & A DESIRABLE IN-TOWN LOCATION.

$560,000

— beds9 baths9,740 sq ft

2 Valley St, Springfield, VT 05156

0.24 acre lot • Built 1834 • Listed 138 days

CONTINGENT

ABOUT THIS HOME
Pending Listing in Windsor County, VT:
$3,000 TOWARDS CLOSING COSTS. MOTIVATED SELLER! Welcome to 306 Camp Brook Road, a charming Vermont home nestled on 1.1 peaceful acres in Bethel. This inviting 3-bedroom, 1.5-bath residence offers a perfect blend of classic New England warmth and comfortable living. Step inside to discover beautiful wide-plank wood floors, an airy open-concept living and dining area, and a cozy wood stove—ideal for gathering on chilly evenings. An extra sitting room is perfect for gatherings. Natural light floods the spacious living room through oversized windows, creating a bright, welcoming atmosphere year-round. The kitchen features plenty of cabinet space, updated appliances, and a breakfast bar fo

$299,500

3 beds1.5 baths1,716 sq ft

306 Camp Brook Rd, Bethel, VT 05032

Updated appliances • Open concept living • Cozy wood stove

CONTINGENT

ABOUT THIS HOME
Pending Listing in Windsor County, VT:
Welcome to this 3-bedroom, 1-bath farmhouse in the heart of West Windsor, VT! Inside, you’ll find a warm and inviting open-concept layout featuring a main floor bedroom, and mudroom. Perfect for gatherings or quiet evenings. Beyond the farmhouse, the property includes a wonderful collection of outbuildings—a classic barn, a 2-car garage, a workshop with a woodstove, and even a sugarhouse—making it ideal for hobbies, homesteading, or simply enjoying the Vermont lifestyle. There is over 18 acres of wide open field, ready for your animals, and you can even have ample hay for feed. With plenty of space indoors and out, this property offers both charm and practicality in a beau

$499,900

3 beds1 bath1,832 sq ft

3738 Brownsville Hartland Rd, West Windsor, VT 05089

Over 18 acres • Classic barn • Mudroom

CONTINGENT

ABOUT THIS HOME
Pending Listing in Windsor County, VT:
Winterplace on Okemo. Welcome to this beautifully updated 3-bedroom, 2-bathroom condo, ideally situated in the highly coveted Winterplace community on Okemo Mountain. This exceptional home offers unparalleled convenience for ski enthusiasts, boasting easy access to Okemo's main base and the summit, all within a short walk to the nearby ski trail. Step inside to discover a spacious open-concept design that seamlessly blends the living, dining, and kitchen areas. The inviting living room, complete with a cozy wood-burning fireplace, sets the perfect ambiance for relaxation. The well-appointed kitchen features a convenient breakfast bar, perfect for casual meals. With three comfortable bedroom

$730,000

3 beds2 baths1,296 sq ft

42 Harrison Ln Unit M 205, Ludlow, VT 05149

Open-concept design • Hot tubs • Breakfast bar

Property at 127 Pleasant St, Cavendish, VT 05142, 4 beds, 2 baths

$549,000

4 beds2 baths2,300 sq ft

127 Pleasant St, Cavendish, VT 05142

Property at 101 Ledgewood Rd Unit G-1 with G-1 Garage, Ludlow, VT 05149, 4 beds, 3 baths

$1,350,000

4 beds3 baths2,138 sq ft

101 Ledgewood Rd Unit G-1 with G-1 Garage, Ludlow, VT 05149

Property at 32 Oak Ln, Springfield, VT 05156, 3 beds, 2 baths

$93,999

3 beds2 baths880 sq ft

32 Oak Ln, Springfield, VT 05156

Property at 17 High St #2, Woodstock, VT 05091, 2 beds, 1 bath

$300,000

2 beds1 bath1,040 sq ft

17 High St #2, Woodstock, VT 05091

Property at 149 Willow Cir, White River Junction, VT 05001, 2 beds, 2 baths

$135,000

2 beds2 baths1,248 sq ft

149 Willow Cir, White River Junction, VT 05001

Property at 5527 Route 106, Weathersfield, VT 05151, 3 beds, 1 bath

$129,900

3 beds1 bath1,064 sq ft

5527 Route 106, Weathersfield, VT 05151

Property at 26 Dorman Rd, Chester, VT 05143, 4 beds, 2 baths

$299,000

4 beds2 baths1,248 sq ft

26 Dorman Rd, Chester, VT 05143

Property at 2179 US Route 4 W, Bridgewater, VT 05034, 2 beds, 1 bath

$550,000

2 beds1 bath1,008 sq ft

2179 US Route 4 W, Bridgewater, VT 05034

Property at 198 Okemo Trailside Rd Unit 43D, Ludlow, VT 05149, 4 beds, 2.5 baths

$665,000

4 beds2.5 baths1,842 sq ft

198 Okemo Trailside Rd Unit 43D, Ludlow, VT 05149

Property at 935 French Meadow Rd, Springfield, VT 05156, 3 beds, 2 baths

$425,000

3 beds2 baths1,809 sq ft

935 French Meadow Rd, Springfield, VT 05156

Property at 501 Gates Rd, Chester, VT 05143, 1 bed, 1 bath

$185,000

1 bed1 bath616 sq ft

501 Gates Rd, Chester, VT 05143

Property at 423 Main St, Chester, VT 05142, 6 beds, 5 baths

$495,000

6 beds5 baths3,217 sq ft

423 Main St, Chester, VT 05142

Property at 129 Ash Ln, Springfield, VT 05156, 2 beds, 1 bath

$89,499

2 beds1 bath746 sq ft

129 Ash Ln, Springfield, VT 05156

Property at 470 Bentley Rd Unit 7-5443, Hartford, VT 05059, 4 beds, 3 baths

$1,070,950

4 beds3 baths1,586 sq ft

470 Bentley Rd Unit 7-5443, Hartford, VT 05059

Property at 1011 Knapp Pond Rd, Cavendish, VT 05142, 2 beds, 2 baths

$114,900

2 beds2 baths1,056 sq ft

1011 Knapp Pond Rd, Cavendish, VT 05142

Property at 2 Highland Ave, Woodstock, VT 05091

$650,000

— beds— baths— sq ft

2 Highland Ave, Woodstock, VT 05091

Property at 0 Leonard Rd, Pomfret, VT 05067

$140,000

— beds— baths— sq ft

0 Leonard Rd, Pomfret, VT 05067

Property at Goulden Ridge Rd, Weathersfield, VT 05030

$125,000

— beds— baths— sq ft

Goulden Ridge Rd, Weathersfield, VT 05030

Property at 0 Mecawee Rd, Bridgewater, VT 05091

$650,000

— beds— baths— sq ft

0 Mecawee Rd, Bridgewater, VT 05091

Property at 00 Chapel Hill Rd #2, Sharon, VT 05065

$290,000

— beds— baths— sq ft

00 Chapel Hill Rd #2, Sharon, VT 05065

Property at 459 Sugar Hill Rd, Bethel, VT 05032

$100,000

— beds— baths— sq ft

459 Sugar Hill Rd, Bethel, VT 05032

Property at 0 Remington Rd #7, Chester, VT 05143

$85,000

— beds— baths— sq ft

0 Remington Rd #7, Chester, VT 05143

Property at 0 Hoey Rd, Cavendish, VT 05142

$125,000

— beds— baths— sq ft

0 Hoey Rd, Cavendish, VT 05142

Property at 0 Town Farm Rd, Norwich, VT 05055

$648,000

— beds— baths— sq ft

0 Town Farm Rd, Norwich, VT 05055

Property at 25 Maxfield Ln, Hartland, VT 05048, 3 beds, 2 baths

$49,500

3 beds2 baths1,120 sq ft

25 Maxfield Ln, Hartland, VT 05048

Property at 76 Colonial Dr #13, White River Junction, VT 05001, 2 beds, 1.5 baths

$239,900

2 beds1.5 baths1,072 sq ft

76 Colonial Dr #13, White River Junction, VT 05001

Property at 152 Webster Rd, Hartland, VT 05048, 2 beds, 1 bath

$399,000

2 beds1 bath1,200 sq ft

152 Webster Rd, Hartland, VT 05048

Property at 397 Thompson Rd, Stockbridge, VT 05772, 1 bed, 0.5 baths

$50,000

1 bed0.5 baths448 sq ft

397 Thompson Rd, Stockbridge, VT 05772

Property at 238 S Hollow Ln, Rochester, VT 05767, 4 beds, 5.5 baths

$1,495,000

4 beds5.5 baths5,177 sq ft

238 S Hollow Ln, Rochester, VT 05767

Property at 336 Piper Hill Rd, Weston, VT 05161, 3 beds, 1.5 baths

$247,000

3 beds1.5 baths1,458 sq ft

336 Piper Hill Rd, Weston, VT 05161

Property at 43 Eastman Rd, Sharon, VT 05065, 3 beds, 1.5 baths

$385,000

3 beds1.5 baths1,875 sq ft

43 Eastman Rd, Sharon, VT 05065

Property at 86 Woodhaven Dr, Hartford, VT 05001, 2 beds, 1.5 baths

$249,000

2 beds1.5 baths1,008 sq ft

86 Woodhaven Dr, Hartford, VT 05001

Property at 5 Clough Ave, West Windsor, VT 05089, 3 beds, 1 bath

$79,900

3 beds1 bath1,392 sq ft

5 Clough Ave, West Windsor, VT 05089

Property at 184 Hazen St, White River Junction, VT 05001, 3 beds, 1.5 baths

$299,500

3 beds1.5 baths1,408 sq ft

184 Hazen St, White River Junction, VT 05001

Property at 48 School St, North Springfield, VT 05150, 2 beds, 1 bath

$205,000

2 beds1 bath676 sq ft

48 School St, North Springfield, VT 05150

Property at 226 Fellows Hill Rd, Springfield, VT 05156, 3 beds, 1 bath

$79,900

3 beds1 bath1,075 sq ft

226 Fellows Hill Rd, Springfield, VT 05156

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Pending Listings in Windsor County

There are currently 152 pending listings for sale in Windsor County at a median listing price of $550K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Windsor County stay on the market for 89 days. This map is refreshed with the newest listings in Windsor County every 15 minutes.

In the past month, 103 homes have been sold in Windsor County. In addition to houses in Windsor County, there were also 105 condos, 4 townhouses, and 26 multi-family units for sale in Windsor County last month. Find your dream home in Windsor County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Windsor County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Windsor County. If you're looking to sell your home in the Windsor County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Windsor County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Copyright 2025 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Tue Dec 02 2025 on the search page

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