Pending Listings in Windsor County, VT

185 homes

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ABOUT THIS HOME
Pending Listing in Windsor County, VT:
If you are seeking a spot to call home where Mother Nature is your neighbor and best friend, look no further. The moment you arrive; you are immediately drawn to the land across the road. Your own grove of trees with brook frontage and your very own swimming hole. You will spend hours every single day sitting or lying in your hammock in the timber frame Creek House. It is the most therapeutic spot you can ever imagine. Head back across the road to the camp compound. The main cabin is decorated exactly like you would imagine your get away to be. .. natural wood, artifacts, artwork. Enter into the living room with full size futon recessed into the wall. There's a foldout LLBean chair that sle

$329,000

2 beds2 baths652 sq ft

729 Davis Rd, Cavendish, VT 05142

Swimming hole • Brook frontage • Guest cottage

CONTINGENT

ABOUT THIS HOME
Pending Listing in Windsor County, VT:
Classic Deck House design meets the Vermont lifestyle in this inviting Quechee Lakes home. Featuring the signature architectural elements that make Deck Houses so desirable, you'll love the soaring wood ceilings, walls of windows, and seamless connection to the natural surroundings. The open-concept floor plan creates a bright and welcoming living space, perfect for entertaining or everyday living. The primary suite offers a private bath, while two additional bedrooms provide plenty of room for family and guests. A dedicated office makes working from home easy, and the spacious family room offers flexible space for recreation, media, or hobbies. Enjoy seasonal views from multiple decks and

$549,000

3 beds2.5 baths2,187 sq ft

477 Morgan Rd, Hartford, VT 05059

Deck house design • Walls of windows • Private bath

CONTINGENT

ABOUT THIS HOME
Pending Listing in Windsor County, VT:
Experience timeless elegance and rural charm at this meticulously crafted country estate, featuring a historical reproduction Shaker style home designed by renowned architect McKee Wing Roth and built in 1991. Set on 15 deeded acres of rolling pastures, this unique estate blends traditional design with modern sustainability. Conveniently located 6.5 miles from the renowned Crown Point Country Club and under 20 miles from Okemo Mountain Resort. The main residence offers authentic Shaker architectural details and quality craftsmanship and detail throughout. A matching Shaker-style barn includes 2 horse stalls, and ample storage for your needs, while a carriage style garage accommodates 3 vehi

$699,000

2 beds3 baths2,250 sq ft

60 Spencer Hollow Rd, Springfield, VT 05156

Horse stalls • Owned solar panels • Cedar horse fencing

CONTINGENTFLOOR PLAN

ABOUT THIS HOME
Pending Listing in Windsor County, VT:
Sunday 8/16 Open House is being CANCELED! Experience the very best of Vermont living in the charming village of Weston, where every season offers something to enjoy. Spend winter days skiing at nearby Stratton, Magic, Bromley, or Okemo, and warmer months hiking scenic trails, horseback riding, swimming in lakes and ponds, or taking in a performance at the Weston Theater Company. Explore local shops, galleries, and restaurants while enjoying the beauty of one of Southern Vermont's most beloved communities. Whether you're seeking outdoor adventure, a vibrant arts community, or simply the peace and beauty of Vermont, this exceptional property places it all within easy reach. Thoughtfully built

$1,199,000

4 beds3 baths4,372 sq ft

278 Lawrence Hill Rd, Weston, VT 05161

Covered front porch • Hot tub • 15.1 acre lot

CONTINGENT

ABOUT THIS HOME
Pending Listing in Windsor County, VT:
This Lake Pauline residence offers an inviting, easygoing retreat in a convenient yet quiet location close to Okemo Mountain Resort. The cottage-style home features an open living and dining area with a cozy gas stove and access to a deck overlooking the water. The lakeside yard provides plenty of room for relaxing, lawn games, swimming, kayaking, and gathering around the firepit. Improvements completed within the past two years include Andersen windows, an updated kitchen and bath, and a new furnace. A delightful four-season getaway where lake and mountain living come together.

$479,999

2 beds1 bath768 sq ft

99 Lake Pauline Rd, Ludlow, VT 05149

Firepit • Lakeside yard • Andersen windows

Property at 26 Abbott St, White River Junction, VT 05001, 1 bed, 1 bath

$269,900

1 bed1 bath819 sq ft

26 Abbott St, White River Junction, VT 05001

Property at 530 West Rd, Barnard, VT 05031, 3 beds, 2 baths

$569,000

3 beds2 baths1,924 sq ft

530 West Rd, Barnard, VT 05031

Property at 1138 Bethel Mountain Rd, Rochester, VT 05767, 3 beds, 3 baths

$450,000

3 beds3 baths2,122 sq ft

1138 Bethel Mountain Rd, Rochester, VT 05767

Property at 1393 Sheddsville Rd, West Windsor, VT 05089, 4 beds, 2.5 baths

$775,000

4 beds2.5 baths3,168 sq ft

1393 Sheddsville Rd, West Windsor, VT 05089

Property at 29 Baker Rd, Springfield, VT 05156, 8 beds, 3.5 baths

$468,500

8 beds3.5 baths3,009 sq ft

29 Baker Rd, Springfield, VT 05156

Property at 583 Hawk Spur Rd, Plymouth, VT 05056, 4 beds, 3 baths

$579,000

4 beds3 baths3,428 sq ft

583 Hawk Spur Rd, Plymouth, VT 05056

Property at 245 Turnpike Rd, Sharon, VT 05070, 4 beds, 3.5 baths

$1,800,000

4 beds3.5 baths3,718 sq ft

245 Turnpike Rd, Sharon, VT 05070

Property at 1013 Jericho Rd, White River Junction, VT 05001, 2 beds, 1 bath

$359,000

2 beds1 bath1,024 sq ft

1013 Jericho Rd, White River Junction, VT 05001

Property at 1407 US Route 5, Springfield, VT 05156, 3 beds, 2 baths

$749,000

3 beds2 baths2,715 sq ft

1407 US Route 5, Springfield, VT 05156

Property at 20 Edwin's Pond Rd, Rochester, VT 05767, 3 beds, 2.5 baths

$415,000

3 beds2.5 baths1,268 sq ft

20 Edwin's Pond Rd, Rochester, VT 05767

Property at 28 Thetford Ln, Bethel, VT 05032, 3 beds, 2 baths

$189,900

3 beds2 baths980 sq ft

28 Thetford Ln, Bethel, VT 05032

Property at 18 Tuckerville Pkwy, Ludlow, VT 05149, 2 beds, 2 baths

$115,000

2 beds2 baths1,008 sq ft

18 Tuckerville Pkwy, Ludlow, VT 05149

Property at 38 Rimrock Rd Unit 3A, Ludlow, VT 05149, 4 beds, 3.5 baths

$649,000

4 beds3.5 baths2,628 sq ft

38 Rimrock Rd Unit 3A, Ludlow, VT 05149

Property at 3051 VT Rt 107, Stockbridge, VT 05772, 3 beds, 1 bath

$385,000

3 beds1 bath1,488 sq ft

3051 VT Rt 107, Stockbridge, VT 05772

Property at 1397 Popple Dungeon Rd, Chester, VT 05143, 3 beds, 2 baths

$299,000

3 beds2 baths1,788 sq ft

1397 Popple Dungeon Rd, Chester, VT 05143

Property at 1607 Massey Rd, Springfield, VT 05156, 4 beds, 2 baths

$695,000

4 beds2 baths4,144 sq ft

1607 Massey Rd, Springfield, VT 05156

Property at 205 Woodhaven Dr Unit 4G, White River Junction, VT 05001, 2 beds, 1.5 baths

$252,000

2 beds1.5 baths1,048 sq ft

205 Woodhaven Dr Unit 4G, White River Junction, VT 05001

Property at 544 Vulture Mountain Rd, Stockbridge, VT 05772, 4 beds, 3 baths

$500,000

4 beds3 baths960 sq ft

544 Vulture Mountain Rd, Stockbridge, VT 05772

Property at 66 Scott's Lndg, Ludlow, VT 05149, 3 beds, 3 baths

$850,000

3 beds3 baths2,294 sq ft

66 Scott's Lndg, Ludlow, VT 05149

Property at 1317 S Hill Rd, Ludlow, VT 05149, 3 beds, 2 baths

$450,000

3 beds2 baths2,400 sq ft

1317 S Hill Rd, Ludlow, VT 05149

Property at 598 E Woodstock Rd, Woodstock, VT 05091, 4 beds, 3 baths

$659,000

4 beds3 baths3,190 sq ft

598 E Woodstock Rd, Woodstock, VT 05091

Property at 191 Route 100 N, Ludlow, VT 05149, 5 beds, 1.5 baths

$455,000

5 beds1.5 baths2,205 sq ft

191 Route 100 N, Ludlow, VT 05149

Property at 207 Hartness Way, Hartford, VT 05059, 3 beds, 2.5 baths

$750,000

3 beds2.5 baths1,972 sq ft

207 Hartness Way, Hartford, VT 05059

Property at 13 Hawthorn St, Hartford, VT 05001, 8 beds, 4 baths

$489,000

8 beds4 baths3,483 sq ft

13 Hawthorn St, Hartford, VT 05001

Property at 339 Ellisons Lake Rd, Ludlow, VT 05149, 4 beds, 4.5 baths

$2,800,000

4 beds4.5 baths5,200 sq ft

339 Ellisons Lake Rd, Ludlow, VT 05149

Property at 133 Baltimore Rd, North Springfield, VT 05150, 4 beds, 2 baths

$525,000

4 beds2 baths2,232 sq ft

133 Baltimore Rd, North Springfield, VT 05150

Property at 663 Depot St, Chester, VT 05143, 3 beds, 2 baths

$390,000

3 beds2 baths1,304 sq ft

663 Depot St, Chester, VT 05143

Property at 12 Archibald Ln, Ludlow, VT 05149, 4 beds, 4.5 baths

$3,200,000

4 beds4.5 baths4,058 sq ft

12 Archibald Ln, Ludlow, VT 05149

Property at 58 Harrison Ln Unit K-102, Ludlow, VT 05149, 3 beds, 2 baths

$800,000

3 beds2 baths1,649 sq ft

58 Harrison Ln Unit K-102, Ludlow, VT 05149

Property at 61 Academy Cir, South Woodstock, VT 05071, 6 beds, 5 baths

$2,500,000

6 beds5 baths5,433 sq ft

61 Academy Cir, South Woodstock, VT 05071

Property at 58 Reservoir Rd, Springfield, VT 05156, 3 beds, 1 bath

$325,000

3 beds1 bath1,474 sq ft

58 Reservoir Rd, Springfield, VT 05156

Property at 11 Blueberry Ledge Rdg Unit L-3, Plymouth, VT 05056, 3 beds, 3 baths

$425,000

3 beds3 baths1,918 sq ft

11 Blueberry Ledge Rdg Unit L-3, Plymouth, VT 05056

Property at 18 Pleasant St #3, Ludlow, VT 05149, 4 beds, 3 baths

$525,000

4 beds3 baths2,407 sq ft

18 Pleasant St #3, Ludlow, VT 05149

Property at 67 Valley St, Springfield, VT 05156

$249,000

— beds— baths3,978 sq ft

67 Valley St, Springfield, VT 05156

Property at 37 Dee Haven Ln, Sharon, VT 05065, 4 beds, 2 baths

$295,000

4 beds2 baths1,992 sq ft

37 Dee Haven Ln, Sharon, VT 05065

Property at 117 Ledgewood Rd Unit F3 w/F4 Garage, Ludlow, VT 05149, 4 beds, 3.5 baths

$1,050,000

4 beds3.5 baths2,585 sq ft

117 Ledgewood Rd Unit F3 w/F4 Garage, Ludlow, VT 05149

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Pending Listings in Windsor County

There are currently 185 pending listings for sale in Windsor County at a median listing price of $572K. 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 77 days. This map is refreshed with the newest listings in Windsor County every 15 minutes.

In the past month, 86 homes have been sold in Windsor County. In addition to houses in Windsor County, there were also 104 condos, 0 townhouses, and 19 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 2026 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 Thu Sep 17 2026 on the search page

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