Luxury homes for sale & real estate in Windsor County, VT

115 homes

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ABOUT THIS HOME
Luxury Home for sale in Windsor County, VT:
Nestled at the end of a quiet dead-end road, this 68-acre private homestead offers exceptional privacy, timeless New England charm, and direct access to over 560 acres of town-owned land—the Hurricane Forest and Hurricane Wildlife Refuge. With conservation land on two sides, this property is a rare blend of seclusion, natural beauty, and convenience—a one mile drive to the intersection of RT 89 and 91, just 20 minutes from Woodstock and within easy reach of all Upper Valley amenities. The Colonial-style home boasts wide pine floors throughout combining classic craftsmanship with the efficiency and comfort of a 21st-century build. The Rumford fireplace in the living room provides

$1,100,000

4 beds3 baths2,640 sq ft

307 Remick Rd, White River Junction, VT 05001

Spacious kitchen • Wide pine floors • Rumford fireplace

VIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in Windsor County, VT:
This beautifully maintained home sits on over three acres in a peaceful setting between Okemo and Killington Mountain Resorts and is truly move-in ready. Originally built in 1985, the home was expanded in 2008 and further enhanced with an oversized two-car garage in 2021. Recent upgrades including a new kitchen, standing seam roof, boiler, updated baths, new appliances, mini splits, carpet, and fresh exterior stain make this property completely turnkey. A graceful curved staircase leads to the lower level, featuring a spacious primary suite, an additional bedroom suite, two more bedrooms, and another bath. The large mudroom provides ample space for all your gear, no matter the season. Enjoy

$885,000

4 beds3.5 baths2,667 sq ft

559 Crimson Hawk Rd, Plymouth, VT 05056

Standing seam roof • New kitchen • Updated baths

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Windsor County, VT:
Welcome to 33 Mountain Avenue – a mid-century modern gem poised perfectly on the edge of Faulkner Park and at the foot of Mt. Tom and once part of the Marianne Faulkner Estate. The spacious one-level design provides a seamless connection between the indoor and outdoor living space which includes two ensuite bedrooms, living/dining room with fireplace, kitchen, family room, office and attached one car garage. An exquisite multi-terraced exterior landscape design is predominately and privately located at the back of the property. Plentiful space for gardening, a fire-pit, or even an i

$1,295,000

2 beds3.5 baths2,280 sq ft

33 Mountain Ave, Woodstock, VT 05091

Trails of mt. tom • 0.8 acre lot • Garage

VIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in Windsor County, VT:
Welcome to your dream getaway! Add your finishing touches to this newly built "South Hill" home. This 5-bedroom, 4-bathroom country home combines timeless craftsmanship with modern comfort, just minutes from Okemo. Step inside to the inviting, open floor plan where natural light pours in. Open concept includes the kitchen, dining, and living areas—a perfect space for entertaining. The kitchen awaits your personal touch, ready for you to install your countertops and appliances, while the living room offers a large stone wood-burning fireplace. Completing the main level is a bonus room that offers the flexibility of a 5th bedroom or home office to suit all your needs. Upstairs

$995,000

5 beds4 baths3,063 sq ft

152 Town Farm Rd, Ludlow, VT 05149

Blue stone patio • Open floor plan • Walk-in closet

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Windsor County, VT:
Beautifully sited just a short walk from Woodstock Village, this 2015 custom-built home blends modern comfort with timeless Vermont charm. Thoughtfully designed for everyday living and entertaining, the main level features an open, light-filled layout, a well-appointed kitchen, and seamless access to a sunny three-season room overlooking the landscaped grounds. The sought-after first-floor primary suite offers ease and convenience, with generous closet space and a private bath. With three additional bedrooms plus a dedicated office, the home offers plenty of room to spread out. The large finished basement provides flexible bonus space—perfect for a playroom, media room, fitness area,

$1,300,000

4 beds4 baths3,195 sq ft

125 Shurtleff Ln, Woodstock, VT 05091

Three season room • Finished basement • Private patio

Property at 650 Francis Rd, Barnard, VT 05031, 2 beds, 5.5 baths

$39,000,000

2 beds5.5 baths9,950 sq ft

650 Francis Rd, Barnard, VT 05031

Property at 332 Cushing Rd, Pomfret, VT 05053, 3 beds, 3.5 baths

$1,295,000

3 beds3.5 baths3,590 sq ft

332 Cushing Rd, Pomfret, VT 05053

Property at 53 Ponus Rd, Ludlow, VT 05149, 5 beds, 3.5 baths

$1,250,000

5 beds3.5 baths3,652 sq ft

53 Ponus Rd, Ludlow, VT 05149

Property at 1362 Barnard Rd, Woodstock, VT 05091, 4 beds, 2 baths

$2,600,000

4 beds2 baths3,000 sq ft

1362 Barnard Rd, Woodstock, VT 05091

Property at 355 Greene Rd, South Woodstock, VT 05071, 7 beds, 8.5 baths

$18,000,000

7 beds8.5 baths12,520 sq ft

355 Greene Rd, South Woodstock, VT 05071

Property at 73 Laber Rd, Bridgewater Corners, VT 05035, 4 beds, 6.5 baths

$1,490,000

4 beds6.5 baths6,269 sq ft

73 Laber Rd, Bridgewater Corners, VT 05035

Property at 60 Spencer Hollow Rd, Springfield, VT 05156, 2 beds, 3 baths

$859,000

2 beds3 baths2,250 sq ft

60 Spencer Hollow Rd, Springfield, VT 05156

Property at 411 Wood Rd, Hartford, VT 05059, 4 beds, 3.5 baths

$1,425,000

4 beds3.5 baths4,204 sq ft

411 Wood Rd, Hartford, VT 05059

Property at 48 Alpine Way Unit D-1, Ludlow, VT 05149, 5 beds, 5.5 baths

$3,150,000

5 beds5.5 baths3,460 sq ft

48 Alpine Way Unit D-1, Ludlow, VT 05149

Property at 17 Linden Hl, Woodstock, VT 05091, 4 beds, 3 baths

$1,200,000

4 beds3 baths2,736 sq ft

17 Linden Hl, Woodstock, VT 05091

Property at 198 Piper Hill Rd, Weston, VT 05161, 4 beds, 2.5 baths

$1,995,000

4 beds2.5 baths3,839 sq ft

198 Piper Hill Rd, Weston, VT 05161

Property at 1 Depot St, Wilder, VT 05088

$999,500

— beds— baths3,218 sq ft

1 Depot St, Wilder, VT 05088

Property at 958 E Woodstock Rd, Woodstock, VT 05091, 3 beds, 2.5 baths

$1,150,000

3 beds2.5 baths2,220 sq ft

958 E Woodstock Rd, Woodstock, VT 05091

Property at 611 Simmons Rd, Chester, VT 05143, 2 beds, 4 baths

$1,995,000

2 beds4 baths3,514 sq ft

611 Simmons Rd, Chester, VT 05143

Property at 187 Hopson Rd, Norwich, VT 05055, 4 beds, 2.5 baths

$1,495,000

4 beds2.5 baths2,710 sq ft

187 Hopson Rd, Norwich, VT 05055

Property at 1877 Willard Rd, Hartford, VT 05059, 4 beds, 3.5 baths

$850,000

4 beds3.5 baths2,970 sq ft

1877 Willard Rd, Hartford, VT 05059

Property at 26 Mt Peg Rd Unit B, Woodstock, VT 05091, 3 beds, 3.5 baths

$995,000

3 beds3.5 baths2,584 sq ft

26 Mt Peg Rd Unit B, Woodstock, VT 05091

Property at 475 Twenty Mile Stream Rd, South Reading, VT 05062, 3 beds, 3 baths

$895,000

3 beds3 baths3,920 sq ft

475 Twenty Mile Stream Rd, South Reading, VT 05062

Property at 513 Deer Brook Way Lot 16, Woodstock, VT 05091, 4 beds, 2.5 baths

$1,295,000

4 beds2.5 baths2,668 sq ft

513 Deer Brook Way Lot 16, Woodstock, VT 05091

Property at 14/16 Summarsell Dr, Hartland, VT 05048

$1,576,000

— beds— baths9,455 sq ft

14/16 Summarsell Dr, Hartland, VT 05048

Property at 509 Church Hl, Woodstock, VT 05091, 3 beds, 3 baths

$915,000

3 beds3 baths2,150 sq ft

509 Church Hl, Woodstock, VT 05091

Property at 593 Red Barn Rd, White River Junction, VT 05001, 5 beds, 4.5 baths

$1,475,000

5 beds4.5 baths3,060 sq ft

593 Red Barn Rd, White River Junction, VT 05001

Property at 18 The Grn, Woodstock, VT 05091, 6 beds, 7 baths

$3,500,000

6 beds7 baths5,142 sq ft

18 The Grn, Woodstock, VT 05091

Property at 41 Pleasant St, Woodstock, VT 05091, 9 beds, 11 baths

$2,599,000

9 beds11 baths5,993 sq ft

41 Pleasant St, Woodstock, VT 05091

Property at 3147 Mount Hunger Rd, Barnard, VT 05031, 5 beds, 8.5 baths

$15,000,000

5 beds8.5 baths9,679 sq ft

3147 Mount Hunger Rd, Barnard, VT 05031

Property at 16 Church St, Woodstock, VT 05091, 4 beds, 3 baths

$1,295,000

4 beds3 baths3,089 sq ft

16 Church St, Woodstock, VT 05091

Property at 85 Pallottas Hill Rd, Ludlow, VT 05149, 4 beds, 2 baths

$5,500,000

4 beds2 baths3,150 sq ft

85 Pallottas Hill Rd, Ludlow, VT 05149

Property at 166 Woods West Rd, Ludlow, VT 05149, 4 beds, 3.5 baths

$1,250,000

4 beds3.5 baths4,177 sq ft

166 Woods West Rd, Ludlow, VT 05149

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

$995,000

4 beds2 baths4,144 sq ft

1607 Massey Rd, Springfield, VT 05156

Property at 7074 Robert Frost Ln #7074, Hartford, VT 05059, 5 beds, 4 baths

$1,625,000

5 beds4 baths3,837 sq ft

7074 Robert Frost Ln #7074, Hartford, VT 05059

Property at 423 Taft Family Rd, Hartford, VT 05059, 5 beds, 5 baths

$1,499,000

5 beds5 baths5,074 sq ft

423 Taft Family Rd, Hartford, VT 05059

Property at 1588 Austin Hill Rd, Rochester, VT 05767, 3 beds, 4.5 baths

$869,000

3 beds4.5 baths4,088 sq ft

1588 Austin Hill Rd, Rochester, VT 05767

Property at 39 Elm St Unit B, Woodstock, VT 05091, 3 beds, 3.5 baths

$1,689,000

3 beds3.5 baths3,294 sq ft

39 Elm St Unit B, Woodstock, VT 05091

Property at 33 Ferndale Dr, Barnard, VT 05031, 3 beds, 2.5 baths

$999,000

3 beds2.5 baths4,289 sq ft

33 Ferndale Dr, Barnard, VT 05031

Property at 254 Town Line Rd, Plymouth, VT 05056, 4 beds, 3.5 baths

$2,499,000

4 beds3.5 baths5,079 sq ft

254 Town Line Rd, Plymouth, VT 05056

Property at 8 Okemo Acres Rd, Ludlow, VT 05194, 3 beds, 3.5 baths

$1,050,000

3 beds3.5 baths2,390 sq ft

8 Okemo Acres Rd, Ludlow, VT 05194

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Luxury Homes for Sale in Windsor County

There are currently 115 luxury homes 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 Fri Nov 28 2025 on the search page

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