Homes with virtual tours for Sale in Windsor County, VT

113 homes

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NEW CONSTRUCTIONVIDEO TOUR

ABOUT THIS HOME
Home with Virtual Tour for sale in Windsor County, VT:
Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 65 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and Killington are viewed from nearly every room. Finished in 2024, this timber frame home channels modern farmhouse warmth with a clean, contemporary edge. The wall-to-wall glass in both gables frames the surrounding landscape like living artwork, while inside, 24-foot ceilings, radiant heat, A/C, and a saun

$6,750,000

4 beds4.5 baths5,087 sq ft

412 Skyland Ln, Woodstock, VT 05091

Timber frame home • 24-foot ceilings • Extraordinary views

3D WALKTHROUGH

ABOUT THIS HOME
Home with Virtual Tour for sale in Windsor County, VT:
BARNARD VILLAGE CAPE- This elegant Cape sits in an ideal location in the idyllic village of Barnard, just a short walk to the Barnard General Store and Silver Lake. The perfect blend of original charm, sophistication, and modern amenities, the house is bright and welcoming with lovely natural woodwork and plenty of space for social gatherings or quiet privacy. A large central living room features magnificent hand hewn ceiling beams that run the length, a paneled central fireplace, built in book shelves, and a sophisticated hidden bar. The well-appointed chef's eat-in kitchen is flanked by a cozy light-filled sitting area and formal dining room. On the second level of the main house are 3 be

$795,000

4 beds3 baths2,099 sq ft

6077 VT Route 12, Barnard, VT 05031

Hidden bar • 0.53 acre lot • 2 garage spots

VIDEO TOUR

ABOUT THIS HOME
Home with Virtual Tour for sale in Windsor County, VT:
Downtown Ludlow Convenience - Welcome to Mill #210, a beautifully updated condo in the heart of Ludlow. Just minutes to Okemo Mountain and directly on the shuttle route, this furnished unit combines comfort with convenience. Inside, you’ll find exposed beams, modern updates throughout, and an open living space that flows seamlessly to a private deck overlooking the Black River. Enjoy the ease of being steps from shops, dining, and village amenities while still feeling tucked away. With a proven rental history, this home offers excellent rental potential as well as a perfect Vermont retreat. Visit the Okemo real estate community today. Taxes are based on the town assessment.

$215,000

2 beds1 bath892 sq ft

145 Main St #210, Ludlow, VT 05149

Private deck • Steps from shops • Updated condo

VIDEO TOUR

ABOUT THIS HOME
Home with Virtual Tour for sale in Windsor County, VT:
TIMBERS IN THE SKY – Featured in Log and Timber Home Living magazine, this one-of-a-kind Vermont timber frame retreat, built in 2022, blends dramatic architecture with refined comfort. Fully furnished with luxury pieces, the open floor plan showcases a soaring great room with vaulted ceilings, walls of glass framing breathtaking mountain views, exposed beams, and a striking tile gas fireplace. The chef’s kitchen offers stainless steel appliances, custom cabinetry, and a generous island, while radiant-heated Italian porcelain floors and rustic wood accents provide warmth and elegance. Four bedrooms and five spa-like baths include a stunning primary suite and a fun bunk room sleep

$1,995,000

4 beds4 baths3,500 sq ft

2391 Music Mountain Rd, Stockbridge, VT 05772

Huge covered deck • Timber frame retreat • Chef's kitchen

VIDEO TOUR

ABOUT THIS HOME
Home with Virtual Tour for sale in Windsor County, VT:
Welcome to this charming home nestled in a small neighborhood along the scenic Black River in Cavendish, Vermont. This inviting property combines classic Vermont character with versatile living spaces, all within walking distance of the town green, shops, restaurants, and more. Step inside through the mudroom. The kitchen offers a warm, welcoming space with a sunny dining area perfect for morning coffee or casual meals. A formal dining room provides space for larger gatherings, while the living room, bathed in morning light, creates a cozy setting to relax and unwind. A first-floor bedroom adds convenience and flexibility for guests or main-level living. Upstairs, you’ll find three ad

$415,000

5 beds3 baths1,976 sq ft

198 Depot St, Proctorsville, VT 05153

First-floor bedroom • Formal dining room • Sunny dining area

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

$1,195,000

3 beds3.5 baths2,592 sq ft

26 Mt Peg Rd Unit A, Woodstock, VT 05091

Property at 7 Slayton Ter, Woodstock, VT 05091, 4 beds, 2.5 baths

$1,495,000

4 beds2.5 baths2,532 sq ft

7 Slayton Ter, Woodstock, VT 05091

Property at 396 S Main St, Bethel, VT 05032, 2 beds, 2 baths

$205,000

2 beds2 baths1,420 sq ft

396 S Main St, Bethel, VT 05032

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 1522 Barnard Rd, Woodstock, VT 05091, 5 beds, 3.5 baths

$1,595,000

5 beds3.5 baths3,648 sq ft

1522 Barnard Rd, Woodstock, VT 05091

Property at 117 Horseshoe Dr, West Windsor, VT 05089, 3 beds, 3 baths

$849,900

3 beds3 baths3,392 sq ft

117 Horseshoe Dr, West Windsor, VT 05089

Property at 2346 Quechee Main St, White River Junction, VT 05059, 3 beds, 3.5 baths

$1,865,000

3 beds3.5 baths3,827 sq ft

2346 Quechee Main St, White River Junction, VT 05059

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

$995,000

3 beds3.5 baths2,584 sq ft

26 Mt Peg Rd Unit C, Woodstock, VT 05091

Property at 652 Tierney Rd, Cavendish, VT 05142, 4 beds, 3.5 baths

$1,499,000

4 beds3.5 baths3,560 sq ft

652 Tierney Rd, Cavendish, VT 05142

Property at 3800 Weston Andover Rd, Andover, VT 05143, 8 beds, 7.5 baths

$5,950,000

8 beds7.5 baths10,062 sq ft

3800 Weston Andover Rd, Andover, VT 05143

Property at 165 Moon Shadow Dr Unit M-15, Ludlow, VT 05149, 5 beds, 4.5 baths

$3,100,000

5 beds4.5 baths7,634 sq ft

165 Moon Shadow Dr Unit M-15, Ludlow, VT 05149

Property at 157 Dartt Hill Rd, Bethel, VT 05032, 5 beds, 3 baths

$949,000

5 beds3 baths2,807 sq ft

157 Dartt Hill Rd, Bethel, VT 05032

Property at 119 Pine Hill Rd, Ludlow, VT 05149, 4 beds, 3.5 baths

$765,000

4 beds3.5 baths2,828 sq ft

119 Pine Hill Rd, Ludlow, VT 05149

Property at 58 Greenbush Rd, Cavendish, VT 05142, 3 beds, 3 baths

$750,000

3 beds3 baths1,432 sq ft

58 Greenbush Rd, Cavendish, VT 05142

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

$1,195,000

3 beds3.5 baths2,385 sq ft

26 Mt Peg Rd Unit D, Woodstock, VT 05091

Property at 140 Lodge Rd #11, Ludlow, VT 05149, 3 beds, 3 baths

$1,390,000

3 beds3 baths1,836 sq ft

140 Lodge Rd #11, Ludlow, VT 05149

Property at 238 Q1 Jackson Gore Inn Unit 238 Q1, Ludlow, VT 05149, 2 beds, 2 baths

$95,000

2 beds2 baths1,025 sq ft

238 Q1 Jackson Gore Inn Unit 238 Q1, Ludlow, VT 05149

Property at 1873 North Rd, Barnard, VT 05031, 5 beds, 4 baths

$1,249,000

5 beds4 baths3,282 sq ft

1873 North Rd, Barnard, VT 05031

Property at 46 Partridge Rd, Ludlow, VT 05149, 5 beds, 4 baths

$2,499,000

5 beds4 baths5,305 sq ft

46 Partridge Rd, Ludlow, VT 05149

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

$995,000

4 beds3.5 baths2,585 sq ft

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

Property at 107 Blueberry Ledge Rdg Unit L-45, Plymouth, VT 05056, 3 beds, 2 baths

$429,000

3 beds2 baths1,428 sq ft

107 Blueberry Ledge Rdg Unit L-45, Plymouth, VT 05056

Property at 513 Giddings St, North Springfield, VT 05150, 5 beds, 3 baths

$325,000

5 beds3 baths2,963 sq ft

513 Giddings St, North Springfield, VT 05150

Property at 115 Eastman Rd, South Woodstock, VT 05071, 3 beds, 3.5 baths

$8,000,000

3 beds3.5 baths5,384 sq ft

115 Eastman Rd, South Woodstock, VT 05071

Property at 168 Trailside Ext Unit 21B, Ludlow, VT 05149, 4 beds, 2.5 baths

$925,000

4 beds2.5 baths2,045 sq ft

168 Trailside Ext Unit 21B, Ludlow, VT 05149

Property at 348 Turtle Hill Rd, Ludlow, VT 05149, 5 beds, 4 baths

$3,650,000

5 beds4 baths5,181 sq ft

348 Turtle Hill Rd, Ludlow, VT 05149

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

$445,000

3 beds3 baths1,918 sq ft

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

Property at 212 QIII Jackson Gore Inn Unit 212 QIII, Ludlow, VT 05149, 1 bath

$55,000

0 beds1 bath390 sq ft

212 QIII Jackson Gore Inn Unit 212 QIII, Ludlow, VT 05149

Property at 51 E Ash Rd, Plymouth, VT 05056, 7 beds, 8.5 baths

$2,950,000

7 beds8.5 baths13,410 sq ft

51 E Ash Rd, Plymouth, VT 05056

Property at 365 Q4 Jackson Gore Inn Rd Unit 365 Q4, Ludlow, VT 05149, 1 bath

$49,000

0 beds1 bath390 sq ft

365 Q4 Jackson Gore Inn Rd Unit 365 Q4, Ludlow, VT 05149

Property at 325 Cemetery Rd, West Windsor, VT 05089, 4 beds, 2 baths

$1,325,000

4 beds2 baths2,554 sq ft

325 Cemetery Rd, West Windsor, VT 05089

Property at 515 Shattuck Hill Rd Unit 515, 513 & 511, West Windsor, VT 05037, 6 beds, 5.5 baths

$1,450,000

6 beds5.5 baths4,225 sq ft

515 Shattuck Hill Rd Unit 515, 513 & 511, West Windsor, VT 05037

Property at 1300 Mountain Rd, Ludlow, VT 05149, 4 beds, 5 baths

$2,000,000

4 beds5 baths2,887 sq ft

1300 Mountain Rd, Ludlow, VT 05149

Property at 37 Village Center Rd #1, Ludlow, VT 05149, 4 beds, 3 baths

$1,675,000

4 beds3 baths1,884 sq ft

37 Village Center Rd #1, Ludlow, VT 05149

Property at 141 Upper Xrd, Ludlow, VT 05149, 3 beds, 2 baths

$525,000

3 beds2 baths1,658 sq ft

141 Upper Xrd, Ludlow, VT 05149

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 49 Burton Rd, Weston, VT 05161, 6 beds, 5.5 baths

$1,250,000

6 beds5.5 baths5,790 sq ft

49 Burton Rd, Weston, VT 05161

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Homes with virtual tours for Sale in Windsor County

There are currently 113 homes with virtual tours 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 102 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 94 condos, 4 townhouses, and 27 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 Sat Dec 13 2025 on the search page

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