Homes with Parking for Sale in Windsor County, VT

220 homes

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ABOUT THIS HOME
Home with Parking for sale in Windsor County, VT:
Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom , 2 bath home offers the character of a traditional New England property with comfortable , move in ready living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace--perfect for cozy Vermont evenings. Freshly painted interiors and updated flooring provide a clean , inviting feel while preserving the home's classic farmhouse charm. An attached barn/ garage offers excellent storage and flexible space for outdoor gear , a workshop, or hobby area--ideal for those who enjoy Vermont's year-round outdoor lifestyle. Located just

$349,000

4 beds2 baths1,617 sq ft

5798 W Woodstock Rd, Woodstock, VT 05091

Attached barn • Spacious dining room • Sunny eat in kitchen

3D WALKTHROUGH

ABOUT THIS HOME
Home with Parking for sale in Windsor County, VT:
Town Line Estate is a once-in-a-generation offering. This extraordinary 22-acre private estate is a testament to master builder craftsmanship and refined living. From the moment you arrive, every detail speaks to an uncompromising standard, classic beams, rich cherry cabinetry, and two Rumford fireplaces create warmth and character throughout. The heart of the home is a restaurant-quality kitchen designed for serious entertaining, flowing seamlessly to a spacious back deck and elegant stone patio. Soak in natural light year-round in the stunning solarium, or retreat to the dramatic tower atrium, an architectural showpiece unlike anything in the market. The estate's grounds are simply breath

$2,250,000

4 beds3.5 baths5,079 sq ft

254 Town Line Rd, Plymouth, VT 05056

Spacious back deck • Elegant stone patio • Stunning solarium

3D WALKTHROUGH

ABOUT THIS HOME
Home with Parking for sale in Windsor County, VT:
"The Plateau", originally part of the Kennedy Biscuit Co. (Nabisco) family estate, is nestled on a plateau at the end of a private road which greets you with open fields, mature trees, beautiful gardens, and a protected front-and-center view of Mt. Ascutney to the West and the Connecticut River to the East. This private peaceful setting includes an inground pool for those hot summer days, and two porches: one open air and one screened-in, with views into the New Hampshire hillsides. Inside, the house is open and bright with a wonderful flow throughout. The large living room features a wood-burning fireplace and plenty of windows streaming in lots of natural light. The formal dinin

$1,399,000

4 beds3.5 baths4,000 sq ft

145 The Plateau, Windsor, VT 05089

Private road • Screened-in porch • Built-in cabinets

ABOUT THIS HOME
Home with Parking for sale in Windsor County, VT:
Set on 157 private acres with sweeping long-range views of the Connecticut River, this meticulously restored circa 1735 Cape offers a rare blend of historic character, refined comfort, and estate-scale amenities. Completely dismantled and rebuilt with care, the post-and-beam residence displays exposed beams, wide-board floors and sheathing, gunstock corner posts, and classic brick fireplaces alongside thoughtful modern upgrades. The inviting, renovated kitchen features an oversized fireplace, high-end appliances, and expansive views of the swimming pond and distant views of the Connecticut River. Three en-suite bedrooms include a gracious first-floor primary suite enhanced by a 30-by-20-foo

$2,790,000

4 beds4.5 baths2,894 sq ft

1726 Skitchewaug Trl, Springfield, VT 05156

Private acres • High-end appliances • Long-range views

ABOUT THIS HOME
Home with Parking for sale in Windsor County, VT:
Stately hilltop home built by Silas Banister c. 1800, recently undergone a complete restoration. Quality materials & craftsmanship throughout. It has gorgeous views of nearby Ascutney Mountain & long-range views of NH. The property consists of 98 acres made up of fields, hard & softwoods, trails, a large sugarbush (potential for a future boiling operation). Conserved by Upper Valley Land Trust, enrolled in Current Use. The main floor offers a new kitchen which boasts a beautiful 11' quartzite island & counters. Dining & Family Room with soapstone woodstove, Living Room with a new Rumford Fireplace with rod iron & glass doors for efficiency. A large Sunroo

$3,150,000

5 beds4 baths3,212 sq ft

166 Jewett Rd, Brownsville, VT 05037

New kitchen • Quartz island • Soapstone woodstove

Property at 99 Heather Dr Unit 8F, White River Junction, VT 05001, 2 beds, 1.5 baths

$347,000

2 beds1.5 baths1,225 sq ft

99 Heather Dr Unit 8F, White River Junction, VT 05001

Property at 58 Lakeshore Dr, Ludlow, VT 05149, 4 beds, 3 baths

$3,500,000

4 beds3 baths2,571 sq ft

58 Lakeshore Dr, Ludlow, VT 05149

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

$1,275,000

4 beds3.5 baths4,204 sq ft

411 Wood Rd, Hartford, VT 05059

Property at 1641 W Hill Rd, Rochester, VT 05767, 3 beds, 3 baths

$640,000

3 beds3 baths2,697 sq ft

1641 W Hill Rd, Rochester, VT 05767

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

$14,900,000

7 beds8.5 baths12,520 sq ft

355 Greene Rd, South Woodstock, VT 05071

Property at 934 Heald Rd, Proctorsville, VT 05153, 3 beds, 2.5 baths

$795,000

3 beds2.5 baths2,416 sq ft

934 Heald Rd, Proctorsville, VT 05153

Property at 42 Cedar Dr, Ludlow, VT 05149, 4 beds, 3.5 baths

$1,350,000

4 beds3.5 baths5,960 sq ft

42 Cedar Dr, Ludlow, VT 05149

Property at 53 Moon Shadow Dr, Ludlow, VT 05149, 7 beds, 6.5 baths

$4,450,000

7 beds6.5 baths6,245 sq ft

53 Moon Shadow Dr, Ludlow, VT 05149

Property at 243 Qtr. I V Jackson Gore Inn, Ludlow, VT 05149, 1 bath

$65,000

Studio1 bath390 sq ft

243 Qtr. I V Jackson Gore Inn, Ludlow, VT 05149

Property at 24 Ledgewood Rd Unit B2/B6 GR, Ludlow, VT 05149, 4 beds, 3 baths

$1,300,000

4 beds3 baths2,871 sq ft

24 Ledgewood Rd Unit B2/B6 GR, Ludlow, VT 05149

Property at 366 Knapp Pond Rd, Cavendish, VT 05142, 4 beds, 2 baths

$1,200,000

4 beds2 baths1,908 sq ft

366 Knapp Pond Rd, Cavendish, VT 05142

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

$779,000

3 beds3 baths3,392 sq ft

117 Horseshoe Dr, West Windsor, VT 05089

Property at 62 Pullman Ln, White River Junction, VT 05001, 3 beds, 2.5 baths

$795,000

3 beds2.5 baths2,066 sq ft

62 Pullman Ln, White River Junction, VT 05001

Property at 1036 N Main St, Bethel, VT 05031, 5 beds, 4.5 baths

$1,150,000

5 beds4.5 baths3,370 sq ft

1036 N Main St, Bethel, VT 05031

Property at 144 Lodge Rd #5, Ludlow, VT 05149, 1 bed, 1.5 baths

$485,000

1 bed1.5 baths1,044 sq ft

144 Lodge Rd #5, Ludlow, VT 05149

Property at 4205 Route 131, Perkinsville, VT 05151, 3 beds, 1.5 baths

$619,900

3 beds1.5 baths1,938 sq ft

4205 Route 131, Perkinsville, VT 05151

Property at 3578 Royalton Turnpike Rd, Barnard, VT 05031, 2 beds, 1 bath

$369,000

2 beds1 bath1,140 sq ft

3578 Royalton Turnpike Rd, Barnard, VT 05031

Property at 1787 Route 100 N, Ludlow, VT 05149, 3 beds, 4 baths

$535,000

3 beds4 baths2,727 sq ft

1787 Route 100 N, Ludlow, VT 05149

Property at 1057 Brockway Mills Rd, Springfield, VT 05156, 3 beds, 1 bath

$350,000

3 beds1 bath2,128 sq ft

1057 Brockway Mills Rd, Springfield, VT 05156

Property at 72 Wood Rd, Hartford, VT 05001, 3 beds, 2 baths

$1,300,000

3 beds2 baths2,334 sq ft

72 Wood Rd, Hartford, VT 05001

Property at 399 Bentley Rd, Hartford, VT 05059, 5 beds, 3.5 baths

$1,490,950

5 beds3.5 baths3,358 sq ft

399 Bentley Rd, Hartford, VT 05059

Property at 1354 Vermont Route 100, Stockbridge, VT 05772, 3 beds, 2.5 baths

$850,000

3 beds2.5 baths4,088 sq ft

1354 Vermont Route 100, Stockbridge, VT 05772

Property at 919 VT Route 100 S, Rochester, VT 05767, 3 beds, 1 bath

$339,000

3 beds1 bath1,144 sq ft

919 VT Route 100 S, Rochester, VT 05767

Property at 505 Deweys Mills Rd, Hartford, VT 05047, 6 beds, 5 baths

$1,275,000

6 beds5 baths4,571 sq ft

505 Deweys Mills Rd, Hartford, VT 05047

Property at 54 Commonwealth Ave, Springfield, VT 05156, 3 beds, 2 baths

$390,000

3 beds2 baths1,214 sq ft

54 Commonwealth Ave, Springfield, VT 05156

Property at 196 Cowdrey Outlook, Bethel, VT 05032, 3 beds, 1 bath

$1,595,000

3 beds1 bath1,708 sq ft

196 Cowdrey Outlook, Bethel, VT 05032

Property at 406 Mt View Loop, Rochester, VT 05767, 2 beds, 1.5 baths

$465,000

2 beds1.5 baths1,008 sq ft

406 Mt View Loop, Rochester, VT 05767

Property at 924 Okemo Ridge Rd Unit S 11, Ludlow, VT 05149, 7 beds, 6.5 baths

$4,775,000

7 beds6.5 baths6,624 sq ft

924 Okemo Ridge Rd Unit S 11, Ludlow, VT 05149

Property at 1009 Route 131, Springfield, VT 05030, 4 beds, 1 bath

$249,000

4 beds1 bath1,738 sq ft

1009 Route 131, Springfield, VT 05030

Property at 310 Pierce Hill Rd, Brownsville, VT 05037, 7 beds, 5 baths

$1,295,000

7 beds5 baths5,774 sq ft

310 Pierce Hill Rd, Brownsville, VT 05037

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

$2,650,000

7 beds8.5 baths13,410 sq ft

51 E Ash Rd, Plymouth, VT 05056

Property at 299 Latham Works Ln, White River Junction, VT 05001, 3 beds, 1 bath

$369,440

3 beds1 bath1,569 sq ft

299 Latham Works Ln, White River Junction, VT 05001

Property at 1589 Main St, Cavendish, VT 05142, 10 beds, 10 baths

$1,400,000

10 beds10 baths7,153 sq ft

1589 Main St, Cavendish, VT 05142

Property at 193 Jackson Gore Rd Unit 739/741, Ludlow, VT 05149, 2 beds, 3 baths

$699,000

2 beds3 baths1,364 sq ft

193 Jackson Gore Rd Unit 739/741, Ludlow, VT 05149

Property at 76 Goldthwaite Rd, Chester, VT 05143, 4 beds, 3 baths

$1,200,000

4 beds3 baths3,308 sq ft

76 Goldthwaite Rd, Chester, VT 05143

Property at Jackson Gore Adams House Unit 717/719 Q1-4, Ludlow, VT 05149, 1 bed, 2 baths

$495,000

1 bed2 baths957 sq ft

Jackson Gore Adams House Unit 717/719 Q1-4, Ludlow, VT 05149

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Homes with Parking for Sale in Windsor County

There are currently 220 homes with parking homes for sale in Windsor County at a median listing price of $575K. 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 85 days. This map is refreshed with the newest listings in Windsor County every 15 minutes.

In the past month, 68 homes have been sold in Windsor County. In addition to houses in Windsor County, there were also 105 condos, 0 townhouses, and 17 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 Sat Oct 10 2026 on the search page

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