Homes with Garages for Sale in Windsor County, VT

210 homes

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NEW 2 HRS AGO

ABOUT THIS HOME
Home with Garage for sale in Windsor County, VT:
Charming 4 Bedroom, 3 Bath home on the shuttle route to the Okemo Resort Base Lodge. Neat and clean, this stand alone home is very close to the base area, so you don't have to go into town at the end of your ski day. Very open kitchen (with island), dining and living room with sliders to the deck. Walk into the airlock mudroom to the main living space along with 2 first floor bedrooms and a full bath. The upper level consists of 2 additional bedrooms (one is set up as a den) with a primary bath and another 3/4 bath. The garage has been converted into a storage area but could be converted back. Plowing, firewood, trash pick up and seasonal house checks are provided by the quarterly dues of t

$625,000

4 beds3 baths1,725 sq ft

122 Chamonix Rd Unit 21 C, Ludlow, VT 05149

Airlock mudroom • Open kitchen • 27 acre lot

ABOUT THIS HOME
Home with Garage for sale in Windsor County, VT:
Much more here than meets the eye. This home had heating efficiency completed with SEVCA, new siding, new hot water heater, chimney and furnace inspected and some new exterior paint. Nice level yard, attached two car garage PLUS detached barn! Close to downtown Chester and 15 minutes to Ludlow and Okemo/Vail resort. There is a large 3-season porch, two spacious bedrooms and large country kitchen. This little gem is just waiting for a little polish and it will make a wonderful home. Easy to view, improvements are listed in documents.

$239,000

2 beds1 bath1,222 sq ft

1374 VT Route 103 N, Chester, VT 05143

New siding • New exterior paint • Chimney inspected

ABOUT THIS HOME
Home with Garage for sale in Windsor County, VT:
This well-appointed 3-bedroom, 2-bath home sits in the heart of Vermont’s recreational corridor and offers the perfect blend of comfort, efficiency, and turn-key investment potential. Just 10 minutes to Killington’s Skyeship Gondola and 20 minutes to Okemo Mountain, this property is a true skier’s paradise with strong year-round short-term rental history. Built in 2008, the home was designed for maximum efficiency with quality heating systems, excellent insulation, and a whole-house Tesla battery backup. Recent upgrades include owned solar panels, bringing the electric bill down to virtually nothing—an ideal benefit for both full-time living and STR profitability. Th

$499,000

3 beds2 baths1,560 sq ft

90 Blueberry Hill Rd, Bridgewater Corners, VT 05035

Open floor plan • Radiant heat • Level 0.78-acre lot

ABOUT THIS HOME
Home with Garage for sale in Windsor County, VT:
Effortless Style Meets Vermont Village Living Sweeping arches, sun-soaked spaces, and vintage charm, this Ludlow Village home is the perfect blend of character and modern comfort. Lovingly cared for over 33 years, it's been thoughtfully renovated to keep the history intact while adding all the upgrades you want. Wake up to southern light streaming into your sunroom, sip coffee on the elevated deck with mountain views, or gather friends around the patio's hot tub and gas fire pit after a day on the slopes. With Okemo Mountain Resort just minutes away, you can ski in winter, golf in summer, and explore pristine lakes all year long. Inside, high-speed internet keeps you connected while heated

$799,000

4 beds2 baths2,516 sq ft

14 Gill Ter, Ludlow, VT 05149

Hot tub • High-speed internet • Elevated deck

ABOUT THIS HOME
Home with Garage for sale in Windsor County, VT:
Welcome to "Valley Brook Farm", a Historic Cape in the middle of Horse country on 12.92 acres with Barns, rolling & level Pasture, a swimming Pond, and Brook. Located in the heart of the nationally renowned Green Mountain Horse Association trail network. Nestled on scenic & bucolic Jenneville Road, this c. 1820 Cape offers the warmth of wide pine floors, post-and-beam character, and sun-filled spaces. The 1.75-story home (2,212+ sq ft) includes 4 bedrooms and 2 full baths. The charming country kitchen features an expansive Family Room area and breakfast nook with a view of the rear meadows. The adjoining pantry, pellet stove, and coat closet make for practical Vermont

$635,000

4 beds2 baths2,212 sq ft

298 Jenneville Rd, Hartland, VT 05048

Swimming pond • 12.92 acres • Barns

Property at 222 Andover St, Ludlow, VT 05149, 5 beds, 3.5 baths

$849,000

5 beds3.5 baths2,890 sq ft

222 Andover St, Ludlow, VT 05149

Property at 224 QIV Jackson Gore Inn Unit 224 QIV, Ludlow, VT 05149, 2 beds, 2 baths

$95,000

2 beds2 baths1,025 sq ft

224 QIV Jackson Gore Inn Unit 224 QIV, Ludlow, VT 05149

Property at 1254 US Route 5, Springfield, VT 05156, 8 beds, 1 bath

$485,000

8 beds1 bath3,500 sq ft

1254 US Route 5, Springfield, VT 05156

Property at 713/715 Qtr. I I I Adams House, Ludlow, VT 05149, 3 beds, 3 baths

$210,000

3 beds3 baths2,001 sq ft

713/715 Qtr. I I I Adams House, Ludlow, VT 05149

Property at 149 W Trottier Rd, South Royalton, VT 05068, 3 beds, 2.5 baths

$519,000

3 beds2.5 baths5,616 sq ft

149 W Trottier Rd, South Royalton, VT 05068

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 106 Contro Rd, Chester, VT 05143, 2 beds, 2.5 baths

$289,000

2 beds2.5 baths1,475 sq ft

106 Contro Rd, Chester, VT 05143

Property at 152 Town Farm Rd, Ludlow, VT 05149, 5 beds, 4 baths

$995,000

5 beds4 baths3,063 sq ft

152 Town Farm Rd, Ludlow, VT 05149

Property at 32 Melview Rdg, Norwich, VT 05055, 3 beds, 3 baths

$799,000

3 beds3 baths2,686 sq ft

32 Melview Rdg, Norwich, VT 05055

Property at 125 Shurtleff Ln, Woodstock, VT 05091, 4 beds, 4 baths

$1,300,000

4 beds4 baths3,195 sq ft

125 Shurtleff Ln, 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 36 Juniper Dr Unit 6B, White River Junction, VT 05001, 2 beds, 1.5 baths

$339,900

2 beds1.5 baths1,225 sq ft

36 Juniper Dr Unit 6B, White River Junction, VT 05001

Property at 219 Wildlife Rd, White River Junction, VT 05001, 3 beds, 2 baths

$595,000

3 beds2 baths2,176 sq ft

219 Wildlife Rd, White River Junction, VT 05001

Property at 307 Remick Rd, White River Junction, VT 05001, 4 beds, 3 baths

$1,100,000

4 beds3 baths2,640 sq ft

307 Remick Rd, White River Junction, VT 05001

Property at 559 Crimson Hawk Rd, Plymouth, VT 05056, 4 beds, 3.5 baths

$885,000

4 beds3.5 baths2,667 sq ft

559 Crimson Hawk Rd, Plymouth, VT 05056

Property at 514 First Ave, Chester, VT 05143, 5 beds, 5 baths

$529,000

5 beds5 baths3,880 sq ft

514 First Ave, Chester, VT 05143

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 143 Spoonerville Rd, Springfield, VT 05150, 3 beds, 2 baths

$369,000

3 beds2 baths1,320 sq ft

143 Spoonerville Rd, Springfield, VT 05150

Property at 333 Music Mountain Rd, Stockbridge, VT 05772, 3 beds, 2 baths

$715,000

3 beds2 baths2,542 sq ft

333 Music Mountain Rd, Stockbridge, VT 05772

Property at 7 Common St, Springfield, VT 05156, 8 beds, 15 baths

$379,000

8 beds15 baths4,936 sq ft

7 Common St, Springfield, VT 05156

Property at 254/256 Qtr. I Jackson Gore Inn, Ludlow, VT 05149, 1 bed, 2 baths

$72,000

1 bed2 baths775 sq ft

254/256 Qtr. I Jackson Gore Inn, Ludlow, VT 05149

Property at 33 Mountain Ave, Woodstock, VT 05091, 2 beds, 3.5 baths

$1,295,000

2 beds3.5 baths2,280 sq ft

33 Mountain Ave, Woodstock, VT 05091

Property at 46 Ledgeside Ter, White River Junction, VT 05001, 2 beds, 1 bath

$175,000

2 beds1 bath1,296 sq ft

46 Ledgeside Ter, White River Junction, VT 05001

Property at 115 Prior Rd, Cavendish, VT 05142, 3 beds, 2.5 baths

$795,000

3 beds2.5 baths2,128 sq ft

115 Prior Rd, Cavendish, VT 05142

Property at 3914 South Rd, Woodstock, VT 05071, 4 beds, 3 baths

$725,000

4 beds3 baths3,584 sq ft

3914 South Rd, Woodstock, VT 05071

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

$795,000

4 beds3 baths3,190 sq ft

598 E Woodstock Rd, Woodstock, VT 05091

Property at 50 Bates Rd, Cavendish, VT 05142, 3 beds, 1 bath

$299,000

3 beds1 bath1,800 sq ft

50 Bates Rd, Cavendish, VT 05142

Property at 215 Elm Hill St, Springfield, VT 05156, 4 beds, 2.5 baths

$379,000

4 beds2.5 baths2,240 sq ft

215 Elm Hill St, Springfield, VT 05156

Property at 418 Qtr. I I I Jackson Gore Inn, Ludlow, VT 05149, 1 bed, 2 baths

$74,000

1 bed2 baths775 sq ft

418 Qtr. I I I Jackson Gore Inn, Ludlow, VT 05149

Property at 105 Williams LN Unit 7f, Hartford, VT 05059, 3 beds, 2.5 baths

$435,000

3 beds2.5 baths1,352 sq ft

105 Williams LN Unit 7f, Hartford, VT 05059

Property at 1873 Old River Rd, White River Junction, VT 05001, 2 beds, 1 bath

$425,000

2 beds1 bath908 sq ft

1873 Old River Rd, White River Junction, VT 05001

Property at 1928 VT. Route 131, Springfield, VT 05156, 4 beds, 1.5 baths

$825,000

4 beds1.5 baths2,200 sq ft

1928 VT. Route 131, Springfield, VT 05156

Property at 198 Depot St, Proctorsville, VT 05153, 5 beds, 3 baths

$415,000

5 beds3 baths1,976 sq ft

198 Depot St, Proctorsville, VT 05153

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 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 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

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Homes with Garages for Sale in Windsor County

There are currently 210 homes with garages 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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