Windsor County VT Homes for Sale with Garage

/40
$465,000
- 3 Beds
- 3 Baths
- 1,600 Sq Ft
2 High St, Woodstock, VT 05091

FLASH OPPORTUNITY AWAITS – Historic c. 1890 1,600 sq/ft. unfinished home in the center of downtown Woodstock. In the heart of everything! LOOKING FOR A FAST SALE - AND A CASH BUYER. The home has been stripped back to framing and is ready for a builder or future investment. It is not currently habitable and will not be able to be sold or shown to someone looking for financing or construction loan

John Bassette Bassette Real Estate Group

2 High St, Woodstock, VT 05091
/44
$629,000
- 1 Bed
- 1.5 Baths
- 1,044 Sq Ft
144 Lodge Rd Unit 5, Ludlow, VT 05149

Slopeside at SouthFace Village Okemo! This may be the nicest one-bedroom condominium currently available on Okemo Mountain. Immaculate and barely used, it comfortably sleeps six and is offered fully furnished, move-in ready for your mountain escape. The interior features stylish quartz countertops, hardwood flooring, built-in shelving, and energy-efficient appliances. Ductless mini-splits provide

Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

144 Lodge Rd Unit 5, Ludlow, VT 05149
/60
$1,250,000
- 5 Beds
- 3.5 Baths
- 2,649 Sq Ft
331 Vermont Route 100, Plymouth, VT 05149

Experience the blend of lakeside tranquility and ski country convenience at Echo View Farm—an exquisitely restored Vermont farmhouse set on 6.7 picture-perfect acres overlooking Echo Lake. Every detail of this five-bedroom, three-and-a-half-bath retreat has been thoughtfully curated to deliver timeless elegance with modern comfort. Step into the heart of the home where a chef’s kitchen, complete

Kevin Barnes William Raveis Real Estate Vermont Properties

331 Vermont Route 100, Plymouth, VT 05149
/42
$985,000
- 5 Beds
- 4 Baths
- 3,625 Sq Ft
1166 Rte 100, Weston, VT 05161

Nearly 5,000 sq ft of flexible living space in one of Vermont’s most desirable towns—perfect for second-home buyers or investors. This unique property offers two distinct living areas under one roof: a beautifully designed walk-out lower level apartment ideal for rental income, in-law suite, or guest quarters, and an updated main level with style and comfort. The main level features a modern

Carrie Mathews Winhall Real Estate

1166 Rte 100, Weston, VT 05161
/52
$798,500
- 3 Beds
- 2 Baths
- 1,573 Sq Ft
6 Ledgewood Rd Unit A-5 w/ A-1 Garage, Ludlow, VT 05149

Ledgewood on Okemo Mountain, discover the allure of Ledgewood where slopeside living becomes a reality. These highly sought-after condominiums, known for their quality craftsmanship featuring masonry fireplaces, solid wood doors, and convenient garages, offer an exceptional opportunity. This particular floor plan boasts generous space perfect for accommodating everyone. Imagine cozy evenings by

Katherine Burns William Raveis Real Estate Vermont Properties

6 Ledgewood Rd Unit A-5 w/ A-1 Garage, Ludlow, VT 05149
/54
$1,395,000
- 2 Beds
- 2.5 Baths
- 2,112 Sq Ft
683 Reservoir Rd, White River Junction, VT 05001

Welcome home to pure perfection, privacy, and magic. This serene setting, with lush gardens and a rolling lawn, boasts a unique twist on a timber frame design, providing modern amenities and comfortable spaces throughout. A beautifully appointed, main floor primary en-suite offers a spacious bathroom with a tiled shower and large soaking tub, plus a large walk-in closet and laundry. The rest of

Zoe Hathorn Washburn Snyder Donegan Real Estate Group

683 Reservoir Rd, White River Junction, VT 05001
/35
$665,000
- 3 Beds
- 2 Baths
- 1,908 Sq Ft
530 West Rd, Barnard, VT 05031

Conveniently located less than a mile from Barnard General Store and Silver Lake, this charming 3 bedroom cape sits on just over 3 acres of land with tiered stone walls and green lawn circling the house. Mature trees surround the yard and there is view potential with minor clearing and thinning. The full length back deck offers private outdoor space including a covered grilling area just steps

Dan Noble Snyder Donegan Real Estate Group

530 West Rd, Barnard, VT 05031
/27
$950,000
- 5 Beds
- 4.5 Baths
- 2,686 Sq Ft
19 Church St Unit EX, Woodstock, VT 05091

Bright and spacious five bedroom, five bath in-village residence with Ottauquechee River frontage and less than 1-minute walk to the Woodstock Green. 2-car attached garage enters into the kitchen via a mud-laundry room. Eat-in kitchen with stainless appliances, granite countertops and a large sunny bay window leads to the formal dining room, and also opens to the patio, perfect for entertaining

John Snyder Snyder Donegan Real Estate Group

19 Church St Unit EX, Woodstock, VT 05091
/34
$349,000
- 3 Beds
- 2 Baths
- 1,453 Sq Ft
724 S Windsor St, South Royalton, VT 05068

This lovely updated three-bedroom two bath Central VT home offers great opportunity for residential use, or for investors as a rental property. At one time a two-unit, the home is less than a mile to Vermont Law School (VLS), and just a half mile to the WRV elementary and High Schools. The lovely Village green, where Community activities and farmers markets are held throughout the year is also

Kate Jarvis Williamson Group Sothebys Intl. Realty

724 S Windsor St, South Royalton, VT 05068
/55
$2,950,000
- 4 Beds
- 4.5 Baths
- 6,548 Sq Ft
657 Town Farm Rd, Ludlow, VT 05149

61 Acre estate with sweeping views and open fields in Ludlow's prestigious South Hill area. Less than 10 minutes to the Okemo ski area and the Ludlow village amenities, this luxury home has received numerous updates in the last several years.Large updated eat-in country kitchen w/ wood cabinetry, stone countertops and updated stainless steel appliances. A gas fireplace with sitting room

Andre Menard Mary W. Davis Realtor & Assoc., Inc.

657 Town Farm Rd, Ludlow, VT 05149
/55
$975,000 Open Sun 1PM - 3PM
- 3 Beds
- 3 Baths
- 1,656 Sq Ft
509 Church Hill Rd, Wood Stock, VT 05091

Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens.The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes ,

Carol Wood Williamson Group Sothebys Intl. Realty

509 Church Hill Rd, Wood Stock, VT 05091
/32
$299,000
- 6 Beds
- 2 Baths
- 2,518 Sq Ft
761 Main St, Cavendish, VT 05153

Location, Location, Location...Large families and investors take note. This classic colonial located on the corner of Main Street and Twenty Mile Stream Road is ready for the next family to enjoy or use for rental income. This was the family's gathering house for 55 years, and now it could be yours. There are 6 bedrooms, a woodstove/fireplace, mudroom, 1 car garage/workshop, and bonus space on

Kevin Barnes William Raveis Real Estate Vermont Properties

761 Main St, Cavendish, VT 05153
/60
$1,597,000
- 6 Beds
- 5.5 Baths
- 4,225 Sq Ft
515 Shattuck Hill Rd Unit 515, 513 & 511, Reading, VT 05062

Nestled in the tranquil hills of West Windsor, Vermont, Rock Haven Estate is a remarkable 33.49-acre country sanctuary offering three separate luxury homes, set along a private drive & surrounded by nature’s beauty. Whether you're looking for a full-time residence with income-generating opportunities or a private family compound, Rock Haven Estate is a rare find! The Rock House - Hilltop Elegance

Kate Jarvis Williamson Group Sothebys Intl. Realty

515 Shattuck Hill Rd Unit 515, 513 & 511, Reading, VT 05062
/54
$1,690,000
- 5 Beds
- 4.5 Baths
- 4,617 Sq Ft
687 S Perry Rd, Woodstock, VT 05091

Privately sited on a knoll to capture sweeping North Westerly views, this expanded Classic Cape has been lovingly stewarded and tastefully updated over the years. Enter through the formal foyer with wainscot, or a convenient mudroom with powder room. Superior craftsmanship throughout featuring a beautifully appointed chef's kitchen with Viking range-top, wall ovens and best quality appliances,

Danny Kogut Williamson Group Sothebys Intl. Realty

687 S Perry Rd, Woodstock, VT 05091
/29
$399,000
- 4 Beds
- 3.5 Baths
- 2,710 Sq Ft
491 Farrar Rd, Chester, VT 05143

Tucked away on a quiet dirt road, this spacious sunny south-facing home offers a peaceful retreat with sweeping views of the surrounding countryside. Step onto the expansive front deck and take in the stunning long-range scenery, including a picturesque pond just beyond the property—yours to enjoy without the upkeep.Inside, the home is open and inviting, with plenty of room to relax or

Daire Gibney Barrett and Valley Associates Inc.

491 Farrar Rd, Chester, VT 05143
/55
$2,695,000
- 5 Beds
- 4.5 Baths
- 3,090 Sq Ft
248 Gird Lot Rd, Weathersfield, VT 05151

This meticulously maintained five-bedroom, four-and-a-half-bath home offers sweeping views of the Connecticut River Valley and New Hampshire mountains. Thoughtfully designed for comfort and flexibility, the open-concept layout includes a main-level living option, hardwood floors, and tall ceilings with abundant and expansive windows that flood the home with natural light.The spacious

Karen DeMas Four Seasons Sotheby's Int'l Realty

248 Gird Lot Rd, Weathersfield, VT 05151
/57
$599,900
- 3 Beds
- 2.5 Baths
- 1,835 Sq Ft
2475 Little Hollow Rd, Rochester, VT 05767

Quintessential VT Mountain Location with privacy & seclusion galore! Surrounded by thousands of acres of locally owned timberland, many abundant recreational opportunities to Mount Cushman and the magnificent Little Hollow recreational area. Absolutely Gorgeous 3 bedroom, 3 bath Modified Cape on 7.1 acres of open and wooded land, that is located at the very end of a Class 3 town maintained road,

Paul H Rea Rural Vermont Real Estate

2475 Little Hollow Rd, Rochester, VT 05767
/60
$2,995,000
- 5 Beds
- 9 Baths
- 8,249 Sq Ft
1497 Bowman Rd, Barnard, VT 05068

Upper Farm- Circa 1799, large antique cape nestled on 12 acres with stream, multiple ponds, stunning waterfalls overlooking a large meadow. Beautiful extensive gardens for all those perennial enthusiasts with multiple stone terraces overlooking an apple orchard with a variety of types of apples. A two level barn for equipment/storage/animals. A brand new expansive 3 bay heated garage with

Gretchjen Smith Williamson Group Sothebys Intl. Realty

1497 Bowman Rd, Barnard, VT 05068
/59
$1,745,000
- 2 Beds
- 3 Baths
- 2,106 Sq Ft
7 North St, Woodstock, VT 05091

Stunning Renovated Antique Cape in the Heart of Woodstock Village!Tucked away on over an acre of beautifully landscaped land directly abutting the Marsh-Billings-Rockefeller National Park, this fully renovated antique Cape offers the rare combination of historic charm, modern efficiency, and unbeatable walkability. Located in the heart of Woodstock Village, you can stroll to the village

Keri Cole Williamson Group Sothebys Intl. Realty

7 North St, Woodstock, VT 05091
/60
$1,995,000
- 3 Beds
- 2.5 Baths
- 5,422 Sq Ft
2334 South Rd, Woodstock, VT 05091

Offered for the first time, the exclusive private residence of one of Woodstock's most notable and prolific builders, Hank Savelberg. Located just five minutes from the Woodstock Village Green, this whimsical, private, contemporary hillside estate was lovingly constructed featuring well thought, connected open spaces with expansive glass walls and dramatic sweeping wooden ceilings. The entire

Danny Kogut Williamson Group Sothebys Intl. Realty

2334 South Rd, Woodstock, VT 05091
/33
$4,490,000
- 5 Beds
- 5.5 Baths
- 8,122 Sq Ft
5685 Vermont 12, Barnard, VT 05031

SEE PROPERTY-SPECIFIC WEBSITE FOR DETAILS, HIGH RESOLUTION PHOTOS, VIDEOS AND MORE. If you’ve been looking for the iconic Vermont home, rarely does an opportunity like this present itself. Welcome to HIGHLAND GLEN, an idyllic Vermont home situated on 12 picturesque acres in the quaint town of Barnard, VT. Upon arrival at Highland Glen, you'll immediately sense the special charm of this

John Snyder Snyder Donegan Real Estate Group

5685 Vermont 12, Barnard, VT 05031
/60
$649,000
- 4 Beds
- 2.5 Baths
- 2,520 Sq Ft
5100 Route 100, Plymouth, VT 05056

(Das Grunebergehaus) The Green Mountain House. First time offered on market since 1978. This gorgeous farmhouse, circa 1831, has been lovingly maintained & updated over the current owner's term of ownership. Previously owned by the Coolidge Family. During the years of Calvin Coolidge's presidency this home was used as a guest house for political figures to come & stay while visiting President

Marni Rieger KW Vermont-Killington

5100 Route 100, Plymouth, VT 05056
/45
$450,000
- 3 Beds
- 2 Baths
- 1,809 Sq Ft
935 French Meadow Rd, Springfield, VT 05156

Nestled in peaceful seclusion on 21.4 acres, this inviting split-level home is ready to welcome its next owners. While privately situated and out of view from the road, the property remains conveniently close to VT Routes 106 and 10, offering the perfect blend of privacy and accessibility.Step inside from the charming covered porch into a spacious mudroom with Vermont slate flooring,

Jessica Landers Barrett and Valley Associates Inc.

935 French Meadow Rd, Springfield, VT 05156
/35
$199,000
- 3 Beds
- 1 Bath
- 1,322 Sq Ft
841 Farrar Rd, Chester, VT 05143

Looking for an opportunity in an ideal location? This property offers unbeatable potential in the sought-after town of Chester. Located on a quiet country road, but still just a couple miles from downtown shopping and dining you get the best of both worlds. This property offers both open and wooded acreage with fruit trees to enjoy! Featuring two generously sized garages, this home is ideal for

Taylor Medeiros-Batey KW Coastal and Lakes & Mountains Realty/Hanover

841 Farrar Rd, Chester, VT 05143
/39
$465,000
- 4 Beds
- 2.5 Baths
- 2,125 Sq Ft
143 Okemo Acres, Ludlow, VT 05149

Charming Fixer-Upper in a Dream Location – Your Canvas Awaits!Step into a world of endless possibilities with this house, nestled in the heart of a picturesque neighborhood just a mere 0.8 miles from the magnificent Okemo Mountain. This property is not just a house; it’s a golden opportunity for those with a vision, a passion for design, and a desire to create a home that reflects their

Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

143 Okemo Acres, Ludlow, VT 05149
/44
$3,275,000
- 4 Beds
- 4.5 Baths
- 3,363 Sq Ft
207 Willey Hill Rd, Norwich, VT 05055

Nestled on a private 17-acre retreat, The Pond at Willey Hill is a quintessentially picturesque estate just a stone’s throw away from Norwich, Hanover, and the best of the Upper Valley. Featuring a wildlife-rich pond as its center, the beautifully landscaped grounds offer seasonal long-range views, a pool, woodland trail, and a park-like fenced area. Expertly renovated by renowned builders O’Hara

David Donegan Snyder Donegan Real Estate Group

207 Willey Hill Rd, Norwich, VT 05055
/48
$575,000
- 9 Beds
- 6 Baths
- 5,054 Sq Ft
12 Commonwealth Ave, Ludlow, VT 05149

A rare find in the heart of the Ludlow Village. This three-family property offers over 5,000 sq. ft. of income-generating space, just steps from the Okemo shuttle and downtown Ludlow! With a strong rental history this property offers both versatility and value. Two of the three units have been beautifully, recently updated and are turn key. One unit used by by the Seller, the second currently

Frank Provance Diamond Realty

12 Commonwealth Ave, Ludlow, VT 05149
/10
$385,000
- 6 Beds
- 4 Baths
- 2,949 Sq Ft
7 Commonwealth Ave, Ludlow, VT 05149

Bring your vision and unlock the potential! This property has been fully gutted and is ready for your transformation. With a new roof, windows and siding and decking on the porch, you're well on your way! Conveniently located in the Village Of Ludlow near skiing, golf, lakes for swimming, and village shopping, it’s the perfect opportunity for contractors, investors, or DIYers. With two separate

Frank Provance Diamond Realty

7 Commonwealth Ave, Ludlow, VT 05149
/48
$4,900,000
- 7 Beds
- 9 Baths
- 8,442 Sq Ft
5893 Stage Rd, Barnard, VT 05031

"LONG WAY HILL" - An elegant and beautifully constructed residence of the highest quality, privately situated on 54 acres with long-range views, lawns, gardens, fields and trails. Beautiful perennial and wildflower gardens offer charming, private views of woods and hills over a half-acre pond. Architect-designed in the style of a traditional New England country home, the main residence has 5

John Snyder Snyder Donegan Real Estate Group

5893 Stage Rd, Barnard, VT 05031
/56
$1,125,000
- 3 Beds
- 2.5 Baths
- 2,668 Sq Ft
32 Old Farm Rd, Norwich, VT 05055

Spring is in full bloom around this beautiful home in the desirable Old Farm neighborhood! With many spaces thoughtfully renovated in recent years by Riverlight Builders, this property features a stunning new kitchen with a center island with bar seating, Quartzite natural stone countertops, and high-end cabinetry, seamlessly open to the main floor living areas, making it ideal for entertaining

Evan Pierce Four Seasons Sotheby's Int'l Realty

32 Old Farm Rd, Norwich, VT 05055
/47
$679,900
- 3 Beds
- 2.5 Baths
- 3,680 Sq Ft
82 Hiram Atkins Byway, Hartford, VT 05001

Price Reduced! Wonderful colonial style home that has been beautifully maintained, updated and nestled on a semi private lot in Quechee Lakes. Membership gives access to one of Vermont's finest 36 hole golf courses, club house, pool, beach area at lake Pineo, quechee ski hill, pickleball, tennis and is a great spot for biking and hiking. Just a short drive to KILLINGTON, Pico, Saskadena Six Ski

Alex DeFelice The Clerkin Agency, P.C.

82 Hiram Atkins Byway, Hartford, VT 05001
/38
$750,000
- 2 Beds
- 3 Baths
- 1,364 Sq Ft
193 Jackson Gore Unit 739/741, Ludlow, VT 05149

Come and experience Vermont at its best! This condo is located in Jackson Gore on Okemo Mountain in Ludlow. This slope side condo unit has stunning views of the mountain and trails. This unit would serve well as a family retreat or rental investment property. It boasts a gas fireplace for cold winter nights. It has 2 bedrooms and 3 bathrooms and offers lock-out capability for separate rental

John Napier TPW Real Estate

193 Jackson Gore Unit 739/741, Ludlow, VT 05149
/51
$695,000
- 4 Beds
- 3 Baths
- 3,100 Sq Ft
35 Stevens Rd, Cavendish, VT 05142

This is a dream come true for someone who is seeking a Vermont nature retreat in every season. Located on the corner of two quiet, town maintained, gravel roads, one of which is a dead end, is the handsome 1800 traditional Cape with two additions! This classic home includes 40+ acres. Only one other house can be seen from the property & you have to know where to look! The views of Mother Nature

Betty McEnaney Diamond Realty

35 Stevens Rd, Cavendish, VT 05142
/42
$345,000
- 3 Beds
- 2 Baths
- 1,492 Sq Ft
2903 Vermont 107, Stockbridge, VT 05772

Come take a look at this 3 bedroom, 1 3/4 bath, well cared for and tastefully updated "Country Charmer". This home has a little bit of everything for everyone. Sited on an amazing well-manicured level lot. There is an additional 2 bay garage w/ample workshop area, a sugar house, and a pony/animal run-in. The first floor has a primary bedroom, 3/4 bath and laundry. Enjoy the sunny, open flow from

Rose Wright Vermont Heritage Real Estate

2903 Vermont 107, Stockbridge, VT 05772
/35
$690,000
- 3 Beds
- 3.5 Baths
- 2,314 Sq Ft
3755 Quechee Main St Unit 11B, Quechee, VT 05059

Unique opportunity to own in the highly sought-after Coach Road condominium complex! This unit is within walking distance to the Quechee Club and all its amenities. Coach Road condos boast what many say is the best location in Quechee. Entering through the front door, you find a generous foyer with ample closet space. High ceilings and full-length windows shower this home with light. The kitchen,

Jennifer Kirkman KW Vermont Woodstock

3755 Quechee Main St Unit 11B, Quechee, VT 05059
/47
$8,000,000
- 3 Beds
- 3.5 Baths
- 5,384 Sq Ft
115 Eastman Rd, Woodstock, VT 05091

Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

Keri Cole Williamson Group Sothebys Intl. Realty

115 Eastman Rd, Woodstock, VT 05091
/38
$690,000
- 4 Beds
- 3 Baths
- 2,557 Sq Ft
144 Butternut Ln, Woodstock, VT 05091

The Harry Emmons House an antique brick cape located in the village of Taftsville sited on an open flat village lot. Through the classic covered farm porch enter a gathering room with a brick fireplace, light-filled high ceilings, exposed beams in comfortably sized rooms, a country kitchen, sunny dining room, and a first-floor bedroom with dressing area. Moving upstairs, the second floor has two

Scott Monahan Williamson Group Sothebys Intl. Realty

144 Butternut Ln, Woodstock, VT 05091
/23
$110,000
- 3 Beds
- 2 Baths
- 1,144 Sq Ft
133 Willow Cir, White River Junction, VT 05001

An affordable 3-bedroom 2-bath double-wide home in one of the Upper Valley’s most sought-after parks, Tall Timbers. One Car garage, lots of storage and more. This home offers laminate flooring, spacious kitchen and laundry area. One of the best lots available with plenty of space, you’ll feel like you live on your own land. The surrounding homes are in great condition and with a little TLC

Richard Ballou RE/MAX Upper Valley

133 Willow Cir, White River Junction, VT 05001
/46
$625,000
- 2 Beds
- 3 Baths
- 1,369 Sq Ft
193 Jackson Gore Unit 640/642, Ludlow, VT 05149

Bixby House 640/642 Whole Ownership. This luxury two-bedroom, valley side home features fully-equipped kitchen with stainless steel appliances, tiled back splash, farm sink and granite counters. The cozy living room includes a dining area and gas fireplace. The tiled foyer entry provides storage for outdoor gear. Primary bedroom has a king bed and a spacious master bath with his and her sinks.

Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

193 Jackson Gore Unit 640/642, Ludlow, VT 05149
/30
$524,000
- 4 Beds
- 2.5 Baths
- 2,238 Sq Ft
141 N Runway Rd, Perkinsville, VT 05151

Welcome to this beautifully maintained expanded Cape, perfectly positioned to capture stunning views of the Hartness runway—an aviation enthusiast's dream! Tucked away on a quiet dead-end road, the property offers just the right balance of privacy and convenience, located only 10 minutes from major grocery stores, entertainment, and other everyday essentials.The main level features a

Allison Griep KW Vermont Woodstock

141 N Runway Rd, Perkinsville, VT 05151

Showing Results 121 - 160, Page 4 of 6

Vermont Windsor County

How to Buy a Home How to Finance a Home How to Sell a Home

Windsor County Types of Homes for Sale

Windsor County Real Estate Listings

Windsor County New Construction Homes

More About Living in Windsor County

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.