Windsor County VT Homes for Sale with Parking

/55
$499,000
- 3 Beds
- 2.5 Baths
- 2,826 Sq Ft
636 Us Route 5, North Hartland, VT 05052

Welcome to this inviting home designed for everyday living & effortless entertaining. Set on a .66-acre flat lot, the outdoor space offers plenty of room for gardening, recreation, & gatherings. The three-car garage features a full second story accessible via a full staircase-ideal for storage! Enter into a spacious mudroom, a practical space for all seasons. Inside, the open kitchen & dining

Dawn Troutman Susan Cole Realty Group, LLC

636 Us Route 5, North Hartland, VT 05052
/60
$1,500,000
- 10 Beds
- 12 Baths
- 5,500 Sq Ft
1589 Main St, Cavendish, VT 05142

Glimmerstone Mansion—an extraordinary legacy estate where timeless elegance meets modern sophistication. Set on 2.4± beautifully landscaped acres, this iconic property—listed on the National Historic Register—has been meticulously restored, thoughtfully upgraded, and exquisitely furnished. At the heart of the estate is the grand 10-bedroom mansion, where nearly every bedroom and gathering space

Kevin Barnes William Raveis Real Estate Vermont Properties

1589 Main St, Cavendish, VT 05142
/41
$465,000
- 3 Beds
- 2 Baths
- 2,432 Sq Ft
17 Bixby Rd, Ludlow, VT 05149

This warm and welcoming home combines classic charm with practical comfort, offering cozy spaces that invite you to unwind and make yourself at home. There’s so much to love here—from the spacious layout and warm interior touches to thoughtful features like the heated driveway and sun-filled rooms.The sun-drenched kitchen features white cabinetry, stainless appliances, and a spacious breakfast

Frank Provance Diamond Realty

17 Bixby Rd, Ludlow, VT 05149
/12
$249,000
- 3 Beds
- 1 Bath
- 1,440 Sq Ft
419 Coach Rd, Chester, VT 05143

Price Reduction! Come see this private 2-acre lot, off a side street close to the picturesque Chester village. This well maintained 1968 mobile home has a bright open concept addition. Close to ski mountains and other snowmobile trails. Make this a Vermont getaway or a permanent home joining a wonderful community.

Amy Carson Lowe's Real Estate, LLC

419 Coach Rd, Chester, VT 05143
/58
$995,000
- 3 Beds
- 3.5 Baths
- 2,544 Sq Ft
725 Flamstead Rd, Chester, VT 05143

Immaculately maintained 2,700+ sq ft home offers privacy, peace, and mountain views—just 15 minutes to Okemo Mountain and 4 minutes to the village of Chester. Step inside to find an open, flowing layout with timeless and gorgeous Brazilian rosewood floors, a wood burning fireplace in the living room, and walls of windows that frame the landscape. The family chef will happily welcome opportunities

Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

725 Flamstead Rd, Chester, VT 05143
/46
$695,000
- 3 Beds
- 3.5 Baths
- 2,274 Sq Ft
5863 Vt Route 14, South Royalton, VT 05068

Overlooking the Second Branch of the White River, a farm field, and 1/2 acre island in the middle of the White River, this classic old cape dates back to the late 1700s. Previously known as the "Hop Vine Tea Room, when travelers stopped for food and refreshment, the dining hall still remains, dated kitchen, and even indoor plumbing. The many updates include plumbing, wiring, insulation,

Dean Goulet Dunrovin Real Estate

5863 Vt Route 14, South Royalton, VT 05068
/49
$1,175,000
- 4 Beds
- 4 Baths
- 3,920 Sq Ft
1847 Trebo Rd, Chester, VT 05143

With only 50 stone homes in all of Vermont, this one stands out as possibly the most beautiful; uniquely situated on 20 acres of gorgeous greenlawn, fields, forest, rolling hills, extensive stone walls. A mere 2 miles to Chester. Since 2020 the house has been transformed & restored w/improvements such as interior & exterior paint, new windows & French Doors, stone steps & walkways, 50 panel

Gary Coger Four Seasons Sotheby's Int'l Realty

1847 Trebo Rd, Chester, VT 05143
/49
$499,000
- 3 Beds
- 2.5 Baths
- 1,764 Sq Ft
200 Butternut Rd, Hartford, VT 05001

Tucked into one of Hartford’s most desirable neighborhoods, this thoughtfully maintained colonial offers space, comfort, and effortless indoor-outdoor living just minutes from the heart of the Upper Valley.Step inside to a bright, open layout where the kitchen, dining, and living areas flow seamlessly together — ideal for hosting friends, gathering for meals, or simply enjoying everyday

Zack Bourque BHHS Verani Upper Valley

200 Butternut Rd, Hartford, VT 05001
/47
$549,000
- 4 Beds
- 2 Baths
- 2,300 Sq Ft
127 Pleasant St, Cavendish, VT 05142

This lovingly restored Arts and Crafts style home is located just 10 minutes from Okemo Mountain. Built in 1928, this home sits on a peaceful, elevated street in Cavendish, just steps from the town’s sledding hill. Owned by the same family for 20 years, the memories made here are priceless. The children learned to ski at Okemo and with everyone grown, the family is ready to pass along this

Tyleen Murray Kelley Real Estate, Inc.

127 Pleasant St, Cavendish, VT 05142
/45
$569,000
- 4 Beds
- 3 Baths
- 4,289 Sq Ft
114 Monument Hill Rd, Springfield, VT 05156

Perfect Location! This Hilltop Homestead/Mini farm boasts 5 acres of mostly open land and a sprawling 4,000 plus sq. ft. ranch style home with a full finished walkout basement with attached 2 car garage and numerous barns and outbuildings. Easy access to Springfield or Chester and I-91. The home features a huge primary bedroom suite, two other bedrooms and another full bath on the main level,

Chris Long BHG Masiello Brattleboro

114 Monument Hill Rd, Springfield, VT 05156
/38
$109,900
- 2 Beds
- 3 Baths
- 1,367 Sq Ft
505/507 Qtr I Adams House, Ludlow, VT 05149

Adams House Unit 505/507 QII: Quarter ownership. This 2 Bedroom, 3 Bathroom lock-out style unit that sleeps 8 in Adams House is in an excellent location. When you park in the heated North garage, you find yourself only steps away from the unit which is located on the first floor. A very short walk down the hall and you pass the owners locker location. Walk into the living room and you'll be

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

505/507 Qtr I Adams House, Ludlow, VT 05149
/35
$1,350,000
- 4 Beds
- 2.5 Baths
- 2,668 Sq Ft
513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091

This traditional New England Colonial home was professionally designed and custom built by the renowned Vermont Vernacular Builders. The home is strategically sited to enjoy the long views of the distant hills and to benefit from its southern exposure. This 4 bedroom is a quintessential classic example of pure Vermont living apparent in this gracious sun-filled home. There are wide board floors

Chris Crowe Quechee Lakes Real Estate Center

513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091
/59
$1,225,000
- 4 Beds
- 4.5 Baths
- 4,420 Sq Ft
2941 Twenty Mile Stream Rd, Cavendish, VT 05142

Experience timeless elegance and modern luxury in this exquisitely renovated 1834 farmhouse, gracefully sited on one of Cavendish’s most sought-after country roads. Thoughtfully updated while preserving its historic charm, this extraordinary residence features a state-of-the-art chef’s kitchen, whole house a/c and an expansive open-concept main level adorned with original hand-hewn beams and

Joseph Karl William Raveis Real Estate Vermont Properties

2941 Twenty Mile Stream Rd, Cavendish, VT 05142
/60
$4,850,000
- 5 Beds
- 6 Baths
- 9,153 Sq Ft
476 Salt Ash Rd, Plymouth, VT 05056

Serena Lodge was inspired by the legendary William Rockefeller estate in the Adirondacks, known as The Point, and thoughtfully designed to reflect its inviting look and warm, rustic elegance. This 9,000+ square foot residence sits atop a knoll beside a lively creek with small waterfalls, creating a peaceful, natural soundtrack.The Great Room is the centerpiece of the home, with a soaring

Debra Staniscia Four Seasons Sotheby's Int'l Realty

476 Salt Ash Rd, Plymouth, VT 05056
/59
$2,395,000
- 3 Beds
- 5 Baths
- 4,329 Sq Ft
719 Walker Hill Rd, Barnard, VT 05068

An exquisite, private retreat for artists, writers, nature-lovers, composers or simply as a quiet, serene getaway gathering house on 66 stunningly beautiful acres with stone walls, gardens, patios, open lawns, a beautiful swimming pond, in-ground heated saltwater pool with stone patio, and a breathtakingly beautiful outdoor screened pergola. The residence was constructed using reclaimed frames

John Snyder Snyder Donegan Real Estate Group

719 Walker Hill Rd, Barnard, VT 05068
/55
$649,000
- 3 Beds
- 2.5 Baths
- 3,040 Sq Ft
656 Main St, Chester, VT 05143

Magnificent Queen Ann Style Victorian with 3 bedrooms, 2.5 baths on .37 acres in Chester Village. The remarkable front porch has a beautiful archway and intricate, colorful ornamentation. A tiled entryway/coatroom leads to the elegant foyer with dramatic stairway and beautiful glass Art Nouveau Newel post light. The living room features a marble fireplace, pocket doors and original stained glass

Geralyn Donohue Engel & Völkers Okemo

656 Main St, Chester, VT 05143
/32
$344,900
- 3 Beds
- 2 Baths
- 1,798 Sq Ft
109 High St, Cavendish, VT 05142

Discover the perfect blend of small-town charm and four-season adventure in the heart of Cavendish. Perched on a sunny corner lot with views of Hawks Mountain, this classic Vermont home offers easy access to everything from skiing at Okemo to hiking, biking, and swimming nearby. Step inside through the thoughtfully planned mudroom and enter a warm, updated eat-in kitchen—complete with

Dana Haley Diamond Realty

109 High St, Cavendish, VT 05142
/60
$595,000
- 6 Beds
- 1 Bath
- 2,308 Sq Ft
525 Route 103 N, Chester, VT 05143

The possibilities are endless with this beautiful property that has been in the same family since 1964! You will not find a nicer piece of Vermont land than this, with approx. 34 acres of open pastureland bordered by hundreds of feet of the Williams River. This stream offers some great summertime activities such as swimming and fishing! The house and attached barns can be a showplace with some

Glenn Olney Barrett and Valley Associates Inc.

525 Route 103 N, Chester, VT 05143
/56
$599,999
- 5 Beds
- 3.5 Baths
- 2,443 Sq Ft
1057 Quarry Rd, Chester, VT 05143

Chester Haven on a Quiet Dead-End Road. Tucked away in a serene neighborhood, this spacious 5-bedroom, 4-bath home offers over 3,400 sq ft of beautifully designed living space—perfect for both everyday comfort and grand entertaining. Located on a peaceful dead-end street, yet just minutes from the charm and convenience of Main Street, this property offers the best of both worlds. Inside,

Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

1057 Quarry Rd, Chester, VT 05143
/58
$1,495,000
- 4 Beds
- 3 Baths
- 2,384 Sq Ft
416 Wood Rd, Hartford, VT 05001

JUNE HILL STABLES - Open House Saturday, July 19 11:30-1:00 See the evening sky! Perched above the village of Quechee with panoramic views of Quechee Lakes, June Hill Stables is a rare 12.51 acre equestrian estate just east of Woodstock, VT. This 4 bedroom, 3 bathroom homestead was once the personal training facility of an Olympic dressage rider with a 13,600 sq. ft. indoor riding and stable

Sandy Reavill Real Broker LLC

416 Wood Rd, Hartford, VT 05001
/39
$635,000
- 3 Beds
- 2.5 Baths
- 1,452 Sq Ft
3361 County Rd, Windsor, VT 05089

Enjoy privacy and lovely views from this well executed contemporary home overlooking copious gardens and mature plantings to a spectacular pond with an arched footbridge (spotlights highlight the bridge after dark) to access your own little island. Beautiful updates throughout the home include new maintenance-free manufactured cedar-tone shingles on the entire house and workshop shed. The kitchen

Danny Kogut Williamson Group Sothebys Intl. Realty

3361 County Rd, Windsor, VT 05089
/38
$425,000
- 4 Beds
- 3 Baths
- 2,220 Sq Ft
74 Dutton District Rd, Springfield, VT 05156

Located on a quiet country road just outside Springfield, this 4 bedroom home has room for you to move right in. Located just off interstate 91, it offers easy access to White River Junction and the rest of the Upper Valley including Dartmouth College and the Dartmouth Hitchcock Medical Center. Springfield itself offers multiple options for dining and food shopping. The main floors of the

John Tolosky Barrett and Valley Associates Inc.

74 Dutton District Rd, Springfield, VT 05156
/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
$1,295,000
- 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
/52
$825,000
- 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
$1,200,000
- 5 Beds
- 4.5 Baths
- 3,486 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
/32
$325,000
- 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
$640,000
- 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
/52
$1,495,000
- 4 Beds
- 3 Baths
- 3,311 Sq Ft
7511 Woodstock Rd, Hartford, VT 05001

Tucked just off Woodstock Road on over five meticulously landscaped acres, this distinguished 4-bedroom, 2.5-bath Colonial in Quechee, Vermont offers an exceptional blend of privacy and convenience — a short, scenic drive to Woodstock, Hanover, and Lebanon, NH, with easy access to I-89, I-91, and Woodstock Road. Inside, discover a gracious formal dining room with a cozy fireplace and a stunning

Richard Higgerson Higgerson & Company

7511 Woodstock Rd, Hartford, VT 05001
/34
$2,199,000
- 4 Beds
- 3.5 Baths
- 3,564 Sq Ft
15 Hathorn Hill Street Extension, Woodstock, VT 05091

An incredibly rare combination of in-Village and country living. 4+ acres and privacy with a pond and heated in-ground pool, yet walk-to-the Green. The residence, designed and built by the well-respected design-build firm Ambrose Construction, offers modern amenities, appliances and construction with a “Vermont Farmhouse” aesthetic. The vaulted ceiling timber frame great-gathering room has

John Snyder Snyder Donegan Real Estate Group

15 Hathorn Hill Street Extension, Woodstock, VT 05091
/60
$3,199,000
- 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

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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.