Windsor County VT Homes for Sale with Parking

/41
$745,000
- 5 Beds
- 2.5 Baths
- 2,717 Sq Ft
1134 Route 106, Reading, VT 05062

Timeless Stone Estate on 36 Acres with Modern Comforts & Rustic Elegance. Welcome to your private countryside retreat—an extraordinary 36-acre estate where historic charm meets modern-day living. Built in the 1800s and thoughtfully updated, this 5-bedroom, 2.5-bath stone home offers the kind of setting most only dream of: expansive rolling land, a private pond and multiple outbuildings for all

Kevin Barnes William Raveis Real Estate Vermont Properties

1134 Route 106, Reading, VT 05062
/38
$650,000
- 2 Beds
- 3 Baths
- 1,367 Sq Ft
193 Jackson Gore Unit 840/842, Ludlow, VT 05149

Discover the perfect balance of comfort, convenience, and stunning valley views in this beautifully appointed 2-bedroom, 3-bathroom residence located in the sought-after Bixby House at Jackson Gore, Okemo Mountain Resort. This spacious and well-designed unit offers an exceptional slopeside experience with direct ski access and all the amenities you need for a relaxing, four-season Vermont

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

193 Jackson Gore Unit 840/842, Ludlow, VT 05149
/46
$52,000
- 1 Bath
- 390 Sq Ft
365 Q4 Jackson Gore Inn Rd Unit 365 Q4, Ludlow, VT 05149

Jackson Gore on Okemo. An excellent opportunity to own a vacation home at Jackson Gore on Okemo, #365 Quarter IV ownership. This option provides an easy way to enjoy a mountain retreat with a minimal investment. This studio property is located within the Jackson Gore Inn, offering slopeside views of the mountain. Owners have access to a wide range of resort amenities, including the pool, hot

Joseph Karl William Raveis Real Estate Vermont Properties

365 Q4 Jackson Gore Inn Rd Unit 365 Q4, Ludlow, VT 05149
/56
$1,125,000
- 4 Beds
- 2.5 Baths
- 2,772 Sq Ft
157 Thompson Rd, Chester, VT 05143

Step back in time and experience the timeless charm of this beautifully preserved historic farm, originally known as Thompson Farm and later operated as Jersey Girl Farm. Dating back to 1830, this remarkable property blends 19th-century character with modern sustainability and comfort. The main house retains its original doors and slate roof, while recent upgrades include a new heating system,

Joe Castaluccio Winhall Real Estate

157 Thompson Rd, Chester, VT 05143
/26
$185,000
- 3 Beds
- 1 Bath
- 1,109 Sq Ft
16 Brierbrook Ln, Springfield, VT 05156

Built in 1954, this classic ranch offers timeless character with modern updates. Nestled beside a tranquil brook in one of the area's most respected neighborhoods, the home combines peaceful surroundings with convenience. Over the past five years, numerous improvements have enhanced comfort and functionality, while leaving room for your personal finishing touches. Features include a one-car

Chelsea Bevis KW Vermont Woodstock

16 Brierbrook Ln, Springfield, VT 05156
/60
$1,500,000
- 10 Beds
- 12 Baths
- 7,153 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
$239,000
- 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
/46
$695,000
- 3 Beds
- 3.5 Baths
- 2,674 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
$1,100,000
- 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
/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
$449,500
- 4 Beds
- 3 Baths
- 4,289 Sq Ft
114 Monument Hill Rd, Springfield, VT 05156

HUGE PRICE REDUCTION! OWNER HAS MOVED SO THE PROPERTY MUST BE SOLD. POSSIBLE OWNER FINANCING!! 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

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
/60
$1,150,000
- 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
/59
$475,000
- 4 Beds
- 3 Baths
- 2,352 Sq Ft
200 Lambert Rd, Springfield, VT 05156

Tucked into a quiet neighborhood in Springfield, this spacious 4-bedroom, 3-bathroom home offers comfort, flexibility, and a long list of recent updates. Set on a peaceful lot with local views, the property features a brand new roof, large newly built deck—perfect for entertaining—and a freshly installed wood stove to keep things cozy in the cooler months. Inside, you'll find new flooring and

Lucas deSousa Vermont Real Estate Company

200 Lambert Rd, Springfield, VT 05156
/41
$337,500
- 3 Beds
- 2 Baths
- 1,798 Sq Ft
109 High St, Cavendish, VT 05142

Upgraded, updated, and ready for you! 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

Dana Haley Diamond Realty

109 High St, Cavendish, VT 05142
/26
$225,000
- 3 Beds
- 1 Bath
- 1,327 Sq Ft
160 Depot St, Chester, VT 05143

Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer,

Joshua Lemieux Remax Summit

160 Depot St, Chester, VT 05143
/60
$495,000
- 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
/39
$575,000
- 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
/41
$375,000
- 4 Beds
- 3 Baths
- 4,012 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
/49
$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
/32
$845,000
- 4 Beds
- 3 Baths
- 3,190 Sq Ft
598 E Woodstock Rd, Woodstock, VT 05091

This stately, rambling gambrel home offers privacy, convenience, antique charm, and room for everyone. Walking distance to the east end of Woodstock village, on 2.9 lush acres including a fenced backyard, a fenced vegetable garden, and extensive perennial beds. The home is a stunning mixture of antique touches and modern functionality, with beautiful built-ins and closet spaces at every turn. The

Geoff Eckler Real Broker LLC

598 E Woodstock Rd, Woodstock, VT 05091
/60
$198,500
- 3 Beds
- 3 Baths
- 1,670 Sq Ft
342/344 Jackson Gore Inn Unit 342/344 Q1, Ludlow, VT 05149

Experience true slopeside living for a fraction of the cost with this quarter-share at Jackson Gore on Okemo—Unit 342/344 QIV. This spacious 3-bedroom, 3-bathroom condo sleeps up to 12 and features a lock-out design, allowing you to use one side and rent the other, use both, or rent both for maximum flexibility and income potential. Highlights include a fully equipped kitchen, two fireplaces,

Sarah Sheehan William Raveis Real Estate Vermont Properties

342/344 Jackson Gore Inn Unit 342/344 Q1, Ludlow, VT 05149
/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
$1,185,000
- 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
$859,000
- 5 Beds
- 4 Baths
- 4,925 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
/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
$639,000
- 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
- 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
/32
$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
$944,999
- 3 Beds
- 3 Baths
- 2,150 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
$1,450,000
- 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
$2,495,000
- 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

Showing Results 121 - 160, Page 4 of 6

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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.