Windsor County VT Homes for Sale with Garage

/56
$3,100,000
- 5 Beds
- 4.5 Baths
- 5,194 Sq Ft
165 Moonshadow Dr Unit M-15, Ludlow, VT 05149

Welcome to your mountain sanctuary in the heart of Solitude Village—Okemo’s premier slopeside community. This luxurious 5-bedroom, 3-bathroom retreat offers true ski-on/ski-off access, allowing you to hit the Rising Star Trail or Moon Shadow right from your doorstep. Step inside to a warm, elegant interior featuring radiant-heated tile and rich hardwood floors throughout. The expansive great

Joseph Karl William Raveis Real Estate Vermont Properties

165 Moonshadow Dr Unit M-15, Ludlow, VT 05149
/34
$550,000
- 1 Bed
- 2 Baths
- 1,112 Sq Ft
193 Jackson Gore Unit 639/641, Ludlow, VT 05149

Escape to mountain luxury with this fully furnished 1-bedroom, 2-bathroom condo located in the heart of the premier Okemo ski resort at Jackson Gore. Perfectly positioned just steps from the slopes, this stylish retreat offers the ultimate blend of comfort, convenience and year round adventure. The open-concept living space features a cozy gas fireplace and large windows with mountains views.

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

193 Jackson Gore Unit 639/641, Ludlow, VT 05149
/29
$299,000
- 3 Beds
- 2 Baths
- 1,232 Sq Ft
842 Main St, Proctorsville, VT 05153

Cared for by one owner for many years, this two-story home on .26 +/- acres was rebuilt in 1977 and would make a very cute ski house, vacation or full-time home. Enter through the enclosed breezeway which is a great space for entertaining or relaxing. The eat-in kitchen includes a breakfast/dining nook and excellent counter space. The living room is spacious and has plenty of natural light. A

Geralyn Donohue Engel & Völkers Okemo

842 Main St, Proctorsville, VT 05153
/27
$470,000
- 3 Beds
- 2.5 Baths
- 1,196 Sq Ft
60 Fletcher Ln, Hartford, VT 05001

Discover this raised ranch nestled on 1.38 acres in the heart of Quechee, Vermont—a four-season destination known for its breathtaking natural beauty, vibrant community, and top-tier amenities. This 3-bedroom, 3-bathroom home offers a functional layout, spacious living areas, and easy access to year-round outdoor recreation.Step inside to find an open-concept living and dining space. The

Evan Russell Real Broker LLC

60 Fletcher Ln, Hartford, VT 05001
/42
$424,900
- 3 Beds
- 2 Baths
- 2,776 Sq Ft
64 Summer Hill St, Springfield, VT 05156

Tucked in one of Springfield’s most sought-after neighborhoods, 64 Summer Hill St offers the perfect blend of comfort, charm, and convenience. This beautifully maintained 3-bedroom, 2-bath home nestled in one of Springfield’s most desirable neighborhoods. Located on a peaceful .28acre lot in the Cherry Hill district, this inviting property offers the perfect balance of comfort and convenience.

Jamie Watson BHG Masiello Keene

64 Summer Hill St, Springfield, VT 05156
/60
$1,950,000
- 4 Beds
- 6.5 Baths
- 4,562 Sq Ft
73 Laber Rd, Bridgewater Corners, VT 05035

Experience elevated Vermont living with this exceptional mountaintop estate, thoughtfully designed for both comfort and flexibility. Set on nearly 30 private acres, the residence combines timeless architectural style with expansive interiors and truly breathtaking panoramic views—including sightlines to 4,000-foot peaks and Killington’s ski trails.Inside, you’ll find a rare level of

Keri Cole Williamson Group Sothebys Intl. Realty

73 Laber Rd, Bridgewater Corners, VT 05035
/24
$400,000
- 3 Beds
- 2 Baths
- 1,360 Sq Ft
17 Larkspur Ln, White River Junction, VT 05001

Welcome to this light-filled 3-bedroom, 2-bath free-standing home in the desirable Courtyard at Hemlock Ridge community. Tucked away in a peaceful, walkable neighborhood, this home offers comfort, style, convenience, and is handicap accessible. Inside, enjoy soaring 9+ foot ceilings that enhance the spacious feel, along with floor-to-ceiling built-in bookshelves that add both function and charm.

Cheryl Herrmann RE/MAX Group One Realtors

17 Larkspur Ln, White River Junction, VT 05001
/57
$985,000
- 3 Beds
- 2 Baths
- 2,760 Sq Ft
616 Rose Hill Rd, Woodstock, VT 05091

This is a rare opportunity to own 10.1 acres of land in a coveted area of Woodstock that includes a 1988 Frizzell Builders house and a detached oversized garage with a second floor for storage . The property was part of the King Farm which is now in Vt. Land Trust as conserved land , until it was split off in the late 1980's when the Colby family came into ownership and built the existing house

Carol Wood Williamson Group Sothebys Intl. Realty

616 Rose Hill Rd, Woodstock, VT 05091
/25
$495,000
- 3 Beds
- 1 Bath
- 895 Sq Ft
121 E Lake Rd, Ludlow, VT 05149

Charming Lake Cottage with Over 113 +/-Feet of Waterfront on Lake Pauline.Lovingly maintained by the same family since the 1940s, this delightful lakefront cottage is a rare find. Step inside to discover original touches like tongue-and-groove paneling and vintage details that evoke a simpler time, all thoughtfully preserved. Modern updates blend seamlessly with its nostalgic charm and

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

121 E Lake Rd, Ludlow, VT 05149
/32
$2,250,000
- 2 Beds
- 4 Baths
- 2,410 Sq Ft
611 Simmons Rd, Chester, VT 05143

Skygate Farm is a historic Vermont farmstead first settled in the 1800s, which today spans over 300 acres of meadows, forests, trails, and weathered stone walls. The setting speaks of an early farmer’s wisdom — sited along a gentle hill to shield against the northwest winds, while opening to the first light of day and the vast mountain views to the east. Found at the end of a winding gravel road,

Dia Jenks LandVest, Inc/Woodstock

611 Simmons Rd, Chester, VT 05143
/60
$1,295,000
- 5 Beds
- 3 Baths
- 3,281 Sq Ft
170 Joshua Rd, White River Junction, VT 05001

Welcome to a rare blend of historic charm and modern comfort. Tucked at the end of a quiet dirt road in Norwich, VT, this expanded 1860 farmhouse offers 3,281 sqft of character-filled living space with 10 rooms, 5 bedrooms, and 3 full baths. Original hand-hewn beams, wide plank floors, and a spacious farmer’s porch set a warm, inviting tone. Thoughtful updates made during the seller’s ownership

Cheryl Herrmann RE/MAX Group One Realtors

170 Joshua Rd, White River Junction, VT 05001
/40
$950,000
- 4 Beds
- 4 Baths
- 3,278 Sq Ft
2904 E Hill Rd, Andover, VT 05143

Perched on 60 acres with views of Okemo Mountain from its second floor, this custom designed contemporary is hitting the market for the first time. Built by an international journalist and his writer wife as a retreat for their family and high profile friends, it now awaits its next lucky stewards. Filled with natural light, the rambling home was inspired by a friend's classic Vermont

Steve Stettler Four Seasons Sotheby's Int'l Realty

2904 E Hill Rd, Andover, VT 05143
/60
$569,000
- 3 Beds
- 2 Baths
- 2,008 Sq Ft
352 Edwins Pond Rd, Rochester, VT 05767

Welcome to Tranquility in Vermont.This charming three-bedroom, two-bath home invites you to unwind and enjoy the peaceful beauty of Vermont living. With both a spacious great room and a cozy living room—each warmed by its own wood stove—you’ll always have the perfect place to relax.The home features wide plank wood floors throughout, a brand-new heating system with on-demand hot

Katie McFadden RE/MAX North Professionals

352 Edwins Pond Rd, Rochester, VT 05767
/60
$3,650,000
- 5 Beds
- 4 Baths
- 5,181 Sq Ft
348 Turtle Hill Rd, Ludlow, VT 05149

Built over the course of two years and completed in 2023, this nearly new custom timberframe home showcases exceptional craftsmanship and fine attention to detail. Privately sited on over 13 acres, the property offers sweeping, panoramic views of southern Vermont's mountains and valleys; vistas that are truly second to none. The home's architectural highlights include hand-hewn Douglas fir beams

Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

348 Turtle Hill Rd, Ludlow, VT 05149
/52
$1,299,000
- 4 Beds
- 4.5 Baths
- 4,009 Sq Ft
320 Old Bow Rd, Springfield, VT 05156

Spacious Country Retreat with Stunning Views! Experience the perfect blend of space, privacy, and scenic beauty in this impressive country home. Set on 13.78 acres, this property offers expansive outdoor and indoor living, with amazing panoramic views. Inside, you'll find large sunlit rooms including oversized bedrooms, a mudroom, and second floor laundry for convenience. The open concept living

Jenn Boyer Coldwell Banker Homes Unlimited

320 Old Bow Rd, Springfield, VT 05156
/60
$3,650,000
- 5 Beds
- 5 Baths
- 3,212 Sq Ft
166 Jewett Rd, Brownsville, VT 05037

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,

Dana Waters Dark Horse Realty

166 Jewett Rd, Brownsville, VT 05037
/42
$359,000
- 3 Beds
- 1 Bath
- 1,144 Sq Ft
919 Vermont Route 100, Rochester, VT 05767

Situated on a sun-drenched, level yard you will find this stunning ranch-style home, equipped with the latest amenities, including new electrical andheating systems, water heater, insulation, windows and doors, siding, interiorwalls, recessed lighting thoughout, hardwood floors, spacous kitchen, and abath featuring a granite vanity. A brand new wood stove offers an additional heating

Christopher King King Real Estate

919 Vermont Route 100, Rochester, VT 05767
/45
$74,000
- 1 Bed
- 2 Baths
- 775 Sq Ft
418 Qtr I Jackson Gore Inn, Ludlow, VT 05149

Top-Floor 1BR/2BA at Jackson Gore – Sleeps 6, Gorgeous Views, Premium Resort AccessExperience the best of slopeside living with this beautifully appointed 1-bedroom, 2-bathroom top-floor unit at Jackson Gore, Okemo Mountain Resort. Perfectly positioned with incredible valley views and a glimpse of the outdoor heated pool, this residence offers both comfort and convenience, just steps from the

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

418 Qtr I Jackson Gore Inn, Ludlow, VT 05149
/54
$985,000
- 3 Beds
- 3 Baths
- 1,920 Sq Ft
72 Oakridge Way, Woodstock, VT 05091

PRIME LOCATION! Tucked away at the end of a peaceful dead-end road in the Westerdale neighborhood is this Vermont Cape Cod home offers the perfect blend of privacy and convenience on just over 6 acres. Surrounded by mature trees and set on a wooded lot overlooking a tranquil pond, you’ll enjoy the calm of nature right outside your doorstep. The freshly installed deck provides a serene spot.

Nancy Greenwood Watson Realty & Associates

72 Oakridge Way, Woodstock, VT 05091
/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
/32
$385,000
- 2 Beds
- 1 Bath
- 768 Sq Ft
68 Advent Hill Rd, Hartland, VT 05048

Country Ranch with Stunning Views in Hartland, VTEscape to the peaceful charm of this 2-bedroom, 1-bath ranch-style home nestled in scenic Hartland. Set on a beautiful country lot, this single-level home offers sweeping views of the surrounding countryside—perfectly enjoyed from the spacious front porch. Inside, you’ll find a bright and efficient layout with cozy living spaces, a

Katie Ladue Gilbert KW Vermont Woodstock

68 Advent Hill Rd, Hartland, VT 05048
/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
$1,249,000
- 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
/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
/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
/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
$489,900
- 4 Beds
- 3 Baths
- 2,289 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
$1,225,000
- 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
- 6,313 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
/41
$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
/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
/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
/39
$575,000 Open Sat 11AM - 1PM
- 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
/51
$399,000
- 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

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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.