Windsor County VT Homes for Sale

/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
/23
$80,000
- Land
- 3.99 Acres
- $20,050 per Acre
00 Simonsville Rd, Andover, VT 05143

3.99 +/- acres in Andover close to year round recreation of surrounding towns. This lot was approved by Vt ww dept. in 2008 for a 4 bedroom home and has being updated with a new survey and a revised engineered plan with relocation of the proposed leach field is in process. Located along almost 1000' of the Williams River, after two major storm events, this lot has not lost much ground. A driveway

Geralyn Donohue Engel & Völkers Okemo

00 Simonsville Rd, Andover, VT 05143
/7
$69,500
- Land
- 1.96 Acres
- $35,459 per Acre
Lot 09-195-003 Winsor Dr, Hartford, VT 05001

Great location with easy access to everything the Upper Valley has to offer. Recreation, Shopping, Dartmouth Hospital, College, and more. State approved Septic design, power at the road, along with cable for internet and TV. Just bring your own home design and you are ready to get started on your dream home.

Richard Ballou RE/MAX Upper Valley

Lot 09-195-003 Winsor Dr, Hartford, VT 05001
/9
$99,000
- Land
- 3.80 Acres
- $26,053 per Acre
20,31,32 Pitt Rd, Stockbridge, VT 05722

Nestled in the Green Mountain National Forest, this 3-lot offering in the Timber Hawk community spans nearly 4 wooded acres with approx. 600 ft of frontage along Pit Road, bordering the scenic White River. This package offers a unique opportunity for homeowners, builders, or investors: build one private home or explore the potential to develop up to three single-family homes. Three individual

Tucker Adirondack Lange Vermont Real Estate Company

20,31,32 Pitt Rd, Stockbridge, VT 05722
/9
$49,000
- Land
- 1.70 Acres
- $28,824 per Acre
LOT #23 Westwind Rd, Stockbridge, VT 05772

Perched above the White River and a 5 minute walk to the Peavine Day Use Area river swim spot, this raw land is perfect to build your Vermont dream home. Enjoy breathtaking views and take in the Vermont countryside located in the Timber Hawk neighborhood.

Tucker Adirondack Lange Vermont Real Estate Company

LOT #23 Westwind Rd, Stockbridge, VT 05772
/10
$100,000
- Land
- 11 Acres
- $8,772 per Acre
459 Sugar Hill Rd, Bethel, VT 05032

11.4 private acres of land at the end of Sugar Hill Road. Mostly wooded and sloped with an active stream at the property roadside. A partially finished two-story building exists on the property waiting to be finished by a new owner with the potential use as a camp or starter home. The building was begun in 2011 and has a drilled well and a septic holding tank. A septic design is available. Much

Stan Butler Four Seasons Sotheby's Int'l Realty

459 Sugar Hill Rd, Bethel, VT 05032
/41
$795,000
- 4 Beds
- 2.5 Baths
- 2,663 Sq Ft
490 W Hill Rd, Ludlow, VT 05149

From mountain views to apres-ski soaks in the hot tub, this home delivers the full Vermont lifestyle with ease. Located on one of Ludlow’s most coveted roads, this custom-built mountain retreat offers the perfect blend of quality, comfort, and convenience. Skip the village traffic and drive straight to the base of Okemo in just minutes! Thoughtfully designed and with so much to love, this

Frank Provance Diamond Realty

490 W Hill Rd, Ludlow, VT 05149
/23
$179,900
- Land
- 4.60 Acres
- $39,109 per Acre
00 Quechee-Hartland Rd, Hartford, VT 05001

Outstanding location with easy access to the entire Upper Valley. Town of Hartland is a great community and very desirable for family living, country living with convenient access to all your needs.This lot is part of a two lot subdivision. Septic Engineering has been done and designed for a 4 bedroom home. Lots are cleared with wonderful local views and East and South East exposure.

Charles Bacon Quechee Lakes Real Estate Center

00 Quechee-Hartland Rd, Hartford, VT 05001
/23
$159,900
- Land
- 1.30 Acres
- $123,000 per Acre
0 Quechee-Hartland Rd, Hartford, VT 05001

Outstanding location with local views and east to south easterly exposure. This lot is part of a two lot subdivision .Septic plans available with each lot being designed for a 4-bedroom house. Driveway will be shared until it splits to each house.Easy access to route 4 North in Quechee or route 5 South in Hartland.These lots are cleared land with elevated sites in a lovely setting with

Charles Bacon Quechee Lakes Real Estate Center

0 Quechee-Hartland Rd, Hartford, VT 05001
/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
- 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
/44
$795,000
- 4 Beds
- 2 Baths
- 2,496 Sq Ft
410 Upper Rd, Bridgewater Corners, VT 05035

This 1892 Farmhouse offers two fully furnished and equipped 2-bedroom residences and is located midway between historic Woodstock Vermont and the Killington and Okemo Mt. ski areas, just 15- and 30-minutes' drive away, respectively. The property is privately sited above the Ottauquechee (an Abenaki name translated as 'Bright Water') River and directly across from Long Trial Brewing where a main

Laird Bradley Williamson Group Sothebys Intl. Realty

410 Upper Rd, Bridgewater Corners, VT 05035
/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
/46
$820,000
- 3 Beds
- 3 Baths
- 2,288 Sq Ft
26 Country Crossing, Ludlow, VT 05149

I'm excited to share details about a truly special property that I believe you'll find incredibly appealing. This tastefully appointed home offers multi-level entertainment spaces, three plus comfortable bedrooms, and three baths, making it perfectly suited for both relaxation and entertaining. The location is truly ideal for anyone looking to embrace the Okemo Valley lifestyle. Situated just

Kevin Barnes William Raveis Real Estate Vermont Properties

26 Country Crossing, Ludlow, VT 05149
/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
/55
$598,000
- 3 Beds
- 3.5 Baths
- 2,391 Sq Ft
3440 Route 44, West Windsor, VT 05037

This well cared for contemporary home has only been used as a second home for the original owners. The house takes advantage of the southwest exposure to be able to bring the outside in with the use of large palladium windows and multiple French doors. Some of the interior features include 3 woodburning fireplaces ,wide pine floors ,vaulted ceilings ,and skylights. The floor plan has an easy

Carol Wood Williamson Group Sothebys Intl. Realty

3440 Route 44, West Windsor, VT 05037
/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
/46
$775,000
- 4 Beds
- 2.5 Baths
- 1,844 Sq Ft
36 Lower IV Unit 48A, Ludlow, VT 05149

Beautifully Updated Okemo Trailside Townhome. This tri-level end unit has the feel of being in a country home surrounded by lush trees, however it is on the private shuttle route or a short walk to the trail. You enter the enlarged and spacious mudroom, then into the open kitchen/living/dining rooms with sliders to the wrap around deck. The wood burning fireplace warms this floor for a ski lodge

Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

36 Lower IV Unit 48A, Ludlow, VT 05149
/7
$35,000
- Land
- 1.71 Acres
- $20,468 per Acre
2-49 E Ash Rd, Plymouth, VT 05056

Looking for an ideal piece of land to build your forever home? If so, don't miss out on this stunning 1.71 acres of land with mountain views! Located on a quiet road this peaceful property offers tons of privacy and views of the VT mountains and the beautiful forestry all around you. Just a short drive off of the main road VT route 100 that takes you easily to all the surrounding attractions and

Daniel Preston KW Vermont Woodstock

2-49 E Ash Rd, Plymouth, VT 05056
/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
/51
$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
/51
$450,000
- Land
- 264 Acres
- $1,708 per Acre
0 Peavine Blvd Unit 5046570, Bethel, VT 05032

First time being offered, a 263-acre parcel of wooded and open land, with local and long-distance views. The topography is level too steep with new and old logging trails that crisscross the property. Multiple house sites have been identified from the recent logging, along with destination locations to admire the views and tranquility that nature offers. For the wildlife enthusiast or hunter,

Terry Davis Williamson Group Sothebys Intl. Realty

0 Peavine Blvd Unit 5046570, Bethel, VT 05032
/29
$275,000
- 3 Beds
- 2 Baths
- 1,232 Sq Ft
81 Trombley Rd, Andover, VT 05143

This beautiful privately located 3 bedroom, 2 bathroom manufactured home is move in ready and just waiting for your finishing touches! It has a wonderful level yard with plenty of space for gardens, room to play, or put in a camp fire to sit around on a lovely Vermont evening. There is an additional gravel pad in place that you could put a tiny home as a rental opportunity or a guest house when

Erin Kendall EXP Realty

81 Trombley Rd, Andover, VT 05143
/25
$207,000
- 3 Beds
- 3 Baths
- 1,604 Sq Ft
295 Hotel Rd Unit 10/10A, Brownsville, VT 05037

This spacious walk-up condominium features 3 bedrooms and 3 full baths, with an inviting open-concept living and dining area anchored by a cozy fireplace. Step out onto your private deck overlooking the tubing hill and take in all the action just outside your door!This vibrant community offers an unbeatable lifestyle with access to approximately 1,300 acres of outdoor fun, including

Allison Griep KW Vermont Woodstock

295 Hotel Rd Unit 10/10A, Brownsville, VT 05037
/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
/32
$899,500
- 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 Jackson Gore Rd 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 Jackson Gore Rd 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
$1,250,000
- 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
/13
$157,500
- Land
- 1.00 Acre
- $157,500 per Acre
160 Greeley Shunpike, Hartford, VT 05001

The house on this property was destroyed by fire in 2020. The two car 22 x 24 garage and 8 x 12 garden shed were not damaged.The 24 x 36 concrete foundation may be suitable for reconstruction. All the infrastructure is in place except the house.

Linda Hicks Quechee Lakes Real Estate Center

160 Greeley Shunpike, Hartford, VT 05001
/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
/40
$399,999
- 3 Beds
- 2 Baths
- 1,116 Sq Ft
32 Route 103 S Unit B8, Ludlow, VT 05149

Brookhaven B8, a delightful three-bedroom, two-bathroom condominium located in the Ludlow Village. This beautifully renovated home offers a fantastic combination of comfort and convenience. You'll be just minutes away from the base of Okemo Mountain and the wonderful restaurants and shops in the village, with the added bonus of a free shuttle to the mountain. Inside, the condo features stylish

Katherine Burns William Raveis Real Estate Vermont Properties

32 Route 103 S Unit B8, Ludlow, VT 05149
/46
$730,000
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
28 Fowler Rd Unit N203, Ludlow, VT 05149

Winterplace at Okemo, discover the perfect blend of mountain luxury and year-round adventure. Winterplace N203 is a beautifully renovated three-bedroom, two-bathroom residence nestled in one of the most desirable locations at Okemo Mountain Resort. This ski-in, ski-out home offers a spacious and stylish interior, thoughtfully designed for comfort after a day on the slopes. Step into the warm,

Katherine Burns William Raveis Real Estate Vermont Properties

28 Fowler Rd Unit N203, Ludlow, VT 05149
/27
$1,295,000
- Land
- 9 Acres
- $143,729 per Acre
0 Newton Ln Unit 5045705, Norwich, VT 05055

110 Acres of Pastoral Beauty with Mountain Views in Hartford and Norwich, Vermont.This rare 110-acre parcel, 101 acres in Hartford and nine in Norwich (see separate MLS listing 5045699), offers rolling meadows, mature hardwoods, and long mountain views in the heart of the Upper Valley. The elevated, west-facing setting is filled with natural light and classic Vermont charm, with open

Karen DeMas Four Seasons Sotheby's Int'l Realty

0 Newton Ln Unit 5045705, Norwich, VT 05055

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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.