Windsor County VT Homes for Sale

/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
/21
$15,000
- Land
- 1.05 Acres
- $14,286 per Acre
0 Vermont Route 100, Plymouth, VT 05056

Discover one of the most affordable ways to get into the Hawk Mountain Resort community. This parcel is located off scenic byway Route 100 and is only minutes to Okemo or Killington. There are 4 lakes all within a few minutes as well. Plenty of hiking, biking, boating, and fishing in the area. All plans and permits must be approved by the Hawk Architectural Review Board. No trailers, yurts, RV's

Kevin Barnes William Raveis Real Estate Vermont Properties

0 Vermont Route 100, Plymouth, VT 05056
/22
$15,000
- Land
- 1.01 Acres
- $14,851 per Acre
0 Crimson Hawk Rd, Plymouth, VT 05056

This parcel is part of the Hawk West side of Hawk Mountain Resort and is one of the most affordable ways to get into the Hawk Mountain Resort Community. Easy access to Route 100 and only minutes to Okemo or Killington. There are 4 lakes all within a few minutes as well. Plenty of hiking, biking, boating, and fishing in the area. All plans and permits must be approved by the Hawk Architectural

Kevin Barnes William Raveis Real Estate Vermont Properties

0 Crimson Hawk Rd, Plymouth, VT 05056
/18
$50,000
- Land
- 2.07 Acres
- $24,155 per Acre
0 E Ash Rd, Plymouth, VT 05056

Welcome to Hawk East lot 2-20. This 2.07 acres lot is one of the closest lots to the Hawk Mountain Resort. There is a nice level area in the middle of the property that would make a nice building site. Easy access to Route 100 and only minutes to Okemo or Killington. There are 4 lakes all within a few minutes as well. Plenty of hiking, biking, boating, and fishing in the area. All plans and

Kevin Barnes William Raveis Real Estate Vermont Properties

0 E Ash Rd, Plymouth, VT 05056
/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
/49
$1,749,000
- 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
/53
$160,000
- Land
- 24 Acres
- $6,723 per Acre
399 Twitchell Settlement, Rochester, VT 05767

OFFER DEADLINE 06/15 SUNDAY 9PM Dreaming of owning a piece of Vermont? This 23.8± acre riverfront parcel offers the perfect blend of natural beauty, privacy, and long-term potential. Set along the scenic White River, the land features a peaceful mix of open meadow and mature forest, ideal for those seeking a flexible escape or investment.The property includes existing electric service and what is

Nick Sicard EXP Realty

399 Twitchell Settlement, Rochester, VT 05767
/60
$1,485,000
- 5 Beds
- 4.5 Baths
- 4,424 Sq Ft
229 Bradley Hill Rd, Norwich, VT 05055

Welcome to this beautifully renovated historic farmhouse, nestled on 3.4 serene acres in picturesque Norwich, VT. Bathed in natural light and brimming with character, this spacious home masterfully blends timeless charm with modern comfort. Carefully restored architectural details complement bright, airy living spaces and updated amenities designed for modern living. Whether you're entertaining,

Heidi Ruth Coldwell Banker LIFESTYLES - Hanover

229 Bradley Hill Rd, Norwich, VT 05055
/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 entertain.

Daire Gibney Barrett and Valley Associates Inc.

491 Farrar Rd, Chester, VT 05143
/23
$420,000
- 4 Beds
- 2 Baths
- 1,917 Sq Ft
13 Overlook Dr, Springfield, VT 05156

Serene Cul-de-Sac Retreat with Elegant Indoor-Outdoor Living in Springfield, Vermont. Tucked at the end of a quiet cul-de-sac in one of the most desirable neighborhoods in Springfield, this beautifully maintained four-bedroom, two-bathroom home offers a rare combination of tranquility, convenience, and charm. With a thoughtfully landscaped yard, mature trees, and a private wooded backdrop, the

Patrick Kelley Four Seasons Sotheby's Int'l Realty

13 Overlook Dr, Springfield, VT 05156
/48
$599,000
- 4 Beds
- 2 Baths
- 2,306 Sq Ft
241 North Rd, Bethel, VT 05032

Welcome to this classic Vermont home in the heart of Barnard Village, directly across from Silver Lake State Park. Enjoy quick access to Silver Lake, the Barnard General Store, Town Hall, and local trails, all within easy walking distance. Set on a private, gently sloped lot, this well-maintained split-level offers four bedrooms, multiple spacious living areas, and inviting indoor and outdoor

Eric Johnston Four Seasons Sotheby's Int'l Realty

241 North Rd, Bethel, VT 05032
/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 kitchen is

Karen DeMas Four Seasons Sotheby's Int'l Realty

248 Gird Lot Rd, Weathersfield, VT 05151
/51
$1,700,000
- 4 Beds
- 3 Baths
- 4,351 Sq Ft
775 E Lake Rd, Ludlow, VT 05149

Spectacular Waterfront Gem on Lake Rescue. Welcome to one of the most coveted locations on Lake Rescue where breathtaking sunsets, serene waters, and panoramic year-round views of Okemo Mountain create the ultimate Vermont lakefront retreat.This rare, true gem offers a sprawling, level yard with direct and effortless water access, an exceptional feature on this picturesque lake. Nestled on the

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

775 E Lake Rd, Ludlow, VT 05149
/49
$945,000
- 4 Beds
- 2.5 Baths
- 2,044 Sq Ft
100 Pomfret Rd, Woodstock, VT 05091

Charming, Unique, and Ideally Located! Welcome to 100 Pomfret Road—a beautifully updated farmhouse set on four level, picturesque acres just a short walk from Mt. Tom, Billings Farm, and the heart of downtown Woodstock. This rare find blends timeless character with everyday convenience in a peaceful, brookside setting.Inside, you’ll find a sun-drenched home featuring four bedrooms, two full

Keri Cole Williamson Group Sothebys Intl. Realty

100 Pomfret Rd, Woodstock, VT 05091
/52
$419,000
- 5,984 Sq Ft
643 Main St, Cavendish, VT 05153

After owning this property for more than 50 years, the Seller is ready to relocate and pass along this classic brick home with lots of square footage and potential. Once having 4 apartments in the main house and an attached barn, the Seller made the upper level of the barn into her own unit. The kitchen was removed from one of the house units and made into a laundry room, so there are currently

Tyleen Murray Kelley Real Estate, Inc.

643 Main St, Cavendish, VT 05153
/52
$1,595,000
- 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
/23
$57,000
- Studio
- 1 Bath
- 390 Sq Ft
240 QII Jackson Gore Inn Unit 240 QII, Ludlow, VT 05149

Jackson Gore 240 Quarter II studio condo on Okemo. This is one of the best values at Jackson Gore for a studio quarter-share condo. Enjoy this fully furnished slopeside retreat with indoor access to the resort's pool, hot tubs, sauna, and steam room. Amenities also include the use of the Spring House fitness center that houses additional pools, hot tubs, a gym, a racketball court, and a classroom

Kevin Barnes William Raveis Real Estate Vermont Properties

240 QII Jackson Gore Inn Unit 240 QII, Ludlow, VT 05149
/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
$3,275,000
- 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
/60
$1,850,000
- 2 Beds
- 3 Baths
- 2,106 Sq Ft
7 North St, Woodstock, VT 05091

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

Keri Cole Williamson Group Sothebys Intl. Realty

7 North St, Woodstock, VT 05091
/27
$450,000
- 3 Beds
- 2 Baths
- 1,989 Sq Ft
107 Winding Brook Ln, White River Junction, VT 05001

Nestled in a serene country setting, this recently refreshed 3-bedroom, 2-bath home offers the perfect blend of privacy, space, and convenience. Set on 5 rolling acres, the property features plenty of maples for making your own syrup and an open field above the home, ideal for horses, livestock, or simply enjoying the wide-open views and Vermont's natural beauty.The kitchen and open living areas

Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

107 Winding Brook Ln, White River Junction, VT 05001
/29
$615,000
- 3 Beds
- 3 Baths
- 2,439 Sq Ft
1140 Murphys Rd Unit 10B, Hartford, VT 05001

Overlooking the Lakeland Golf course, a golf-cart ride to the Club, this highly desirable 3-bedroom, 3-bathroom condominium offers room for spacious gatherings and privacy on all three levels, filled with natural light. A wide deck off the living and dining areas is ideal for entertaining. The living room's gas fireplace will enhance your winter evenings and Apres-Ski experience. Quechee Land

Barbara Ruel Coldwell Banker LIFESTYLES - Quechee

1140 Murphys Rd Unit 10B, Hartford, VT 05001
/25
$130,000
- 1 Bed
- 1 Bath
- 829 Sq Ft
276 Connecticut River Rd, Springfield, VT 05156

Here's your chance to own a very unique property located next to the historic Crown Point Military Rd is this 1960 Quonset hut. Set on top of a walk-out full foundation, with lots of natural light and a fireplace on ground level, kitchen, bath, bedroom and dining on upper floor this property is ready for your ideas. Home would make a great getaway for someone looking for a getaway just minutes

Julie Buffum Buffum Realty

276 Connecticut River Rd, Springfield, VT 05156
/60
$2,200,000
- 3 Beds
- 2.5 Baths
- 5,422 Sq Ft
2334 South Rd, Woodstock, VT 05091

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

Danny Kogut Williamson Group Sothebys Intl. Realty

2334 South Rd, Woodstock, VT 05091
/49
$2,195,000
- 3 Beds
- 3 Baths
- 2,997 Sq Ft
9671 Vt Route 12, Barnard, VT 05031

[See the property specific website with video, hi-rez photos and more]. SPRING HILL FARM – A Storied Vermont Estate with Timeless Appeal. Set amidst the rolling hills of Barnard, Vermont, Spring Hill Farm is a distinguished country estate where historic charm and thoughtful stewardship come together across 207 acres of beautifully maintained landscape. Anchoring the property is a stately brick

Susan Hickey Snyder Donegan Real Estate Group

9671 Vt Route 12, Barnard, VT 05031
/39
$535,000
- 3 Beds
- 2.5 Baths
- 1,933 Sq Ft
222 Parkview Rd, Springfield, VT 05156

Delayed showings - showings begin June 1st! Tucked away on 3.87 acres of open lawns and mixed woods, this turnkey home offers peace, privacy, and distant views of Okemo, which is located only 25 minutes away. Thoughtfully designed for single-level living, it features granite countertops, stainless steel appliances, and a cozy Vermont Soapstone wood stove that complements the efficient Buderus

Holly Hall Hall Collins Real Estate Group

222 Parkview Rd, Springfield, VT 05156
/36
$1,650,000
- 3 Beds
- 3.5 Baths
- 2,614 Sq Ft
938 Stigers Rd, Chester, VT 05143

Welcome to 938 Stigers Road, a masterpiece in the mountains! Discover a stunning fusion of artistry and craftsmanship in this exquisite timber frame home, tucked away in the serene beauty of the mountains.This residence is the inspired creation of a visionary artist and a skilled builder, resulting in a one-of-a-kind retreat where design and nature are in perfect harmony.Fall in love with the

Liz Moore Four Seasons Sotheby's Int'l Realty

938 Stigers Rd, Chester, VT 05143
/60
$375,000
- 4 Beds
- 2 Baths
- 2,425 Sq Ft
44 Watershed Rd, Bethel, VT 05032

TAMARACK FARM - Historic, very attractive 1.5 story brick cape with attached two-car garage, overlooking a deep ravine leading to a lower second acre on Route 12 perfect for equestrian pursuits. Nestled in a picturesque Vermont countryside, this classic 4-bedroom, 2-bath home showcases wide-board pine floors, exposed ceiling beams, and period details throughout. The first floor country kitchen

John Bassette Bassette Real Estate Group

44 Watershed Rd, Bethel, VT 05032
/34
$435,000
- 4 Beds
- 2 Baths
- 2,352 Sq Ft
35 Depot St, Hartford, VT 05001

Right in town, private and ready for you. first time home buyers, investors, people looking to downsize or want to be closer to amenities and public transportation, this is your opportunity. You are only a short walk to Kilowatt Park and the paths that lead to the water on the Vermont side of Wilder Dam. The house is comfortable and roomy with many options for the new owners. One could turn it

Josh Hunt Snyder Donegan Real Estate Group

35 Depot St, Hartford, VT 05001
/18
$255,000
- 3 Beds
- 2 Baths
- 1,743 Sq Ft
66 Union St, Windsor, VT 05089

Welcome to this beautifully maintained New Englander nestled in the historic town of Windsor — Vermont's first capital and a gem of the Upper Valley. This classic 3-bedroom, 2-bath home blends timeless charm with thoughtful updates, offering a perfect retreat in a vibrant, small-town setting.Located within walking distance to Windsor’s shops, restaurants, schools, and the picturesque Connecticut

Katie Ladue Gilbert KW Vermont Woodstock

66 Union St, Windsor, VT 05089
/33
$4,490,000
- 5 Beds
- 5.5 Baths
- 8,122 Sq Ft
5685 Vermont 12, Barnard, VT 05031

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

John Snyder Snyder Donegan Real Estate Group

5685 Vermont 12, Barnard, VT 05031
/22
$375,000
- 3 Beds
- 1 Bath
- 1,069 Sq Ft
879 Dairy Hill Rd, South Royalton, VT 05068

Located less than five minutes from the center of South Royalton, this well-cared-for ranch offers a peaceful setting with easy access off a paved, publicly maintained road to everything the Upper Valley has to offer. Vermont Law School is just down the road and S. Royalton is known for its tight-knit community, local food scene, and walkable village center — with Worthy Burger, a co-op, and a

Franchesca Collins Hall Collins Real Estate Group

879 Dairy Hill Rd, South Royalton, VT 05068
/37
$995,000
- 2 Beds
- 2.5 Baths
- 2,176 Sq Ft
4 River St, Woodstock, VT 05091

This impeccably restored 1847 Woodstock village cape set upon a captivating river front landscape is truly magical! The complete and meticulous efficiency upgrades and renovations combined with the perfect village location offers an incomparable opportunity for those buyers coveting a village location. All new windows and red birch floors set the stage for the interior design. The sun-filled

Mary Mayhew Snyder Donegan Real Estate Group

4 River St, Woodstock, VT 05091
/60
$499,000
- 5 Beds
- 7 Baths
- 5,546 Sq Ft
472 Main St, Chester, VT 05143

The Laurin Whiting House, circa 1850, is a Greek Revival style home with 5 bedrooms and 7 baths on 1 +/- acre. The curved, multi-bay veranda wraps around the front of the house with neo-classical columns and an oculus that punctuates the front gable end. A light-filled living room has French doors that open to the lovely porch and adjoin a large bedroom and full bath. The formal dining room

Geralyn Donohue Engel & Völkers Okemo

472 Main St, Chester, VT 05143
/45
$350,000
- 4 Beds
- 2 Baths
- 2,484 Sq Ft
47 Dell Rd, Springfield, VT 05156

Welcome to a home that truly has it all! Perfectly positioned on a cul-de-sac, this property is steps away from the trailhead of Hartness Park where you can enjoy 3 miles of trails in the 85 acre town forest. A seamless blend of privacy whilst still being in town - what more can you ask for? This beautifully maintained property offers the rare and coveted convenience of first-floor living—with

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

47 Dell Rd, Springfield, VT 05156
/58
$635,000
- 3 Beds
- 3.5 Baths
- 2,203 Sq Ft
44 Freeman Rd Unit B2, Cavendish, VT 05153

The Castle Hill Resort & Spa is an award winning destination located just minutes from Okemo Mountain Resort. This ground floor 3br +loft & den features 3.5 baths. This townhouse condo has floor to ceiling windows that provide natural light throughout. The open living room, dining room, and kitchen offer an inviting atmosphere for gatherings. The ground floor patio offers outdoor seating and has

Joseph Karl William Raveis Real Estate Vermont Properties

44 Freeman Rd Unit B2, Cavendish, VT 05153
/42
$199,000
- 5 Beds
- 1 Bath
- 1,898 Sq Ft
54 Bridge St, Springfield, VT 05156

Owners say it's time to move on from this large, 5BR family home that has had loads of mechanical upgrades. All rooms are spaciously sized, formal dining room, enclosed front porch 3 car garage, solar panels, lots of storage with a dry basement and attic storage. Other improvements include re-insulation and sheetrock in some rooms, fresh paint, new flooring and a bath off the primary 2nd floor

Julie Buffum Buffum Realty

54 Bridge St, Springfield, VT 05156
/43
$499,000
- 3 Beds
- 2 Baths
- 1,809 Sq Ft
935 French Meadow Rd, Springfield, VT 05156

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

Jessica Landers Barrett and Valley Associates Inc.

935 French Meadow Rd, Springfield, VT 05156
/36
$995,000
- 4 Beds
- 3.5 Baths
- 3,650 Sq Ft
126 Primrose Ln, Hartford, VT 05047

126 PRIMROSE LANE- Spacious, well-built, and updated colonial in desirable location just a few minutes from the Quechee Club. A newer premium kitchen with direct access to a large west facing deck that wraps the back of the house, abutting great room with a vaulted ceiling centered around a beautiful stone fireplace, and a formal dining room adjacent the kitchen make for an ideal layout for

David Donegan Snyder Donegan Real Estate Group

126 Primrose Ln, Hartford, VT 05047
/35
$199,000
- 3 Beds
- 1 Bath
- 1,322 Sq Ft
841 Farrar Rd, Chester, VT 05143

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

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

841 Farrar Rd, Chester, VT 05143

Showing Results 81 - 120, Page 3 of 11

Vermont Windsor County

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

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

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

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