Windsor County VT Homes for Sale with Parking

/59
$1,850,000
- 4 Beds
- 6 Baths
- 4,764 Sq Ft
77 Newton Rd, Reading, VT 05062

Welcome to this private property on a quiet country road in desirable Reading, VT, just 4 miles from South Woodstock. Only 30 minutes to Okemo Mountain Resort and 35 minutes to Killington Ski Area! This spacious 4-bedroom, 6-bathroom home comfortably sleeps 12. This home was made for entertaining! The updated kitchen features high-end appliances, leading to a dining area. Off the kitchen, an

Susan Hickey

Snyder Donegan Real Estate Group

(802) 536-6644

77 Newton Rd, Reading, VT 05062
/42
$600,000
- 3 Beds
- 3 Baths
- 1,826 Sq Ft
789 Hammond Hill Rd, West Windsor, VT 05089

“The Hideaway House”. . . An Oasis of Tranquility. Nestled away in a bowl of woods & set back over 200 feet from the road, this 3-bedroom, 3-full-bath home with attached 2-car garage & extremely high-speed fiber optic Internet offers sanctuary-like privacy situated on 5.52 hillside acres in fashionable West Windsor, VT. This welcoming residence is secluded serenity at its best & is located in

Ross Doody

Century 21 Highview Realty

(802) 461-4869

789 Hammond Hill Rd, West Windsor, VT 05089
/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

(802) 491-4915

9671 Vt Route 12, Barnard, VT 05031
/30
$249,000
- 3 Beds
- 2 Baths
- 1,792 Sq Ft
95 Union St, Springfield, VT 05156

Large home on generously sized lot with lots of room to romp this 3BR/2BA home has lots of space indoors and out. Roomy and sun filled kitchen flows right into the dining room. Living room is cozy with the pellet stove glowing. Good sized mud room could be used as a small office or reading room or a place to do homework. 1st floor full bath and laundry for your convenience. 2nd floor has a

Julie Buffum

Buffum Realty

(802) 644-3166

95 Union St, Springfield, VT 05156
/33
$499,000 New Construction
- 3 Beds
- 2 Baths
- 1,334 Sq Ft
216 Quechee-Hartland Rd, Hartford, VT 05059

New construction in Quechee, VT with no HOA fees. This country-style ranch offers the perfect blend of comfort and charm.Featuring 3 bedrooms and 2 full baths, this home features an open-concept design, seamlessly connecting the living room, dining area, and kitchen—ideal for modern living and entertaining. The first level primary suite includes a spacious walk-in closet and a private

Melissa Robinson

Coldwell Banker LIFESTYLES - Hanover

(802) 644-7200

216 Quechee-Hartland Rd, Hartford, VT 05059
/42
$669,000
- 3 Beds
- 2.5 Baths
- 2,303 Sq Ft
145 Stearns Dr, Bethel, VT 05032

Welcome to 145 Stearns Drive, a beautifully crafted single-level home nestled on 8.8 private acres between Bethel and Barnard. This three-bedroom, two and one-half-bath property features radiant heat throughout, an open-concept layout, and warm oak finishes that provide timeless charm.The light-filled kitchen boasts custom cabinetry, stainless appliances, a wine cooler, island workspace,

Eric Johnston Four Seasons Sotheby's Int'l Realty

145 Stearns Dr, Bethel, VT 05032
/49
$1,595,000
- 5 Beds
- 3.5 Baths
- 3,648 Sq Ft
1522 Barnard Rd, Woodstock, VT 05091

Just 2 miles from Woodstock Village, this gracious brick cape on 6 open acres offers space, comfort, and classic Vermont charm. The expanded chef’s kitchen opens to a gracious gathering room ideal for entertaining, while 3 fireplaces—wood-burning, brick, and gas-ready—provide cozy warmth throughout. Upstairs, find 3–4 bedrooms including one with its own fireplace, plus a private guest room or

Keri Cole Williamson Group Sothebys Intl. Realty

1522 Barnard Rd, Woodstock, VT 05091
/59
$3,300,000
- 4 Beds
- 5 Baths
- 5,000 Sq Ft
1279 Old Bridgewater Hill Rd, Bridgewater, VT 05035

Asa Greene traveled to Vermont in 1783 to establish a farm in the high hills in Bridgewater after serving in the American Revolution. 242 Years later the farmhouse still stands at the end of Old Bridgewater Hill Road after nearly 50 years of careful restoration and renovations made to accommodate an active, growing family. Creatively blending old & new the farmhouse takes advantage of an

Laird Bradley Williamson Group Sothebys Intl. Realty

1279 Old Bridgewater Hill Rd, Bridgewater, VT 05035
/32
$1,965,000
- 3 Beds
- 3.5 Baths
- 3,827 Sq Ft
2346 Quechee Main St, White River Junction, VT 05001

A beautifully constructed residence, designed to take in breathtaking views of the river, the Lakeland course of the Quechee club golf course, the Quechee ski slopes, and lake Pinneo. The house offers high-quality details inside and out including porches, stone patios, octagonal viewing/sitting rooms and more. Gourmet kitchen of with a large walk-in pantry, 2 river stone fireplaces, tigerwood

John Snyder Snyder Donegan Real Estate Group

2346 Quechee Main St, White River Junction, VT 05001
/57
$1,415,000
- 5 Beds
- 3.5 Baths
- 3,925 Sq Ft
18 Elm St, Norwich, VT 05055

Charming Norwich Village Farmhouse Blending Historic Character with Modern ComfortLocated in the heart of Norwich Village, this timeless Vermont farmhouse—originally built in 1810—has been thoughtfully renovated to preserve its rich history while incorporating modern conveniences. From original exposed beams and antique doors to tucked-away nooks, every detail tells a story.The

Julie Davis KW Vermont Woodstock

18 Elm St, Norwich, VT 05055
/48
$1,749,000
- 3 Beds
- 3.5 Baths
- 3,294 Sq Ft
39 Elm St Unit B, Woodstock, VT 05091

The Richmond House – Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a distinguished brick Federal with a softly weathered, rose-hued patina and elegant architectural details. Set on over an acre behind a classic white picket fence, this historic property—reimagined under the direction of Laurence Rockefeller—comprises three luxurious residences

Zoe Hathorn Washburn Snyder Donegan Real Estate Group

39 Elm St Unit B, Woodstock, VT 05091
/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
/36
$995,000
- 4 Beds
- 3.5 Baths
- 3,394 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
/54
$1,049,000
- 3 Beds
- 2.5 Baths
- 4,289 Sq Ft
33 Ferndale Dr, Bethel, VT 05032

Welcome to this exceptional Colonial post-and-beam home nestled off the scenic North Road in the heart of Barnard, Vermont. Thoughtfully designed and beautifully maintained, this three-bedroom, two-and-a-half-bath residence blends timeless craftsmanship with modern comfort across three spacious levels of living.Inside, warm wood tones and custom finishes create a welcoming atmosphere

Eric Johnston Four Seasons Sotheby's Int'l Realty

33 Ferndale Dr, Bethel, VT 05032
/60
$599,000
- 5 Beds
- 5.5 Baths
- 2,336 Sq Ft
311 Old Route 12, Bethel, VT 05032

Tucked at the edge of a stunning park-like lawn, this spacious home offers both privacy and convenience—just minutes from the Barnard General Store, Silver Lake, Woodstock, and Bethel. Surrounded by landscaped grounds with ponds, rock walls, and gardens, it's a true Vermont retreat. Enjoy the peaceful setting from the deck or the covered porch.The sun-filled main level features a bright

Lucas deSousa Vermont Real Estate Company

311 Old Route 12, Bethel, VT 05032
/60
$949,000
- 6 Beds
- 6 Baths
- 5,497 Sq Ft
31 Huntington Place Unit 1,2 & 3, Rochester, VT 05767

Charming 1900s Village Building, Three Condo Units, One Incredible Opportunity!In the heart of Rochesters picturesque village, this beautifully restored early 1900s building is a rare investment opportunity, offered as a single property with three fully furnished condo units. Perfect for an owner-occupant, a multi-generational retreat, or a savvy investor, this historic gem blends classic

Kate Cassidy Four Seasons Sotheby's Int'l Realty

31 Huntington Place Unit 1,2 & 3, Rochester, VT 05767
/46
$825,000
- 3 Beds
- 3 Baths
- 1,432 Sq Ft
58 Greenbush Rd, Cavendish, VT 05142

Charming Cape Cod Home in a Serene Country Setting – 10.10 AcresWelcome to this beautifully transformed Cape Cod-style home, nestled on just over 10 acres of picturesque countryside. Offering a perfect blend of classic charm and modern convenience, this inviting property is ideal for those seeking tranquility and space. Step onto the welcoming front porch, where you can relax and

Katie Ladue Gilbert KW Vermont Woodstock

58 Greenbush Rd, Cavendish, VT 05142
/16
$425,000
- 6 Beds
- 4 Baths
- 2,243 Sq Ft
3 MacE Hill Rd, Hartland, VT 05048

Strong Cash Flow! Profitable Investment Opportunity! This fully leased three unit multifamily property is an excellent chance for investors to add a consistent cash flowing property to their portfolio or for an onsite owner to occupy one unit and let the extra additional rents help pay for your housing. A low maintenance property with nice updates over the years which include separate electrical

Alex DeFelice The Clerkin Agency, P.C.

3 MacE Hill Rd, Hartland, VT 05048
/40
$3,500,000
- 6 Beds
- 6 Baths
- 5,433 Sq Ft
61 Academy Cir, Woodstock, VT 05071

Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The

Carol Wood Williamson Group Sothebys Intl. Realty

61 Academy Cir, Woodstock, VT 05071
/60
$799,000
- 4 Beds
- 3.5 Baths
- 2,729 Sq Ft
419 Baileys Mills Rd, Reading, VT 05062

Welcome to this enchanting, historic Cape nestled on 75.56 pristine acres along the scenic Mill Brook. Ideally located just five miles from GMHA, the property spans both sides of Baileys Mill Road, offering abundant opportunities for equestrians, hobby farmers & nature lovers alike. The land is a rare mix of open pastures, mature woodlands, flowing streams, and panoramic valley views. A network

Kate Jarvis Williamson Group Sothebys Intl. Realty

419 Baileys Mills Rd, Reading, VT 05062
/37
$1,185,000
- 4 Beds
- 3 Baths
- 2,785 Sq Ft
1782 Randall Rd, Woodstock, VT 05091

This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide

Wade Treadway Wade I Treadway Real Estate

1782 Randall Rd, Woodstock, VT 05091
/30
$1,200,000
- 3 Beds
- 2 Baths
- 2,118 Sq Ft
124 Turner Rd, Weston, VT 05161

A mountain retreat surrounded on three sides by the Green Mountain National Forest and yet only a few miles from the village green in Weston and the Weston Playhouse. Big views to breathe in. Turner Farm is located on a dead end road above the trout club. The 134 acre parcel covers the eastern slope of Peabody Hill; the land climbs to an elevation of 2,770 feet and is threaded with trails for

Dia Jenks LandVest, Inc/Woodstock

124 Turner Rd, Weston, VT 05161
/50
$750,000
- 4 Beds
- 4 Baths
- 1,800 Sq Ft
477 Dunham Rd, Bethel, VT 05032

A work of modern art. Words cannot describe the feeling you get when your eyes settle on this amazing place. Future owners need only appreciate the unique, creative, and thought provoking touches in this very interesting home.The builder/owners have created a family atmosphere centered around the massive stone fireplace, maple floor, open kitchen with impressive island, dining area, and a

Dean Goulet Dunrovin Real Estate

477 Dunham Rd, Bethel, VT 05032
/49
$795,000
- 3 Beds
- 2.5 Baths
- 2,235 Sq Ft
228 Leonard Rd, Sharon, VT 05065

Welcome to your private Vermont retreat on nearly 24 acres of open meadows, woods, and a pristine spring-fed pond. Tucked away in complete seclusion and surrounded by 500 acres of undeveloped maple forest, this peaceful property offers unrivaled privacy and natural beauty. The charming 3-bedroom home features hardwood floors, a cozy wood stove, and a beautifully renovated kitchen with granite

Mandolyn McIntyre Real Broker LLC

228 Leonard Rd, Sharon, VT 05065
/59
$1,750,000 Open Sat 1PM - 3PM
- 5 Beds
- 4 Baths
- 3,862 Sq Ft
699 Spear Cemetery Rd, Reading, VT 05062

Situated amongst the finest equine estates in the region, Tuacknback Farm is an iconic landmark, best known as the most popular hold along the famed Vermont 100 ride. Located on a scenic country road, accessing the most extensive trail systems in New England, the entire property was impeccably orchestrated for ease with direct walk-in access to the connected stable and hay loft, and a wide

Danny Kogut Williamson Group Sothebys Intl. Realty

699 Spear Cemetery Rd, Reading, VT 05062
/52
$785,000
- 4 Beds
- 3.5 Baths
- 2,828 Sq Ft
119 Pine Hill Rd, Ludlow, VT 05149

Nestled in the desirable Okemo Pines community, this 4-bedroom, 3.5-bath home offers the perfect blend of comfort, charm, and convenience, only minutes from Okemo Mountain Resort. Thoughtfully designed for year-round enjoyment, the home features multiple seasonal living areas, including a large deck with Okemo views, a sunroom, and a covered porch with mountain views. The house offers privacy

Joseph Karl William Raveis Real Estate Vermont Properties

119 Pine Hill Rd, Ludlow, VT 05149
/34
$895,000
- 3 Beds
- 5 Baths
- 3,590 Sq Ft
1104 Main St, Cavendish, VT 05142

Situated on the bank of the Black River at the edge of the Village Of Proctorsville is this three bedroom all ensuite, 5 bath log home. The Great Room boasts a floor to cathedral ceiling wood burning fireplace where you can sit and relax after a day on the slopes. Then take in river views from the formal dining room. Also on the first floor is a primary ensuite. Upstairs the huge lofted area is

Frank Provance Diamond Realty

1104 Main St, Cavendish, VT 05142
/48
$1,275,000
- 4 Beds
- 3 Baths
- 3,332 Sq Ft
204 High Ridge Rd, Brownsville, VT 05037

This hidden gem is one of the best kept secrets in West Windsor. Sited at the end of a private road with rolling green lawns, and a tree top view of Mount Ascutney, this lovingly stewarded home was impeccably constructed and orchestrated with flowing wide open, bright spaces. The perfect home for full or part time living, and entertaining. The living room is anchored by a painted brick Rumford

Danny Kogut Williamson Group Sothebys Intl. Realty

204 High Ridge Rd, Brownsville, VT 05037
/32
$875,000
- 3 Beds
- 3.5 Baths
- 3,189 Sq Ft
233 Brothers Rd, Hartland, VT 05048

The idyllic Hartland countryside is the setting for this handsome cape. A delightful three season porch is entered by way of the attached two car garage or directly by a lovely landscaped pathway. Once inside you will be greeted by a warm and inviting kitchen detailed with cherry cabinetry, the dining room with a bay window view of the gardens,a living room with fireplace, and a spacious

Mary Mayhew Snyder Donegan Real Estate Group

233 Brothers Rd, Hartland, VT 05048
/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
/36
$799,900
- 4 Beds
- 4 Baths
- 1,960 Sq Ft
5 Malagash Rd, South Reading, VT 05153

Set on a spacious and level lot in the scenic countryside of Reading, Vermont, this raised ranch offers room to spread out both inside and out. With 4 bedrooms and 4 bathrooms, the home provides flexible living options across two levels—perfect for larger households, multi-generational living, or hosting guests. The bright main floor features an open layout with a comfortable living area, an

Katie Ladue Gilbert KW Vermont Woodstock

5 Malagash Rd, South Reading, VT 05153
/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
/39
$875,000
- 3 Beds
- 5 Baths
- 3,000 Sq Ft
151 Smokerise, Ludlow, VT 05149

Entertain in Style in this VERY spacious home on 3.52 acres of paradise. Make memories and invite all of your friends and family to this tasteful home with room for everyone and more. Large living room, with wood burning stone fireplace, lovely views and a slider to the wrap around expanded deck. Inviting custom country kitchen with island and granite countertops along with 2 bedrooms and a full

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

151 Smokerise, Ludlow, VT 05149
/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
/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
/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
/56
$750,000
- 6 Beds
- 4 Baths
- 3,127 Sq Ft
8 Pond St, Ludlow, VT 05149

Village Charmer - Experience the allure of village living in the heart of Ludlow with this recently renovated 6-bedroom, 4-bathroom residence. Ideal for your comfort and convenience, the property is within walking distance of Ludlow's shopping and dining amenities and just a short drive (a few minutes) to the base of Okemo. Boasting not one, but two mudrooms, it provides ample space for all your

Sarah Sheehan William Raveis Real Estate Vermont Properties

8 Pond St, Ludlow, VT 05149
/38
$750,000
- 3 Beds
- 2 Baths
- 2,568 Sq Ft
75 Lyon Rd, South Royalton, VT 05068

Return to yesteryear in this Late 1700s Colonial on 35 acres+-. Attention hobby farmers with goats, sheep, etc. This mini- farm features a modern milking parlor with equipment. this classic home has five fireplaces, spacious rooms, two full baths, and numerous improvements, making this a traditional treasure in Royalton, Vt. A 24 x 24 garage/workshop/ storage, and modern wood boiler are only

Dean Goulet Dunrovin Real Estate

75 Lyon Rd, South Royalton, VT 05068
/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
/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

Showing Results 1 - 40, Page 1 of 6

Vermont Windsor County

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

Windsor County Types of Homes for Sale

Windsor County Real Estate Listings

Windsor County New Construction Homes

More About Living in Windsor County

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.