Windsor County VT Homes for Sale

/36
$367,000
- Land
- 11 Acres
- $34,754 per Acre
0 Valley View Dr, Ludlow, VT 05149

Elevate Your Lifestyle at Summit Ridge - Tucked away in a private, gated community just minutes from the slopes of Okemo and our Lakes Region, this homesite is the perfect canvas for your mountain dream home. Imagine waking up to panoramic, long-range mountain views in every direction—serenity, space, and stunning scenery, all wrapped into one unbeatable location with 10.56 acres. You're just a

Sarah Sheehan

William Raveis Real Estate Vermont Properties

(802) 424-8692

0 Valley View Dr, Ludlow, VT 05149
/47
$395,000
- 3 Beds
- 2 Baths
- 1,116 Sq Ft
32 Route 103 S Unit D4, Ludlow, VT 05149

Brookhaven condo D4 is located in the village of Ludlow and just a few minutes to the slopes at Okemo Mountain. This four-season destination is convenient to our lake’s region, restaurants, Fox Run Golf Club, shopping, and more. Enjoy easy access to the mountain with the Okemo Village Shuttle stopping in the Brookhaven parking lot. This top floor three-bedroom, two-full-bathroom condominium looks

Sarah Sheehan

William Raveis Real Estate Vermont Properties

(802) 705-0113

32 Route 103 S Unit D4, Ludlow, VT 05149
/55
$895,000
- 4 Beds
- 4.5 Baths
- 2,769 Sq Ft
104 Main St, Ludlow, VT 05149

Discover one of Ludlow Village’s true gems—now beautifully reimagined into a stunning 4-bedroom, 4.5-bathroom residence that perfectly balances classic charm with modern luxury. Whether you’re searching for a primary home, vacation retreat, or an investment opportunity, this timeless property offers it all. Step inside to an inviting open-concept living space, with soaring ceilings and abundant

Sarah Sheehan

William Raveis Real Estate Vermont Properties

(802) 898-8861

104 Main St, Ludlow, VT 05149
/60
$875,000
- 7 Beds
- 5 Baths
- 3,192 Sq Ft
65 Andover St, Ludlow, VT 05149

This stunning, turnkey three-unit property is perfect as a family compound, investment opportunity, or live/rent scenario. The main home features two updated units: a 3-bedroom, 2-bath lower-level apartment with a beautiful covered porch, and a 3-bedroom, 2-bath upper-level apartment with its own smaller porch. Behind the main home sits a two-story 1-bedroom carriage house with radiant electric

Sarah Sheehan

William Raveis Real Estate Vermont Properties

(802) 523-2035

65 Andover St, Ludlow, VT 05149
/16
$150,000
- Land
- 6 Acres
- $25,253 per Acre
0 Brook Rd, Springfield, VT 05156

This beautiful 5.94 acre lot set high upon a hill has complete privacy! A half mile long driveway leads through the trees to a landing with mowed field to build your Vermont dream home. Gorgeous sunset views and lots of wildlife! The land is very fertile and has been farmed for over 100 years. Power on site. Nearby to town, country club, and rec center. **Land is behind 341 Brook Road in

Lisa Friedman

Great American Dream Realty

(802) 454-3572

0 Brook Rd, Springfield, VT 05156
/28
$375,000
- Land
- 10 Acres
- $37,955 per Acre
0 Turtle Hill Rd, Ludlow, VT 05149

Build Your Dream Home with Breathtaking Okemo Views! This exceptional nearly 10-acre parcel offers the perfect balance of privacy and convenience, just minutes from town. Enjoy some of the finest views of Okemo while designing your Vermont retreat. Nestled on a private road, this is the perfect spot for your four-season getaway—close to world-class skiing, the lakes region, top-rated restaurants,

Sarah Sheehan

William Raveis Real Estate Vermont Properties

(802) 348-2304

0 Turtle Hill Rd, Ludlow, VT 05149
/14
$230,000
- Land
- 6 Acres
- $36,918 per Acre
1090 New Boston Rd, Norwich, VT 05055

Build your dream home on the hill of this sunny 6.23 acre parcel in Norwich. A building site has been cleared for the highest point of the property with a view. An engineer has completed a wetlands study and an application is ready to be submitted for approvals. There is a camp on the property in need of a septic, should you keep it. Just minutes from Dartmouth College and the Upper Valley.

Melissa Robinson

Coldwell Banker LIFESTYLES - Hanover

(802) 808-6490

1090 New Boston Rd, Norwich, VT 05055
/37
$495,000
- 3 Beds
- 1.5 Baths
- 1,630 Sq Ft
19 Prospect St, Ludlow, VT 05149

Step into the charm of Ludlow village living with this captivating gem on Prospect St! Nestled on a serene street, this village charmer seamlessly blends historic allure with modern convenience, offering a lifestyle of ease and elegance. Enjoy easy access to the Okemo shuttle, local shops, and delectable dining options, all while relishing the tranquility of this picturesque neighborhood. Indulge

Sarah Sheehan

William Raveis Real Estate Vermont Properties

(802) 278-6550

19 Prospect St, Ludlow, VT 05149
/57
$2,300,000
- 6 Beds
- 4 Baths
- 4,301 Sq Ft
126 Route 66, Ludlow, VT 05149

Ski-in, ski-out from this exceptional home located directly on the Sachem Trail at Okemo Mountain. Fully renovated with a spacious addition in 2018, this two-family property offers flexibility, comfort, and incredible slope-side living. The main residence spans three levels with 4 bedrooms and 3 bathrooms, featuring an open-concept kitchen and dining area perfect for entertaining. Expansive

Sarah Sheehan

William Raveis Real Estate Vermont Properties

(802) 551-3239

126 Route 66, Ludlow, VT 05149
/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

(802) 810-8520

8 Pond St, Ludlow, VT 05149
/44
$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
/32
$1,199,000
- 5 Beds
- 2.5 Baths
- 2,662 Sq Ft
63 Shiloh Ln, Norwich, VT 05055

Tucked away on magical Shiloh Lane, this 21.5-acre property offers a peaceful, park-like setting with beautifully landscaped grounds, two potential pond sites, horse barn, greenhouse, garden space and trails. Step inside from the covered front porch or the stone patio and discover a thoughtfully cared for home filled with warmth and character. The 2023 kitchen renovation includes striking Mexican

Melissa Robinson

Coldwell Banker LIFESTYLES - Hanover

(802) 810-8665

63 Shiloh Ln, Norwich, VT 05055
/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

(802) 696-6705

342 Jackson Gore Rd Unit 342/344 Q1, Ludlow, VT 05149
/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
/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
/46
$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
- 3,650 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
/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
$630,000
- 5 Beds
- 5.5 Baths
- 5,478 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
/22
$645,000
- 3 Beds
- 1.5 Baths
- 1,468 Sq Ft
187 Dana Rd, Woodstock, VT 05091

This delightful gambrel cape offers a wonderful combination of thoughtful and charming updates, energy efficient upgrades, and a coveted and convenient location! An intelligent interior design offers an all-season functional flow for everyday living as well as entertaining. Step inside by way of a spacious entryway/mudroom that also has direct entry from the attached garage. One will find the

Mary Mayhew Snyder Donegan Real Estate Group

187 Dana Rd, Woodstock, VT 05091
/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
/40
$2,675,000
- 6 Beds
- 6 Baths
- 7,619 Sq Ft
5518 Vermont 12, Woodstock, VT 05091

An historic brick residence prominently located in an affluent and growing community! Conveniently situated within walking distance to the Elementary School, to year round recreation on beloved Silver Lake and to the classic Barnard General Store. All the amenities of Woodstock Village are just minutes away! World class medical care at Dartmouth Hitchcock Hospital and year round cultural events

John Wetmore Wetmore Real Estate

5518 Vermont 12, Woodstock, VT 05091
/42
$15,000,000
- 5 Beds
- 10 Baths
- 9,679 Sq Ft
3147 Mount Hunger Rd, Barnard, VT 05031

Honey Hill Farm is a rare and distinguished Vermont estate, encompassing over 300 acres of pastoral beauty, panoramic mountain views, trails, and a spring-fed pond. The main residence has been masterfully reimagined with a full-scale renovation, marrying timeless craftsmanship with the highest standard of modern luxury. At its heart lies an expansive gourmet kitchen—designed with custom marble

Keri Cole Williamson Group Sothebys Intl. Realty

3147 Mount Hunger Rd, Barnard, VT 05031
/42
$8,000,000
- 3 Beds
- 3.5 Baths
- 6,096 Sq Ft
115 Eastman Rd, South Woodstock, VT 05071

Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

Keri Cole

115 Eastman Rd, South Woodstock, VT 05071
/23
$329,900
- Land
- 142 Acres
- $2,323 per Acre
0 Chateauguay Rd Unit 22557682, Woodstock, VT 05091

Interested in this property? Call, text, or email us today for more details!(540) 824-3372Feel free to visit the property any time, no need to set up an appointment, this property has no address.Subscribe to email alerts by texting your e-mail address to (541) 375-0012 and be the first to know when we get a great deal in.By texting (541) 375-0012 you authorize Country Land

Luke Harris Country Land Sellers

0 Chateauguay Rd Unit 22557682, Woodstock, VT 05091
/15
$237,000
- Land
- 221 Acres
- $1,072 per Acre
0 New Boston Rd, Thetford, VT 05074

IntroductionThe ownership is selling their property in two separate parcels, divided by the town line. The +/-60 acre Strafford parcel is well suited to future home development with paved town road frontage and roadside electric service. The +/-220 acre Thetford parcel is well suited to a camp or seasonal off-grid home development with beautiful local views.Both parcels have

John Latham Fountains Land

0 New Boston Rd, Thetford, VT 05074
/43
$420,000
- 2 Beds
- 2.5 Baths
- 1,445 Sq Ft
60 Spaulding Rd Unit J1, Cavendish, VT 05153

Nestled on a quaint hillside in the Okemo Valley, the Castle Hill Resort offers an abundance of amenities with ownership in the resort community. This rare two-bedroom condominium provides ample space for everyone with extra windows for light and views. This is rare as most buildings are Quad-plexes and this building is a top and bottom Duplex, sharing no walls with neighbors! Enjoy an on-suite

Joseph Karl William Raveis Real Estate Vermont Properties

60 Spaulding Rd Unit J1, Cavendish, VT 05153
/35
$675,000
- 3 Beds
- 2.5 Baths
- 2,230 Sq Ft
28 Webster Rd, Hartland, VT 05048

Nestled in the picturesque countryside of Hartland, VT, this classic 3-bedroom, 3-bath Colonial offers the perfect blend of charm, comfort, and rural tranquility. Set on a spacious lot surrounded by rolling hills and open skies, the home welcomes you with a traditional layout featuring a warm and inviting living room, a functional eat-in kitchen with ample storage, and a formal dining area for

Katie Ladue Gilbert KW Vermont Woodstock

28 Webster Rd, Hartland, VT 05048
/43
$849,000
- 3 Beds
- 5 Baths
- 2,805 Sq Ft
1130 Safford Rd, Hartford, VT 05001

Well-built modern residence is well-maintained and works perfectly fo 2 or for 10. Beautifully landscaped property with stone patios, walkways and extensive gardens, the house is situated near the end of a quiet road, and the miles of walking trails on Trailhead B, just a few doors down from the house. The house offers a vaulted ceiling living room with wood-burning fireplace that opens to the

John Snyder Snyder Donegan Real Estate Group

1130 Safford Rd, Hartford, 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
/49
$800,000
- 3 Beds
- 2.5 Baths
- 1,439 Sq Ft
17 Daybreak Dr Unit F205, Ludlow, VT 05149

Solitude Village on Okemo Mountain with Unbeatable Ski Access & Amenities! Nestled in the heart of Solitude Village, this exceptional 3-bedroom, 2.5-bath condominium presents a rare opportunity for quintessential Vermont living. Perched directly on the Promenade Trail, imagine stepping out your door onto the slopes, or relaxing on your expansive deck, soaking in panoramic views that transform

Katherine Burns William Raveis Real Estate Vermont Properties

17 Daybreak Dr Unit F205, Ludlow, VT 05149
/53
$798,000
- 2 Beds
- 2 Baths
- 1,308 Sq Ft
392 Gully Rd, Woodstock, VT 05091

Built in 2019, this charming Cape-style home is nestled on five sunny, private acres just minutes from Woodstock Village. Thoughtfully designed and beautifully constructed, the home offers efficient, low-maintenance living in a coveted location. With excellent solar exposure, stunning sunset views, and lovely hillside scenery, it’s bright, warm, and welcoming year-round.The interior

Keri Cole Williamson Group Sothebys Intl. Realty

392 Gully Rd, Woodstock, VT 05091
/51
$649,000
- 3 Beds
- 2.5 Baths
- 1,788 Sq Ft
162 Bear Hill Rd, Plymouth, VT 05056

Beautifully renovated 3-bedroom, 2.5-bath chalet perched on the slope of the former Plymouth Notch Ski Area. This move-in-ready home combines mountain charm with modern comfort. Interior upgrades include new flooring, fully renovated bathrooms, stylish lighting, and a refreshed kitchen with granite countertops, tile backsplash, pot filler, and all-new stainless steel appliances. The open-concept

Debra Staniscia Four Seasons Sotheby's Int'l Realty

162 Bear Hill Rd, Plymouth, VT 05056

Showing Results 1 - 40, Page 1 of 12

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.