Windsor County VT Houses for Sale

/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
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/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
$1,299,000
- 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
/54
$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
/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
/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
/57
$1,415,000 Open Fri 4PM - 6PM
- 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
/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
/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
/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
/2
$1,249,000
- 4 Beds
- 2.5 Baths
- 2,772 Sq Ft
157 Thompson Rd, Chester, VT 05143

Step back in time and experience the timeless charm of this beautifully preserved historic farm, originally known as Thompson Farm and later operated as Jersey Girl Farm. Dating back to 1830, this remarkable property blends 19th-century character with modern sustainability and comfort. The main house retains its original doors and slate roof, while recent upgrades include a new heating system,

Joe Castaluccio Winhall Real Estate

157 Thompson Rd, Chester, VT 05143
/39
$850,000
- 4 Beds
- 3.5 Baths
- 4,336 Sq Ft
166 Robbins Hill, Hartford, VT 05059

This sun-soaked Quechee Lakes home offers the privacy of single-family living with the added benefits of country club amenities. It sits at the end of a quiet road and offers on-site access to wooded walking trails, perfect for hiking or snowshoeing. Walk in through the front door to a warm foyer, which leads directly to the architecturally dramatic sunken living room featuring a stone fireplace

Jennifer Falvey KW Vermont Woodstock

166 Robbins Hill, Hartford, VT 05059
/60
$1,500,000
- 10 Beds
- 12 Baths
- 7,153 Sq Ft
1589 Main St, Cavendish, VT 05142

Glimmerstone Mansion—an extraordinary legacy estate where timeless elegance meets modern sophistication. Set on 2.4± beautifully landscaped acres, this iconic property—listed on the National Historic Register—has been meticulously restored, thoughtfully upgraded, and exquisitely furnished. At the heart of the estate is the grand 10-bedroom mansion, where nearly every bedroom and gathering space

Kevin Barnes William Raveis Real Estate Vermont Properties

1589 Main St, Cavendish, VT 05142
/58
$995,000
- 3 Beds
- 3.5 Baths
- 2,744 Sq Ft
725 Flamstead Rd, Chester, VT 05143

Inspired by Frank Lloyd Wright’s “The Cottage,” where simplicity, warmth, and a deep connection to nature come together in perfect balance. Immaculately maintained 2,700+ sq ft home offers privacy, peace, and mountain views—just 15 minutes to Okemo Mountain and 4 minutes to the village of Chester. Step inside to find an open, flowing layout with timeless and gorgeous Brazilian rosewood floors, a

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

725 Flamstead Rd, Chester, VT 05143
/40
$695,000
- 3 Beds
- 3.5 Baths
- 2,674 Sq Ft
5863 Vt Route 14, South Royalton, VT 05068

Overlooking the Second Branch of the White River, a farm field, and 1/2 acre island in the middle of the White River, this classic old cape dates back to the late 1700s. Previously known as the "Hop Vine Tea Room, when travelers stopped for food and refreshment, the dining hall still remains, dated kitchen, and even indoor plumbing. The many updates include plumbing, wiring, insulation,

Dean Goulet Dunrovin Real Estate

5863 Vt Route 14, South Royalton, VT 05068
/20
$1,175,000
- 4 Beds
- 4 Baths
- 3,920 Sq Ft
1847 Trebo Rd, Chester, VT 05143

With only 50 stone homes in all of Vermont, this one stands out as possibly the most beautiful; uniquely situated on 20 acres of gorgeous greenlawn, fields, forest, rolling hills, extensive stone walls. A mere 2 miles to Chester. Since 2020 the house has been transformed & restored w/improvements such as interior & exterior paint, new windows & French Doors, stone steps & walkways, 50 panel

Gary Coger Four Seasons Sotheby's Int'l Realty

1847 Trebo Rd, Chester, VT 05143
/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 après-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
/48
$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
/60
$599,000
- 7 Beds
- 3.5 Baths
- 3,850 Sq Ft
534 Elm St, Chester, VT 05143

Have you been waiting to buy just the right property? An impressive home in a special town in an amazing state might be perfect. This well-loved Victorian has 4 bedrooms in the main house and another 3 bedrooms in the carriage house unit. There is a storage room in between the two spaces with doors to open to easily connect the units. The beautiful main house has a farmhouse-style kitchen, formal

Tyleen Murray Kelley Real Estate, Inc.

534 Elm St, Chester, VT 05143
/60
$795,000
- 5 Beds
- 3 Baths
- 3,627 Sq Ft
5 Whispering Pines Rd, Ludlow, VT 05149

Experience the Best of Country Living on North HillLocated just 1.9 miles from Okemo, this charming 5-bedroom contemporary home offers the perfect balance of privacy and convenience. Whether you're hitting the slopes in winter or teeing off in summer, world-class skiing and golf are just moments away. Plus, Main Street's pubs, pizza parlors, fine dining, and unique shops are all within easy

Diane Rousseau Four Seasons Sotheby's Int'l Realty

5 Whispering Pines Rd, Ludlow, VT 05149
/55
$669,000
- 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
/56
$629,000
- 5 Beds
- 3.5 Baths
- 3,470 Sq Ft
1057 Quarry Rd, Chester, VT 05143

Chester Haven on a Quiet Dead-End Road. Tucked away in a serene neighborhood, this spacious 5-bedroom, 4-bath home offers over 3,400 sq ft of beautifully designed living space—perfect for both everyday comfort and grand entertaining. Located on a peaceful dead-end street, yet just minutes from the charm and convenience of Main Street, this property offers the best of both worlds. Inside,

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

1057 Quarry Rd, Chester, VT 05143
/39
$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 cedar shingles on the entire house, garage and workshop shed. The kitchen features custom oak

Danny Kogut Williamson Group Sothebys Intl. Realty

3361 County Rd, Windsor, VT 05089
/35
$665,000
- 3 Beds
- 2 Baths
- 1,908 Sq Ft
530 West Rd, Barnard, VT 05031

Conveniently located less than a mile from Barnard General Store and Silver Lake, this charming 3 bedroom cape sits on just over 3 acres of land with tiered stone walls and green lawn circling the house. Mature trees surround the yard and there is view potential with minor clearing and thinning. The full length back deck offers private outdoor space including a covered grilling area just steps

Dan Noble Snyder Donegan Real Estate Group

530 West Rd, Barnard, VT 05031
/24
$800,000
- 2 Beds
- 1 Bath
- 679 Sq Ft
38 Northshore Dr, Ludlow, VT 05149

Same family owned for several decades and now it's time for another family to see the benefits of lakeside living. This cottage is located on private Northshore Drive on beautiful Lake Rescue. Use as-is for summer fun, then plan your future new build or winterize this home. Expand the existing footprint to suit your family's needs. The waterfront gazebo and storage building is your access to

Katherine Burns William Raveis Real Estate Vermont Properties

38 Northshore Dr, Ludlow, VT 05149
/27
$650,000
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
952 Scout Camp Rd, Plymouth, VT 05056

This is a little bit of heaven right here. Located on the backside of quiet Lake Amherst is a home that is much more than a summer camp. Built in 2015, so there are virtually no headaches to be expected. The structure is in great shape and so are the mechanicals. There is a porch across the entire front of the house to overlook the lake...room for dining, sleeping or relaxing in the rockers with

Betty McEnaney Diamond Realty

952 Scout Camp Rd, Plymouth, VT 05056
/32
$779,000
- 4 Beds
- 4 Baths
- 2,912 Sq Ft
168 Thorn Apple Ln, Hartford, VT 05047

Sweet 4 bedroom / 4 bath home nestled between Hillside and High Pastures Road. Accessed by a private road, you will find this property to be located in a great setting that’s quiet and has views of the Woodstock hillside. This home offers nice generous size rooms throughout and a wonderful floor plan. On the main floor, there is a nice size kitchen open to a large living room with a wood burning

Lisa Baldwin Coldwell Banker LIFESTYLES - Hanover

168 Thorn Apple Ln, Hartford, VT 05047
/57
$640,000
- 3 Beds
- 2.5 Baths
- 1,835 Sq Ft
2475 Little Hollow Rd, Rochester, VT 05767

Quintessential VT Mountain Location with privacy & seclusion galore! Surrounded by thousands of acres of locally owned timberland, many abundant recreational opportunities to Mount Cushman and the magnificent Little Hollow recreational area. Absolutely Gorgeous 3 bedroom, 3 bath Modified Cape on 7.1 acres of open and wooded land, that is located at the very end of a Class 3 town maintained road,

Paul H Rea Rural Vermont Real Estate

2475 Little Hollow Rd, Rochester, VT 05767
/39
$775,000
- 3 Beds
- 2.5 Baths
- 1,850 Sq Ft
17 Golf Pond, Woodstock, VT 05091

Nestled in the heart of the picturesque Village of Woodstock, this beautiful 3-bedroom, 2.5-bath home offers a perfect blend of classic Vermont charm and modern comfort. Overlooking a serene pond, the home boasts an open floor plan on the main level..Step inside to find warm wood floors throughout, a welcoming fireplace that anchors the spacious living area, a thoughtfully laid out kitchen

Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

17 Golf Pond, Woodstock, VT 05091
/35
$765,000
- 3 Beds
- 3 Baths
- 2,247 Sq Ft
62 Highland Views N, Ludlow, VT 05149

Motivated sellers...Don't miss out!! This is the best of both worlds...convenient location and privacy all at the same time. This home is in absolutely perfect condition. Just 2 years old, there will be no headaches for the next owner. Three levels of living space for you to enjoy. The wall of windows brings the outside in. The woods surrounding the house give you solitude, but there are

Betty McEnaney Diamond Realty

62 Highland Views N, Ludlow, VT 05149
/36
$829,000
- 3 Beds
- 2 Baths
- 2,868 Sq Ft
840 Sugar Hill Rd, Bethel, VT 05032

Located at the end of a dead end road in Bethel, Vermont, this 129 acre property is totally unique in many ways. Comprised of acres of rolling hills with distant mountain views, a mature apple orchard, two water falls and acres of forest with extensive walking/ATV/horse trails. Several small streams meander through the property providing multiple great pond site opportunities. The main house and

Stan Butler Four Seasons Sotheby's Int'l Realty

840 Sugar Hill Rd, Bethel, VT 05032
/46
$769,000
- 4 Beds
- 3 Baths
- 3,179 Sq Ft
31 Plumley Ave, Ludlow, VT 05149

Charming Country Retreat in Ludlow – Minutes from Okemo MountainDon’t miss this rare opportunity to enjoy the peace of country living in the heart of Ludlow, a quintessential Vermont ski town and home to Okemo Mountain Resort. This meticulously maintained home has been lovingly cared for by the same owner for over 30 years. Designed for easy living, this move-in-ready property features

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

31 Plumley Ave, Ludlow, VT 05149

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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.