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

8 Pond St, Ludlow, VT 05149
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/39
$790,000
- 4 Beds
- 3.5 Baths
- 3,347 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
/46
$695,000
- 3 Beds
- 3.5 Baths
- 2,274 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
/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
/25
$195,000
- 2 Beds
- 1 Bath
- 1,152 Sq Ft
15 Randall St, Springfield, VT 05156

Nestled near the end of a quiet dead-end road, this Cape-style home offers both tranquility and convenience. Featuring beautiful oak hardwood floors, this property is filled with character and potential. The spacious deck invites you to enjoy outdoor living, while the attached 2-car garage adds both practicality and ease. Inside, the main level boasts a formal dining room, a cozy living room, and

Chelsea Richardson Barrett and Valley Associates Inc.

15 Randall St, Springfield, VT 05156
/35
$399,000
- 3 Beds
- 3.5 Baths
- 2,038 Sq Ft
1497 Route 100a, Plymouth, VT 05056

Talk about a convenient location! Central to Killington, Woodstock, and Ludlow. This home is absolutely suitable for full time living or vacation usage. Once upon a time, this was an old schoolhouse. Since then, it was reborn as a home. The floorplan is tremendously flexible with a den/office/TV room upstairs and down along with bedrooms both upstairs and down. A couple of really nice bay

Betty McEnaney Diamond Realty

1497 Route 100a, Plymouth, VT 05056
/39
$275,000
- 3 Beds
- 2 Baths
- 1,785 Sq Ft
36 Graham St, Bethel, VT 05032

Tucked away on a quiet street just off Route 107, this 3-bedroom, 2-bath home offers a great mix of privacy, practicality, and convenience in the heart of Bethel. Inside, you'll find a functional layout with a spacious laundry room, a recently installed dishwasher, and a pellet stove that efficiently heats the entire home, with oil radiator heat as a backup option. The detached two-car garage

Jacob Barnes EXP Realty

36 Graham St, Bethel, VT 05032
/56
$1,950,000
- 3 Beds
- 3.5 Baths
- 1,844 Sq Ft
161 Fishing Access Rd, Ludlow, VT 05149

Spectacular Lakefront Living in Ludlow, Vermont. Welcome to your ultimate four-season escape — a rare lakefront treasure tucked at the end of a quiet private road on the peaceful Round Pond section of Lake Rescue. With a private swimming area and boat docks just steps from your door, this home offers unparalleled privacy, natural beauty, and direct water access. Take in panoramic lake views from

Katherine Burns William Raveis Real Estate Vermont Properties

161 Fishing Access Rd, Ludlow, VT 05149
/40
$1,650,000
- 4 Beds
- 3 Baths
- 2,619 Sq Ft
441 Spruce Way, Woodstock, VT 05091

441 SPRUCE WAY - Easily accessible to the village, yet tucked away on over 24 acres is this unique, modern/contemporary residence designed by Boston architect Ken McKinzie and sited perfectly to take in south-facing long range mountain views. The house was designed to be perfect for two, with the primary bedroom suite on the main living level, yet with two bedrooms and a bath at the other end of

John Snyder Snyder Donegan Real Estate Group

441 Spruce Way, Woodstock, VT 05091
/34
$275,000
- 4 Beds
- 1.5 Baths
- 1,616 Sq Ft
10 Derby Ct, Springfield, VT 05156

This bright and inviting Gambrel home sits on a corner lot and offers a lovely, fenced backyard, to grow your garden, or play toss with the kids. This home features a welcoming, large foyer, a generous living room and a formal dining room for those family dinners. The kitchen features an island to enjoy the morning coffee. With four bedrooms 1 full bathroom and one 1.4 baths, there is plenty of

Carol Cole BHG Masiello Brattleboro

10 Derby Ct, Springfield, VT 05156
/40
$219,000
- 2 Beds
- 2 Baths
- 1,420 Sq Ft
396 S Main St, Bethel, VT 05032

Just minutes from downtown Bethel this home has everything you’re looking for! The sunny, gently sloping yard is ideal for gardening, or hosting gatherings.Inside, you'll find two bedrooms and two full bathrooms, a spacious living room, and a bright kitchen that opens to a large dining room with sliding doors leading to a private deck overlooking the backyard.Both bedrooms are

Lindsay Cimadon

396 S Main St, Bethel, VT 05032
/24
$289,000
- 3 Beds
- 2 Baths
- 1,890 Sq Ft
89 Lyon Rd, South Royalton, VT 05068

A perfect ‘SoRo’ location, minutes from the charm of South Royalton Village and privacy off a dead -end road, make this country property a must see. The 2000+/- sqft of living space includes a large kitchen/family room, functional mudroom, office/study, large bedrooms, and two storage sheds on property. In warmer months, the large front deck provides additional living and entertaining space.

Seth Barbiero EXP Realty

89 Lyon Rd, South Royalton, VT 05068
/59
$439,000
- 4 Beds
- 2 Baths
- 2,264 Sq Ft
264 Elm Hill St, Springfield, VT 05156

This beautiful post and beam built, 4 bedroom, 2 bath 1791 farmhouse is the third oldest in the town of Springfield. Located at the top of Elm Hill with stone walls and hill views, is only one mile from the center of town. The main floor includes a nice workable kitchen with an adjoining sitting room with a wood stove and the triple window on the east provides full morning sun as you enjoy your

Carol Cole BHG Masiello Brattleboro

264 Elm Hill St, Springfield, VT 05156
/48
$200,000
- 3 Beds
- 1 Bath
- 1,556 Sq Ft
234 Harvard St, Springfield, VT 05156

Discover timeless charm & everyday comfort in the heart of Springfield with this inviting home, where classic character meets modern ease. From the whimsical stucco exterior and detached two-car garage (currently set up as a workshop) to the one-of-a-kind walrus-shaped mailbox - this home is full of personality. Step inside to discover hardwood floors, natural light, & flexible layout that suits

Isabella Luhrs BHG Masiello Keene

234 Harvard St, Springfield, VT 05156
/44
$410,000
- 3 Beds
- 2 Baths
- 1,304 Sq Ft
663 Depot St, Chester, VT 05143

Everything you’ve been looking for in a Vermont home—completely renovated with care and character. Nearly every aspect of this Chester property is new: electrical, plumbing, heating, insulation, drywall, windows, and more—offering the low-maintenance peace of mind homeowners crave. The kitchen features a stylish farmhouse sink and stone countertops, while the upstairs bathroom includes a

Betsy Adamovich Real Broker LLC

663 Depot St, Chester, VT 05143
/48
$350,000
- 5 Beds
- 4 Baths
- 2,963 Sq Ft
513 Giddings St, Springfield, VT 05150

Nestled on over an acre +/- of level land, this well-maintained home offers a wealth of space and potential for any lifestyle. With a large shed, a 3-car carport/workshop, and even a chicken coop, you'll have plenty of room to store, work, and play. The first floor features a generously-sized bedroom with bay windows, a beautifully refinished bathroom with a walk-in shower, a large kitchen,

Chelsea Richardson Barrett and Valley Associates Inc.

513 Giddings St, Springfield, VT 05150
/33
$525,000
- 3 Beds
- 2.5 Baths
- 2,152 Sq Ft
17 Vermont 12, Hartland, VT 05048

1850 home re-furbished top to bottom for modern amenities with antique charm. New roof, floors, kitchen, bathrooms, windows, electrical, plumbing, and heating throughout. Very large flat yard located right downtown.

Derek Eisenberg Continental Real Estate Group, Inc.

17 Vermont 12, Hartland, VT 05048
/32
$2,300,000
- 4 Beds
- 4.5 Baths
- 2,948 Sq Ft
134 Chester Arthur Rd, Hartford, VT 05047

A quality residence with 4.69 landscaped acres beautifully complimenting the estate! Entering into the grounds a graceful drive meanders through landscaped lawns to arrive at a stone patio and an appealing New England style residence. Conveniently, there is option to enter an attached garage with direct entrance to the residence. After crossing the stone patio, passing through the front door

John Wetmore Wetmore Real Estate

134 Chester Arthur Rd, Hartford, VT 05047
/34
$475,000
- 3 Beds
- 2 Baths
- 1,489 Sq Ft
6852 Us Route 4, Bridgewater, VT 05034

This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont

Laird Bradley Williamson Group Sothebys Intl. Realty

6852 Us Route 4, Bridgewater, VT 05034
/31
$379,900
- 3 Beds
- 2 Baths
- 1,584 Sq Ft
34 Fox Chair Terrace, Springfield, VT 05156

Welcome to 34 Fox Chair Terrace, a peaceful, private three-bedroom, two-bath home set on a full acre just minutes from downtown Springfield and charming Chester, Vermont. Tucked away in a quiet rural setting, this spacious property offers the best of both worlds: privacy and nature, with easy access to shopping, schools, the local hospital, and other area amenities.Step inside to find a

Patrick Kelley Four Seasons Sotheby's Int'l Realty

34 Fox Chair Terrace, Springfield, VT 05156
/33
$329,000
- 3 Beds
- 2 Baths
- 864 Sq Ft
1159 Ski Tow Rd, Brownsville, VT 05037

Located near the end of a country cul-de-sac at Ascutney Mountain this Split entry has 3BR/2BA it is configured as two units with separate entries & 2 kitchens but has been used as a single-family home, as well. It has 2 nice brick fireplaces; one with a VT Castings woodstove insert, the other has a wood stove hook up. Recent updates include a new Rinnai direct vent propane heater, 2 Tesla Power

Dana Waters Dark Horse Realty

1159 Ski Tow Rd, Brownsville, VT 05037
/37
$549,000
- 4 Beds
- 2 Baths
- 2,541 Sq Ft
106 Vermont Route 100, Weston, VT 05161

This historic property located on Weston Island, the original settlement of the village of Weston, was once home to the area's beloved country doctor. Rich in antique farmhouse allure, it has been thoughtfully updated for modern living. The first floor features a generous mudroom, a living room with wide plank floors and wood stove, and a den with built ins and a wood burning fireplace that could

Steve Stettler Four Seasons Sotheby's Int'l Realty

106 Vermont Route 100, Weston, VT 05161
/38
$1,999,000
- 6 Beds
- 6 Baths
- 7,619 Sq Ft
5518 Vt Route 12, Barnard, VT 05031

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 of the well known amenities of Woodstock Village are just minutes away! World class medical care at Dartmouth Hitchcock Hospital and year round

John Wetmore Wetmore Real Estate

5518 Vt Route 12, Barnard, VT 05031
/25
$379,000
- 2 Beds
- 2 Baths
- 1,451 Sq Ft
78 Division St, Hartford, VT 05001

Right in the heart of Wilder, this cozy home is near trails, water, public transportation and schools. Only a 15 minute drive to the Hanover Green or the Lebanon Green. The house has a generous boot room that flows into the kitchen then the living space. Several upgrades, including the hardwood staircase and railing, have added value to the interior. The back yard offers a nice shaded place to

Josh Hunt Snyder Donegan Real Estate Group

78 Division St, Hartford, VT 05001
/29
$299,000
- 5 Beds
- 3.5 Baths
- 3,465 Sq Ft
600 N Windsor St, South Royalton, VT 05068

Just 3⁄4 of a mile from the heart of South Royalton and Vermont Law School, this versatile property offers tremendous rental potential with some TLC. With three separate units—each with its own private entrance—this is the perfect opportunity to renovate and generate strong rental income. The main unit in the house has 3 bedrooms and 1 1/2 baths. The second unit in the main house is a 1 bed 1

Franchesca Collins Hall Collins Real Estate Group

600 N Windsor St, South Royalton, VT 05068
/33
$225,000
- 2 Beds
- 1 Bath
- 864 Sq Ft
2579 Vermont Route 100, Plymouth, VT 05056

Tucked among the trees in beautiful Plymouth, this rustic getaway offers a peaceful setting with easy access to outdoor recreation. This property offers unbeatable access to some of Vermont’s best recreation. Just a short drive to both Killington and Okemo for world-class skiing, and minutes from Echo Lake and Plymouth State Park, this is a four-season location ideal for outdoor lovers.The home

Frank Provance Diamond Realty

2579 Vermont Route 100, Plymouth, VT 05056
/34
$250,000
- 1 Bed
- 1 Bath
- 617 Sq Ft
413 Hidden Heights Rd, Chester, VT 05143

Until this last winter this was a really sweet 16 x 24 log cabin. Then it became fire damaged and now the owner would love to have someone bring it back to its former glory. Nice, private area on a town-maintained country road. All utilities are underground, including a 330-gallon propane tank, electric power from the street, and water from the 230' drilled well. The cabin has 1 bath, a

Glenn Olney Barrett and Valley Associates Inc.

413 Hidden Heights Rd, Chester, VT 05143
/52
$599,900
- 4 Beds
- 3.5 Baths
- 2,068 Sq Ft
266 Barlow Rd, Springfield, VT 05156

This beautiful property has so much to offer! This extremely well maintained home is both private and serene, tucked away on top of the world. Outside the home features, a large back deck, standing seam roof, expansive space for gardens and the privacy of 33.19+/- acres. Going inside the home features full picture windows allowing plenty of natural light, two Gas fireplaces perfect for

Thaddeus Abare Barrett and Valley Associates Inc.

266 Barlow Rd, Springfield, VT 05156
/49
$450,000
- 4 Beds
- 2 Baths
- 2,040 Sq Ft
281 Evergreen Terrace, Springfield, VT 05156

This delightful home is sure to please. Set in a lovely wooded cul-de-sac, surround yourself with lovely, terraced landscaping, stone walls and a peaceful wooded setting to while away the hours. This beautiful well cared home features many delightful settings. The living room features a cathedral ceiling and stone fireplace, with a wood stove insert, along with many windows to bring in the

Carol Cole BHG Masiello Brattleboro

281 Evergreen Terrace, Springfield, VT 05156
/59
$1,750,000
- 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
/17
$140,000
- 1 Bed
- 1 Bath
- 266 Sq Ft
32 Pond St Unit 1, Ludlow, VT 05149

Charming One-Bedroom Efficiency in the Heart of Ludlow VillageThis beautifully remodeled ground-floor efficiency offers the perfect opportunity to own in Ludlow, just moments from Main Street and the Okemo slopes. Enjoy easy access with a private covered porch entrance and the convenience of walking to local shops and restaurants or catching the Okemo Shuttle just steps away.Inside,

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

32 Pond St Unit 1, Ludlow, VT 05149
/60
$240,000
- 3 Beds
- 1 Bath
- 1,024 Sq Ft
442 Vermont 103, Chester, VT 05143

Adorable Village Home in the Heart of Chester, VermontThis charming 3-bedroom, 1-bath home is packed with personality and Vermont village charm! Set on a sunny quarter-acre lot, this sweet property features an oversized deck perfect for summer barbecues, a great yard for play or gardening, and a convenient attached garage.Inside, you’ll love the warm, inviting living space with

Rachael Rogala Rachael Rogala Inc.

442 Vermont 103, Chester, VT 05143
/34
$375,000
- 4 Beds
- 2 Baths
- 1,300 Sq Ft
12 Meadow Dr, Springfield, VT 05156

This delightful ranch home located in a desirable cul-de-sac neighborhood, is where you can enjoy a nice evening walk and chat with the neighbors. Enter from the front porch to the bright living room with a lovely fireplace and hardwood floors, to enjoy a fire on those cool evenings. The nice sized kitchen adjoins the lovely dining room which features easy access to the large screened-in porch,

Carol Cole BHG Masiello Brattleboro

12 Meadow Dr, Springfield, VT 05156
/57
$2,190,000
- 4 Beds
- 3.5 Baths
- 3,073 Sq Ft
7 Norman Dr, Ludlow, VT 05149

This is a rare opportunity to own a stunning year-round residence on the shores of Lake Rescue, nestled within a sought-after community that includes Okemo Mountain Ski Resort—offering the ultimate four-season lifestyle. Ideally located on the coveted east side of the lake, the home is perfectly positioned to capture afternoon sun and dramatic sunsets over the water.Beautifully landscaped

Boris Lavanovich Mary W. Davis Realtor & Assoc., Inc.

7 Norman Dr, Ludlow, VT 05149
/30
$480,000
- 2 Beds
- 1 Bath
- 768 Sq Ft
37 Atwood Ave, Woodstock, VT 05091

Charming, updated, and perfectly located—this turnkey gem is your ticket to easy living in one of the area’s most adorable neighborhoods! With all the major systems recently upgraded - including a new furnace, hot water heater, Tesla Powerwall, and water purification system - this efficient home is move-in ready.Inside, you’ll love the fresh renovations: a modern kitchen with

Keri Cole Williamson Group Sothebys Intl. Realty

37 Atwood Ave, Woodstock, VT 05091
/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
/16
$250,000
- 5 Beds
- 2 Baths
- 1,728 Sq Ft
101 Mount Vernon St, Springfield, VT 05156

Built as a duplex, this and last owner have used it as a single family. Therefore there are no traditional figures for income and expenses. Easy to transform into the duplex for income by adding appliances to the upstairs apartment. This home has many upgrades including siding, windows, decks/railings/stairway (outside). Drive is paved and there looks to be room to replace the shed. Perfect

Christine Lewis Brattleboro Area Realty

101 Mount Vernon St, Springfield, VT 05156
/33
$325,000
- 2 Beds
- 1 Bath
- 1,000 Sq Ft
85 Slawson Rd, Weston, VT 05161

This adorable Weston home offers more than meets the eye – come check it out! The house sits on just shy of 2.5 acres and is adjacent to thousands of conserved acres in the Okemo State Forest and the Mount Holly Conservation Trust. Slawson Road is a quiet neighborhood with a nice mix of primary and vacation homes, offering true peace and quiet, and is located almost equidistant to Weston and

Claudia Harris Mary Mitchell Miller Real Estate

85 Slawson Rd, Weston, VT 05161
/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
/19
$379,900
- 2 Beds
- 1 Bath
- 900 Sq Ft
302 Davidson Hill Rd, Chester, VT 05143

This Cozy cabin tucked away along the outskirts of Chester is sure to impress. With a brand new roof, heating system and more this is the perfect turn key retreat. The property features both open lawn and forest to explore, just up the road from snowmobiling and hiking trails this property has the ability to be your home base for all your favorite activities year around. Including close proximity

Thaddeus Abare Barrett and Valley Associates Inc.

302 Davidson Hill Rd, Chester, VT 05143

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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.