Windsor County VT Homes for Sale with Parking

/34
$1,295,000
- 3 Beds
- 3 Baths
- 2,764 Sq Ft
766 Masterson Rd, Bethel, VT 05032

Tucked at the end of a quiet country road, Sugar Bowl Farm is a modern farmhouse set on 124 private acres. Completed in 2025, the home is beautifully finished and filled with natural light, especially in the cathedral-ceilinged great room where south and east facing windows catch the shifting light throughout the day. This airy central space flows effortlessly to the veranda, deck, and gardens

Dia Jenks LandVest, Inc/Woodstock

766 Masterson Rd, Bethel, VT 05032
/52
$667,500 Open House 9/20
- 4 Beds
- 3 Baths
- 2,794 Sq Ft
95 Church St, Chester, VT 05143

Charming Renovated Farmhouse in the Heart of ChesterThis beautifully renovated farmhouse sits on a level half-acre lot just steps from Chester’s Village Green, shops, and local amenities. Offering the perfect blend of historic charm and modern updates, this 4-bedroom, 3-bath home is ideal for year-round living or a Vermont getaway.Inside, enjoy a spacious kitchen with custom

McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

95 Church St, Chester, VT 05143
/58
$1,400,000
- 6 Beds
- 5 Baths
- 4,571 Sq Ft
505 Deweys Mills Rd, Hartford, VT 05047

The Dewey House joins timeless elegance with contemporary convenience. Situated on a quiet road adjacent to the Quechee Gorge waterfall in the charming town of Quechee, this property offers easy access to I-89, I-91, and Route 4. Nearby walking trails and direct water access lend themselves to outdoor pursuits, while the views from the house and its decks over the mill pond and hills create the

Jennifer Falvey KW Vermont Woodstock

505 Deweys Mills Rd, Hartford, VT 05047
/38
$449,000
- 4 Beds
- 2.5 Baths
- 2,272 Sq Ft
96 Dairy Ln, Windsor, VT 05089

Before the leaves have fallen, the PRICE on this one has! Nestled on 1.34 picturesque acres in historic Windsor, this classic 4-bedroom Colonial blends timeless charm with comfortable living. Set back from the road, the home offers privacy and space to enjoy Vermont’s natural beauty while being just minutes from town amenities, schools, and I-91.Inside, you'll find a traditional floor

Katie Ladue Gilbert KW Vermont Woodstock

96 Dairy Ln, Windsor, VT 05089
/31
$79,500
- 1 Bed
- 2 Baths
- 775 Sq Ft
368/370 Qtr I V Jackson Gore Inn, Ludlow, VT 05149

368/370 Qtr. IV~Enjoy two coveted winter weeks —including Christmas and New Year’s(2025-26)—at this spacious 1-bedroom, 2-bathroom lockout unit at the Jackson Gore Inn at Okemo. Located on the third floor and just steps from the Round House, this unit offers beautiful valley views and ideal proximity to lifts, pools, and dining. Unit C Features: 1 bedroom, sleeps eight, lock-out

Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

368/370 Qtr I V Jackson Gore Inn, Ludlow, VT 05149
/18
$625,000
- 3 Beds
- 3 Baths
- 1,248 Sq Ft
37 Sargent St, Norwich, VT 05055

Privacy and convenience all in one. This delightful home on .32 of an acre has both. Move right in to this 1969 built 3 bedroom 3 bathroom with a bonus room on the lower level and enjoy being so close to downtown Norwich, whilst being tucked away on the end of the cul sde sac that is Sargent St. Wood floors throughout, some under carpet. The kitchen is adjacent to dining room and spacious deck

Liam McCarthy Coldwell Banker LIFESTYLES - Hanover

37 Sargent St, Norwich, VT 05055
/43
$260,000
- 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
/57
$1,800,000
- 4 Beds
- 4 Baths
- 2,310 Sq Ft
37 Village Center Rd Unit 4 Blue Spruce, Ludlow, VT 05149

SouthFace Village, Blue Spruce #4 is the newest development on Okemo Mountain. Discover the ultimate ski-in, ski-out living with this stunning 4-bedroom, 4-bathroom condominium nestled in the heart of a prestigious gated community with direct access to the Suncatcher Trail and Sunshine Chairlift Quad. This beautifully furnished home is designed for your comfort and enjoyment. Upon entering the

Joseph Karl William Raveis Real Estate Vermont Properties

37 Village Center Rd Unit 4 Blue Spruce, Ludlow, VT 05149
/38
$69,900
- 1 Bed
- 2 Baths
- 957 Sq Ft
709/711 Qtr I Adams House, Ludlow, VT 05149

Adams 709/711 Qtr. I: Rare opportunity to own a top-floor 1-bedroom, 2-bathroom lockout unit in the sought-after Adams House at Jackson Gore. This spacious, slope-facing residence offers stunning mountain views and ultimate ski-in/ski-out convenience. This luxury one-bedroom condo sleeps 8 with the flexibility of a lock-out option. Features include two baths, including one with a jetted tub, two

Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

709/711 Qtr I Adams House, Ludlow, VT 05149
/60
$695,000
- 2 Beds
- 1 Bath
- 1,196 Sq Ft
691 Dartt Hill Rd, Bethel, VT 05032

With long range views to Mount Moosilauke in NH, this property offers endless opportunities for either primary or vacation home use, short- or long-term rental potential, family legacy/ample guest spaces, or a home business to name a few of the possibilities. The charming 2-bedroom log home has been renovated with premier kitchen and bathroom finishes. Natural woodwork glows warmly throughout the

Terry Davis Williamson Group Sothebys Intl. Realty

691 Dartt Hill Rd, Bethel, VT 05032
/59
$439,000
- 4 Beds
- 2 Baths
- 2,264 Sq Ft
264 Elm Hill St, Springfield, VT 05156

No words describe this property better than a peaceful, bright, historic gentleman farm. This classic post and beam home, the third oldest in Springfield was built in the early 1790's by James Litchfield when he settled in Springfield to farm 64 acres atop of Elm Hill. Although the land was farmed, currently, the site has been reduced to a manageable 1.2 acres. The original axe-cut posts and

Carol Cole BHG Masiello Brattleboro

264 Elm Hill St, Springfield, VT 05156
/51
$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
/51
$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
- 3,524 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
/49
$615,000
- 3 Beds
- 3 Baths
- 2,680 Sq Ft
1643 Hammond Hill Rd, West Windsor, VT 05089

Welcome to your private 8-acre retreat in West Windsor, where craftsmanship, comfort, and self-sufficiency meet everyday adventure. Explore wooded trails, swim in the peaceful pond, or sip coffee on the sunny porch. Evenings glow around the fire pit, while a sturdy treehouse sparks play and gardens of flowers bloom through the seasons. Stone stairways, wooden benches, and camping spots complete

Eric Johnston Four Seasons Sotheby's Int'l Realty

1643 Hammond Hill Rd, West Windsor, VT 05089
/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
/31
$68,500
- 1 Bed
- 2 Baths
- 775 Sq Ft
434 Qtr. I V Jackson Gore Inn, Ludlow, VT 05149

Jackson Gore Inn, Unit 434 QIV. Quarter Ownership. This top floor residence has beautiful valley facing views. Unit B Features: one bedroom with king bed, queen sleep sofa and queen wall bed, full kitchen, jetted tub, fireplace, entertainment center. This unit sleeps six and includes 1 locker for year round use. Other features include a large master bath offering his and her sinks, gas fireplace

Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

434 Qtr. I V Jackson Gore Inn, Ludlow, VT 05149
/60
$749,000
- 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

Laird Bradley 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
/56
$750,000
- 4 Beds
- 4 Baths
- 3,300 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
/29
$169,500
- 2 Beds
- 1 Bath
- 1,500 Sq Ft
1438 Gravelin Rd, Perkinsville, VT 05151

Country Setting on a shared drive surrounded by 3 acres w/ a small pond. First floor has 1 BR, full bath, kitchen/dining area and living room. Lower level has 1 BR and laundry room. Heat is a propane Rannai direct vent, plus a lower-level pellet stove. Property is in need of repair but livable. This is an ideal candidate for a 203K loan.

Don Chabot Town and Country Realty

1438 Gravelin Rd, Perkinsville, VT 05151
/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
/57
$995,000
- 4 Beds
- 3.5 Baths
- 2,585 Sq Ft
117 Ledgewood Rd Unit F3 w/F4 Garage, Ludlow, VT 05149

Ledgewood on Okemo, a spacious condominium located in one of the most sought-after communities on Okemo Mountain. This property offers an abundance of space, featuring two en-suites and two additional bedrooms. The expansive great room opens to a large family kitchen with two breakfast bars, providing ample seating for the whole family. You'll also appreciate the private ski-in/ski-out access and

Katherine Burns William Raveis Real Estate Vermont Properties

117 Ledgewood Rd Unit F3 w/F4 Garage, Ludlow, VT 05149
/57
$2,190,000
- 4 Beds
- 3.5 Baths
- 4,313 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
/48
$1,275,000
- 4 Beds
- 3 Baths
- 3,796 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
/56
$3,100,000
- 5 Beds
- 4.5 Baths
- 7,634 Sq Ft
165 Moonshadow Dr Unit M-15, Ludlow, VT 05149

Welcome to your mountain sanctuary in the heart of Solitude Village—Okemo’s premier slopeside community. This luxurious 5-bedroom, 3-bathroom retreat offers true ski-on/ski-off access, allowing you to hit the Rising Star Trail or Moon Shadow right from your doorstep. Step inside to a warm, elegant interior featuring radiant-heated tile and rich hardwood floors throughout. The expansive great

Joseph Karl William Raveis Real Estate Vermont Properties

165 Moonshadow Dr Unit M-15, Ludlow, VT 05149
/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
/34
$289,000
- 3 Beds
- 2 Baths
- 1,232 Sq Ft
842 Main St, Proctorsville, VT 05153

Cared for by one owner for many years, this two-story 3 bedroom, 2 bath home on .26 +/- acres was built in 1977 and would make a very cute ski house or full-time home. Enter through the enclosed breezeway, a great space for entertaining and relaxing. The eat-in kitchen includes a breakfast/dining nook and excellent counter space. The living room is spacious and has plenty of natural light. A

Geralyn Donohue Engel & Völkers Okemo

842 Main St, Proctorsville, VT 05153
/42
$414,900
- 3 Beds
- 2 Baths
- 2,776 Sq Ft
64 Summer Hill St, Springfield, VT 05156

Tucked in one of Springfield’s most sought-after neighborhoods, 64 Summer Hill St offers the perfect blend of comfort, charm, and convenience. This beautifully maintained 3-bedroom, 2-bath home nestled in one of Springfield’s most desirable neighborhoods. Located on a peaceful .28acre lot in the Cherry Hill district, this inviting property offers the perfect balance of comfort and convenience.

Jamie Watson BHG Masiello Keene

64 Summer Hill St, Springfield, VT 05156
/60
$1,850,000
- 4 Beds
- 6.5 Baths
- 6,269 Sq Ft
73 Laber Rd, Bridgewater Corners, VT 05035

Experience elevated Vermont living with this exceptional mountaintop estate, thoughtfully designed for both comfort and flexibility. Set on nearly 30 private acres, the residence combines timeless architectural style with expansive interiors and truly breathtaking panoramic views—including sightlines to 4,000-foot peaks and Killington’s ski trails.Inside, you’ll find a rare level of

Keri Cole Williamson Group Sothebys Intl. Realty

73 Laber Rd, Bridgewater Corners, VT 05035
/25
$495,000
- 3 Beds
- 1 Bath
- 895 Sq Ft
121 E Lake Rd, Ludlow, VT 05149

Charming Lake Cottage with Over 113 +/-Feet of Waterfront on Lake Pauline.Lovingly maintained by the same family since the 1940s, this delightful lakefront cottage is a rare find. Step inside to discover original touches like tongue-and-groove paneling and vintage details that evoke a simpler time, all thoughtfully preserved. Modern updates blend seamlessly with its nostalgic charm and

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

121 E Lake Rd, Ludlow, VT 05149
/32
$2,250,000
- 2 Beds
- 4 Baths
- 3,514 Sq Ft
611 Simmons Rd, Chester, VT 05143

Skygate Farm is a historic Vermont farmstead first settled in the 1800s, which today spans over 300 acres of meadows, forests, trails, and weathered stone walls. The setting speaks of an early farmer’s wisdom — sited along a gentle hill to shield against the northwest winds, while opening to the first light of day and the vast mountain views to the east. Found at the end of a winding gravel road,

Dia Jenks LandVest, Inc/Woodstock

611 Simmons Rd, Chester, VT 05143
/60
$549,000
- 3 Beds
- 2 Baths
- 2,008 Sq Ft
352 Edwins Pond Rd, Rochester, VT 05767

Welcome to Tranquility in Vermont.This charming three-bedroom, two-bath home invites you to unwind and enjoy the peaceful beauty of Vermont living. With both a spacious great room and a cozy living room—each warmed by its own wood stove—you’ll always have the perfect place to relax.The home features wide plank wood floors throughout, a brand-new heating system with on-demand hot

Katie McFadden RE/MAX North Professionals

352 Edwins Pond Rd, Rochester, VT 05767
/60
$3,650,000
- 5 Beds
- 4 Baths
- 5,181 Sq Ft
348 Turtle Hill Rd, Ludlow, VT 05149

Built over the course of two years and completed in 2023, this nearly new custom timberframe home showcases exceptional craftsmanship and fine attention to detail. Privately sited on over 13 acres, the property offers sweeping, panoramic views of southern Vermont's mountains and valleys; vistas that are truly second to none. The home's architectural highlights include hand-hewn Douglas fir beams

Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

348 Turtle Hill Rd, Ludlow, VT 05149
/52
$1,099,000
- 4 Beds
- 4.5 Baths
- 4,009 Sq Ft
320 Old Bow Rd, Springfield, VT 05156

Spacious Country Retreat with Stunning Views! Experience the perfect blend of space, privacy, and scenic beauty in this impressive country home. Set on 13.78 acres, this property offers expansive outdoor and indoor living, with amazing panoramic views. Inside, you'll find large sunlit rooms including oversized bedrooms, a mudroom, and second floor laundry for convenience. The open concept living

Jenn Boyer Coldwell Banker Homes Unlimited

320 Old Bow Rd, Springfield, VT 05156
/60
$3,650,000
- 5 Beds
- 5 Baths
- 3,212 Sq Ft
166 Jewett Rd, Brownsville, VT 05037

Stately hilltop home built by Silas Banister c.1800, recently undergone a complete restoration. Quality materials & craftsmanship throughout. It has gorgeous views of nearby Ascutney Mountain & long-range views of NH. The property consists of 98 acres made up of fields, hard & softwoods, trails, a large sugarbush (potential for a future boiling operation). Conserved by Upper Valley Land Trust,

Dana Waters Dark Horse Realty

166 Jewett Rd, Brownsville, VT 05037
/43
$359,000
- 3 Beds
- 1 Bath
- 1,144 Sq Ft
919 Vermont Route 100, Rochester, VT 05767

Situated on a sun-drenched, level yard you will find this stunning ranch-style home, equipped with the latest amenities, including new electrical andheating systems, water heater, insulation, doors, siding, interiorwalls, double pane windows, recessed lighting thoughout, hardwood floors, spacous kitchen, and a bath featuring a granite vanity. A brand new wood stove offers an additional

Christopher King King Real Estate

919 Vermont Route 100, Rochester, VT 05767
/45
$74,000
- 1 Bed
- 2 Baths
- 775 Sq Ft
418 Qtr I Jackson Gore Inn, Ludlow, VT 05149

Top-Floor 1BR/2BA at Jackson Gore – Sleeps 6, Gorgeous Views, Premium Resort AccessExperience the best of slopeside living with this beautifully appointed 1-bedroom, 2-bathroom top-floor unit at Jackson Gore, Okemo Mountain Resort. Perfectly positioned with incredible valley views and a glimpse of the outdoor heated pool, this residence offers both comfort and convenience, just steps from the

Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

418 Qtr I Jackson Gore Inn, Ludlow, VT 05149
/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

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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.