Windsor County VT Homes for Sale with Parking

/50
$945,000
- 4 Beds
- 2.5 Baths
- 2,044 Sq Ft
100 Pomfret Rd, Woodstock, VT 05091

Charming, Unique, and Ideally Located! Welcome to 100 Pomfret Road—a beautifully updated farmhouse set on four level, picturesque acres just a short walk from Mt. Tom, Billings Farm, and the heart of downtown Woodstock. This rare find blends timeless character with everyday convenience in a peaceful, brookside setting.Inside, you’ll find a sun-drenched home featuring four

Keri Cole Williamson Group Sothebys Intl. Realty

100 Pomfret Rd, Woodstock, VT 05091
/60
$2,995,000
- 5 Beds
- 9 Baths
- 8,249 Sq Ft
1497 Bowman Rd, Barnard, VT 05068

Upper Farm- Circa 1799, large antique cape nestled on 12 acres with stream, multiple ponds, stunning waterfalls overlooking a large meadow. Beautiful extensive gardens for all those perennial enthusiasts with multiple stone terraces overlooking an apple orchard with a variety of types of apples. A two level barn for equipment/storage/animals. A brand new expansive 3 bay heated garage with

Gretchjen Smith Williamson Group Sothebys Intl. Realty

1497 Bowman Rd, Barnard, VT 05068
/59
$1,745,000
- 2 Beds
- 3 Baths
- 2,106 Sq Ft
7 North St, Woodstock, VT 05091

Stunning Renovated Antique Cape in the Heart of Woodstock Village!Tucked away on over an acre of beautifully landscaped land directly abutting the Marsh-Billings-Rockefeller National Park, this fully renovated antique Cape offers the rare combination of historic charm, modern efficiency, and unbeatable walkability. Located in the heart of Woodstock Village, you can stroll to the village

Keri Cole Williamson Group Sothebys Intl. Realty

7 North St, Woodstock, VT 05091
/33
$4,490,000
- 5 Beds
- 5.5 Baths
- 8,122 Sq Ft
5685 Vermont 12, Barnard, VT 05031

SEE PROPERTY-SPECIFIC WEBSITE FOR DETAILS, HIGH RESOLUTION PHOTOS, VIDEOS AND MORE. If you’ve been looking for the iconic Vermont home, rarely does an opportunity like this present itself. Welcome to HIGHLAND GLEN, an idyllic Vermont home situated on 12 picturesque acres in the quaint town of Barnard, VT. Upon arrival at Highland Glen, you'll immediately sense the special charm of this

John Snyder Snyder Donegan Real Estate Group

5685 Vermont 12, Barnard, VT 05031
/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
/60
$649,000
- 4 Beds
- 2.5 Baths
- 2,520 Sq Ft
5100 Route 100, Plymouth, VT 05056

(Das Grunebergehaus) The Green Mountain House. First time offered on market since 1978. This gorgeous farmhouse, circa 1831, has been lovingly maintained & updated over the current owner's term of ownership. Previously owned by the Coolidge Family. During the years of Calvin Coolidge's presidency this home was used as a guest house for political figures to come & stay while visiting President

Marni Rieger KW Vermont-Killington

5100 Route 100, Plymouth, VT 05056
/54
$450,000
- 3 Beds
- 2 Baths
- 1,809 Sq Ft
935 French Meadow Rd, Springfield, VT 05156

Nestled in peaceful seclusion on 21.4 acres, this inviting split-level home is ready to welcome its next owners. While privately situated and out of view from the road, the property remains conveniently close to VT Routes 106 and 10, offering the perfect blend of privacy and accessibility.Step inside from the charming covered porch into a spacious mudroom with Vermont slate flooring,

Jessica Landers Barrett and Valley Associates Inc.

935 French Meadow Rd, Springfield, VT 05156
/39
$465,000
- 4 Beds
- 2.5 Baths
- 2,125 Sq Ft
143 Okemo Acres, Ludlow, VT 05149

Charming Fixer-Upper in a Dream Location – Your Canvas Awaits!Step into a world of endless possibilities with this house, nestled in the heart of a picturesque neighborhood just a mere 0.8 miles from the magnificent Okemo Mountain. This property is not just a house; it’s a golden opportunity for those with a vision, a passion for design, and a desire to create a home that reflects their

Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

143 Okemo Acres, Ludlow, VT 05149
/60
$3,275,000
- 4 Beds
- 4.5 Baths
- 4,708 Sq Ft
207 Willey Hill Rd, Norwich, VT 05055

Nestled on a private 17-acre retreat, The Pond at Willey Hill is a quintessentially picturesque estate just a stone’s throw away from Norwich, Hanover, and the best of the Upper Valley. Featuring a wildlife-rich pond as its center, the beautifully landscaped grounds offer seasonal long-range views, a pool, woodland trail, and a park-like fenced area. Expertly renovated by renowned builders O’Hara

David Donegan Snyder Donegan Real Estate Group

207 Willey Hill Rd, Norwich, VT 05055
/48
$575,000
- 9 Beds
- 6 Baths
- 5,054 Sq Ft
12 Commonwealth Ave, Ludlow, VT 05149

A rare find in the heart of the Ludlow Village. This three-family property offers over 5,000 sq. ft. of income-generating space, just steps from the Okemo shuttle and downtown Ludlow! With a strong rental history this property offers both versatility and value. Two of the three units have been beautifully, recently updated and are turn key. One unit used by by the Seller, the second currently

Frank Provance Diamond Realty

12 Commonwealth Ave, Ludlow, VT 05149
/48
$4,900,000
- 7 Beds
- 9 Baths
- 9,464 Sq Ft
5893 Stage Rd, Barnard, VT 05031

"LONG WAY HILL" - An elegant and beautifully constructed residence of the highest quality, privately situated on 54 acres with long-range views, lawns, gardens, fields and trails. Beautiful perennial and wildflower gardens offer charming, private views of woods and hills over a half-acre pond. Architect-designed in the style of a traditional New England country home, the main residence has 5

John Snyder Snyder Donegan Real Estate Group

5893 Stage Rd, Barnard, VT 05031
/47
$679,900
- 3 Beds
- 2.5 Baths
- 3,680 Sq Ft
82 Hiram Atkins Byway, Hartford, VT 05001

Price Reduced! Wonderful colonial style home that has been beautifully maintained, updated and nestled on a semi private lot in Quechee Lakes. Membership gives access to one of Vermont's finest 36 hole golf courses, club house, pool, beach area at lake Pineo, quechee ski hill, pickleball, tennis and is a great spot for biking and hiking. Just a short drive to KILLINGTON, Pico, Saskadena Six Ski

Alex DeFelice The Clerkin Agency, P.C.

82 Hiram Atkins Byway, Hartford, VT 05001
/43
$750,000
- 2 Beds
- 3 Baths
- 1,364 Sq Ft
193 Jackson Gore Unit 739/741, Ludlow, VT 05149

Come and experience Vermont at its best! This condo is located in Jackson Gore on Okemo Mountain in Ludlow. This slope side condo unit has stunning views of the mountain and trails. This unit would serve well as a family retreat or rental investment property. It boasts a gas fireplace for cold winter nights. It has 2 bedrooms and 3 bathrooms and offers lock-out capability for separate rental

John Napier TPW Real Estate

193 Jackson Gore Unit 739/741, Ludlow, VT 05149
/51
$725,000
- 3 Beds
- 3.5 Baths
- 3,240 Sq Ft
149 Arnold Rd, Bethel, VT 05032

PRICE IMPROVEMENT-Motivated Seller!Charming Country Log Home on 35 Private AcresOffered for the first time on the market, this beautifully crafted 2012 log home offers the perfect blend of rustic charm and modern comfort. Thoughtfully designed, the home features 3 spacious bedrooms and 4 bathrooms, with flexible layout options to suit your lifestyle. Two generously sized bedrooms on the

Eric Kenyon Rural Vermont Real Estate

149 Arnold Rd, Bethel, VT 05032
/51
$695,000
- 4 Beds
- 3 Baths
- 3,100 Sq Ft
35 Stevens Rd, Cavendish, VT 05142

This is a dream come true for someone who is seeking a Vermont nature retreat in every season. Located on the corner of two quiet, town maintained, gravel roads, one of which is a dead end, is the handsome 1800 traditional Cape with two additions! This classic home includes 40+ acres. Only one other house can be seen from the property & you have to know where to look! The views of Mother Nature

Betty McEnaney Diamond Realty

35 Stevens Rd, Cavendish, VT 05142
/47
$8,000,000
- 3 Beds
- 3.5 Baths
- 5,384 Sq Ft
115 Eastman Rd, Woodstock, VT 05091

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 Williamson Group Sothebys Intl. Realty

115 Eastman Rd, Woodstock, VT 05091
/38
$629,000
- 4 Beds
- 3 Baths
- 2,557 Sq Ft
144 Butternut Ln, Woodstock, VT 05091

The Harry Emmons House an antique brick cape located in the village of Taftsville sited on an open flat village lot. Through the classic covered farm porch enter a gathering room with a brick fireplace, light-filled high ceilings, exposed beams in comfortably sized rooms, a country kitchen, sunny dining room, and a first-floor bedroom with dressing area. Moving upstairs, the second floor has two

Scott Monahan Williamson Group Sothebys Intl. Realty

144 Butternut Ln, Woodstock, VT 05091
/46
$625,000
- 2 Beds
- 3 Baths
- 1,369 Sq Ft
193 Jackson Gore Unit 640/642, Ludlow, VT 05149

Bixby House 640/642 Whole Ownership. This luxury two-bedroom, valley side home features fully-equipped kitchen with stainless steel appliances, tiled back splash, farm sink and granite counters. The cozy living room includes a dining area and gas fireplace. The tiled foyer entry provides storage for outdoor gear. Primary bedroom has a king bed and a spacious master bath with his and her sinks.

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

193 Jackson Gore Unit 640/642, Ludlow, VT 05149
/30
$515,000
- 4 Beds
- 2.5 Baths
- 2,238 Sq Ft
141 N Runway Rd, Perkinsville, VT 05151

Welcome to this beautifully maintained expanded Cape, perfectly positioned to capture stunning views of the Hartness runway—an aviation enthusiast's dream! Tucked away on a quiet dead-end road, the property offers just the right balance of privacy and convenience, located only 10 minutes from major grocery stores, entertainment, and other everyday essentials.The main level features a

Allison Griep KW Vermont Woodstock

141 N Runway Rd, Perkinsville, VT 05151
/19
$639,000
- 3 Beds
- 2 Baths
- 3,300 Sq Ft
23 Brookside Dr, Norwich, VT 05055

Walk to Dan & Whits and elementary school from this 3 BR, 2 bath village home with pastoral viewsRare opportunity for country-like living and views within the quiet village of Norwich, a picturesque, quintessential Vermont town across the river from Dartmouth College and world-class Medical Center in Hanover, NH. Walk to Dan & Whits and elementary school from this 3 BR, 2 bath home with

Jason Saphire www.HomeZu.com

23 Brookside Dr, Norwich, VT 05055
/60
$875,000
- 7 Beds
- 4.5 Baths
- 4,733 Sq Ft
107 Baker Rd, Springfield, VT 05156

Welcome to this spacious and beautifully expanded Gambrel-style home, set on a stunning 9.55-acre property with mountain views in the heart of Springfield, Vermont. Offering classic New England charm with thoughtful modern upgrades, this property is not just a home, but a contemporary and comfortable living space. The main home, built in 1955, was expanded with a large addition in 2009, including

Jeremy Collins Ridgeline Real Estate

107 Baker Rd, Springfield, VT 05156
/19
$174,900
- 2 Beds
- 1 Bath
- 1,217 Sq Ft
654 Us Route 5, North Hartland, VT 05052

This home has a good size lawn, is close to Hartford (4 miles from the VA) easy access to I91 and I89 short travel to skiing, hiking, boating, swimming, shopping. A nice incentive is the slab rent from the mobile home next door. This property is being sold AS-IS,

Mary Chamberlin Dave Walthour Real Estate

654 Us Route 5, North Hartland, VT 05052
/26
$199,000
- 2 Beds
- 1 Bath
- 1,192 Sq Ft
1568 S Hill Rd, Ludlow, VT 05149

Cozy home on 2.3+/- acres. Great location out in the country on South Hill. Stone wall and lovely meadow visible from the living room picture window. Open floor plan, wide board wood floors. Just 10 minutes to Okemo Mountain Resort. Water intrusion in basement caused settling and damage. Foundation likely needs extensive repairs or replacement. Being sold "as-is". Current owner is ready to move

Alexandra Eatmon Kelley Real Estate, Inc.

1568 S Hill Rd, Ludlow, VT 05149
/38
$230,000
- 3 Beds
- 1 Bath
- 1,679 Sq Ft
707 Skitchewaug Trail, Springfield, VT 05156

Discover opportunity and flexibility at 707 Skitchewaug Trail in Springfield. This 3-bedroom, 1-bath home sits on 2.8 private acres, combining open yard space and wooded surroundings to create the perfect country setting. With a spacious kitchen and dining area, cozy wood stove in the living room, and first-floor bedroom, bath, and laundry, the layout supports a variety of living needs, from

Nick Sicard EXP Realty

707 Skitchewaug Trail, Springfield, VT 05156
/33
$179,900
- 2 Beds
- 1 Bath
- 856 Sq Ft
982 Vermont 14, Royalton, VT 05068

Welcome to this cozy and well-maintained home, perfectly situated close to local shops and restaurants for ultimate convenience. Step inside to a convenient mudroom area, with plenty of space to take off those muddy boots. The home opens into a nicely sized living room and kitchen with an island that offers additional prep and seating space. Two bedrooms down the hall share a full bathroom and

Shenia Covey Lyford Coldwell Banker LIFESTYLES - Hanover

982 Vermont 14, Royalton, VT 05068
/31
$74,000
- 1 Bed
- 2 Baths
- 775 Sq Ft
228/230 Qtr I Jackson Gore Inn, Ludlow, VT 05149

Great location! This one bedroom lockout unit with a deck is looking right over the outdoor pool and hot tubs with a beautiful valley view! Direct access to the elevator/stairs to the private owner's locker room where you store your skis in your personal locker. Unit C Features: 1 bedroom, sleeps eight, lock-out capabilities, 2 fixed Queen beds, Queen sleep sofa, Queen wall bed, full

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

228/230 Qtr I Jackson Gore Inn, Ludlow, VT 05149
/51
$1,375,000
- 6 Beds
- 5.5 Baths
- 5,790 Sq Ft
49 Burton Rd, Weston, VT 05161

Location, Views, and Room for Everyone – It’s All Here and Waiting for You! Offering maximum warmth, comfort, and charm, this beautifully-built and well-maintained home features traditional New England architecture on 7+ picturesque and tranquil acres just outside the delightful village of Weston. The inviting layout features classic design and rich architectural details with formal and informal

Claudia Harris Mary Mitchell Miller Real Estate

49 Burton Rd, Weston, VT 05161
/58
$549,000
- 8 Beds
- 1 Bath
- 3,500 Sq Ft
1254 U S 5, Springfield, VT 05156

Welcome to the former Danforth Inn! Take a trip back in time to 1780 as you look at this extremely original old building that was built in Weathersfield Bow in 1780 by Gideon Lyman. In 1789 Joseph Danforth moved to the Bow and he leased and then bought the Inn, changing the name to the Danforth Inn. This property will need some love, but it has never been spoiled in its originality, and it's just

Glenn Olney Barrett and Valley Associates Inc.

1254 U S 5, Springfield, VT 05156
/59
$410,000
- 2 Beds
- 2 Baths
- 2,400 Sq Ft
54 Twitchell Settlement, Rochester, VT 05767

"Nestled on over three private acres, this Vermont retreat exudes rustic charm and modern comfort. The soaring cathedral ceilings and floor-to-ceiling arched windows in the great room flood the space with natural light, creating a warm and inviting atmosphere. The open-concept layout seamlessly connects the kitchen, dining, and living areas, ideal for gatherings or quiet moments by the pellet

Nick Sicard EXP Realty

54 Twitchell Settlement, Rochester, VT 05767
/54
$525,000
- 3 Beds
- 2 Baths
- 2,246 Sq Ft
9 Deeplawn Ct, Ludlow, VT 05149

Set on a knoll overlooking the elementary school and view beyond, this three bedroom, two bath contemporary cape is within 5 min. of Okemo and features a sleek, renovated kitchen with quartz counters and upgraded appliances. A large, light-filled living/dining area perfect for entertaining and a cozy tv room (which could function as a first floor bedroom) and full bath with updated vanity

Geralyn Donohue Engel & Völkers Okemo

9 Deeplawn Ct, Ludlow, VT 05149
/31
$66,000
- 1 Bed
- 2 Baths
- 775 Sq Ft
274/276 Qtr I Jackson Gore Inn, Ludlow, VT 05149

A wonderful 1 bedroom, 2 bath with optional lockout opportunity at Jackson Gore! Sleeping 8, it is located on the 2nd floor with valley views and close to the Round House Restaurant. Features include 2 queen beds, a queen sleep sofa, a queen wall bed, full kitchen, a jetted bath tub, a gas fireplace and a deck. All Jackson Gore amenities including Spring House fitness center, indoor and outdoor

Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

274/276 Qtr I Jackson Gore Inn, Ludlow, VT 05149
/48
$395,000
- 3 Beds
- 1 Bath
- 1,064 Sq Ft
125 W Hill Rd, Ludlow, VT 05149

125 West Hill Road, per google maps it's 2 minutes to the Okemo base .07 miles away. AND just a one minute walk to the West Hill Recreation Area. This throwback ranch home has been well cared for and loved by the original family who built the house. Pull into the two car garage and unload your gear into the breezeway that could be the ultimate mudroom/playroom. Step into the eat in kitchen

Frank Provance Diamond Realty

125 W Hill Rd, Ludlow, VT 05149
/43
$71,000
- 1 Bed
- 2 Baths
- 775 Sq Ft
456 QIV Jackson Gore Inn Unit 456 QIV, Ludlow, VT 05149

Jackson Gore 1 bedroom 2 bath condo 456 quarter IV on Okemo. This top-floor Jackson Gore Inn condo with incredible valley views is now available and it can easily sleep 6 guests with a king bedroom en suite, a queen sleeper sofa, and a queen Murphy bed. The kitchen has full-size stainless appliances and the living room is a great gathering space with a gas fireplace. Many amenities are just a

Kevin Barnes William Raveis Real Estate Vermont Properties

456 QIV Jackson Gore Inn Unit 456 QIV, Ludlow, VT 05149
/37
$529,500
- 4 Beds
- 2.5 Baths
- 2,200 Sq Ft
56 Main St, Ludlow, VT 05149

Great opportunity for all. The hard work of setting up an Airbnb has been done! Welcome to Bears Den!! This is a terrific location for those looking for convenience whether it be for a second home or investment property. Great location opposite Okemo Mountain School, Okemo shuttle stop. Walking or riding distance to shops, restaurants and the new Ludlow Area Sporting Trails located behind

Betty McEnaney Diamond Realty

56 Main St, Ludlow, VT 05149
/40
$795,000
- 6 Beds
- 3 Baths
- 3,325 Sq Ft
29-31 High St, Ludlow, VT 05149

Location, Location, Location! GENERATING $76,800.00 PER YEAR! In the heart of the village, on the coveted, much sought after, quiet High St. is this three family beautiful property. A short stroll to downtown Ludlow and all it has to offer. Two beautiful units in the main house with hardwood flooring, updated kitchens and both with 3 season sun porches. A cozy two bedroom apartment above the

Frank Provance Diamond Realty

29-31 High St, Ludlow, VT 05149
/35
$1,895,000
- 5 Beds
- 4.5 Baths
- 4,214 Sq Ft
10 College Hill Rd, Woodstock, VT 05091

10 College Hill is the perfect in-village residence, off the main road yet walk-to-everything. The original, historic residence was designed in 1916 by renowned architect John Russell Pope whose accomplishments include the Jefferson Memorial, and master plans for Dartmouth and Yale. It also enjoys modern additions and updates including a stunning first-level primary bedroom suite designed in

John Snyder Snyder Donegan Real Estate Group

10 College Hill Rd, Woodstock, VT 05091
/19
$359,000
- 4 Beds
- 3 Baths
- 2,144 Sq Ft
25 Independent Dr, Hartland, VT 05048

Affordable, Large multi family building on 6.36+/- acres currently being used as 3 units but has a 4th unit which will need to be finished and updated. This property has lots of space and many options for rental revenue. Add this property to your rental portfolio and rent all four units or Live on site in one unit and have the other three units help pay for your living expenses. This property is

Alex DeFelice The Clerkin Agency, P.C.

25 Independent Dr, Hartland, VT 05048
/20
$799,000
- 6 Beds
- 3.5 Baths
- 3,900 Sq Ft
35 Railroad Row Unit C3-2, Hartford, VT 05001

Here is a great opportunity to buy a co-living business in White River Junction, VT, that is a turn key operation. The living spaces are sunny and very bright with a large spacious kitchen and a cozy living room. There are 6 individual large studio-type rooms and 4 baths, one with a laundry area. A buyer could choose to live there and run the business or manage it from afar. Another option would

Linde McNamara LindeMac Real Estate

35 Railroad Row Unit C3-2, Hartford, VT 05001
/41
$299,000
- 4 Beds
- 1 Bath
- 1,554 Sq Ft
2 Pond St, Ludlow, VT 05149

This charming home, cherished by one family since the mid-1950s, presents a wonderful opportunity for renovation and personalization. This nine room home has 4 bedrooms, 1 bath, and an eat-in kitchen. The location is ideally situated within walking distance of Dorsey Park and Ludlow Village. Catch the shuttle bus to Okemo for a day of skiing or walk to the restaurants, grocery store and all the

Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

2 Pond St, Ludlow, VT 05149
/43
$1,950,000
- 5 Beds
- 3.5 Baths
- 3,502 Sq Ft
4945 South Rd, Woodstock, VT 05071

The John Arnold Cottle House is a landmark residence in the heart of South Woodstock, a rare blend of village convenience and country living. Built in 1811 by one of the area's earliest settlers, this stately Federal-style brick home has been thoughtfully restored to honor its historic charm while integrating modern comforts. Set on 2.7 acres, the property features 450 ft of frontage on Kedron

Story Jenks LandVest, Inc/Woodstock

4945 South Rd, Woodstock, VT 05071

Showing Results 161 - 200, Page 5 of 6

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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.