Windsor, VT Homes

/26
$489,500 Pending
- 2 Beds
- 1.5 Baths
- 930 Sq Ft
11A Prospect St, Woodstock, VT 05091

Walk to everything Woodstock village has to offer from this sunny condo! Within an easy stroll of the Woodstock Inn, downtown restaurants, farmer's markets, and the Marsh Billings Rockefeller National Park, 11A Prospect is ideal for enjoying the charms of village living. Elevated above the Route 4 on a bucolic neighborhood side street, this well-kept home offers historic details with modern

Keri Cole Williamson Group Sothebys Intl. Realty

11A Prospect St, Woodstock, VT 05091
/18
$70,000 Sold Nov 01, 2024
- 1,124 Sq Ft
- $62/SF
- 141 Days On Market
- 2 Beds
- 2 Baths
- Built 1977
257 Riverbend Way, Woodstock, VT 05091

A wonderful opportunity in the amazing community of Woodstock, Vermont. Only 10 minutes to the charming Woodstock village is this Spacious 2-Bedroom Mobile Home located in Riverside MHP. This home offers an abundance of space and desirable features, making it an ideal retreat for those seeking comfort, convenience, and outdoor adventure. Two Bedrooms, Two Full Bathrooms With bedrooms located at

Heather Ashline BHHS Verani Upper Valley

257 Riverbend Way, Woodstock, VT 05091

/30
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,640 Sq Ft
157 Brownsville Rd, Windsor, VT 05089

157 Brownsville Rd, Windsor, VT 05089

/55
$1,095,000 Pending
- 4 Beds
- 3.5 Baths
- 2,710 Sq Ft
2 Maple St, Woodstock, VT 05091

Located in the Heart of Woodstock Village- fantastic location at the foot of the Mtn Peg trail system with easy access to Vail field and all of towns amenities. This beautifully renovated home is completely new. Handsome farmhouse vernacular style home with traditional slate floors, sliding barn doors and wood floors throughout first floor with an open concept for entertaining and all new

Gretchjen Smith Williamson Group Sothebys Intl. Realty

2 Maple St, Woodstock, VT 05091
/33
$975,000 Sold Oct 29, 2024
- 2,988 Sq Ft
- $326/SF
- 6 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2003
5434 Rush Meadow Rd, West Windsor, VT 05089

5434 RUSH MEADOW- Lovely reproduction Cape in prime Rush Meadow neighborhood. This is a wonderful, peaceful setting- a perfect balance of bright sunshine, pasture, and wooded landscape. The house is immaculate and well designed with an open floor plan and historic touches throughout. The first floor master suite is spacious with a private deck. There are two large bedrooms on the second floor, a

David Donegan Snyder Donegan Real Estate Group

5434 Rush Meadow Rd, West Windsor, VT 05089

/27
Est $429,109 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,355 Sq Ft
125 Brownsville Rd, Hartland, VT 05048

125 Brownsville Rd, Hartland, VT 05048

/44
$1,800,000 Pending
- 3 Beds
- 2.5 Baths
- 2,423 Sq Ft
2090 Randall Rd, Woodstock, VT 05091

Constructed in 2007 with a nod to the Gothic Style Vermont Farmhouse vernacular, this beautifully composed country home creatively integrates curated period detail with modern conveniences and systems. Conveniently located at the end of a picturesque tree lined dirt road just minutes from the Villages of both Woodstock and South Woodstock offering privacy and tranquility. The interior spaces of

Danny Kogut Williamson Group Sothebys Intl. Realty

2090 Randall Rd, Woodstock, VT 05091
/25
$380,000 Sold Oct 25, 2024
- 1,140 Sq Ft
- $333/SF
- 8 Days On Market
- 3 Beds
- 1 Bath
- Built 1970
46 Yodel Valley Rd, West Windsor, VT 05089

Please join us for an OPEN HOUSE Saturday, September 14th 10 AM - 12 PM! Nestled at the end of a private road amidst the tranquil woods, this charming chalet-style home offers a serene escape on 3 acres and just moments from Ascutney Mountain. Whether you seek a private getaway, year round living, or an investment opportunity (the current owners proving a successful and conservative AirBnB income

Tyler Hall BHHS Verani Upper Valley

46 Yodel Valley Rd, West Windsor, VT 05089

/38
Est $1,493,397 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,350 Sq Ft
2876 Hartland Hill Rd, Woodstock, VT 05091

2876 Hartland Hill Rd, Woodstock, VT 05091

/40
$695,000 Pending
- 4 Beds
- 3 Baths
- 3,584 Sq Ft
3914 South Rd, Woodstock, VT 05091

This South Woodstock contemporary residence was designed by the original architect-owner to showcase Vermont’s changing seasons and capture views of the Kedron Brook as it wanders through the property past small meadows tucked in along the banks. The home can be accessed privately at grade level through the heated garage and mudroom, while guests enter via a covered entry to the upper level.

Laird Bradley Williamson Group Sothebys Intl. Realty

3914 South Rd, Woodstock, VT 05091
/2
$650,000 Sold Oct 22, 2024
- 2,016 Sq Ft
- $322/SF
- 69 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1980
157 Deer Ridge Way, Woodstock, VT 05091

Welcome to this beautifully renovated 3-bedroom, 2.5 bathroom home situated on a private road just minutes from the Woodstock Village. This property has undergone extensive remodeling to provide modern comfort and style. The primary suite is featured with a heat pump for heating and cooling, a tastefully tiled bathroom with a heated floor, a walk-in closet, as well as a laundry room. The living

Andrew Kimbell Hall Collins Real Estate Group

157 Deer Ridge Way, Woodstock, VT 05091

/39
Est $1,724,417 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 4,216 Sq Ft
343 Spruce Way, Woodstock, VT 05091

343 Spruce Way, Woodstock, VT 05091

/40
$1,875,000 Pending
- 10 Beds
- 12 Baths
- 7,769 Sq Ft
2709 W Woodstock Rd, Woodstock, VT 05091

INVESTMENT, MULTI-GENERATIONAL, MULTI FAMILY AND COMMERCIAL OPPORTUNITY .. priced below appraised value on land and buildings providing instant equity. Experience the charm of Woodstock, VT with its quaint Main Street and enjoy the proximity to Killington Resort, just a short drive away. This exceptional property offers a unique blend of natural beauty and year-round recreational opportunities,

Susan Bishop Four Seasons Sotheby's Int'l Realty

2709 W Woodstock Rd, Woodstock, VT 05091
/22
$131,000 Sold Oct 18, 2024
- 1,013 Sq Ft
- $129/SF
- 194 Days On Market
- 3 Beds
- 2 Baths
- Built 2023
7 Park View Way Unit 32, Woodstock, VT 05091

A wonderful opportunity for affordable living in the charming community of Woodstock Vermont. Need help with down payment Champlain Housing Trust may be able to help you, up to $30,000 in deferred loan program for qualified buyers. Home is on site after a long rainy summer ready for the new owner. 2023 Single Wide Mobile home 3 bedrooms 2 bath. Buyers application for Park approval under

Jenna Luce RE/MAX Upper Valley

7 Park View Way Unit 32, Woodstock, VT 05091

/40
Est $452,447 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,574 Sq Ft
1880 South Rd, Woodstock, VT 05091

1880 South Rd, Woodstock, VT 05091

/40
$1,875,000 Pending
- 10 Beds
- 11 Baths
- 7,769 Sq Ft
2709 W Woodstock Rd, Woodstock, VT 05091

INVESTMENT, MULTI-GENERATIONAL, MULTI FAMILY AND COMMERCIAL OPPORTUNITY .. priced below appraised value on land and buildings providing instant equity. Experience the charm of Woodstock, VT with its quaint Main Street and enjoy the proximity to Killington Resort, just a short drive away. This exceptional property offers a unique blend of natural beauty and year-round recreational opportunities,

Susan Bishop Four Seasons Sotheby's Int'l Realty

2709 W Woodstock Rd, Woodstock, VT 05091
/12
$475,000 Sold Oct 17, 2024
- Land
- 4.17 Acres
- $113,909 per Acre
- 64 Days On Market
0 Rose Hill Rd, Woodstock, VT 05091

Secluded and desirable. This parcel boasts privacy despite its unrivaled distance to the happenings of downtown Woodstock, Vermont and even closer proximity to Woodstock's Recreation Center. Break ground into the life you've always dreamed of. Piping has been brought in for town sewer and additional piping is ready for underground electricity to be installed. This 4.17 acre lot provides ample

Taylor Medeiros-Batey KW Coastal and Lakes & Mountains Realty/Hanover

0 Rose Hill Rd, Woodstock, VT 05091

/33
Est $625,274 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,654 Sq Ft
4165 Hartland Hill Rd, Woodstock, VT 05091

4165 Hartland Hill Rd, Woodstock, VT 05091

/40
$1,650,000 Under Contract
- 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
/40
$725,000 Sold Oct 15, 2024
- 1,296 Sq Ft
- $559/SF
- 101 Days On Market
- 3 Beds
- 2 Baths
- Built 1989
64 Fowler Rd Unit Q104, Ludlow, VT 05149

Winterplace on Okemo Mountain! Nestled in the heart of winter wonder, Winterplace Q104 presents an enticing opportunity for mountain living at its finest. This meticulously maintained three-bedroom, two-bathroom condo is your key to slope-side serenity. Step into spacious comfort as the open kitchen seamlessly flows into the inviting living room, offering ample space for gatherings and

Joseph Karl William Raveis Real Estate Vermont Properties

64 Fowler Rd Unit Q104, Ludlow, VT 05149

/26
Est $1,538,757 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 3,043 Sq Ft
76 Grove Hill Rd, Woodstock, VT 05091

76 Grove Hill Rd, Woodstock, VT 05091

/43
$495,000 Under Contract
- 3 Beds
- 2 Baths
- 2,616 Sq Ft
371 Vermont 12, Hartland, VT 05048

- Gingerbread Cottage on 12 Acres Near Woodstock & Quechee - Gingerbread Cottage on 12 Acres Near Woodstock & Quechee – Lovingly maintained by its current owner, this 3-bedroom, 2-bath home sits on 12 private acres of open land, woods, and trails. With over 2,500 sq. ft., the home blends character and comfort - featuring wide pine floors, vintage custom cabinetry, and a living room with

Keri Cole Williamson Group Sothebys Intl. Realty

371 Vermont 12, Hartland, VT 05048
/35
$595,000 Sold Oct 11, 2024
- 1,146 Sq Ft
- $519/SF
- 38 Days On Market
- 2 Beds
- 1 Bath
- Built 1950
93 Blackbriar Rd, Woodstock, VT 05091

Privately sited on 1.90 landscaped and wooded acres in downtown Woodstock, this newly renovated mid-century Bungalow offers the perfect combination of original charm, modern amenities, and locational convenience. Renovations were extensive and include new kitchen cabinets, countertops, appliances, and fixtures, bathroom tile shower enclosure, hearthstone for the wood-burning fireplace, and

David Donegan Snyder Donegan Real Estate Group

93 Blackbriar Rd, Woodstock, VT 05091

/37
Est $480,958 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,919 Sq Ft
3328 Brownsville Hartland Rd, West Windsor, VT 05089

3328 Brownsville Hartland Rd, West Windsor, VT 05089

/33
$768,500 Under Contract
- 3 Beds
- 3 Baths
- 2,552 Sq Ft
3 Hathorn Hill St Unit 3, Woodstock, VT 05091

Rare opportunity to own in Hathorn Hill Condos. Private, quiet with lovely fern grove and stonewalls with views to the East. This unit has an de-attached 2 bay garage with easy access to extra parking. Upper level consist of an open floor plan, abundance of natural light with slider doors across the front for nice views off balcony. Living room anchored by a handsome wood burning fireplace

Gretchjen Smith Williamson Group Sothebys Intl. Realty

3 Hathorn Hill St Unit 3, Woodstock, VT 05091
/37
$2,350,000 Sold Oct 11, 2024
- 3,925 Sq Ft
- $599/SF
- 70 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1910
182 Rose Hill Rd, Woodstock, VT 05091

This historic home was built in 1904 by John Cotton Dana for his family around 1904. The Danas were a prominent family in Woodstock . The Dana House , home of the Woodstock Historical Society, is a major landmark in Woodstock. The house has recently undergone a comprehensive renovation. The large open rooms ,enveloped with light and lovely views , create a sophisticated yet cozy setting. The

Carol Wood Williamson Group Sothebys Intl. Realty

182 Rose Hill Rd, Woodstock, VT 05091

/40
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 3,135 Sq Ft
418 Fletcher Hill Rd, South Woodstock, VT 05071

418 Fletcher Hill Rd, South Woodstock, VT 05071

/34
$2,199,000 Under Contract
- 4 Beds
- 3.5 Baths
- 2,934 Sq Ft
15 Hathorn Hill Street Extension, Woodstock, VT 05091

An incredibly rare combination of in-Village and country living. 4+ acres and privacy with a pond and heated in-ground pool, yet walk-to-the Green. The residence, designed and built by the well-respected design-build firm Ambrose Construction, offers modern amenities, appliances and construction with a “Vermont Farmhouse” aesthetic. The vaulted ceiling timber frame great-gathering room has

John Snyder Snyder Donegan Real Estate Group

15 Hathorn Hill Street Extension, Woodstock, VT 05091
/40
$410,000 Sold Oct 11, 2024
- 2,030 Sq Ft
- $202/SF
- 94 Days On Market
- 3 Beds
- 2 Baths
- Built 1965
148 E Hill Rd Unit A, South Woodstock, VT 05071

A rare opportunity to own an iconic, contemporary condo in the heart of South Woodstock's bucolic horse country. Less than a mile from the Kedron Valley Inn and Ransom Tavern and just six miles from Woodstock village, this extraordinary four-floor, light-filled, open-concept condo has been updated with thoughtful, longterm investments, including roofs and windows. Surrounded by pristine

Keri Cole Williamson Group Sothebys Intl. Realty

148 E Hill Rd Unit A, South Woodstock, VT 05071

/37
Est $3,158,662 Not Listed For Sale
- 6 Beds
- 6.5 Baths
- 4,700 Sq Ft
592 Quinn Rd, Woodstock, VT 05091

592 Quinn Rd, Woodstock, VT 05091

/39
$775,000 Under Contract
- 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
/40
$2,000,000 Sold Oct 07, 2024
- 2,411 Sq Ft
- $830/SF
- 35 Days On Market
- 3 Beds
- 2 Baths
- Built 2009
1106 Church Hill Rd, Woodstock, VT 05091

Travel a mile south of Woodstock Village on Church Hill Road and you’ll discover a rural refuge that combines seclusion with proximity to village life. Two dwellings, a modern home and a separate cottage sheltered by woodland are discreetly sited overlooking a sparkling two-acre spring-fed pond. Each residence offers three bedrooms and two baths with open floor plans and single level living. The

Laird Bradley Williamson Group Sothebys Intl. Realty

1106 Church Hill Rd, Woodstock, VT 05091

/39
Est $877,334 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,460 Sq Ft
46 Stewart Ln Unit P305, Ludlow, VT 05149

46 Stewart Ln Unit P305, Ludlow, VT 05149

/39
$649,000 Under Contract
- 3 Beds
- 2.5 Baths
- 1,958 Sq Ft
5851 South Rd, Woodstock, VT 05071

This charming home is an amazing opportunity to own a piece of history in the lovely village of South Woodstock , Vermont. Starting its life as the garage and home of Clyde Wood it has evolved over time with the present owners into a beautiful , meticulous residence. Much attention to detail can be found in every room from wide pine flooring to cathedral ceiling in the great room. The home is

Carol Wood Williamson Group Sothebys Intl. Realty

5851 South Rd, Woodstock, VT 05071
/37
$935,000 Sold Sep 27, 2024
- 1,800 Sq Ft
- $519/SF
- 14 Days On Market
- 3 Beds
- 2 Baths
- Built 1900
13 High St, Woodstock, VT 05091

Prime Woodstock Village Location. Fabulous spot. Walk to everything in town from this absolutely adorable, renovated 3 bedroom/ 2 full bath home. Formally the town Blacksmith shop. This charming property has an open concept floor plan ideal for entertaining. Beautiful wood floors and loads of light throughout. Spacious smooth fenced in yard with frontage on the Kedron Brook. Sit on the deck and

Marni Rieger KW Vermont-Killington

13 High St, Woodstock, VT 05091

/40
Est $887,987 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,324 Sq Ft
917 Carlton Hill Rd, Woodstock, VT 05091

917 Carlton Hill Rd, Woodstock, VT 05091

/39
$1,499,000 Under Contract
- Land
- 4.57 Acres
- $328,009 per Acre
458 Woodstock Rd, Wood Stock, VT 05091

It has been said that the highest and best use of this landmark Woodstock property would be a combination of constructing multiple residential units, in the private rear acreage, and commercial development, of the highly visible Route 4 road frontage. There is no question of the unlimited potential! Highly visible! Well located, on the East End entrance route to Woodstock Village! This property

John Wetmore Wetmore Real Estate

458 Woodstock Rd, Wood Stock, VT 05091
/28
$835,000 Sold Sep 06, 2024
- 3,394 Sq Ft
- $246/SF
- 37 Days On Market
- 6 Beds
- 3 Baths
- Built 1971
86 Willow Brook Rd, Woodstock, VT 05091

This classic expanded Cape Style Home is located on a quiet dirt road within walking distance to The Village Green, and just steps to King Farm and the Mt Tom Trail system. Plenty of room to sprawl about in the generous common spaces. The living room has oversized windows and anchored by a brick fireplace flanked by built in book shelves with a propane stove insert. The dining room has a wood

Danny Kogut Williamson Group Sothebys Intl. Realty

86 Willow Brook Rd, Woodstock, VT 05091

/38
Est $1,181,000 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,492 Sq Ft
506 Westerdale Rd, Woodstock, VT 05091

506 Westerdale Rd, Woodstock, VT 05091

/40
$358,000 Sold Sep 03, 2024
- 1,728 Sq Ft
- $207/SF
- 43 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1982
21 Townhouse Way, Woodstock, VT 05091

The location and setting for this spacious brick home makes it one of the most desirable neighborhoods in Woodstock. The setting is private surrounded by woods and open, landscaped gardens. An easy drive to the Woodstock Green and walkable to the Woodstock Middle and High Schools as well as the Union Arena. The eat in kitchen leads out to a lovely deck that offers a private setting for outdoor

Carol Wood Williamson Group Sothebys Intl. Realty

21 Townhouse Way, Woodstock, VT 05091

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