Windsor County VT Homes for Sale

/60
$1,995,000
- 3 Beds
- 2.5 Baths
- 5,422 Sq Ft
2334 South Rd, Woodstock, VT 05091

Offered for the first time, the exclusive private residence of one of Woodstock's most notable and prolific builders, Hank Savelberg. Located just five minutes from the Woodstock Village Green, this whimsical, private, contemporary hillside estate was lovingly constructed featuring well thought, connected open spaces with expansive glass walls and dramatic sweeping wooden ceilings. The entire

Danny Kogut Williamson Group Sothebys Intl. Realty

2334 South Rd, Woodstock, VT 05091
/35
$729,000
- 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
/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
/44
$495,000
- 4 Beds
- 3 Baths
- 1,400 Sq Ft
934 E Ash Rd Unit 14, Plymouth, VT 05056

Charming Condominium Retreat!Welcome to your dream retreat nestled amid breathtaking natural beauty! This stunning condominium offers an unparalleled blend of modern comfort and serene surroundings, making it the perfect sanctuary for those seeking both relaxation and adventure.Step inside and be greeted by an updated kitchen, complete with stylish fixtures and ample space for

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

934 E Ash Rd Unit 14, Plymouth, VT 05056
/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
/58
$635,000
- 3 Beds
- 3.5 Baths
- 2,203 Sq Ft
44 Freeman Rd Unit B2, Cavendish, VT 05153

The Castle Hill Resort & Spa is an award winning destination located just minutes from Okemo Mountain Resort. This ground floor 3br +loft & den features 3.5 baths. This townhouse condo has floor to ceiling windows that provide natural light throughout. The open living room, dining room, and kitchen offer an inviting atmosphere for gatherings. The ground floor patio offers outdoor seating and has

Joseph Karl William Raveis Real Estate Vermont Properties

44 Freeman Rd Unit B2, Cavendish, VT 05153
/45
$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
/35
$199,000
- 3 Beds
- 1 Bath
- 1,322 Sq Ft
841 Farrar Rd, Chester, VT 05143

Looking for an opportunity in an ideal location? This property offers unbeatable potential in the sought-after town of Chester. Located on a quiet country road, but still just a couple miles from downtown shopping and dining you get the best of both worlds. This property offers both open and wooded acreage with fruit trees to enjoy! Featuring two generously sized garages, this home is ideal for

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

841 Farrar Rd, Chester, VT 05143
/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
/44
$3,495,000
- 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
/10
$385,000
- 6 Beds
- 4 Baths
- 2,949 Sq Ft
7 Commonwealth Ave, Ludlow, VT 05149

Bring your vision and unlock the potential! This property has been fully gutted and is ready for your transformation. With a new roof, windows and siding and decking on the porch, you're well on your way! Conveniently located in the Village Of Ludlow near skiing, golf, lakes for swimming, and village shopping, it’s the perfect opportunity for contractors, investors, or DIYers. With two separate

Frank Provance Diamond Realty

7 Commonwealth Ave, Ludlow, VT 05149
/11
$119,000
- Land
- 16 Acres
- $7,589 per Acre
00 E Hill Rd, Andover, VT 05143

Rooted in along scenic East Hill Road in the bucolic town of Andover, this 16-acre parcel offers a rare opportunity to create your own private haven in one of Southern Vermont’s most peaceful and charming settings. Just minutes from Ludlow and the slopes of Okemo Mountain, this location strikes the perfect balance between quiet countryside and convenient access to skiing, shopping, dining, and

Daire Gibney Barrett and Valley Associates Inc.

00 E Hill Rd, Andover, VT 05143
/20
$250,000
- Land
- 28 Acres
- $8,772 per Acre
00 Chapel Hill Rd, Sharon, VT 05065

Located on a class IV road, right after the end of the publicly maintained section of Chapel Hill Road, this 28.5 acre parcel has potential for a camp, off-grid home, or as a recreational getaway. The Seller has roughed in a driveway to a level spot about 600 feet from the town maintained road. Build here or clear at the top of the land for incredible views of Mt. Ascutney, Killington, and

Tami Sullivan Snyder Donegan Real Estate Group

00 Chapel Hill Rd, Sharon, VT 05065
/6
$299,000
- Land
- 116 Acres
- $2,573 per Acre
00 Grout Rd, Weathersfield, VT 05153

A large private parcel of land located in Cavendish on the Weathersfield line. This 116+- acres is a mix of woods and cleared areas that has beautiful mountain views that can be accessed from Grout road. There is road frontage on scenic vermont route 131 that can access the land with grading. These 2 lot have been surveyed and there are multiple possible building sites. This property is close

John Napier TPW Real Estate

00 Grout Rd, Weathersfield, VT 05153
/19
$695,000
- Land
- 61 Acres
- $11,474 per Acre
0 Noah Wood Rd, Woodstock, VT 05071

Incredible location! 60+ acres situated on the corner of South Rd. (106) and Noah Wood Rd. in beautiful South Woodstock. The land rises from the roads to the crest of the hilltop with amazing view potential looking to the Northeast. Multiple building sites can be found throughout the property which offers great recreational opportunities including direct access to the VAST trail on the lower

Dan Noble Snyder Donegan Real Estate Group

0 Noah Wood Rd, Woodstock, VT 05071
/52
$627,500
- 3 Beds
- 2.5 Baths
- 1,868 Sq Ft
2510 E Hill Rd, Chester, VT 05143

This home on East Hill Road commands one of the area's best views all the way to Stratton! It is one of those spots where the view is different every day & spectacular! The home sits on 14 acres & it overlooks land protected by the Vermont Land Trust and mountains beyond. From the moment you enter, you won't want to leave. It is immaculate and ready to go. A large mudroom with a slate floor &

Betty McEnaney Diamond Realty

2510 E Hill Rd, Chester, VT 05143
/31
$481,500
- 4 Beds
- 3 Baths
- 2,074 Sq Ft
111 Forest Ln, Rochester, VT 05767

Located in the sought after Great Hawk community of Rochester is this 4 bedroom, 3 bath home with updates that make maintaining this home easy on your checkbook. Solar array reduces power bill to minimum fee for 9 months out of the year. Heat pumps further reduce energy costs. This home could use some cosmetic updating as owner put home investment into the utility of the home, new roof and new

Patricia Harvey Xsell Realty LLC

111 Forest Ln, Rochester, VT 05767
/37
$699,000
- Land
- 52 Acres
- $13,365 per Acre
00 Granite Ledge, Pomfret, VT 05059

Pristine Pomfret land with view of Ascutney! Build your dream home on this unspoiled parcel in one of Pomfret's most beautifully preserved and scenic locales. Surrounded by large landholdings and conserved farmland, but only ten minutes from Woodstock and with excellent access to Route 4 and Quechee, this land comprises historic rock walls, mature hardwoods, a stream, and offers the potential for

Keri Cole Williamson Group Sothebys Intl. Realty

00 Granite Ledge, Pomfret, VT 05059
/15
$150,000
- Land
- 2.58 Acres
- $58,140 per Acre
0 Cedar Dr, Ludlow, VT 05149

Discover the perfect canvas for your dream home on this serene 2.5+/-acre lot, ideally located at the end of a cul-de-sac on Cedar Drive in Ludlow, VT. Nestled in a peaceful subdivision, this wooded parcel offers the privacy, natural beauty, and tranquility that define Vermont living. With power conveniently available at the street, this property is ready for your vision—whether that’s a mountain

Katherine Burns William Raveis Real Estate Vermont Properties

0 Cedar Dr, Ludlow, VT 05149
/48
$4,900,000
- 7 Beds
- 9 Baths
- 8,442 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
/56
$1,125,000
- 3 Beds
- 2.5 Baths
- 2,668 Sq Ft
32 Old Farm Rd, Norwich, VT 05055

Spring is in full bloom around this beautiful home in the desirable Old Farm neighborhood! With many spaces thoughtfully renovated in recent years by Riverlight Builders, this property features a stunning new kitchen with a center island with bar seating, Quartzite natural stone countertops, and high-end cabinetry, seamlessly open to the main floor living areas, making it ideal for entertaining

Evan Pierce Four Seasons Sotheby's Int'l Realty

32 Old Farm Rd, Norwich, VT 05055
/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
/3
$15,000
- Land
- 1.39 Acres
- $10,791 per Acre
00 Salt Ash Rd, Plymouth, VT 05056

Escape to Serenity: Your Dream Vacant Land Awaits!Welcome to a slice of paradise where nature’s beauty meets boundless potential! Nestled in an excellent location, this 1.39-acre vacant land is your blank canvas, ready to become the sanctuary you’ve always envisioned. Imagine waking up surrounded by the whispers of nature, with the promise of stunning potential views waiting just beyond

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

00 Salt Ash Rd, Plymouth, VT 05056
/59
$289,500
- 2 Beds
- 1 Bath
- 816 Sq Ft
1084 Rush Meadow Rd, West Windsor, VT 05037

Attractive two bedroom, 1 bath ranch style home on a serene 1.08-acre parcel nestled along scenic Rush Meadow Road in West Windsor. Right in the heart of Horse Country! The kitchen has upgraded cabinetry and there is overflow third bedroom space in the lower level that can be turned into home office or den usage. Bathroom was upgraded as well. Nothing to do! This gently sloping lot offers a

John Bassette Bassette Real Estate Group

1084 Rush Meadow Rd, West Windsor, VT 05037
/38
$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
$749,000
- 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
/5
$80,000
- Land
- 4.30 Acres
- $18,605 per Acre
00 N Hill Rd, Andover, VT 05143

The first step in building your Vermont Dream home is finding the perfect piece of land. Look no further! Situated on quiet country road of North Hill this parcel offers great building site, quiet location, easy access to skiing at Vail/Okemo resort (only minutes away), VAST access, close to Weston village with the Vermont Country Store and the Weston Playhouse. Soil tests were conducted years

Lisa Kelley Cummings & Co

00 N Hill Rd, Andover, VT 05143
/42
$345,000
- 3 Beds
- 2 Baths
- 1,492 Sq Ft
2903 Vermont 107, Stockbridge, VT 05772

Come take a look at this 3 bedroom, 1 3/4 bath, well cared for and tastefully updated "Country Charmer". This home has a little bit of everything for everyone. Sited on an amazing well-manicured level lot. There is an additional 2 bay garage w/ample workshop area, a sugar house, and a pony/animal run-in. The first floor has a primary bedroom, 3/4 bath and laundry. Enjoy the sunny, open flow from

Rose Wright Vermont Heritage Real Estate

2903 Vermont 107, Stockbridge, VT 05772
/35
$730,000
- 3 Beds
- 3.5 Baths
- 2,314 Sq Ft
3755 Quechee Main St Unit 11B, Quechee, VT 05059

Unique opportunity to own in the highly sought-after Coach Road condominium complex! This unit is within walking distance to the Quechee Club and all its amenities. Coach Road condos boast what many say is the best location in Quechee. Entering through the front door, you find a generous foyer with ample closet space. High ceilings and full-length windows shower this home with light. The kitchen,

Jennifer Kirkman KW Vermont Woodstock

3755 Quechee Main St Unit 11B, Quechee, VT 05059
/60
$699,000
- 5 Beds
- 4.5 Baths
- 3,507 Sq Ft
33 Acorn St, White River Junction, VT 05001

Located in a quiet, walkable neighborhood with gorgeous views, this home has it all! With 5 bedrooms and a partially finished basement, there are multiple flexible-use spaces for your office, playroom, or guest suite, including the option of a first floor bedroom. The second floor primary features an enormous walk-in closet, en-suite bathroom with shower and separate jetted tub, and spacious

Tami Sullivan Snyder Donegan Real Estate Group

33 Acorn St, White River Junction, VT 05001
/32
$199,999
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
35 Family Cir, Hartland, VT 05001

Brand New 3-Bedroom, 2-Bath Double-Wide Home in Hartland, VT – Move-In Ready! Discover the comfort and convenience of this beautifully designed home featuring an open-concept layout with a bright and spacious living area, complete with built-in storage. Modern Kitchen & Dining: Cook and entertain with ease in the stylish kitchen boasting a large center island and a generous walk-in corner pantry.

Jenna Luce RE/MAX Upper Valley

35 Family Cir, Hartland, VT 05001
/15
$835,000
- Land
- 150 Acres
- $5,567 per Acre
0 Walker Hill Rd, Bridgewater, VT 05091

150 acres of recreational paradise! Absolute and total privacy! Enjoy long views of mountain peaks showing criss crossed ski trails, pristine cascading streams with mesmerizing waterfalls over large rock outcroppings, mature woodland which hasn't been logged in over 50 years, a fully equipped camper trailer with propane fired generator for off grid living and even a 4 wheeler outfitted with

John Wetmore Wetmore Real Estate

0 Walker Hill Rd, Bridgewater, VT 05091
/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
/21
$290,000
- Land
- 30 Acres
- $9,555 per Acre
00 Chapel Hill Rd, Sharon, VT 05065

Located at the end of publicly maintained Chapel Hill Road, this lot consists of 20.85 acres in Sharon and 9.5 acres in Norwich. A woods road or future driveway leads to the height of land with unparalleled panoramic, southwesterly views of Mt. Ascutney, Killington, and beyond. There is no power on this section of Chapel Hill Rd., but the lot would be perfect for a solar home, camp, or just a

Tami Sullivan Snyder Donegan Real Estate Group

00 Chapel Hill Rd, Sharon, VT 05065
/46
$1,325,000
- 4 Beds
- 2 Baths
- 2,554 Sq Ft
325 Cemetery Rd, West Windsor, VT 05089

Farm at Gaelic Crossing is an equestrian property set on 26.72± acres, has dramatic views of Mount Ascutney and, after summer showers, the frequent and magical appearance of rainbows—often even double rainbows—across the wide, open sky.This updated c.1842 New England Cape offers 2,554 square feet of finished living space, including four bedrooms—two conveniently located on the first

Story Jenks LandVest, Inc/Woodstock

325 Cemetery Rd, West Windsor, VT 05089
/38
$690,000
- 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
/23
$110,000
- 3 Beds
- 2 Baths
- 1,144 Sq Ft
133 Willow Cir, White River Junction, VT 05001

An affordable 3-bedroom 2-bath double-wide home in one of the Upper Valley’s most sought-after parks, Tall Timbers. One Car garage, lots of storage and more. This home offers laminate flooring, spacious kitchen and laundry area. One of the best lots available with plenty of space, you’ll feel like you live on your own land. The surrounding homes are in great condition and with a little TLC

Richard Ballou RE/MAX Upper Valley

133 Willow Cir, White River Junction, VT 05001

Showing Results 281 - 320, Page 8 of 14

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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.