Windsor County VT Homes for Sale with View

/41
$344,900
- 3 Beds
- 2 Baths
- 1,798 Sq Ft
109 High St, Cavendish, VT 05142

Discover the perfect blend of small-town charm and four-season adventure in the heart of Cavendish. Perched on a sunny corner lot with views of Hawks Mountain, this classic Vermont home offers easy access to everything from skiing at Okemo to hiking, biking, and swimming nearby. Step inside through the thoughtfully planned mudroom and enter a warm, updated eat-in kitchen—complete with

Dana Haley Diamond Realty

109 High St, Cavendish, VT 05142
/60
$495,000
- 6 Beds
- 1 Bath
- 2,308 Sq Ft
525 Route 103 N, Chester, VT 05143

The possibilities are endless with this beautiful property that has been in the same family since 1964! You will not find a nicer piece of Vermont land than this, with approx. 34 acres of open pastureland bordered by hundreds of feet of the Williams River. This stream offers some great summertime activities such as swimming and fishing! The house and attached barns can be a showplace with some

Glenn Olney Barrett and Valley Associates Inc.

525 Route 103 N, Chester, VT 05143
/56
$599,999
- 5 Beds
- 3.5 Baths
- 2,443 Sq Ft
1057 Quarry Rd, Chester, VT 05143

Chester Haven on a Quiet Dead-End Road. Tucked away in a serene neighborhood, this spacious 5-bedroom, 4-bath home offers over 3,400 sq ft of beautifully designed living space—perfect for both everyday comfort and grand entertaining. Located on a peaceful dead-end street, yet just minutes from the charm and convenience of Main Street, this property offers the best of both worlds. Inside,

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

1057 Quarry Rd, Chester, VT 05143
/7
$35,000
- Land
- 1.71 Acres
- $20,468 per Acre
2-49 E Ash Rd, Plymouth, VT 05056

Looking for an ideal piece of land to build your forever home? If so, don't miss out on this stunning 1.71 acres of land with mountain views! Located on a quiet road this peaceful property offers tons of privacy and views of the VT mountains and the beautiful forestry all around you. Just a short drive off of the main road VT route 100 that takes you easily to all the surrounding attractions and

Daniel Preston KW Vermont Woodstock

2-49 E Ash Rd, Plymouth, VT 05056
/39
$635,000
- 3 Beds
- 2.5 Baths
- 1,452 Sq Ft
3361 County Rd, Windsor, VT 05089

Enjoy privacy and lovely views from this well executed contemporary home overlooking copious gardens and mature plantings to a spectacular pond with an arched footbridge (spotlights highlight the bridge after dark) to access your own little island. Beautiful updates throughout the home include new maintenance-free manufactured cedar-tone shingles on the entire house and workshop shed. The kitchen

Danny Kogut Williamson Group Sothebys Intl. Realty

3361 County Rd, Windsor, VT 05089
/51
$425,000
- 4 Beds
- 3 Baths
- 2,220 Sq Ft
74 Dutton District Rd, Springfield, VT 05156

Located on a quiet country road just outside Springfield, this 4 bedroom home has room for you to move right in. Located just off interstate 91, it offers easy access to White River Junction and the rest of the Upper Valley including Dartmouth College and the Dartmouth Hitchcock Medical Center. Springfield itself offers multiple options for dining and food shopping. The main floors of the

John Tolosky Barrett and Valley Associates Inc.

74 Dutton District Rd, Springfield, VT 05156
/51
$450,000
- Land
- 264 Acres
- $1,708 per Acre
0 Peavine Blvd Unit 5046570, Bethel, VT 05032

First time being offered, a 263-acre parcel of wooded and open land, with local and long-distance views. The topography is level too steep with new and old logging trails that crisscross the property. Multiple house sites have been identified from the recent logging, along with destination locations to admire the views and tranquility that nature offers. For the wildlife enthusiast or hunter,

Terry Davis Williamson Group Sothebys Intl. Realty

0 Peavine Blvd Unit 5046570, Bethel, VT 05032
/25
$207,000
- 3 Beds
- 3 Baths
- 1,604 Sq Ft
295 Hotel Rd Unit 10/10A, Brownsville, VT 05037

This spacious walk-up condominium features 3 bedrooms and 3 full baths, with an inviting open-concept living and dining area anchored by a cozy fireplace. Step out onto your private deck overlooking the tubing hill and take in all the action just outside your door!This vibrant community offers an unbeatable lifestyle with access to approximately 1,300 acres of outdoor fun, including

Allison Griep KW Vermont Woodstock

295 Hotel Rd Unit 10/10A, Brownsville, VT 05037
/60
$198,500
- 3 Beds
- 3 Baths
- 1,670 Sq Ft
342 Jackson Gore Rd Unit 342/344 Q1, Ludlow, VT 05149

Experience true slopeside living for a fraction of the cost with this quarter-share at Jackson Gore on Okemo—Unit 342/344 QIV. This spacious 3-bedroom, 3-bathroom condo sleeps up to 12 and features a lock-out design, allowing you to use one side and rent the other, use both, or rent both for maximum flexibility and income potential. Highlights include a fully equipped kitchen, two fireplaces,

Sarah Sheehan William Raveis Real Estate Vermont Properties

342 Jackson Gore Rd Unit 342/344 Q1, Ludlow, VT 05149
/60
$1,250,000
- 5 Beds
- 3.5 Baths
- 2,649 Sq Ft
331 Vermont Route 100, Plymouth, VT 05149

Experience the blend of lakeside tranquility and ski country convenience at Echo View Farm—an exquisitely restored Vermont farmhouse set on 6.7 picture-perfect acres overlooking Echo Lake. Every detail of this five-bedroom, three-and-a-half-bath retreat has been thoughtfully curated to deliver timeless elegance with modern comfort. Step into the heart of the home where a chef’s kitchen, complete

Kevin Barnes William Raveis Real Estate Vermont Properties

331 Vermont Route 100, Plymouth, VT 05149
/52
$798,500
- 3 Beds
- 2 Baths
- 1,573 Sq Ft
6 Ledgewood Rd Unit A-5 w/ A-1 Garage, Ludlow, VT 05149

Ledgewood on Okemo Mountain, discover the allure of Ledgewood where slopeside living becomes a reality. These highly sought-after condominiums, known for their quality craftsmanship featuring masonry fireplaces, solid wood doors, and convenient garages, offer an exceptional opportunity. This particular floor plan boasts generous space perfect for accommodating everyone. Imagine cozy evenings by

Katherine Burns William Raveis Real Estate Vermont Properties

6 Ledgewood Rd Unit A-5 w/ A-1 Garage, Ludlow, VT 05149
/46
$730,000
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
28 Fowler Rd Unit N203, Ludlow, VT 05149

Winterplace at Okemo, discover the perfect blend of mountain luxury and year-round adventure. Winterplace N203 is a beautifully renovated three-bedroom, two-bathroom residence nestled in one of the most desirable locations at Okemo Mountain Resort. This ski-in, ski-out home offers a spacious and stylish interior, thoughtfully designed for comfort after a day on the slopes. Step into the warm,

Katherine Burns William Raveis Real Estate Vermont Properties

28 Fowler Rd Unit N203, Ludlow, VT 05149
/27
$1,295,000
- Land
- 9 Acres
- $143,729 per Acre
0 Newton Ln Unit 5045705, Norwich, VT 05055

110 Acres of Pastoral Beauty with Mountain Views in Hartford and Norwich, Vermont.This rare 110-acre parcel, 101 acres in Hartford and nine in Norwich (see separate MLS listing 5045699), offers rolling meadows, mature hardwoods, and long mountain views in the heart of the Upper Valley. The elevated, west-facing setting is filled with natural light and classic Vermont charm, with open

Karen DeMas Four Seasons Sotheby's Int'l Realty

0 Newton Ln Unit 5045705, Norwich, VT 05055
/27
$1,295,000
- Land
- 101 Acres
- $12,822 per Acre
0 Newton Ln, Hartford, VT 05001

110 Acres of Pastoral Beauty with Mountain Views in Hartford and Norwich, Vermont.This rare 110-acre parcel, 101 acres in Hartford and nine in Norwich (see separate MLS listing #5045705), offers rolling meadows, mature hardwoods, and long mountain views in the heart of the Upper Valley. The elevated, west-facing setting is filled with natural light and classic Vermont charm, with open

Karen DeMas Four Seasons Sotheby's Int'l Realty

0 Newton Ln, Hartford, VT 05001
/54
$1,395,000
- 2 Beds
- 2.5 Baths
- 2,112 Sq Ft
683 Reservoir Rd, White River Junction, VT 05001

Welcome home to pure perfection, privacy, and magic. This serene setting, with lush gardens and a rolling lawn, boasts a unique twist on a timber frame design, providing modern amenities and comfortable spaces throughout. A beautifully appointed, main floor primary en-suite offers a spacious bathroom with a tiled shower and large soaking tub, plus a large walk-in closet and laundry. The rest of

Zoe Hathorn Washburn Snyder Donegan Real Estate Group

683 Reservoir Rd, White River Junction, VT 05001
/16
$149,500
- Land
- 17 Acres
- $8,846 per Acre
00 Day Rd, Sharon, VT 05065

A wonderful opportunity to build in the quaint town of Sharon, VT. This unique acreage consists of a smaller open meadow that feeds into a picturesque and private roughed in logging road wrapping around a larger thinned out wooded area - offering a variety of potential locations to build your dream home. Potential for lovely views. The location is off a private dead-end road with I-89 only a few

Zoe Hathorn Washburn Snyder Donegan Real Estate Group

00 Day Rd, Sharon, VT 05065
/37
$845,000
- 2 Beds
- 1.5 Baths
- 1,714 Sq Ft
403 Horse Shoe Way, Woodstock, VT 05071

Totally secluded on a rolling hillside, just 10 minutes from the Woodstock Village Green, this storybook Post and Beam cottage awaits your vision. From the reclaimed centuries old barn frame to the massive fieldstone fireplace, every detail is well thought, and impeccably executed honoring the Vermont tradition of reclaiming and utilizing locally sourced materials.The home was carefully, and

Danny Kogut Williamson Group Sothebys Intl. Realty

403 Horse Shoe Way, Woodstock, VT 05071
/35
$665,000
- 3 Beds
- 2 Baths
- 1,908 Sq Ft
530 West Rd, Barnard, VT 05031

Conveniently located less than a mile from Barnard General Store and Silver Lake, this charming 3 bedroom cape sits on just over 3 acres of land with tiered stone walls and green lawn circling the house. Mature trees surround the yard and there is view potential with minor clearing and thinning. The full length back deck offers private outdoor space including a covered grilling area just steps

Dan Noble Snyder Donegan Real Estate Group

530 West Rd, Barnard, VT 05031
/27
$1,200,000
- 5 Beds
- 4.5 Baths
- 2,686 Sq Ft
19 Church St Unit EX, Woodstock, VT 05091

Bright and spacious five bedroom, five bath in-village residence with Ottauquechee River frontage and less than 1-minute walk to the Woodstock Green. 2-car attached garage enters into the kitchen via a mud-laundry room. Eat-in kitchen with stainless appliances, granite countertops and a large sunny bay window leads to the formal dining room, and also opens to the patio, perfect for entertaining

John Snyder Snyder Donegan Real Estate Group

19 Church St Unit EX, Woodstock, VT 05091
/15
$129,000
- Land
- 3.24 Acres
- $39,815 per Acre
Lot 3 Mattson Rd, Chester, VT 05143

Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn—ideal for storage, hobbies, or future expansion.As you move toward the back of the property, the land gently slopes up to a wooded hillside that levels out

Jessica Citera Cummings & Co

Lot 3 Mattson Rd, Chester, VT 05143
/24
$750,000
- 2 Beds
- 1 Bath
- 679 Sq Ft
38 Northshore Dr, Ludlow, VT 05149

Same family owned for several decades and now it's time for another family to see the benefits of lakeside living. This cottage is located on private Northshore Drive on beautiful Lake Rescue. Use as-is for summer fun, then plan your future new build or winterize this home. Expand the existing footprint to suit your family's needs. The waterfront gazebo and storage building is your access to

Katherine Burns William Raveis Real Estate Vermont Properties

38 Northshore Dr, Ludlow, VT 05149
/55
$2,950,000
- 4 Beds
- 4.5 Baths
- 6,548 Sq Ft
657 Town Farm Rd, Ludlow, VT 05149

61 Acre estate with sweeping views and open fields in Ludlow's prestigious South Hill area. Less than 10 minutes to the Okemo ski area and the Ludlow village amenities, this luxury home has received numerous updates in the last several years.Large updated eat-in country kitchen w/ wood cabinetry, stone countertops and updated stainless steel appliances. A gas fireplace with sitting room

Andre Menard Mary W. Davis Realtor & Assoc., Inc.

657 Town Farm Rd, Ludlow, VT 05149
/40
$349,000
- 4 Beds
- 1.5 Baths
- 1,792 Sq Ft
94 Perley Farm Rd, South Royalton, VT 05068

Step into a unique piece of Vermont history with this beautifully converted brick schoolhouse, now a warm and inviting 4-bedroom, 1.5-bath home. Perfectly blending classic charm with modern comforts, this one-of-a-kind property offers character, space, and serenity in a picturesque setting.From the moment you arrive, the handsome brick exterior and original architectural details set the

Holly Hall Hall Collins Real Estate Group

94 Perley Farm Rd, South Royalton, VT 05068
/16
$399,000
- Land
- 13 Acres
- $29,776 per Acre
00 N Hill Pent Rd, Ludlow, VT 05149

Opportunity awaits with these two connected wooded building lots totaling 13.44 acres, offering easy access to the VAST snowmobile trail network. Located on a quiet, dead-end country road, this peaceful setting is ideal for those seeking a private getaway with four-season recreational opportunities right at your doorstep. Lot A is 4.67 acres and lot B is 8.77 acres. Both parcels include

Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

00 N Hill Pent Rd, Ludlow, VT 05149
/21
$15,000
- Land
- 1.05 Acres
- $14,286 per Acre
0 Vermont Route 100, Plymouth, VT 05056

Discover one of the most affordable ways to get into the Hawk Mountain Resort community. This parcel is located off scenic byway Route 100 and is only minutes to Okemo or Killington. There are 4 lakes all within a few minutes as well. Plenty of hiking, biking, boating, and fishing in the area. All plans and permits must be approved by the Hawk Architectural Review Board. No trailers, yurts, RV's

Kevin Barnes William Raveis Real Estate Vermont Properties

0 Vermont Route 100, Plymouth, VT 05056
/18
$50,000
- Land
- 2.07 Acres
- $24,155 per Acre
0 E Ash Rd, Plymouth, VT 05056

Welcome to Hawk East lot 2-20. This 2.07 acres lot is one of the closest lots to the Hawk Mountain Resort. There is a nice level area in the middle of the property that would make a nice building site. Easy access to Route 100 and only minutes to Okemo or Killington. There are 4 lakes all within a few minutes as well. Plenty of hiking, biking, boating, and fishing in the area. All plans and

Kevin Barnes William Raveis Real Estate Vermont Properties

0 E Ash Rd, Plymouth, VT 05056
/60
$1,597,000
- 6 Beds
- 5.5 Baths
- 4,225 Sq Ft
515 Shattuck Hill Rd Unit 515, 513 & 511, Reading, VT 05062

Nestled in the tranquil hills of West Windsor, Vermont, Rock Haven Estate is a remarkable 33.49-acre country sanctuary offering three separate luxury homes, set along a private drive & surrounded by nature’s beauty. Whether you're looking for a full-time residence with income-generating opportunities or a private family compound, Rock Haven Estate is a rare find! The Rock House - Hilltop Elegance

Kate Jarvis Williamson Group Sothebys Intl. Realty

515 Shattuck Hill Rd Unit 515, 513 & 511, Reading, VT 05062
/54
$1,690,000
- 5 Beds
- 4.5 Baths
- 4,617 Sq Ft
687 S Perry Rd, Woodstock, VT 05091

Privately sited on a knoll to capture sweeping North Westerly views, this expanded Classic Cape has been lovingly stewarded and tastefully updated over the years. Enter through the formal foyer with wainscot, or a convenient mudroom with powder room. Superior craftsmanship throughout featuring a beautifully appointed chef's kitchen with Viking range-top, wall ovens and best quality appliances,

Danny Kogut Williamson Group Sothebys Intl. Realty

687 S Perry Rd, Woodstock, VT 05091
/55
$2,695,000
- 5 Beds
- 4.5 Baths
- 3,090 Sq Ft
248 Gird Lot Rd, Weathersfield, VT 05151

This meticulously maintained five-bedroom, four-and-a-half-bath home offers sweeping views of the Connecticut River Valley and New Hampshire mountains. Thoughtfully designed for comfort and flexibility, the open-concept layout includes a main-level living option, hardwood floors, and tall ceilings with abundant and expansive windows that flood the home with natural light.The spacious

Karen DeMas Four Seasons Sotheby's Int'l Realty

248 Gird Lot Rd, Weathersfield, VT 05151
/57
$599,900
- 3 Beds
- 2.5 Baths
- 1,835 Sq Ft
2475 Little Hollow Rd, Rochester, VT 05767

Quintessential VT Mountain Location with privacy & seclusion galore! Surrounded by thousands of acres of locally owned timberland, many abundant recreational opportunities to Mount Cushman and the magnificent Little Hollow recreational area. Absolutely Gorgeous 3 bedroom, 3 bath Modified Cape on 7.1 acres of open and wooded land, that is located at the very end of a Class 3 town maintained road,

Paul H Rea Rural Vermont Real Estate

2475 Little Hollow Rd, Rochester, VT 05767
/34
$2,199,000
- 4 Beds
- 3.5 Baths
- 3,564 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
/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
/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
/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

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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.