Windsor County VT Homes for Sale

/12
$39,000
- Land
- 1.58 Acres
- $24,684 per Acre
Lot 1-26 Madison Brook Ln, Stockbridge, VT 05772

Attractive building lot in the desirable Highwood community. This lot offers potential long range views and includes sewer rights in the Our World/Highwood community sewer system, sufficient for a three-bedroom residence. Architectural review and protective covenants ensure that the quality of life in this small community is always preserved. Adjacent to the Green Mountain Trail network for

Kyle Kershner Killington Pico Realty

Lot 1-26 Madison Brook Ln, Stockbridge, VT 05772
/28
$239,000
- 3 Beds
- 1,984 Sq Ft
18 Oak Chapel Rd, Bridgewater, VT 05035

Discover the potential of this unique fixer-upper property nestled on 0.64 acres, featuring not one, but two distinct buildings awaiting your vision.Step into the main 3-bedroom white house, a fixer-upper's dream filled with endless possibilities. The front porch offers a seasonal retreat with stunning Vermont mountain views - envision it transformed into a year-round haven with a few

Chelsea Bevis KW Vermont Woodstock

18 Oak Chapel Rd, Bridgewater, VT 05035
/40
$1,600,000
- 3 Beds
- 2 Baths
- 3,291 Sq Ft
265 Depot St, Proctorsville, VT 05153

Welcome to your new home and business headquarters in Cavendish, Vermont. This expansive property near Okemo Mountain Resort blends residential comfort and commercial opportunity. Imagine a chef’s dream kitchen with double ovens, refrigerators, and cooktops, perfect for culinary creativity. The home features three large bedrooms, spacious living areas, and a large deck for relaxation and

Daire Gibney Barrett and Valley Associates Inc.

265 Depot St, Proctorsville, VT 05153
/9
$125,000
- Land
- 0.07 Acre
- $1,785,714 per Acre
83 Main St, Ludlow, VT 05149

Prime downtown location! Once home to one of the few stone houses in Ludlow. Walk to everything on Main St. The lot is in the preservation district and may be deemed unbuildable do diligence will be required to determine properties usability. Town Planners suggested a public charging station? First of it's kind in Ludlow!

Frank Provance Diamond Realty

83 Main St, Ludlow, VT 05149
/36
$846,000
- 3 Beds
- 3.5 Baths
- 1,840 Sq Ft
49 Vt Rt 12, Pomfret, VT 05053

Discover the possibilities with this beautifully crafted three bedroom, three and one half bath home and versatile Post and Beam barn/studio, set between Woodstock and Silver Lake in scenic Barnard. The main residence features an airy great room with vaulted ceilings, warm wood accents, and expansive windows that invite natural light and frame peaceful views. Thoughtful design and quality

Eric Johnston Four Seasons Sotheby's Int'l Realty

49 Vt Rt 12, Pomfret, VT 05053
/19
$275,000
- Land
- 5.00 Acres
- $55,000 per Acre
95 Jenne Rd, Hartland, VT 05048

5 acres of peacefully quiet land that are situated in an area well known to the equestrian community! Both the surrounding neighbors, on this seldom traveled country road, and numerous other properties in this broad community present as substantial privately sited homes. As you meander up Jenne Road to reach the parcel the classic large maple trees that typify the borders of pastoral Vermont

John Wetmore Wetmore Real Estate

95 Jenne Rd, Hartland, VT 05048
/24
$95,000
- Land
- 10 Acres
- $9,135 per Acre
0 Snell Rd, Chester, VT 05143

This rolling, wooded 10.4+/- acre surveyed parcel in Chester offers 244 feet of road frontage and gently rolling land with a mix of hardwoods and pine. A lovely stream meanders through the property which is also dotted with interesting large boulders and old stone walls. If you are looking for privacy, there is potential for a secluded home site set back from the road. Utility pole is at the road

Geralyn Donohue Engel & Völkers Okemo

0 Snell Rd, Chester, VT 05143
/29
$449,000
- 3 Beds
- 2 Baths
- 840 Sq Ft
2225 Connecticut River Rd, Springfield, VT 05156

Discover the unparalleled luxury of living along the scenic Connecticut River with this wonderfully renovated 3-bedroom, 2-bath home. Positioned above a picturesque bend in the river, enjoy breathtaking views both upstream and downstream from this prime waterfront location.The open-concept kitchen and living area, complete with a cozy fireplace, seamlessly flow onto a spacious deck

Daire Gibney Barrett and Valley Associates Inc.

2225 Connecticut River Rd, Springfield, VT 05156
/37
$495,000
- 3 Beds
- 1.5 Baths
- 1,630 Sq Ft
19 Prospect St, Ludlow, VT 05149

Step into the charm of Ludlow village living with this captivating gem on Prospect St! Nestled on a serene street, this village charmer seamlessly blends historic allure with modern convenience, offering a lifestyle of ease and elegance. Enjoy easy access to the Okemo shuttle, local shops, and delectable dining options, all while relishing the tranquility of this picturesque neighborhood. Indulge

Sarah Sheehan William Raveis Real Estate Vermont Properties

19 Prospect St, Ludlow, VT 05149
/3
$590,000
- 17 Beds
- 2,768 Sq Ft
1185 U S 5 S, Windsor, VT 05089

Introducing a prime investment opportunity nestled on 1.44 acres of picturesque countryside just moments away from the convenience of town living. Whether you're a seasoned investor seeking a lucrative addition to your portfolio or a newcomer to the world of real estate investment, this 8-unit property presents an attractive proposition. With its idyllic location, modern updates, and reliable

Katie Ladue Gilbert KW Vermont Woodstock

1185 U S 5 S, Windsor, VT 05089
/16
$72,500
- 1 Bed
- 2 Baths
- 775 Sq Ft
434 Qtr. I Jackson Gore Inn, Ludlow, VT 05149

Jackson Gore Inn, Unit 434 Q I. 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

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

434 Qtr. I Jackson Gore Inn, Ludlow, VT 05149
/4
$200,000
- Land
- 0.90 Acre
- $222,222 per Acre
00 Okemo Acres Rd, Ludlow, VT 05149

Nestled in a nice neighborhood off of the Okemo Resort access road, with almost an acre and a view of the slopes! You can purchase the lot or you can have the builder/owner build a custom home designed for you. There are drawings that are approved for a 3 bedroom home with the possibility of a garage if you choose. The land is level with open and wooded areas. Build your own home or have it

Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

00 Okemo Acres Rd, Ludlow, VT 05149
/39
$70,000
- 1 Bed
- 2 Baths
- 775 Sq Ft
448 QIV Jackson Gore Inn Unit 448 QIV, Ludlow, VT 05149

Jackson Gore Village at Okemo Mountain Resort. Jackson Gore Inn on Okemo, Quarter Share Ownership, Unit 448 Quarter IV. Whether seeking a weekend getaway or a seasonal retreat, Jackson Gore Inn offers the perfect blend of luxury, comfort, and convenience. With quarter-share ownership, you can enjoy the benefits of mountain living without the full-time commitment. This 1 bedroom, 2 bathroom

Joseph Karl William Raveis Real Estate Vermont Properties

448 QIV Jackson Gore Inn Unit 448 QIV, Ludlow, VT 05149
/40
$799,000
- 7 Beds
- 6 Baths
- 5,028 Sq Ft
52 Upper, Bridgewater, VT 05035

A "turn-key" commercial opportunity in a highly visible location! Being well situated between the world class skiing of Killington and the numerous amenities of historic Woodstock Village entrepreneurial dreams for this diverse property can easily take flight! Within this classic New England style structure are a professionally appointed and immaculate commercial kitchen, spacious dining rooms,

John Wetmore Wetmore Real Estate

52 Upper, Bridgewater, VT 05035
/8
$169,000
- 2 Beds
- 1 Bath
- 900 Sq Ft
3052 Vermont 107, Stockbridge, VT 05772

Small home in need of rehab. House has been vacant for several years and is in need of an interior floor system. Located on Rt 107 for easy access to ski areas and I89 exit 3. Commercially zones area. Property goes up the hillside for further development and views. Should be purchased with cash or construction loan and should be verified with town as an approved homestead. Comes with a

Patricia Harvey Xsell Realty LLC

3052 Vermont 107, Stockbridge, VT 05772
/37
$765,000
- 3 Beds
- 2.5 Baths
- 1,842 Sq Ft
224 Okemo Trailside Extension Unit 46 C, Ludlow, VT 05149

Sitting atop the Okemo Trailside community just below the Catnap ski trail and abutting the Okemo State Forest. Three bedroom plus family room townhome offering magnificent panoramic mountain views to the east. Large and well equipped kitchen with vaulted ceiling and breakfast bar. Open dining and living areas centered by a woodburning fireplace with cathedral ceilings leading out to a large

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

224 Okemo Trailside Extension Unit 46 C, Ludlow, VT 05149
/13
$110,000
- Land
- 10 Acres
- $10,891 per Acre
000 W Hill Rd, Barnard, VT 05031

Located just 1/2 mile from the Barnard General Store and Silver Lake on the right side so West Road with beautiful long range mountain views. The lot is mostly wooded with a section cleared to expose the views. Private setting for a home site. Close to snowmobile trail which is also used in winter for hiking, dog walking, cross county skiing and snowshoeing. Barnard elementary school and

Stan Butler Four Seasons Sotheby's Int'l Realty

000 W Hill Rd, Barnard, VT 05031
/26
$219,000
- Land
- 28 Acres
- $7,878 per Acre
00 Quarry Rd, Chester, VT 05143

Explore this 27.8 acre+/- hillside parcel with mountain views and an approved VT state permit for a 4 bedroom family residence, close to the Village of Chester and adjoining Chester Town land. An easily accessed preliminary site has already been cleared. At the top of the ridge, a nice cleared plateau would be a fabulous spot for an off-the-grid bonus cabin retreat with amazing views! This parcel

Geralyn Donohue Engel & Völkers Okemo

00 Quarry Rd, Chester, VT 05143
/13
$1,789,000
- Land
- 100 Acres
- $17,890 per Acre
5000 Vermont 106, Reading, VT 05062

Beautiful building lot of approximately 100 acres just 5 mins to South Woodstock, and privately situated with a driveway entrance directly on VT 106 for easy access. The parcel includes woods roads and trails, ancient stone walls, brooks, ponds and some cleared areas as potential future building sites with lovely southern exposure and long-range views of distant hills. The property contains two

John Snyder Snyder Donegan Real Estate Group

5000 Vermont 106, Reading, VT 05062
/21
$480,000
- 2 Beds
- 2 Baths
- 1,178 Sq Ft
145 Okemo Trailside Extension Unit 23C, upper, Ludlow, VT 05149

Walk to the Sachem Trail from this recently remodeled, warm and charming, 2 bedroom, 2 bath, 2 level condominium. Easy maintenance with an open floor plan (kitchen, dining and living room with wood burning fireplace and slider to the deck). Updates include: new kitchen cabinets, granite countertops, wood plank flooring, carpet, and paint. The new bathrooms have large format tiling and frameless

Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

145 Okemo Trailside Extension Unit 23C, upper, Ludlow, VT 05149
/49
$849,000
- 7 Beds
- 6 Baths
- 4,642 Sq Ft
41 Lawrence Hill Rd, Weston, VT 05161

This charming historic home, nestled on a hillside in the heart of Weston Village, offers a unique blend of old-world character and modern comfort. Built in the 1800s, the house is rich with architectural details, including aged barn wood accents, warm pine floors, and sunlit rooms that create a welcoming atmosphere for family and friends.The spacious living area is perfect for

Jessica Citera Cummings & Co

41 Lawrence Hill Rd, Weston, VT 05161
/13
$749,000
- 11 Beds
- 6 Baths
- 6,000 Sq Ft
23-25 Depot, Ludlow, VT 05149

Okemo-LudlowUnique commercial property in the center of Ludlow Village. Presently 6 apartment units, plus an 8-bay garage. This property has high visibility and plenty of off-street parking, offering many commercial opportunities.Trustee, seller is a Licensed Real Estate Broker. Siding is asbestos shingle.48 Hours advanced notice needed to show, best times late morning & early

Frank Ellison Ellison Real Estate, Inc.

23-25 Depot, Ludlow, VT 05149
/17
$19,999
- Land
- 1.90 Acres
- $10,526 per Acre
223 Falcon Loop Rd E Unit T-76, Rochester, VT 05767

Attention outdoor enthusiasts, this is your chance to build your dream home/getaway on this private wooded building lot in the desirable Great Hawk community. Nestled in the Green Mountains with southwest exposure and welcome sunlight year-round. This is a fabulous place to build your mountain retreat. Close to some of Vermont's premier ski resorts including Killington/Pico, Sugarbush,

Marybeth Tevis Home Town Realty, Inc.

223 Falcon Loop Rd E Unit T-76, Rochester, VT 05767
/6
$119,000
- Land
- 11 Acres
- $11,163 per Acre
00 Norrie Davies Rd, Cavendish, VT 05142

This property is in two parcels, see survey. The 5.82 acre parcel with the pond sets between Tarbell Hill Rd and Norrie Davies Rd. The 4.84 acre building lot parcel is directly across and is entirely on Norrie Davies Rd. The building lot is wooded with 1200+ feet of road frontage and has a state permit for a 4 bedroom septic system. The lovely pond offer a pleasant place to relax and enjoy.

Frank Ellison Ellison Real Estate, Inc.

00 Norrie Davies Rd, Cavendish, VT 05142
/4
$195,000
- 5 Beds
- 3.5 Baths
- 4,011 Sq Ft
70-74 State St, Windsor, VT 05089

The Stephen Jacob House is an extremely important historic residence in a town known for its historic architecture. Built in 1784 in the Georgian/Federal style, the residence was sited on the rise of State Street from the Village of Windsor. It's commanding presence was embellished with cornice dentil detailing and possibly a Palladian window. Having been used for many purposes over the

Wade Treadway Wade I Treadway Real Estate

70-74 State St, Windsor, VT 05089
/11
$579,000
- Land
- 6 Acres
- $89,628 per Acre
0 Barnard Rd, Woodstock, VT 05091

A truly unique 6 acre parcel of land conveniently located in the heart of Woodstock! Tremendous development potential! Zoning allows both COMMERCIAL and RESIDENTIAL use! The 6 acres visually divide into 2 components with 2 diverse personalities. The 1st component is an extraordinary private building lot in the heart of Woodstock! Access to this 4 acre component initially leads through a pleasant

John Wetmore Wetmore Real Estate

0 Barnard Rd, Woodstock, VT 05091
/14
$845,000
- 2 Beds
- 1 Bath
- 600 Sq Ft
234 Randall Rd, Wood Stock, VT 05091

Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm

Wade Treadway Wade I Treadway Real Estate

234 Randall Rd, Wood Stock, VT 05091
/33
$164,500
- Land
- 5.00 Acres
- $32,900 per Acre
0 Route 155 Unit 4905774, Weston, VT 05161

OWNER TERMS POSSIBLE FOR THE RIGHT BUYER! Driveway has been improved to drive up to a cleared potential house site!Two parcels with two installed septic systems being sold as one offering. These parcels are private, yet convenient to to the Village of Weston, Okemo for skiing, and near the Priory.The land behind these lots is a large parcel owned by the neighbor.There is access

Tyleen Murray Kelley Real Estate, Inc.

0 Route 155 Unit 4905774, Weston, VT 05161
/5
$248,000
- Land
- 58 Acres
- $4,291 per Acre
00 Christian St, Hartford, VT 05001

PRICE REDUCED!! Excellent Investment Opportunity to own a large Christian Street parcel in Hartford!Known as part of the Old Stone Farm years ago this 57.8 acres of land would be a great place to build your dream home with tons of privacy in the heart of Hartford or it could possibly be the next amazing development to provide some much needed housing units here in the upper valley. This

Alex DeFelice The Clerkin Agency, P.C.

00 Christian St, Hartford, VT 05001
/2
$325,000
- Land
- 10 Acres
- $31,863 per Acre
369 West, Barnard, VT 05031

10.2 private, mostly wooded acres with a well designed and professionally built gravel driveway from the road to the house site. One-half mile to Barnard General Store and Silver Lake. Everything is in place to build and just waiting for your creativity. There is a 28' x 40' capped and insulated concrete walk out foundation with drainage, plumbing and radiant heat already in the floor. A four

Stan Butler Four Seasons Sotheby's Int'l Realty

369 West, Barnard, VT 05031
/2
$650,000
- 5 Beds
- 2 Baths
- 2,947 Sq Ft
108 Main St, Ludlow, VT 05149

Wonderful investment opportunity in the Ludlow village. 2 unit multi-family with great rental history. Units are in excellent shape. First floor features a spacious 3 bedroom with hardwood floors. The second unit has 2 bedrooms also with Hardwood floors, both in move in ready condition. Units are currently rented and producing income. Just a mile from the Okemo access road and right in the

Gary Coger Four Seasons Sotheby's Int'l Realty

108 Main St, Ludlow, VT 05149
/2
$35,000
- Land
- 4.03 Acres
- $8,685 per Acre
00 Cavendish Gulf Rd, Cavendish, VT 05142

Judy Thompson Walnut Hill Realty

00 Cavendish Gulf Rd, Cavendish, VT 05142
/16
$96,232 New Construction
- 2 Beds
- 2 Baths
- 777 Sq Ft
9 Walnut St, Hartford, VT 05001

Welcome to 9 Walnut Street, Wilder, VT, where modern comfort meets affordability in Olcott Falls MHP! This brand-new Redman 25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

Kate Barry EXP Realty

9 Walnut St, Hartford, VT 05001
/16
$96,232 New Construction
- 2 Beds
- 2 Baths
- 777 Sq Ft
11 Cubb Ct, Windsor, VT 05089

Welcome to 11 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

Kate Barry EXP Realty

11 Cubb Ct, Windsor, VT 05089
/11
$87,826 New Construction
- 1 Bed
- 1 Bath
- 643 Sq Ft
23 Cubb Ct, Windsor, VT 05089

Welcome to 23 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 1 bedroom, 1 bathroom, and 643 sq. ft. (13'4"x48) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

Kate Barry EXP Realty

23 Cubb Ct, Windsor, VT 05089
/16
$96,232 New Construction
- 2 Beds
- 2 Baths
- 777 Sq Ft
517 Back Mountain Rd, Windsor, VT 05089

Welcome to 517 Back Mountain Rd., Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

Kate Barry EXP Realty

517 Back Mountain Rd, Windsor, VT 05089
/15
$98,995 New Construction
- 3 Beds
- 2 Baths
- 880 Sq Ft
84 Cubb Ct, Windsor, VT 05089

Welcome to 84 Cubb Court, , Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-66 model manufactured home offers 3 bedrooms, 2 bathrooms, and 880 sq. ft. (13'4"x66) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

Kate Barry EXP Realty

84 Cubb Ct, Windsor, VT 05089
/23
$375,000 New Construction
- 3 Beds
- 2 Baths
- 1,493 Sq Ft
6 Rockwood St, Hartland, VT 05052

Be the first to own this brand-new 3-bedroom, 2-bath manufactured home situated on its own land in desirable Hartland, Vermont. Set on a spacious and private ±0.37-acre lot, the property offers a peaceful setting just minutes from the VA hospital and all Upper Valley conveniences.The interior features a large, modern kitchen with a center island and large pantry—perfect for cooking and

Jenna Luce RE/MAX Upper Valley

6 Rockwood St, Hartland, VT 05052
/23
$1,200,000 New Construction
- 4 Beds
- 3.5 Baths
- 2,530 Sq Ft
228 Town Farm Rd, Ludlow, VT 05149

If you're looking for a custom designed ski house built by a premier builder with Okemo views and minutes to downtown Ludlow, look no more. This house is designed with a ski family in mind. Walk in to the custom mudroom to stash all of your gear. Then embrace the open living concept that will be flooded with natural light and winter mountain views to include Okemo. This four bedroom, two

Frank Provance Diamond Realty

228 Town Farm Rd, Ludlow, VT 05149
/19
$325,000 New Construction
320 W Rowe Hill Rd, West Windsor, VT 05037

Wonderful unfinished 24'x34' pole building originally planned to be a stable with an efficiency apartment above now permitted to be a 2 bedroom, 2 bath residence on 9.4 tranquil acres on W Rowe Hill Rd. Sellers say zoning will permit either style.Check out the views at the height of the land or sit by the babbling brook as you plan the completion of this project. The sellers have used all quality

Dana Waters Dark Horse Realty

320 W Rowe Hill Rd, West Windsor, VT 05037

Showing Results 481 - 520, Page 13 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.