Windsor County VT Homes for Sale

/57
$419,000
- 2 Beds
- 2 Baths
- 1,832 Sq Ft
55 Horseshoe Ave, Hartford, VT 05001

Excellent opportunity to own a Wilder village / Frost Park area duplex! This single family conversion home features a wonderful, level, spacious in town neighborhood lot, convenient location, possibility of single level living, and income potential all make this home a rare find! This multi-family home has 2 units, each with 1 bedroom and 1 bath. The kitchen, dining & living room areas have a

Alex DeFelice The Clerkin Agency, P.C.

55 Horseshoe Ave, Hartford, VT 05001
/13
$169,900
- 9 Beds
- 3 Baths
- 2,901 Sq Ft
66 Valley St, Springfield, VT 05156

INVESTMENT PROPERTY, with two 4 BR's apts. and one 1 BR's apt. Walk to town locations. Gross rent, $43,140.00, total expenses $19,992.00, net $23,140.00. Current cap rate is 13.6%. Requires a minimum of 48-hour notice to show.

Don Chabot Town and Country Realty

66 Valley St, Springfield, VT 05156
/15
$269,000
- Land
- 10 Acres
- $27,393 per Acre
00 Chapel Hill Rd, Sharon, VT 05065

Fantastic land lot for the construction of your new home! This shovel-ready site in Sharon, VT is just over the Norwich town line in the Beaver Meadow neighborhood. No further tree clearing is needed. The hardpack driveway leads up to a beautiful and private setting where 200-amp electrical service from GMP has already been installed (underground), along with a 4-bedroom spec septic system and

Josh Hunt Snyder Donegan Real Estate Group

00 Chapel Hill Rd, Sharon, VT 05065
/18
$398,000
- Land
- 14 Acres
- $29,265 per Acre
87 Aldrich Farm Rd, Sharon, VT 05065

This stunning 13.6-acre property on Aldrich Farm Road boasts long-range westerly views of the Green Mountains, including Killington and Pico peaks. The land features a gently sloping open meadow (approximately 5 acres), a mixed hardwood forest, and a babbling brook that flows into a small pond. A carefully reconstructed historic stone wall at the southwestern edge enhances the classic New England

David White OwnerEntry.com

87 Aldrich Farm Rd, Sharon, VT 05065
/16
$89,000
- Land
- 1.14 Acres
- $78,070 per Acre
1087 Pleasant Valley Rd, Springfield, VT 05156

Here's a revised, polished version with a touch more excitement:This ready-to-build lot is a dream come true! Complete with septic, power, a well, and stunning stone terraced walls, it’s all set for you to add the finishing touches. Whether you’re looking for a full-time residence or a private getaway, this property offers the ideal blend of seclusion and convenience on a well-maintained

Daire Gibney Barrett and Valley Associates Inc.

1087 Pleasant Valley Rd, Springfield, VT 05156
/6
$54,900
- Land
- 29 Acres
- $1,893 per Acre
0 Rt 7 (Db 94 Dp 399), Royalton, KY 41464

These 29 acres, per PVA map, are located in southern Magoffin County in Royalton, Kentucky, with the acreage running along both sides of RT 7. The property is located in the Salt Lick area outside Royalton and includes property on both sides of Salt Lick Road as well. The property is undeveloped but electric and public water are available. For those with visions of homesteading, the Licking River

Doug Wireman First Choice Realty & Assoc.

0 Rt 7 (Db 94 Dp 399), Royalton, KY 41464
/10
$37,000
- Land
- 2.36 Acres
- $15,678 per Acre
TBD Vermont Route 100, Plymouth, VT 05056

This surveyed 2.3 acre parcel is perfectly situated between Okemo and Killington Mountains and the beautiful Plymouth lakes. It has easy access off Route 100 and power at the road. This land is ready for you to enjoy unlimited outdoor recreation in a great location. Come see this lot today and bring your imagination.

Mendi Michael Engel & Völkers Okemo

TBD Vermont Route 100, Plymouth, VT 05056
/59
$595,000
- 5 Beds
- 4.5 Baths
- 4,244 Sq Ft
37 Breezy Hill Rd, Springfield, VT 05156

Step into this beautifully crafted home and leave your cares at the door. Originally built in 1940, it has had new additions to the original house along with renovations in 1988 and a new kitchen in 2018. The welcoming foyer, with beautiful stonework leads to a gracious living room with beautiful built-ins, with a propane fireplace to keep you warm. The wet bar makes for convenient hosting. This

Carol Cole BHG Masiello Brattleboro

37 Breezy Hill Rd, Springfield, VT 05156
/7
$314,000
- 4,077 Sq Ft
96 Chester Rd, Springfield, VT 05156

DON'T MISS THIS GREAT INVESTMENT OPPORTUNITY. 5 UNITS PLUS 3 GARAGE SPACES. 3- 2 BR's, 1- 3 BR's UNIT and 1- 1BR's UNIT. ACTUAL CAP RATE 11.55%, PROFORMA CAP 14.29%. SHOWING APPOINTMENTS REQUIRE 48 HOUR NOTICE TO TENANTS. PRICE IS NEGOTIABLE FOR CASH OFFERS AND QUICK CLOSING!

Don Chabot Town and Country Realty

96 Chester Rd, Springfield, VT 05156
/22
$275,000
- Land
- 91 Acres
- $3,022 per Acre
000 Green Mountain Turnpike, Andover, VT 05143

91± Acres with Stunning Mountain Views in Chester, VermontDiscover a breathtaking 91± acre property just minutes from the charming village of Chester, Vermont. This expansive parcel features stunning alpine views of Fox Chair Mountain, over 3,000 feet of road frontage, and power and internet access along more than half the frontage. Located on the historic Green Mountain Turnpike, this

Daire Gibney Barrett and Valley Associates Inc.

000 Green Mountain Turnpike, Andover, VT 05143
/60
$1,850,000
- 4 Beds
- 3.5 Baths
- 5,000 Sq Ft
2706 E Woodstock Rd, Woodstock, VT 05091

INVESTMENT & RESIDENTIAL OPPORTUNITY - Rare historic building (The Taftsville Country Store - Woodstock VT) available for owner occupancy with multiple additional income units in the village of Taftsville. Just five minutes to the quintessential downtown New England Village of Woodstock! Property includes storefront space (approved for restaurant, cafe, or retail store), Post Office (with current

John Bassette Bassette Real Estate Group

2706 E Woodstock Rd, Woodstock, VT 05091
/56
$985,000
- 5 Beds
- 2.5 Baths
- 2,200 Sq Ft
109 Upper Loop, Ludlow, VT 05149

Escape to this spacious 5-bedroom, 3-bathroom home nestled on Okemo Mountain, offering the perfect blend of comfort and convenience. The inviting lower level welcomes you with a cozy family room featuring a two story, wood-burning fireplace, two bedrooms, and a full bathroom—ideal for guests or a private retreat. The main living area on the second level boasts an open kitchen and dining area,

Joseph Karl William Raveis Real Estate Vermont Properties

109 Upper Loop, Ludlow, VT 05149
/14
$239,000
- Land
- 10 Acres
- $23,663 per Acre
0 Christian St Unit 5019436, Hartford, VT 05001

Beautiful, in town location. A very rare opportunity to own an in town Christian Street parcel of land. If you've been having a hard time finding the right home in this very tight housing market Or if you've been dreaming about new construction in the Hartford / Upper Valley area than look no further. This building lot is conveniently located only minutes from Downtown White River Junction. This

Alex DeFelice The Clerkin Agency, P.C.

0 Christian St Unit 5019436, Hartford, VT 05001
/34
$65,000
- 1 Bed
- 2 Baths
- 737 Sq Ft
262 Qtr I V Jackson Gore Inn, Ludlow, VT 05149

Jackson Gore Inn Unit 262 Quarter IV: Quarter ownership. Handicap accessible condo offering a larger bathroom and an open layout. This is a one bedroom residence with a living area that offers a deck with valley views and a gas fireplace. It is centrally located just steps from the owners lounge, library and lobby elevator providing access to the front desk, Coleman Brook Tavern and lobby bar.

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

262 Qtr I V Jackson Gore Inn, Ludlow, VT 05149
/53
$899,000
- 5 Beds
- 3.5 Baths
- 2,890 Sq Ft
222 Andover Rd, Ludlow, VT 05149

Nestled on a peaceful 10.59 acre parcel, this stunning home is just 9 minutes to the Okemo Base Lodge, making it an ideal retreat for outdoor enthusiasts. The spacious layout features open kitchen, dining, and living room with gas fireplace, adorned with beautiful beams and a large kitchen island, making it perfect for entertaining. Key features of the property include:A welcoming mudroom

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

222 Andover Rd, Ludlow, VT 05149
/60
$865,000
- 4 Beds
- 2 Baths
- 2,516 Sq Ft
14 Gill Terrace, Ludlow, VT 05149

Engaging and inviting! Sweeping arches inside and out create warm, subtle elegance filled with natural light from the southern exposure. Lovingly maintained by the owner of 33 years, every detail has been meticulously cared for through extensive renovations that preserve the vintage character while adding modern comforts. Enjoy expansive views from the sunroom or elevated deck, perfect for

Diane Rousseau Four Seasons Sotheby's Int'l Realty

14 Gill Terrace, Ludlow, VT 05149
/59
$895,000
- 3 Beds
- 2.5 Baths
- 2,128 Sq Ft
115 Prior Rd, Cavendish, VT 05142

Entrepreneurs take notice! This home business could be yours. A well know mechanic/woodworker is moving on. This custom built log home and mechanics/woodworking shop is a turn key home and business situated on over 19 acres. This could also be a dream of a snowmobile enthusiast. Located on the VAST trail system on a dead end road. The log home was hand built by the current owner with custom

Frank Provance Diamond Realty

115 Prior Rd, Cavendish, VT 05142
/27
$295,000
- 1 Bed
- 1 Bath
- 675 Sq Ft
2940 Route 103 Unit 158, Cavendish, VT 05142

A Rare Find...1 bedroom condominium at Castle Point, only 3 miles to Okemo Mountain Resort.This condo can be rented out or used whenever you like, it is a full ownership property and fully furnished. It is located in the back away from the hotel lobbies, but has access to the pool and gym facilities. On the first floor the condo has an open living room with a gas fireplace, dining room, and a

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

2940 Route 103 Unit 158, Cavendish, VT 05142
/15
$139,900
- Land
- 49 Acres
- $2,843 per Acre
00 Eaton Ave, Springfield, VT 05156

Prime Development Opportunity: 49+ Acres in Springfield, VTUnlock the potential of this expansive 49+ acre parcel, ideally situated just minutes from downtown Springfield, VT. This prime land boasts considerable road frontage and direct access to town water and sewer, making it a developer's dream. Springfield is a thriving community surrounded by stunning landscapes, with easy access to

Daire Gibney Barrett and Valley Associates Inc.

00 Eaton Ave, Springfield, VT 05156
/18
$99,900
- 1 Bed
- 528 Sq Ft
324 Sunrise Rd, Bethel, VT 05032

Attention outdoor enthusiasts! Rustic secluded cabin on 10 acres in the woods. Overlooking a little open patch of field with natural sunlight makes for peaceful days sitting on the front porch enjoying all the nature that surrounds you. Start a fire in the wood stove and cozy up for those cool fall/winter nights. This property comes with deeded septic rights on adjacent lot. It also offers

Keane Yandow CENTURY 21 North East

324 Sunrise Rd, Bethel, VT 05032
/26
$1,275,000
- 3 Beds
- 2 Baths
- 2,573 Sq Ft
701 Turnpike Rd, Norwich, VT 05055

Discover The Norwich Farm, a 6-acre property featuring multiple barns built in the late 1990s, designed to support dairy and breeding operations. An additional renovated antique barn enhances the character and functionality of the property, offering various opportunities for ventures and recreational activities. At the center of the farm is a thoughtfully renovated antique farmhouse. This

Susan Zak Four Seasons Sotheby's Int'l Realty

701 Turnpike Rd, Norwich, VT 05055
/41
$180,000
- 3 Beds
- 3 Baths
- 1,854 Sq Ft
705/707 Qtr I V Adams House, Ludlow, VT 05149

Adams 705/707 Quarter IV: Quarter ownership. This top floor, 3 bedroom unit is in a wonderful location with magical mountain views up the Jackson Gore Peak! This is a lockout condominium with two bedrooms on one side and one bedroom on the lockout side with incredible ski access. The large Primary Bedroom boasts a King sized Bed, a fireplace and beautiful en-suite bathroom. The second

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

705/707 Qtr I V Adams House, Ludlow, VT 05149
/41
$6,950,000
- 8 Beds
- 7.5 Baths
- 8,262 Sq Ft
3800 Weston-Andover Rd, Andover, VT 05143

Escape to Moosewalk Lane, a fully furnished and equipped luxury estate in Andover, Vermont, set on 384 acres in the iconic Green Mountains. This one of a kind property offers a rare blend of seclusion, natural beauty, and timeless craftsmanship. The custom built 10,062 square foot main house features an expansive open concept design. Crafted with post and beam timber frame construction, the

Steve Stettler Four Seasons Sotheby's Int'l Realty

3800 Weston-Andover Rd, Andover, VT 05143
/31
$300,000
- 2 Beds
- 1.5 Baths
- 1,070 Sq Ft
27 Lawrence Hill Rd Unit 5, Weston, VT 05161

Tuttle Barn Unit 5 enjoys one of Weston's best views overlooking the West River waterfalls and historic Mill with lovely meadows and mountains beyond! The handsome c. 1907 barn was converted to condos in 1983 and, with just five units “the barn” offers the best of in-town living with a small footprint and low-to-no maintenance demands. This charming unit offers two bedrooms (plus a loft) and

Claudia Harris Mary Mitchell Miller Real Estate

27 Lawrence Hill Rd Unit 5, Weston, VT 05161
/32
$300,000
- 2 Beds
- 1.5 Baths
- 1,070 Sq Ft
27 Lawrence Hill Rd Unit 5, Weston, VT 05161

Tuttle Barn Unit 5 enjoys one of Weston's best views overlooking the West River waterfalls and historic Mill with lovely meadows and mountains beyond! The handsome c. 1907 barn was converted to condos in 1983 and, with just five units “the barn” offers the best of in-town living with a small footprint and low-to-no maintenance demands. This charming unit offers two bedrooms (plus a loft) and

Claudia Harris Mary Mitchell Miller Real Estate

27 Lawrence Hill Rd Unit 5, Weston, VT 05161
/37
$580,000
- 5 Beds
- 3 Baths
- 2,142 Sq Ft
223 Hillcrest Terrace, White River Junction, VT 05001

This gem of a home is ready for you to live in, enjoy, and show off to your guests. It is an easy walk or bike ride to the thriving town of White River Junction and close to the interstate for easy access to the Upper Valley. The two levels of covered porches encourage an outdoor morning coffee or relaxing after work. A lovely mix of style, history, and modern amenities, the high ceilings, open

Josh Hunt Snyder Donegan Real Estate Group

223 Hillcrest Terrace, White River Junction, VT 05001
/33
$275,000
- Land
- 1.03 Acres
- $266,990 per Acre
0 Gill Terrace Unit 5014671, Ludlow, VT 05149

New Price Improvement and bundle option!!! Ludlow Village lot with just over an acre and a 2 story carriage house. Imagine the possibilities with the classic lines of the vintage carriage house that has 3 sets of swinging bay doors and an entry door as well. There are stairs to the second level that has 2 sets of dormered windows and tons of storage space. The large village lot provides many

Kevin Barnes William Raveis Real Estate Vermont Properties

0 Gill Terrace Unit 5014671, Ludlow, VT 05149
/17
$114,900
- 2 Beds
- 2 Baths
- 1,056 Sq Ft
1011 Knapp Pond Rd, Cavendish, VT 05142

Welcome to 1011 Knapp Pond Rd, a two-bedroom, two-bathroom mobile home nestled in a serene setting alongside Knapp Pond Road. This property boasts a breathtaking backdrop, with a wildlife preserve directly across the street, making it a perfect haven for nature enthusiasts. Just a leisurely stroll away, you can enjoy the scenic beauty of Knapp Pond, offering tranquil views and outdoor activities.

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

1011 Knapp Pond Rd, Cavendish, VT 05142
/38
$419,000
- 3 Beds
- 2 Baths
- 1,428 Sq Ft
107 Blueberry Ledge Ridge Unit 45, Plymouth, VT 05056

Motivated seller, ready to move in 3BDR + 1 bonus room 14x11 possible 4th BDR, all elegant furnished, everything included(furniture + all housing equipment), private cull-de-sac on top of Hawk Mountain Resort In between Okemo and Killington, with amaizing views of the sunset through the woods and mountain from all rooms. 5 star resort finishing May 2026 , no special assessments added

Ralph Harvey Listwithfreedom.com

107 Blueberry Ledge Ridge Unit 45, Plymouth, VT 05056
/40
$495,000
- 2,280 Sq Ft
1377 Vermont 103, Chester, VT 05143

Chester Vt 1377 VTRT 103. , Multi Family , Many good uses for property. One and two-family residential and professional office, retail store if it were a home occupation or home business. There are 2 separate buildings. One needs to be finished, main building 3 floor could be finished for more living space.

Mike England Michael England Real Estate

1377 Vermont 103, Chester, VT 05143
/6
$100,000
- Land
- 0.65 Acre
- $153,846 per Acre
36 Chestnut St, Hartford, VT 05001

Price Reduced! Motivated Seller!! A Nice .65 acre + / - in town lot located on Chestnut Street in Wilder village. Just minutes to Dartmouth College, Dartmouth Hitchcock Medical Center, the VA Hospital , I 89 & I 91. This property is located in the R1 town zoning district so has lots of potential for a single family home. A great place to build a home with close proximity to schools and walking

Alex DeFelice The Clerkin Agency, P.C.

36 Chestnut St, Hartford, VT 05001
/38
$2,650,000
- 5 Beds
- 5.5 Baths
- 3,862 Sq Ft
113 N Village Rd Unit 25, Ludlow, VT 05149

This beautiful and very spacious newly constructed home, with energy efficient upgrades, has over 6,000 square feet of living space on three levels. Within walking distance to the slopes, located close to the Base Lodge area, this home has everything a ski home needs. Enter through the carefully crafted front door into one of the two mudrooms, or through the two car garage or by the side mudroom

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

113 N Village Rd Unit 25, Ludlow, VT 05149
/35
$595,000
- 1 Bed
- 2 Baths
- 957 Sq Ft
717/719 Quarters I and I V, Ludlow, VT 05149

Unit 717/719 Quarters I, II, III and IV: An amazing opportunity to own all four quarters in the Adams House, offering your family a Vermont vacation on your schedule! This luxury top-floor, corner residence with a one bedroom lock-out has a great view of the Bright Star Basin up to the peaks of Jackson Gore. Features include two baths, two queen beds, a wall bed, and a sleep sofa. Enjoy the

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

717/719 Quarters I and I V, Ludlow, VT 05149
/10
$129,000
- Land
- 3.00 Acres
- $43,000 per Acre
0 Goldcoast Rd, Bridgewater, VT 05034

Come see this beautiful piece of Vermont!! Conveniently located in the town of Bridgewater that boasts no zoning. Enjoy all the outdoor adventures that Vermont has to offer nearby, minutes to world class skiing and riding, mountain biking, surrounded by snowmobiling trails, golf, Long Trail Brewery, Plymouth’s trio of lakes, and the quintessential Vermont town of Woodstock. Visualize your own

Will Spanos KW Vermont-Killington

0 Goldcoast Rd, Bridgewater, VT 05034
/34
$105,000
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
246/248 Qtr I Jackson Gore Inn, Ludlow, VT 05149

Unit 246/248, Quarter I: Quarter ownership. Located on the second floor, convenient to the pool, fitness room and the ski base areas! Great two bedroom / lock-out capabilities. Unit J Features:2 Bedrooms, Sleeps eight, Lock out capability, King bed, Queen bed, Queen sleep sofa, Double sleep sofa, full kitchen, covered balcony, jetted bath tub, fireplace, entertainment center. Come and enjoy

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

246/248 Qtr I Jackson Gore Inn, Ludlow, VT 05149
/21
$185,000
- Land
- 14 Acres
- $13,252 per Acre
0 Valley View Dr Unit 5009431, Andover, VT 05143

This piece of land offers a unique combination of privacy and expansive long-range views at an elevation of 2000+ feet, making it an ideal location for your dream home in Southern Vermont. Nestled within a serene community of fine homes, this lot is one of the few remaining opportunities to build in this desirable area. The land has a waste water permit and comes with a community leach field

Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

0 Valley View Dr Unit 5009431, Andover, VT 05143
/60
$3,350,000
- 6 Beds
- 4.5 Baths
- 4,204 Sq Ft
400 Ruusunen Rd, Springfield, VT 05156

Wild Trails Farm offers unparalleled privacy, encompassing 436 acres of natural splendor. At the heart of this retreat is a 5,600+ sq ft lodge that is both luxurious and eco-friendly, powered by solar and geothermal. It features 6 spacious bedrooms, 4.5 bathrooms, a gourmet kitchen with dual dining areas, common rooms, and sauna. The 2-car garage is currently utilized as a yoga studio, but could

Debra Staniscia Four Seasons Sotheby's Int'l Realty

400 Ruusunen Rd, Springfield, VT 05156
/41
$295,000
- 4 Beds
- 1.5 Baths
- 2,640 Sq Ft
15 Gill Terrace, Ludlow, VT 05149

New improved price and bundle option. Who doesn't love a stately home in Ludlow? This one is a classic with many craftsman details throughout. The fireplace is stunning and the summer sleeping porch on the second floor is something from years gone by. There are hardwood floors in almost every room and decorative panels on many walls. With 4 bedrooms, 2 baths, and some bonus rooms, there is plenty

Kevin Barnes William Raveis Real Estate Vermont Properties

15 Gill Terrace, Ludlow, VT 05149
/43
$189,000
- 4 Beds
- 4 Baths
- 3,024 Sq Ft
515 Main St, Chester, VT 05143

Looking to live near the Chester Green? This may be the home for you! Currently used as a four-unit apartment building I believe that the highest and best use would be to return it to a single-family home with one accessory apartment in the back. The house is in need of renovation however, the style and location would lend well to that investment, or renovate the four units as your next venture,

John Tolosky Barrett and Valley Associates Inc.

515 Main St, Chester, VT 05143
/27
$150,000
- Land
- 1.00 Acre
- $150,000 per Acre
00 Town Farm Rd, Ludlow, VT 05149

South Hill is a sought-after location in Ludlow and here is your chance to build your dream home less than a mile to the center of Ludlow and less than 2 miles to Okemo. This lot was partially cleared and is part of the Scott's Corner's development. There are covenants to protect the value of the property. You could have some nice views of Okemo depending on where you site the home. Access to the

Kevin Barnes William Raveis Real Estate Vermont Properties

00 Town Farm Rd, Ludlow, VT 05149

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Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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.