Windsor County VT Homes for Sale

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  /17

  $825,000

  • Land
  • 150 Acres
  • $5,500 per Acre

  0 Walker Hill Rd Unit 5039522, 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 Unit 5039522, Bridgewater, VT 05091
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  /52

  $2,495,000

  • 5 Beds
  • 4.5 Baths
  • 4,800 Sq Ft

  248 Gird Lot Rd, Weathersfield, VT 05151

  Perched above the Connecticut River Valley with sweeping views to the New Hampshire mountains, this meticulously maintained five bedroom, four and a half bath home offers a rare opportunity just 30 minutes to Hanover, NH, Dartmouth College, and Dartmouth Hitchcock Medical Center. For medical professionals relocating to the Upper Valley, this property provides privacy, acreage, and panoramic views

  Karen DeMas Four Seasons Sotheby's Int'l Realty

  248 Gird Lot Rd, Weathersfield, VT 05151
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  /60

  $3,100,000

  • 5 Beds
  • 4.5 Baths
  • 7,634 Sq Ft

  165 Moonshadow Dr Unit M-15, Ludlow, VT 05149

  Welcome to your mountain sanctuary in the heart of Solitude Village—Okemo’s premier slopeside community. This luxurious 5-bedroom, 3-bathroom retreat offers true ski-on/ski-off access, allowing you to hit the Rising Star Trail or Moon Shadow right from your doorstep. Step inside to a warm, elegant interior featuring radiant-heated tile and rich hardwood floors throughout. The expansive great

  Joseph Karl William Raveis Real Estate Vermont Properties

  165 Moonshadow Dr Unit M-15, Ludlow, VT 05149
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  /25

  $185,000

  • 2 Beds
  • 2 Baths
  • 944 Sq Ft

  184 South St, Springfield, VT 05156

  You will be amazed when you see the condition of this older 1988 mobile home. The owners have maintained it meticulously since they moved it to this location in 2006. Walking distance to the high school and downtown, and near the Springfield hospital as well. There is a large bedroom on each end of the structure, each with a full bath. This would be a perfect property for anyone needing one level

  Glenn Olney Barrett and Valley Associates Inc.

  184 South St, Springfield, VT 05156
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  /26

  $649,000

  • 2 Beds
  • 2 Baths
  • 1,349 Sq Ft

  19 Kettlebrook Rd Unit D-5, Ludlow, VT 05149

  Direct ski-on, ski-off two-bedroom top-floor unit in the Kettlebrook community. Nicely updated throughout. Enclosed mudroom entrance with built-ins, laundry, and exterior ski closet. The main level includes a well-designed kitchen and a separate dining area with a newly installed slider leading out to the deck, which looks out to the slopes; a living room with a wood burning fireplace and

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

  19 Kettlebrook Rd Unit D-5, Ludlow, VT 05149
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  /58

  $2,950,000

  • 5 Beds
  • 5.5 Baths
  • 3,460 Sq Ft

  48 Alpine Way Unit D-1, Ludlow, VT 05149

  Show Stopper—this five-bedroom slopeside townhouse sits just steps from the trails and offers three private suites across three levels of beautifully curated living space. Completely reimagined by a talented local designer, it features an organic palette, thoughtful details, and a true move-in-ready feel—just hang your artwork and your skis. The chef’s kitchen showcases a Dekton waterfall

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

  48 Alpine Way Unit D-1, Ludlow, VT 05149
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  /41

  $1,495,000

  • 4 Beds
  • 2.5 Baths
  • 2,532 Sq Ft

  7 Slayton Terrace, Woodstock, VT 05091

  A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors—just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully

  Keri Cole Williamson Group Sothebys Intl. Realty

  7 Slayton Terrace, Woodstock, VT 05091
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  /26

  $225,000

  • 3 Beds
  • 1 Bath
  • 1,327 Sq Ft

  160 Depot St, Chester, VT 05143

  Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer,

  Joshua Lemieux Remax Summit

  160 Depot St, Chester, VT 05143
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  /60

  $475,000

  • 4 Beds
  • 5 Baths
  • 3,350 Sq Ft

  7868 Pomfret Rd, North Pomfret, VT 05053

  CASH FLOW POSITIVE - PRICE REDUCTION! A rare opportunity to own a piece of Vermont history - The North Pomfret Store & Post Office, c.1830. This 3-story New Englander offers charm, character, and a solid income stream on 3.25 picturesque acres. With 5 total units, the property includes 3 residential apartments (one 2-bedroom, one 1-bedroom, and an Efficiency), a ground-floor commercial office

  John Bassette Bassette Real Estate Group

  7868 Pomfret Rd, North Pomfret, VT 05053
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  /47

  $490,000

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft

  400 E Lake Rd, Ludlow, VT 05149

  Versatile Ludlow retreat on 9 acres with proven short-term rental history, offering flexible living options ideal for owner-occupants or investors seeking income near Okemo Mountain. This property is configured as a single-family residence with two distinct living levels, each featuring private entrances and amenities that allow for multiple use scenarios. The ground floor living area includes a

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

  400 E Lake Rd, Ludlow, VT 05149
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  /27

  $199,000

  • 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
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  /8

  $248,000

  • Land
  • 57.8 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
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  /21

  $110,000

  • Land
  • 1.13 Acres
  • $97,345 per Acre

  00 Evergreen Acres, Ludlow, VT 05149

  Located just 3.5 miles from Okemo Mountain, this prime parcel offers endless potential for your dream home. With selective clearing, enjoy breathtaking views of Okemo Mountain. The property comes with an existing Vermont Wastewater permit for a 3-bedroom residence, making it ready for your plans. Whether you're looking to build your perfect retreat or a year-round residence, this location is

  Kevin Barnes William Raveis Real Estate Vermont Properties

  00 Evergreen Acres, Ludlow, VT 05149
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  /40

  $2,950,000

  • 6 Beds
  • 6 Baths
  • 5,433 Sq Ft

  61 Academy Cir, Woodstock, VT 05071

  Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The

  Carol Wood Williamson Group Sothebys Intl. Realty

  61 Academy Cir, Woodstock, VT 05071
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  /60

  $3,650,000

  • 5 Beds
  • 4 Baths
  • 5,181 Sq Ft

  348 Turtle Hill Rd, Ludlow, VT 05149

  Built over the course of two years and completed in 2023, this nearly new custom timberframe home showcases exceptional craftsmanship and fine attention to detail. Privately sited on over 13 acres, the property offers sweeping, panoramic views of southern Vermont's mountains and valleys; vistas that are truly second to none. The home's architectural highlights include hand-hewn Douglas fir beams

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  348 Turtle Hill Rd, Ludlow, VT 05149
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  /49

  $695,000

  • 2 Beds
  • 2.5 Baths
  • 1,166 Sq Ft

  81 Daybreak Dr Unit I 103, Ludlow, VT 05149

  Solitude I103 Experience the ease of true slopeside living at Solitude Village, one of the most sought-after communities at Okemo Mountain Resort. This inviting ground-floor condominium offers the perfect blend of comfort, convenience, and year-round mountain enjoyment. Enter through a practical mudroom—ideal for storing ski equipment and outdoor gear—before stepping into the welcoming interior.

  Katherine Burns William Raveis Real Estate Vermont Properties

  81 Daybreak Dr Unit I 103, Ludlow, VT 05149
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  /17

  $149,000

  • Land
  • 1.83 Acres
  • $81,421 per Acre

  00 Raymond Rd, Ludlow, VT 05149

  LAND PARCEL WITH LAKE RESCUE ACCESS....This parcel is the last undeveloped lot available that has lake access, shared with a small association, SUNNY VALLEY, with only (8) properties. The building envelope is level and power is at the road. The lot overlooks a pretty meadow with undeveloped woodlands as a backdrop. The Sunny Valley privileges at Lake Rescue include (2) deck platforms overlooking

  Roger Danyew Diamond Realty

  00 Raymond Rd, Ludlow, VT 05149
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  /26

  $465,000

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  57 Townhouse Way Unit 9, Woodstock, VT 05091

  This beautiful Woodstock West Townhouse offers effortless, low-maintenance living in one of Vermont’s most charming four-season destinations. The main level welcomes you with a cozy living area centered around a fireplace, creating the perfect space to unwind. A sun-filled kitchen and dining area flow seamlessly onto a private deck—ideal for relaxing or entertaining. Upstairs, two generously

  Mary Mayhew Snyder Donegan Real Estate Group

  57 Townhouse Way Unit 9, Woodstock, VT 05091
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  /59

  $275,000

  • 2 Beds
  • 2 Baths
  • 2,400 Sq Ft

  54 Twitchell Settlement, Rochester, VT 05767

  PRICE REDUCTION TODAY - NOW OFFERED AT $325,000 (PREVIOUSLY $410,000). Set in Rochester, this chalet-style single family home pairs a dramatic vaulted great room with cathedral ceilings and an arched window wall that pours in natural light and captures seasonal mountain views. The setting spans 3.20 acres with a mix of open field and wooded privacy, giving you room to spread out while enjoying a

  Nick Sicard EXP Realty

  54 Twitchell Settlement, Rochester, VT 05767
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  /60

  $999,000

  • 6 Beds
  • 7.5 Baths
  • 5,588 Sq Ft

  726 E Ash Rd, Plymouth, VT 05056

  Nestled on a 3-acre private lot at Hawk Resort in Vermont’s Lakes Region, this expansive custom residence offers an exceptional mountain retreat. Thoughtfully designed across four levels--each accessible by elevator--the home provides outstanding separation of space, perfect for hosting family and guests.Designed by architect Robert Carl Williams, the home showcases signature craftsmanship,

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  726 E Ash Rd, Plymouth, VT 05056
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  /53

  $540,000

  • 1 Bed
  • 2 Baths
  • 957 Sq Ft

  717/719 Q1-4 Jackson Gore Adams House Unit 717/719 Q1-4, Ludlow, VT 05149

  Located in the heart of Jackson Gore at Okemo Mountain Resort, Adams House 717/719 Q1–4 presents a rare opportunity to own 100% interest in a traditionally quarter-share residence—all four quarters conveyed together, offering full ownership with excellent rental flexibility. This turn-key, ski-on/ski-off residence is being sold fully furnished, allowing a new owner to step right into the winter

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  717/719 Q1-4 Jackson Gore Adams House Unit 717/719 Q1-4, Ludlow, VT 05149
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  /32

  $445,000

  • 3 Beds
  • 3 Baths
  • 2,074 Sq Ft

  259 Jay Hill Rd, Hartford, VT 05001

  Bright, easy to maintain and furnished 3 bedroom, 3 bath house with all that Quechee Lakes has to offer. This home includes newer floors. kitchen appliances, 2 remodeled bathrooms, a whole house generator, and a garage with an electric car charger. Enjoy the outdoors with a large deck and an electric dog fence around the whole house.

  Sandra Dell KW Coastal and Lakes & Mountains Realty/Hanover

  259 Jay Hill Rd, Hartford, VT 05001
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  /35

  $939,000

  • Land
  • 101 Acres
  • $9,297 per Acre

  0 Newton Ln Unit 3 5045699, Hartford, VT 05001

  A rare opportunity to own 110 acres of pastoral Vermont landscape in sought-after Hartford and Norwich, VT. With 101 acres in Hartford (MLS # 5045705) and 9 acres in Norwich (see MLS #5045699), this expansive parcel offers rolling meadows, mature hardwood forest, and long west-facing mountain views in the heart of the Upper Valley. The elevated setting captures exceptional natural light and

  Karen DeMas Four Seasons Sotheby's Int'l Realty

  0 Newton Ln Unit 3 5045699, Hartford, VT 05001
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  /46

  $540,000

  • 1 Bed
  • 2 Baths
  • 1,112 Sq Ft

  193 Jackson Gore Unit 639/641, Ludlow, VT 05149

  Escape to mountain luxury with this fully furnished 1-bedroom, 2-bathroom condo located in the heart of the premier Okemo ski resort at Jackson Gore. Perfectly positioned just steps from the slopes, this stylish retreat offers the ultimate blend of comfort, convenience and year round adventure. The open-concept living space features a cozy gas fireplace and large windows with mountains views. The

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

  193 Jackson Gore Unit 639/641, Ludlow, VT 05149
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  /53

  $359,900

  • 3 Beds
  • 1 Bath
  • 1,608 Sq Ft

  531 Main St, Chester, VT 05143

  Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Chester, Vermont. Perfectly situated within walking distance to local shops, schools, and restaurants, this property offers the ideal blend of convenience and small-town charm. Step inside to find a spacious mudroom and laundry area — a practical entryway for Vermont living. The open kitchen and dining area

  Katherine Burns William Raveis Real Estate Vermont Properties

  531 Main St, Chester, VT 05143
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  /20

  $249,000

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  574 Willard Rd Unit 4A, Quechee, VT 05059

  Experience the ultimate Vermont lifestyle in this stunning end-unit condominium, where modern elegance meets trailside serenity. This home offers a rare sense of privacy, featuring a spacious deck that wraps around the the condo, providing a front-row seat to the soothing sounds of the nearby brook and the quiet beauty of the surrounding woods. Inside, the residence is completely move-in ready

  Linda Hicks Quechee Lakes Real Estate Center

  574 Willard Rd Unit 4A, Quechee, VT 05059
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  /12

  $137,000

  • Land
  • 5.39 Acres
  • $25,417 per Acre

  0 Woodlawn Dr Unit 2 & 3 5063379, Hartford, VT 05001

  5.39+/- acre Parcels of land (when combined) in HARTFORD / WHITE RIVER JUNCTION, VT. located on Woodlawn Drive just off the VA Cut Off Road! 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. These building lots are conveniently located only 1 mile

  Alex DeFelice The Clerkin Agency, P.C.

  0 Woodlawn Dr Unit 2 & 3 5063379, Hartford, VT 05001
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  /44

  $519,000

  • 1 Bed
  • 1.5 Baths
  • 1,044 Sq Ft

  144 Lodge Rd Unit 5, Ludlow, VT 05149

  Slopeside at SouthFace Village Okemo! This may be the nicest one-bedroom condominium currently available on Okemo Mountain. Immaculate and barely used, it comfortably sleeps six and is offered fully furnished, move-in ready for your mountain escape. The interior features stylish quartz countertops, hardwood flooring, built-in shelving, and energy-efficient appliances. Ductless mini-splits provide

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  144 Lodge Rd Unit 5, Ludlow, VT 05149
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  /35

  $425,000

  • 2 Beds
  • 1 Bath
  • 1,208 Sq Ft

  3078 N Hollow Rd, Rochester, VT 05767

  Nestled in the picturesque hollows of Rochester, Vermont, this charming and fully updated home offers the ease of one-level living in a modest yet wonderfully comfortable package. Antique softwood floors, knotty pine ceilings, and a large bay window framing beautiful North Hollow views create a warm and inviting atmosphere, while the open floor plan is equally suited for entertaining and intimate

  Kyle Kershner Killington Pico Realty

  3078 N Hollow Rd, Rochester, VT 05767
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  /27

  $639,000

  • 3 Beds
  • 2 Baths
  • 2,183 Sq Ft

  19 Davry Way, Woodstock, VT 05091

  You know that feeling when you walk through a door and you can already see future memories being made? That's what you feel as you turn every corner of this gem. This thoughtfully updated raised ranch blends comfort, style, and convenience seamlessly with plenty of natural light filling much of the home. Recent improvements include beautifully renovated bathrooms, gleaming hardwood floors, a new

  Julie Davis KW Vermont Woodstock

  19 Davry Way, Woodstock, VT 05091
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  /41

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  22 Rimrock Rd Unit 4B, Ludlow, VT 05149

  Affordable Okemo Trailside 3 bedroom plus den end unit. In great condition and ready to be your ski get-a-way this season. Updates include kitchen, main level bathroom and a brand new wood burning fireplace installed in the Fall of 2025. On 2 levels, there is an open kitchen/dining/living area, bath and bedroom on the main level, 2 bedrooms, bath, laundry and a cozy den finish the lower level.

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

  22 Rimrock Rd Unit 4B, Ludlow, VT 05149
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  /19

  $595,000

  • Land
  • 220.11 Acres
  • $2,703 per Acre

  0 Markham Mountain Rd, Andover, VT 05143

  Discover 220± acres of pristine woodland offering the ultimate blend of privacy, recreation, and opportunity. With a mix of gently level terrain and elevated ridgelines that may offer sweeping mountain views, this remarkable parcel provides endless possibilities — from a private estate setting to potential subdivision. The VAST snowmobile trail runs directly through a portion of the property,

  Kevin Barnes William Raveis Real Estate Vermont Properties

  0 Markham Mountain Rd, Andover, VT 05143
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  /36

  $521,400

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  169 Butternut Rd, Hartford, VT 05001

  This brand-new, never lived in Ranch style home in Hartford is for the folks who want to spend their weekends living, not chasing down a contractor. Skip the renovation stress. It’s new, it’s ready, and you get a clean, 3-bedroom, 2-bathroom single-level-living layout with the ultimate convenience: laundry on the main floor. No hauling baskets up and down stairs ever again. The kitchen has a

  Holly Hall Hall Collins Real Estate Group

  169 Butternut Rd, Hartford, VT 05001
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  /18

  $265,000

  • 2 Beds
  • 1.5 Baths
  • 1,063 Sq Ft

  445 Old Quechee Rd Unit 10C, Hartford, VT 05001

  Welcome to this sun-filled Mill Run Unit 10C in Quechee Lakes. Enjoy beautiful field views from this bright and inviting condo featuring a spacious open floor plan with cathedral ceilings, a cozy wood-burning stove, and access to a private deck where you can relax, listen to the nearby stream, and take in the peaceful field views. The main level offers an updated, fully applianced kitchen along

  Heather Ashline BHHS Verani Upper Valley

  445 Old Quechee Rd Unit 10C, Hartford, VT 05001
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  /60

  $1,250,000

  • 6 Beds
  • 5.5 Baths
  • 5,790 Sq Ft

  49 Burton Rd, Weston, VT 05161

  “Meadow & Mountain View” is the Vermont home you’ve been waiting for! Situated just outside of the charming village of Weston, this impressive property offers one of the area’s most delightful and picturesque locations with fantastic views, beautiful grounds, and a warm and welcoming house designed so that you can relax and truly enjoy your Vermont Life. The inviting layout features classic New

  Claudia Harris Mary Mitchell Miller Real Estate

  49 Burton Rd, Weston, VT 05161
• 

  

  /25

  $539,000

  • 2,304 Sq Ft

  81 High St, Cavendish, VT 05142

  Do you love antique homes? Come and take a look and decide how that you would like to use this property. This renovated 1850's home is currently set up as two income-producing units (a three-bedroom unit upstairs and a two-bedroom (could be three) unit on the main level). There is even additional space on the third floor that could be finished too. By simply removing a piece of sheetrock in the

  Tyleen Murray Kelley Real Estate, Inc.

  81 High St, Cavendish, VT 05142
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  /58

  $385,000

  • 4 Beds
  • 2 Baths
  • 2,554 Sq Ft

  1806 Vermont Route 100, Rochester, VT 05767

  This historic cape, circa 1785, is one of the oldest homes in Rochester, VT, blending timeless charm with modern updates. Centrally located to Sugarbush Resort along with Killington Resort and Pico Mountain. Its exposed beams, hand-built doors, and wide pine plank floors evoke classic New England architecture, while recent upgrades ensure comfort and convenience. Major enhancements include new

  Nathan Mastroeni

  1806 Vermont Route 100, Rochester, VT 05767
• 

  

  /37

  $699,000

  • Land
  • 52.3 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
• 

  

  /44

  $650,000

  • 2 Beds
  • 2 Baths
  • 1,044 Sq Ft

  35 White Loop Unit B101, Ludlow, VT 05149

  Winterplace on Okemo Mountain. This is a must see condominium at an unbeatable location on Okemo. Located at the top of the A & B quad which brings you directly to the Sunburst Six summit chairlift. Natural light fills the bright living space with an open floor plan for the living room, kitchen, and dining area. There is plenty of space for family and friends to gather. A few key features include

  Katherine Burns William Raveis Real Estate Vermont Properties

  35 White Loop Unit B101, Ludlow, VT 05149
• 

  

  /55

  $340,000

  • 3 Beds
  • 1 Bath
  • 2,096 Sq Ft

  335 North St, Chester, VT 05143

  Welcome to a charming village retreat in the heart of Chester, perfectly situated on Main Street in the historic Chester Stone Village. This inviting home blends classic Vermont character with comfortable, year-round living. Enter through a practical mudroom with ample space for all your seasonal gear—ideal for embracing Vermont’s four-season lifestyle. To the right, at the front of the home,

  Brendan McNamara William Raveis Real Estate Vermont Properties

  335 North St, Chester, VT 05143

Showing Results 121 - 160, Page 4 of 10