Windsor County VT Homes for Sale

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  /51

  $410,000

  • 3 Beds
  • 2 Baths
  • 1,304 Sq Ft

  663 Depot St, Chester, VT 05143

  Everything you’ve been looking for in a Vermont home—completely renovated with care and character. Nearly every aspect of this Chester property is new: electrical, plumbing, heating, insulation, drywall, windows, and more—offering the low-maintenance peace of mind homeowners crave. The kitchen features a stylish farmhouse sink and stone countertops, while the upstairs bathroom includes a

  Betsy Adamovich Real Broker LLC

  663 Depot St, Chester, VT 05143
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  /60

  $869,000

  • 4 Beds
  • 4.5 Baths
  • 4,088 Sq Ft

  1588 Austin Hill Rd, Rochester, VT 05767

  An iconic Robert Carl Williams design, completely reimagined by Robson Bilgen Architects in 1999, this one-of-a-kind masterpiece in Rochester’s Great Hawk community is a work of art inside and out. Perfectly sited on 2.7 acres of lush, landscaped grounds, it feels like a private sanctuary, with sweeping pagoda-inspired rooflines, recirculating ponds and waterfalls, dramatic stonework, and vibrant

  Kyle Kershner Killington Pico Realty

  1588 Austin Hill Rd, Rochester, VT 05767
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  /51

  $325,000

  • 5 Beds
  • 4 Baths
  • 2,963 Sq Ft

  513 Giddings St, Springfield, VT 05150

  Nestled on over an acre +/- of level land, this well-maintained home offers a wealth of space and potential for any lifestyle. With a large shed, a 3-car carport/workshop, and even a chicken coop, you'll have plenty of room to store, work, and play. The first floor features a generously-sized bedroom with bay windows, a beautifully refinished bathroom with a walk-in shower, a large kitchen,

  Chelsea Richardson Barrett and Valley Associates Inc.

  513 Giddings St, Springfield, VT 05150
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  /33

  $495,000

  • 3 Beds
  • 2.5 Baths
  • 2,152 Sq Ft

  17 Vermont 12, Hartland, VT 05048

  Classic 1850 home re-furbished top to bottom for modern amenities with antique charm. New roof, windows, kitchen, bathrooms, floors, electrical, plumbing, and heating throughout. First floor master bedroom and bathroom with large walk in closet. Three season porch overlooking big flat yard located right in downtown Hartland.

  Derek Eisenberg Continental Real Estate Group, Inc.

  17 Vermont 12, Hartland, VT 05048
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  /50

  $1,495,000

  • 4 Beds
  • 2.5 Baths
  • 1,938 Sq Ft

  360 Okemo Trailside Extension Unit 37E, Ludlow, VT 05149

  Exceptional Slopeside Living at Okemo. This premier 4-bedroom end unit in Okemo’s coveted Trailside community offers some of the best ski-on/ski-off access on the mountain. Step out your door and ski straight to the high-speed Sunburst Six bubble chair— or walk directly to the Glades Peak Quad, then return home to stunning, unobstructed mountain views.Fully reimagined with a focus on luxury,

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

  360 Okemo Trailside Extension Unit 37E, Ludlow, VT 05149
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  /32

  $2,300,000

  • 4 Beds
  • 4.5 Baths
  • 3,524 Sq Ft

  134 Chester Arthur Rd, Hartford, VT 05047

  A quality residence with 4.69 landscaped acres beautifully complimenting the estate! Entering into the grounds a graceful drive meanders through landscaped lawns to arrive at a stone patio and an appealing New England style residence. Conveniently, there is option to enter an attached garage with direct entrance to the residence. After crossing the stone patio, passing through the front door

  John Wetmore Wetmore Real Estate

  134 Chester Arthur Rd, Hartford, VT 05047
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  /60

  $200,000

  • Land
  • 6.63 Acres
  • $30,166 per Acre

  00 Vermont 103, Andover, VT 05143

  Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With aproposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offersample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

  Rachael Rogala Rachael Rogala Inc.

  00 Vermont 103, Andover, VT 05143
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  /48

  $615,000

  • 3 Beds
  • 3 Baths
  • 2,680 Sq Ft

  1643 Hammond Hill Rd, West Windsor, VT 05089

  Welcome to your private 8-acre retreat in West Windsor, where craftsmanship, comfort, and self-sufficiency meet everyday adventure. Explore wooded trails, swim in the peaceful pond, or sip coffee on the sunny porch. Evenings glow around the fire pit, while a sturdy treehouse sparks play and gardens of flowers bloom through the seasons. Stone stairways, wooden benches, and camping spots complete

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  1643 Hammond Hill Rd, West Windsor, VT 05089
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  /34

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,489 Sq Ft

  6852 Us Route 4, Bridgewater, VT 05034

  This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont

  Laird Bradley Williamson Group Sothebys Intl. Realty

  6852 Us Route 4, Bridgewater, VT 05034
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  /30

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft

  34 Fox Chair Terrace, Springfield, VT 05156

  Welcome to 34 Fox Chair Terrace, a peaceful, private three-bedroom, two-bath home set on a full acre just minutes from downtown Springfield and charming Chester, Vermont. Tucked away in a quiet rural setting, this spacious property offers the best of both worlds: privacy and nature, with easy access to shopping, schools, the local hospital, and other area amenities.Step inside to find a

  Patrick Kelley Four Seasons Sotheby's Int'l Realty

  34 Fox Chair Terrace, Springfield, VT 05156
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  /60

  $115,000

  • Land
  • 3.28 Acres
  • $35,061 per Acre

  00 Vt Route 103 N, Chester, VT 05143

  Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With a proposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life.The lot offers ample space for parking and potential for mountain or woodland views with some strategic tree clearing.

  Rachael Rogala Rachael Rogala Inc.

  00 Vt Route 103 N, Chester, VT 05143
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  /2

  $475,000

  2577 Hartford Ave, Hartford, VT 05001

  Commercial lot - Approximately 1⁄2 acre lot that borders the I-91 highway between the Wilder, VT exit and the Hanover NH/Norwich VT exit. Located on route 5 approximately a quarter mile from Dothan Brook School and 3-4 miles from the Dartmouth green. Property is across the street from walking and biking path, and there is an Advanced Transit bus stop close by as well. There is a separate listing

  Jason Saphire www.HomeZu.com

  2577 Hartford Ave, Hartford, VT 05001
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  /38

  $1,999,000

  • 6 Beds
  • 6 Baths
  • 7,619 Sq Ft

  5518 Vt Route 12, Barnard, VT 05031

  An historic brick residence prominently located in an affluent and growing community! Conveniently situated within walking distance to the Elementary School, to year round recreation on beloved Silver Lake and to the classic Barnard General Store. All of the well known amenities of Woodstock Village are just minutes away! World class medical care at Dartmouth Hitchcock Hospital and year round

  John Wetmore Wetmore Real Estate

  5518 Vt Route 12, Barnard, VT 05031
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  /25

  $359,000

  • 2 Beds
  • 2 Baths
  • 1,451 Sq Ft

  78 Division St, Hartford, VT 05001

  This cozy, well cared for New Englander is move in ready. Enjoy the passive income as a two unit, or use it as a single family home. The choice is yours. The house has a nice boot room to organize all of those winter layers leading into a kitchen that flows into the living room. The first floor bedroom is a nice option. Public transportation is nearby and so are biking trails. Kilowatt field is a

  Josh Hunt Snyder Donegan Real Estate Group

  78 Division St, Hartford, VT 05001
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  /60

  $749,000

  • 4 Beds
  • 3.5 Baths
  • 2,729 Sq Ft

  419 Baileys Mills Rd, Reading, VT 05062

  Welcome to this enchanting, historic Cape nestled on 75.56 pristine acres along the scenic Mill Brook. Ideally located just five miles from GMHA, the property spans both sides of Baileys Mill Road, offering abundant opportunities for equestrians, hobby farmers & nature lovers alike. The land is a rare mix of open pastures, mature woodlands, flowing streams, and panoramic valley views. A network

  Laird Bradley Williamson Group Sothebys Intl. Realty

  419 Baileys Mills Rd, Reading, VT 05062
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  /37

  $1,185,000

  • 4 Beds
  • 3 Baths
  • 2,785 Sq Ft

  1782 Randall Rd, Woodstock, VT 05091

  This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide

  Wade Treadway Wade I Treadway Real Estate

  1782 Randall Rd, Woodstock, VT 05091
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  /56

  $750,000

  • 4 Beds
  • 4 Baths
  • 3,300 Sq Ft

  477 Dunham Rd, Bethel, VT 05032

  A work of modern art. Words cannot describe the feeling you get when your eyes settle on this amazing place. Future owners need only appreciate the unique, creative, and thought provoking touches in this very interesting home.The builder/owners have created a family atmosphere centered around the massive stone fireplace, maple floor, open kitchen with impressive island, dining area, and a

  Dean Goulet Dunrovin Real Estate

  477 Dunham Rd, Bethel, VT 05032
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  /32

  $74,900

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  185 Riverbend Way, Woodstock, VT 05091

  Start your Vermont dream with this affordable 3-bedroom, 2-bath mobile home just minutes from downtown Woodstock, VT. Located in a quiet, private community with stunning mountain views and direct river frontage on the Ottauquechee, this home is a rare opportunity to enjoy scenic living at a budget-friendly price. Perfect as a first home, vacation getaway, or investment, this property is also

  Mendi Michael Engel & Völkers Okemo

  185 Riverbend Way, Woodstock, VT 05091
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  /29

  $169,500

  • 2 Beds
  • 1 Bath
  • 1,500 Sq Ft

  1438 Gravelin Rd, Perkinsville, VT 05151

  Country Setting on a shared drive surrounded by 3 acres w/ a small pond. First floor has 1 BR, full bath, kitchen/dining area and living room. Lower level has 1 BR and laundry room. Heat is a propane Rannai direct vent, plus a lower-level pellet stove. Property is in need of repair but livable. This is an ideal candidate for a 203K loan.

  Don Chabot Town and Country Realty

  1438 Gravelin Rd, Perkinsville, VT 05151
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  /59

  $1,750,000

  • 5 Beds
  • 4 Baths
  • 3,862 Sq Ft

  699 Spear Cemetery Rd, Reading, VT 05062

  Situated amongst the finest equine estates in the region, Tuacknback Farm is an iconic landmark, best known as the most popular hold along the famed Vermont 100 ride. Located on a scenic country road, accessing the most extensive trail systems in New England, the entire property was impeccably orchestrated for ease with direct walk-in access to the connected stable and hay loft, and a wide

  Danny Kogut Williamson Group Sothebys Intl. Realty

  699 Spear Cemetery Rd, Reading, VT 05062
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  /37

  $449,000

  • 4 Beds
  • 3 Baths
  • 1,920 Sq Ft

  1226 E Ash Rd Unit L-34, Plymouth, VT 05056

  PRICE IMPROVEMENT on this Mountain Retreat in Plymouth – Between Killington & OkemoWelcome to your Vermont getaway! This spacious four-bedroom, three-bathroom condo is nestled in the scenic hills of Plymouth, perfectly located between Killington and Okemo for easy access to world-class skiing, snowboarding and year-round mountain and lake adventures.Enjoy breathtaking winter views

  Katie McFadden RE/MAX North Professionals

  1226 E Ash Rd Unit L-34, Plymouth, VT 05056
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  /57

  $995,000

  • 4 Beds
  • 3.5 Baths
  • 2,585 Sq Ft

  117 Ledgewood Rd Unit F3 w/F4 Garage, Ludlow, VT 05149

  Ledgewood on Okemo, a spacious condominium located in one of the most sought-after communities on Okemo Mountain. This property offers an abundance of space, featuring two en-suites and two additional bedrooms. The expansive great room opens to a large family kitchen with two breakfast bars, providing ample seating for the whole family. You'll also appreciate the private ski-in/ski-out access and

  Katherine Burns William Raveis Real Estate Vermont Properties

  117 Ledgewood Rd Unit F3 w/F4 Garage, Ludlow, VT 05149
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  /42

  $945,000

  • 3 Beds
  • 2.5 Baths
  • 1,700 Sq Ft

  360 Okemo Trailside Extension Unit 37B, Ludlow, VT 05149

  It Truly is About Location! Sitting directly on the Sachem Trail this 3 bedroom townhome is one of the best locations on Okemo Mountain. You can access the trail either through the enlarged custom designed mudroom or step out onto the snow from the lower level sliding door. Either way this is the location that you are looking for! The kitchen is spacious, updated and open to the light-filled

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

  360 Okemo Trailside Extension Unit 37B, Ludlow, VT 05149
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  /60

  $225,000

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft

  442 Vermont 103, Chester, VT 05143

  Adorable Village Home in the Heart of Chester, VermontThis charming 3-bedroom, 1-bath home is packed with personality and Vermont village charm! Set on a sunny quarter-acre lot, this sweet property features an oversized deck perfect for summer barbecues, a great yard for play or gardening, and a convenient attached garage.Inside, you’ll love the warm, inviting living space with

  Rachael Rogala Rachael Rogala Inc.

  442 Vermont 103, Chester, VT 05143
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  /34

  $265,000

  • 2 Beds
  • 1.5 Baths
  • 1,140 Sq Ft

  104 Deer Run Rd Unit C13, Brownsville, VT 05037

  Welcome to this nicely maintained 2-bedroom + loft condo offering direct access to the renowned Ascutney Trails—perfect for mountain biking, skiing, hiking, and trail running. Enjoy stunning mountain views from the spacious living room, which features two large sliding glass doors that flood the space with natural light. The open loft above the living area offers even more scenic vistas and

  Daniel Preston KW Vermont Woodstock

  104 Deer Run Rd Unit C13, Brownsville, VT 05037
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  /54

  $725,000

  • 3 Beds
  • 2.5 Baths
  • 1,842 Sq Ft

  182 Okemo Trailside Extension Unit 42 D, Ludlow, VT 05149

  This nicely updated 3 bedroom plus family room townhome has stunning views to the east in a mid- mountain setting.Enjoy the large updated kitchen with wood cabinetry, stone countertops, and wood crafted breakfast bar. The open living area with cathedral ceiling centered by a woodburning fireplace, leads out to a covered deck and hot tub offering spectacular mountain views. The private primary

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

  182 Okemo Trailside Extension Unit 42 D, Ludlow, VT 05149
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  /57

  $1,990,000

  • 4 Beds
  • 3.5 Baths
  • 4,313 Sq Ft

  7 Norman Dr, Ludlow, VT 05149

  This is a rare opportunity to own a stunning year-round residence on the shores of Lake Rescue, nestled within a sought-after community that includes Okemo Mountain Ski Resort—offering the ultimate four-season lifestyle. Ideally located on the coveted east side of the lake, the home is perfectly positioned to capture afternoon sun and dramatic sunsets over the water.Beautifully landscaped

  Boris Lavanovich Mary W. Davis Realtor & Assoc., Inc.

  7 Norman Dr, Ludlow, VT 05149
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  /30

  $465,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  37 Atwood Ave, Woodstock, VT 05091

  Charming, updated, and perfectly located—this turnkey gem is your ticket to easy living in one of the area’s most adorable neighborhoods! With all the major systems recently upgraded - including a new furnace, hot water heater, Tesla Powerwall, and water purification system - this efficient home is move-in ready.Inside, you’ll love the fresh renovations: a modern kitchen with

  Keri Cole Williamson Group Sothebys Intl. Realty

  37 Atwood Ave, Woodstock, VT 05091
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  /36

  $895,000

  • 3 Beds
  • 5 Baths
  • 3,590 Sq Ft

  1104 Main St, Cavendish, VT 05142

  Situated on the bank of the Black River at the edge of the Village Of Proctorsville is this three bedroom all ensuite, 5 bath log home. The Great Room boasts a floor to cathedral ceiling wood burning fireplace where you can sit and relax after a day on the slopes. Then take in river views from the formal dining room. Also on the first floor is a primary ensuite. Upstairs the huge lofted area is

  Frank Provance Diamond Realty

  1104 Main St, Cavendish, VT 05142
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  /48

  $1,275,000 Open Sat 10:30AM - 12PM

  • 4 Beds
  • 3 Baths
  • 3,796 Sq Ft

  204 High Ridge Rd, Brownsville, VT 05037

  This hidden gem is one of the best kept secrets in West Windsor. Sited at the end of a private road with rolling green lawns, and a tree top view of Mount Ascutney, this lovingly stewarded home was impeccably constructed and orchestrated with flowing wide open, bright spaces. The perfect home for full or part time living, and entertaining. The living room is anchored by a painted brick Rumford

  Danny Kogut Williamson Group Sothebys Intl. Realty

  204 High Ridge Rd, Brownsville, VT 05037
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  /16

  $250,000

  • 5 Beds
  • 2 Baths
  • 1,728 Sq Ft

  101 Mount Vernon St, Springfield, VT 05156

  Built as a duplex, this and last owner have used it as a single family. Therefore there are no traditional figures for income and expenses. Easy to transform into the duplex for income by adding appliances to the upstairs apartment. This home has many upgrades including siding, windows, decks/railings/stairway (outside). Drive is paved and there looks to be room to replace the shed. Perfect

  Christine Lewis Brattleboro Area Realty

  101 Mount Vernon St, Springfield, VT 05156
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  /6

  $195,000

  • Land
  • 4.3 Acres
  • $45,349 per Acre

  51 Loveland Rd, Norwich, VT 05055

  Fantastic opportunity to build your dream home on this 4.3 -acre lot in Norwich, Vermont, complete with full architectural plans for the exact home the sellers were planning to build, as shown in the photos and renderings. The property has already undergone significant preparation, including completed building designs and preliminary plans for the water and septic system along with other

  Spenser Molloy Nexthome Modern Realty

  51 Loveland Rd, Norwich, VT 05055
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  /19

  $379,000

  • 2 Beds
  • 3 Baths
  • 1,494 Sq Ft

  1856 Quechee Main St Unit U7, Hartford, VT 05001

  Charming Barn Conversion in the Heart of Quechee Village!!Welcome to this beautifully reimagined barn on Main Street, now home to thoughtfully designed condominiums that blend rustic character with modern convenience. This spacious unit features two primary ensuite bedrooms, a third full bathroom, a versatile loft, and in-unit laundry for easy living. Exposed beams and soaring ceilings

  Megan Moseley Mint Real Estate Group

  1856 Quechee Main St Unit U7, Hartford, VT 05001
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  /2

  $450,000

  • Land
  • 119 Acres
  • $3,782 per Acre

  00 Bradley Hill Rd, Norwich, VT 05055

  Unusually large parcel of land in Norwich. 119 +/- ac with over 2500' of road frontage on delightful Bradley Hill Road. Close to town yet calm and quiet.

  Jane Darrach Martha E. Diebold/Hanover

  00 Bradley Hill Rd, Norwich, VT 05055
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  /14

  $249,000

  • Land
  • 27.1 Acres
  • $9,188 per Acre

  00 Albin Hill Rd, Braintree, VT 05060

  Imagine waking up to sweeping vistas of Vermont’s Green Mountains, surrounded by 27.1 acres of pure tranquility. This rare parcel offers the perfect canvas for your dream estate, luxury retreat, or off-the-grid sanctuary. Perched at an impressive 1,800 feet in elevation, the property offers stunning panoramic views and unparalleled privacy, while still being just minutes from amenities, shopping

  Will Spanos KW Vermont-Killington

  00 Albin Hill Rd, Braintree, VT 05060
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  /32

  $875,000

  • 3 Beds
  • 3.5 Baths
  • 3,592 Sq Ft

  233 Brothers Rd, Hartland, VT 05048

  The idyllic Hartland countryside is the setting for this handsome cape. A delightful three season porch is entered by way of the attached two car garage or directly by a lovely landscaped pathway. Once inside you will be greeted by a warm and inviting kitchen detailed with cherry cabinetry, the dining room with a bay window view of the gardens,a living room with fireplace, and a spacious

  Mary Mayhew Snyder Donegan Real Estate Group

  233 Brothers Rd, Hartland, VT 05048
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  /19

  $359,900

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  302 Davidson Hill Rd, Chester, VT 05143

  This Cozy cabin tucked away along the outskirts of Chester is sure to impress. With a brand new roof, heating system and more this is the perfect turn key retreat. The property features both open lawn and forest to explore, just up the road from snowmobiling and hiking trails this property has the ability to be your home base for all your favorite activities year around. Including close proximity

  Thaddeus Abare Barrett and Valley Associates Inc.

  302 Davidson Hill Rd, Chester, VT 05143
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  /21

  $150,000

  • Land
  • 3.6 Acres
  • $41,667 per Acre

  263 High Ridge Rd, Cavendish, VT 05142

  Good land has been hard to find lately. Good land with a view of Okemo even more so. This double lot has huge westerly views towards Okemo. The driveway is roughed in and the septic is designed and permitted for parcel #71. This lot has a septic design for a 3br home plus an additional allocation for a 1br apartment over the garage. You can combine the two and build a 4 bedroom home should you

  Joseph Karl William Raveis Real Estate Vermont Properties

  263 High Ridge Rd, Cavendish, VT 05142
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  /56

  $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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  /34

  $550,000

  • 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.

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

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

Showing Results 201 - 240, Page 6 of 14