Windsor County VT Homes for Sale

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  /33

  $525,000

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

  17 Vermont 12, Hartland, VT 05048

  1850 home re-furbished top to bottom for modern amenities with antique charm. New roof, floors, kitchen, bathrooms, windows, electrical, plumbing, and heating throughout. Very large flat yard located right downtown.

  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
  • 1,170 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
  • 2,948 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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  /26

  $312,000

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  130 Bryant Rd, Bethel, VT 05032

  This 3 bedroom, 2 bath mfg. home is located on a picturesque 9.9 acre lot and is absolutely stunning. It offers level fields, a bit of woods and close to the VAST trail system. If you are thinking horses, farming or just convenience to central Vermont, this is your place. Only 1.7 miles of dirt rd. driving. There is a chicken coop/small animal shed and a small barn for extra storage or

  Rose Wright Vermont Heritage Real Estate

  130 Bryant Rd, Bethel, VT 05032
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  /60

  $200,000

  • Land
  • 7 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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  /34

  $475,000

  • 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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  /31

  $379,900

  • 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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  /18

  $239,500

  • 1 Bed
  • 1 Bath
  • 856 Sq Ft

  56 Heritage Condo Way Unit 9, Woodstock, VT 05091

  Lots of upgrades to this quiet, two level condo, with lovely views off back baloney. Bonus- new mini split heat pump providing both air conditioning and heat. Kitchen has some upgraded as well with a new dishwasher. This open floor concept condo provides lots of natural sunlight. Cozy up in the living room/dining room and read a book during the winter months overlooking the spacious

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  56 Heritage Condo Way Unit 9, Woodstock, VT 05091
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  /33

  $329,000

  • 3 Beds
  • 2 Baths
  • 864 Sq Ft

  1159 Ski Tow Rd, Brownsville, VT 05037

  Located near the end of a country cul-de-sac at Ascutney Mountain this Split entry has 3BR/2BA it is configured as two units with separate entries & 2 kitchens but has been used as a single-family home, as well. It has 2 nice brick fireplaces; one with a VT Castings woodstove insert, the other has a wood stove hook up. Recent updates include a new Rinnai direct vent propane heater, 2 Tesla Power

  Dana Waters Dark Horse Realty

  1159 Ski Tow Rd, Brownsville, VT 05037
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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
• 

  

  /37

  $549,000

  • 4 Beds
  • 2 Baths
  • 2,541 Sq Ft

  106 Vermont Route 100, Weston, VT 05161

  This historic property located on Weston Island, the original settlement of the village of Weston, was once home to the area's beloved country doctor. Rich in antique farmhouse allure, it has been thoughtfully updated for modern living. The first floor features a generous mudroom, a living room with wide plank floors and wood stove, and a den with built ins and a wood burning fireplace that could

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  106 Vermont Route 100, Weston, VT 05161
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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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  /31

  $68,500

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft

  434 Qtr. I V Jackson Gore Inn, Ludlow, VT 05149

  Jackson Gore Inn, Unit 434 QIV. 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

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

  434 Qtr. I V Jackson Gore Inn, Ludlow, VT 05149
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  /25

  $379,000

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

  78 Division St, Hartford, VT 05001

  Right in the heart of Wilder, this cozy home is near trails, water, public transportation and schools. Only a 15 minute drive to the Hanover Green or the Lebanon Green. The house has a generous boot room that flows into the kitchen then the living space. Several upgrades, including the hardwood staircase and railing, have added value to the interior. The back yard offers a nice shaded place to

  Josh Hunt Snyder Donegan Real Estate Group

  78 Division St, Hartford, VT 05001
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  /29

  $299,000

  • 5 Beds
  • 3.5 Baths
  • 3,465 Sq Ft

  600 N Windsor St, South Royalton, VT 05068

  Just 3⁄4 of a mile from the heart of South Royalton and Vermont Law School, this versatile property offers tremendous rental potential with some TLC. With three separate units—each with its own private entrance—this is the perfect opportunity to renovate and generate strong rental income. The main unit in the house has 3 bedrooms and 1 1/2 baths. The second unit in the main house is a 1 bed 1

  Franchesca Collins Hall Collins Real Estate Group

  600 N Windsor St, South Royalton, VT 05068
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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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  /8

  $169,000

  • 4 Beds
  • 1 Bath
  • 1,746 Sq Ft

  7 Berry Rd, Springfield, VT 05150

  Spacious Home in a Peaceful Setting – Finish to Your TasteTucked away in a quiet location, this large home offers a great opportunity for someone ready to roll up their sleeves and complete the work that’s already well underway. Many major updates have been started, and plenty of supplies are already on site and included with the sale—saving you time and money.What’s

  Linda Benoit Highland Realty

  7 Berry Rd, Springfield, VT 05150
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  /33

  $225,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  2579 Vermont Route 100, Plymouth, VT 05056

  Tucked among the trees in beautiful Plymouth, this rustic getaway offers a peaceful setting with easy access to outdoor recreation. This property offers unbeatable access to some of Vermont’s best recreation. Just a short drive to both Killington and Okemo for world-class skiing, and minutes from Echo Lake and Plymouth State Park, this is a four-season location ideal for outdoor lovers.The home

  Frank Provance Diamond Realty

  2579 Vermont Route 100, Plymouth, VT 05056
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  /34

  $250,000

  • 1 Bed
  • 1 Bath
  • 617 Sq Ft

  413 Hidden Heights Rd, Chester, VT 05143

  Until this last winter this was a really sweet 16 x 24 log cabin. Then it became fire damaged and now the owner would love to have someone bring it back to its former glory. Nice, private area on a town-maintained country road. All utilities are underground, including a 330-gallon propane tank, electric power from the street, and water from the 230' drilled well. The cabin has 1 bath, a

  Glenn Olney Barrett and Valley Associates Inc.

  413 Hidden Heights Rd, Chester, VT 05143
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  /32

  $80,000

  • 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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  /49

  $450,000

  • 4 Beds
  • 2 Baths
  • 2,040 Sq Ft

  281 Evergreen Terrace, Springfield, VT 05156

  This delightful home is sure to please. Set in a lovely wooded cul-de-sac, surround yourself with lovely, terraced landscaping, stone walls and a peaceful wooded setting to while away the hours. This beautiful well cared home features many delightful settings. The living room features a cathedral ceiling and stone fireplace, with a wood stove insert, along with many windows to bring in the

  Carol Cole BHG Masiello Brattleboro

  281 Evergreen Terrace, Springfield, VT 05156
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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

  $469,000

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

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

  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 from this top-level,

  Katie McFadden RE/MAX North Professionals

  1226 E Ash Rd Unit L-34, Plymouth, VT 05056
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  /58

  $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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  /23

  $175,000

  • 1 Bed
  • 1 Bath
  • 520 Sq Ft

  32 Pond St Unit 5, Ludlow, VT 05149

  Charming One-Bedroom Condo in the Heart of Ludlow VillageThis freshly updated condo offers the perfect opportunity to own in Ludlow, just moments from Main Street and the Okemo slopes. Enjoy easy access with a private covered porch entrance and the convenience of walking to local shops and restaurants or catching the Okemo Shuttle just steps away.Inside, you'll find a charming interior

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

  32 Pond St Unit 5, Ludlow, VT 05149
• 

  

  /15

  $130,000

  • 1 Bed
  • 1 Bath
  • 266 Sq Ft

  32 Pond St Unit 3, Ludlow, VT 05149

  Charming One-Bedroom Efficiency in the Heart of Ludlow VillageThis beautifully remodeled efficiency offers the perfect opportunity to own in Ludlow, just moments from Main Street and the Okemo slopes. Enjoy easy access with a private covered porch entrance and the convenience of walking to local shops and restaurants or catching the Okemo Shuttle just steps away.Inside, you'll find a

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

  32 Pond St Unit 3, Ludlow, VT 05149
• 

  

  /17

  $140,000

  • 1 Bed
  • 1 Bath
  • 266 Sq Ft

  32 Pond St Unit 1, Ludlow, VT 05149

  Charming One-Bedroom Efficiency in the Heart of Ludlow VillageThis beautifully remodeled ground-floor efficiency offers the perfect opportunity to own in Ludlow, just moments from Main Street and the Okemo slopes. Enjoy easy access with a private covered porch entrance and the convenience of walking to local shops and restaurants or catching the Okemo Shuttle just steps away.Inside,

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

  32 Pond St Unit 1, Ludlow, VT 05149
• 

  

  /22

  $275,000

  • 2 Beds
  • 2 Baths
  • 790 Sq Ft

  32 Pond St Unit 2, Ludlow, VT 05149

  This is a versatile remodeled and completely move-in ready condo. This two bedroom, two bath condominium is within walking distance to Main Street. The condo has an interior privacy door that can close off a bedroom with private bath and a kitchenette allowing both sides to be used/rented separately as two -1 bedrooms condos spaces. There are two exterior ski lockers and two parking spaces. This

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

  32 Pond St Unit 2, Ludlow, VT 05149
• 

  

  /35

  $189,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  134 Fellows Hill, Springfield, VT 05156

  Welcome to easy one-level living at this well-maintained 2-bedroom, 1-bath home on a half-acre lot in a convenient Springfield location. With low-maintenance vinyl siding and a durable metal roof, this home is built for simplicity and comfort. Step inside from the freshly painted back deck, where you'll find a functional layout perfect for first-time buyers or those looking to downsize. The

  Betsy Adamovich Real Broker LLC

  134 Fellows Hill, Springfield, VT 05156
• 

  

  /15

  $55,000

  • Land
  • 0.35 Acre
  • $157,143 per Acre

  150 Parker Ave, Proctorsville, VT 05153

  Tucked among mature maples and just a short drive from Ludlow and Chester,this classic New England barn offers a rare opportunity to own a piece of Vermont history. With its weathered wood siding, original beams, and classic gable roofline, the structure stands as a testament to traditional craftsmanship. Inside, exposed timber framing and a partial stone foundation highlight its old-world

  Frank Provance Diamond Realty

  150 Parker Ave, Proctorsville, VT 05153
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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
• 

  

  /60

  $240,000

  • 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
• 

  

  /34

  $375,000

  • 4 Beds
  • 2 Baths
  • 1,300 Sq Ft

  12 Meadow Dr, Springfield, VT 05156

  This delightful ranch home located in a desirable cul-de-sac neighborhood, is where you can enjoy a nice evening walk and chat with the neighbors. Enter from the front porch to the bright living room with a lovely fireplace and hardwood floors, to enjoy a fire on those cool evenings. The nice sized kitchen adjoins the lovely dining room which features easy access to the large screened-in porch,

  Carol Cole BHG Masiello Brattleboro

  12 Meadow Dr, Springfield, VT 05156
• 

  

  /34

  $275,000

  • 2 Beds
  • 1.5 Baths
  • 660 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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  /45

  $560,000

  • 9,740 Sq Ft

  2 Valley St, Springfield, VT 05156

  EXCELLENT INVESTMENT PROPERTY CONSISTS OF 2 COMMERCIAL GROUND FLOOR LEVEL SPACES & 7 APARTMENTS. WELL MAINTAINED WITH A GOOD RENTAL HISTORY & A DESIRABLE IN-TOWN LOCATION.

  Don Chabot Town and Country Realty

  2 Valley St, Springfield, VT 05156
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  /7

  $180,000

  • Land
  • 23 Acres
  • $7,725 per Acre

  1718 Brown Schoolhouse Rd, Reading, VT 05062

  Tucked away in the hills of Reading, this 23+ acre private paradise offers the perfect blend of seclusion and possibility. With 2 acres already cleared, the land is ideal for your future dream home, mountain getaway, or nature-rich homestead.Surrounded by forest, wildlife, and stunning seasonal beauty, this property invites hiking, snowshoeing, or quiet reflection right outside your door.

  Patrick Kelley Four Seasons Sotheby's Int'l Realty

  1718 Brown Schoolhouse Rd, Reading, VT 05062
• 

  

  /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
• 

  

  /57

  $2,190,000

  • 4 Beds
  • 3.5 Baths
  • 3,073 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
• 

  

  /30

  $480,000

  • 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
• 

  

  /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

Showing Results 81 - 120, Page 3 of 14