Windsor County VT Homes for Sale

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  /37

  $375,000

  • 3 Beds
  • 1 Bath
  • 2,128 Sq Ft

  1057 Brockway Mills Rd, Springfield, VT 05156

  Conveniently located between Rockingham, Springfield, and Chester, this sweet 3-bedroom ranch sits on 1.5 +/- acres of mostly open, level land. The home has seen many recent upgrades, including fresh paint inside and out, beautifully refinished wood floors in select rooms, and new click-lock flooring in others. What was once attic space has been thoughtfully converted into additional finished

  Chelsea Richardson Barrett and Valley Associates Inc.

  1057 Brockway Mills Rd, Springfield, VT 05156
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  /53

  $850,000

  • 3 Beds
  • 3 Baths
  • 2,294 Sq Ft

  66 Scott's Landing, Ludlow, VT 05149

  Nestled among the trees in a serene country setting, this inviting home with walls of windows is filled with abundant natural light and offers the perfect balance of peaceful retreat and year-round recreation. Enjoy lake living with your own dock, with a dock slip, ideal for boating, relaxing, and taking in the tranquil surroundings. Located near Okemo Mountain Resort, this property is a true

  Katherine Burns William Raveis Real Estate Vermont Properties

  66 Scott's Landing, Ludlow, VT 05149
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  /51

  $1,649,000

  • 4 Beds
  • 3.5 Baths
  • 3,456 Sq Ft

  140 Echo View Dr, Ludlow, VT 05149

  Experience the perfect blend of luxury, comfort, and Vermont charm in this exceptional 3,456-square-foot home. Built with superior craftsmanship and meticulous attention to detail, this residence reflects a commitment to quality where every finish was carefully selected and thoughtfully executed. No detail was overlooked, with premium materials and high-end finishes throughout, creating a home

  Mendi Michael Engel & Völkers Okemo

  140 Echo View Dr, Ludlow, VT 05149
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  /23

  $95,000

  • 1 Bed
  • 1 Bath
  • 542 Sq Ft

  145 Main St Unit 308, Ludlow, VT 05149

  Location, location! Enjoy convenient living in the heart of the Okemo Valley on the Okemo Mountain shuttle route. This top-floor one-bedroom condominium offers an ideal in-town location close to skiing, dining, shopping, and year-round recreation. The complex is known for easy ownership with association fees that include heat and hot water. An excellent opportunity at an attractive price point.

  Katherine Burns William Raveis Real Estate Vermont Properties

  145 Main St Unit 308, Ludlow, VT 05149
• 

  

  

  /56

  $455,000

  • 5 Beds
  • 1.5 Baths
  • 2,205 Sq Ft

  191 Route 100 N, Ludlow, VT 05149

  Nestled between Okemo Mountain and the lakes region, this inviting 5-bedroom home sits on 2 peaceful acres framed by mature trees and an expansive open yard. Filled with warmth and character, the home is a charming reminder of simpler times, offering large sun-filled rooms and generous gathering spaces throughout. At the heart of the home is the open kitchen and family room, where a cozy wood

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

  191 Route 100 N, Ludlow, VT 05149
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  /60

  $2,300,000

  • 6 Beds
  • 4.5 Baths
  • 8,656 Sq Ft

  55 Cherry Hill, Springfield, VT 05156

  Steeped in history and timeless elegance, this extraordinary circa-1860 Georgian Colonial estate offers over 8,000 square feet of refined living space where classic architecture meets remarkable craftsmanship. From the moment you enter, you are greeted by stunning period details including exquisite crown moldings, grand proportions, soaring ceilings, and beautifully preserved finishes that

  Joe Castaluccio Winhall Real Estate

  55 Cherry Hill, Springfield, VT 05156
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  /59

  $495,000

  • 4 Beds
  • 3.5 Baths
  • 3,356 Sq Ft

  990 Main St, Cavendish, VT 05142

  If you're looking for the ultime village ski house look no more! This four bedroom three and a half bath TURN KEY home is nestled in the village of Proctorsville. Home to Singletons Store, Outer Limits Brewery, Murdoch's On The Green and much more walking distance away. Step into this lovely well appointed home and you'll feel right at home. The kitchen boasts granite counters with a large

  Frank Provance Diamond Realty

  990 Main St, Cavendish, VT 05142
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  /32

  $153,000

  • Land
  • 4.7 Acres
  • $32,553 per Acre

  250 Fenton Rd, Chester, VT 05143

  Welcome to a place where the sound of the river becomes part of your daily rhythm. This 4.7-acre parcel with an end-of-road location offers an extraordinary 1,400 feet of frontage on the Williams River, creating a private and tranquil retreat just five minutes from the quintessential Vermont charm of Chester Village. The land unfolds beautifully: wide, flat, sun-filled fields stretch toward the

  Rachel Febbie EXP Realty

  250 Fenton Rd, Chester, VT 05143
• 

  

  /10

  $115,000

  • Land
  • 2.58 Acres
  • $44,574 per Acre

  Lot 30 Cedar, Ludlow, VT 05149

  End of cul de sac 2.5 +/- acre lot on town sewer in well established neighborhood. Rare building lot opportunity on town sewer with close proximity to Okemo, the lakes region, golf, and village amenities.

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

  Lot 30 Cedar, Ludlow, VT 05149
• 

  

  /19

  $195,000

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,338 Sq Ft

  16 Harlow Rd, Springfield, VT 05156

  Perfect location, nice neighborhood, near the hospital, downtown and minutes to the interstate! Featuring a first floor bed and 3/4 bath, it is perfect for aging in place. Eat in kitchen/dining convenient for those who love to cook. And, the living room is huge. Sporting a front porch, a bit of a yard and extra parking in the back, there is plenty of room for gatherings. This home still has some

  Christine Lewis Brattleboro Area Realty

  16 Harlow Rd, Springfield, VT 05156
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  /8

  $375,000

  $24K PRICE DROP

  • Land
  • 22.1 Acres
  • $16,968 per Acre

  1985 Gee Hill Rd, Royalton, VT 05068

  This breathtaking parcel is ready for you to hit the ground running—literally. The driveway is in, the house site is cleared, and the sweeping mountain views are already on full display from ground level. Designed with a walk-out basement in mind, the layout is perfect for maximizing both light and landscape. Fully permitted for a 5-bedroom septic system, with a second 5-bedroom design underway

  Holly Hall Hall Collins Real Estate Group

  1985 Gee Hill Rd, Royalton, VT 05068
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  /33

  $695,000

  $55K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,285 Sq Ft

  47 Pleasant St, Woodstock, VT 05091

  Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space downstairs (which previously has been living spacce), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used

  John Snyder Snyder Donegan Real Estate Group

  47 Pleasant St, Woodstock, VT 05091
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  /41

  $5,150,000

  • 8 Beds
  • 7.5 Baths
  • 10,062 Sq Ft

  3800 Weston-Andover Rd, Andover, VT 05143

  Bringing generations together in a place that inspires connection, adventure, celebration, work and stewardship, Moosewalk Lane is a purpose built multigenerational family compound. Created over two decades and set on 384 private acres in Vermont's Green Mountains, Moosewalk Lane is offered fully furnished and equipped. Anchored by a 10,062 square foot timber frame home, guest house, writer's

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  3800 Weston-Andover Rd, Andover, VT 05143
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  /57

  $3,495,000

  $254K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 8,122 Sq Ft

  5685 Vermont 12, Barnard, VT 05031

  “HIGHLAND GLEN” – Rarely does a property capture the essence of Vermont as beautifully as Highland Glen. Set on twelve picturesque acres in the charming town of Barnard, this extraordinary estate blends timeless New England character with exceptional comfort, privacy, and recreation.Arrive by the iconic red barn and discover stunning gardens, apple orchard, meandering stone walls, flowing

  John Snyder Snyder Donegan Real Estate Group

  5685 Vermont 12, Barnard, VT 05031
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  /58

  $724,000

  $25K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,697 Sq Ft

  1641 W Hill Rd, Rochester, VT 05767

  Welcome to The Birches — a peaceful end-of-road retreat where serenity, privacy, and Vermont’s natural beauty come together. Surrounded by more than 7,000 acres of conserved national forest land, this exceptional property offers unmatched tranquility, abundant wildlife, and direct access to outdoor adventure in every season.Set in a quiet mountain setting, this thoughtfully designed

  Brandon Fowler RE/MAX North Professionals

  1641 W Hill Rd, Rochester, VT 05767
• 

  

  /19

  $250,000

  • 2 Beds
  • 1 Bath
  • 968 Sq Ft

  133 Colonial Dr Unit 403, White River Junction, VT 05001

  *OFFER DEADLINE - 5/26 AT 5PM* Welcome to Oak Knoll Condominiums in White River Junction, VT. This 2 bedroom, 1 bathroom condo has been well updated and is ready for its next owner. New flooring on both levels, new appliances, and a custom laundry closet. The furnace is under four years old and the hot water tank was replaced two years ago, so the big ticket items are already done. Come check out

  Devin Josler Black House Real Estate

  133 Colonial Dr Unit 403, White River Junction, VT 05001
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  /36

  $399,000

  $80K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,094 Sq Ft

  75 Naulahka Ln, Hartford, VT 05059

  This Quechee retreat feels like a tree house. Combining three lots provides a level of privacy that is becoming increasingly rare in the Upper Valley, and the vertical layout makes excellent use of that wooded backdrop.By placing the Great Room behind two large picture windows, the design creates a seamless visual transition between the interior and the forest canopy.With a bedroom and full bath

  Linda Hicks Quechee Lakes Real Estate Center

  75 Naulahka Ln, Hartford, VT 05059
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  /43

  $360,000

  • 4 Beds
  • 3 Baths
  • 2,180 Sq Ft

  879 E Ash Rd Unit 8, Plymouth, VT 05056

  Ledges 8 at Hawk Resort offers the ultimate Vermont mountain retreat, featuring sweeping westerly views and year-round recreation. This spacious 4-bedroom, 3-bath end-unit townhouse spans three levels and is filled with natural light throughout. After a day on the slopes or trails, relax by the striking stone fireplace or unwind on the deck while taking in the mountain scenery. Start and end each

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  879 E Ash Rd Unit 8, Plymouth, VT 05056
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  /45

  $599,999

  • 6 Beds
  • 5 Baths
  • 4,184 Sq Ft

  49 Pleasant St, Ludlow, VT 05149

  If you are a skier, this is your hop-on-the shuttle to Okemo location. If you want to park your car and walk to restaurants and shops, this is a great home base to scoot out from. If you want to generate rental income, this is a property that can allow you to have your cake and eat it too. An easy keeper, without a lot of landscape to take care of, this large residence has hardwood floors and

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  49 Pleasant St, Ludlow, VT 05149
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  /6

  $250,000

  • Land
  • 16 Acres
  • $15,625 per Acre

  13 Happy Hollow Rd, South Royalton, VT 05068

  White River frontage, high and dry house site offering pleasant view over Vermont Law School and level hay field.

  Dean Goulet Dunrovin Real Estate

  13 Happy Hollow Rd, South Royalton, VT 05068
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  /58

  $1,395,000

  $100K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,648 Sq Ft

  1522 Barnard Rd, Woodstock, VT 05091

  Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef’s kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add

  Keri Cole Williamson Group Sothebys Intl. Realty

  1522 Barnard Rd, Woodstock, VT 05091
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  /49

  $134,900

  $15K PRICE DROP

  • 2,361 Sq Ft

  110 Valley St, Springfield, VT 05156

  2 unit investment property features a 4 bedroom and a 2 bedroom unit. Both units are up down configurations. The first unit features decent kitchen with washer and dryer, living room, 3/4 bath, 2 first floor bedrooms and 2 upstairs bedrooms with a covered porch in the rear. The second unit has a living room, large kitchen with washer/dryer hookups, large 3/4 bath, deck, bedroom down, and a

  Steve Schoppmeyer BHG Masiello Brattleboro

  110 Valley St, Springfield, VT 05156
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  /27

  $285,000

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

  253 Old Quechee Rd Unit 5C, Hartford, VT 05001

  This classy and cozy two bedroom Mill Run condominium is beautifully decorated and has been well maintained by the owners since 2004. Sit by the woodstove and relax. Have cocktails on the deck and enjoy the outdoors. Tiled bathrooms, updated kitchen, washer/dryer and more have been added and improved to create a cozy well-equipped vacation spot.The second bedroom has been re-designed to have four

  Jackie Jameson Jameson Real Estate

  253 Old Quechee Rd Unit 5C, Hartford, VT 05001
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  /12

  $389,000

  • Land
  • 4.73 Acres
  • $82,241 per Acre

  5209 Willard Rd, Hartford, VT 05059

  A thoughtfully assembled 4.73-acre homesite in Quechee Lakes’ Upper Willard Road neighborhood. Created from two combined lots, this property offers uncommon scale, privacy, and flexibility in one of the area’s more established settings. The land has been carefully curated by the current owner to take advantage of the natural Vermont landscape, with a mix of wooded surroundings and potential

  Richard Higgerson Higgerson & Company

  5209 Willard Rd, Hartford, VT 05059
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  /36

  $510,000

  $25K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 4,933 Sq Ft

  2 Pine St, Windsor, VT 05089

  Come see and appreciate this recently rejuvenated and extraordinary home that includes 6 bedrooms and 4 bathrooms as well as a 2 car garage! Located just off the downtown village area, this unique property features historical charm and character with vintage woodwork, custom wood floors, high ceilings, spacious rooms and the nooks and crannies a classic home has to offer! Relax on the rear porch

  Susan Bellville Bellville Realty

  2 Pine St, Windsor, VT 05089
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  /37

  $475,000

  • 2,056 Sq Ft

  57 Pleasant St, Ludlow, VT 05149

  Located in the heart of the Village of Ludlow, this versatile multi-family property features three well-appointed apartments with excellent rental potential. The property includes a private one-bedroom unit tucked away at the rear of the home with an upper-level bedroom retreat, plus two spacious two-bedroom apartments offering comfortable living areas and functional layouts. Enjoy a prime

  Katherine Burns William Raveis Real Estate Vermont Properties

  57 Pleasant St, Ludlow, VT 05149
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  /38

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  847 Simonsville Rd, Andover, VT 05143

  Looking to find your own peaceful piece of the Vermont countryside? Look no further than this move in ready homestead on 51.2 rolling acres with twopaddocks already fenced and ready waiting for your animals. Also complete with two spacious sheds for animals or storage, and a chicken coop ready to house them. Established asparagus patch, garden plot,blueberry bushes, apple trees, and even

  Erin Kendall EXP Realty

  847 Simonsville Rd, Andover, VT 05143
• 

  

  /13

  $158,000

  • Land
  • 17,424 Sq Ft
  • $395,000 per Acre

  29 Mill St, Hartland, VT 05048

  Superb IN-town North Hartland building lot with charming VT. sugar house to use for storage or maple sugaring! Also enjoy Hartlands benefit of school choice for high school students! Don't miss this opportunity to build your new home in the 2026 building season. A very Nice .40+/- acre in town parcel situated just across from Currier recreation park in North Hartland, VT. This lot is mostly level

  Alex DeFelice The Clerkin Agency, P.C.

  29 Mill St, Hartland, VT 05048
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  /48

  $395,000

  • 2 Beds
  • 1 Bath
  • 680 Sq Ft

  38 Northshore Dr, Ludlow, VT 05149

  Lake Rescue Retreat.Embrace the lakeside lifestyle in this quintessential Vermont cottage on Lake Rescue. Nestled on a spacious lot, this property perfectly blends historic character with future opportunity. You can choose to use the existing structure as your ultimate summer escape, remodel it to your exact taste, or build your brand-new dream lakeside home from the ground up.A fully

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

  38 Northshore Dr, Ludlow, VT 05149
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  /59

  $2,395,000

  • 3 Beds
  • 5 Baths
  • 4,329 Sq Ft

  719 Walker Hill Rd, Barnard, VT 05068

  An exquisite, private retreat for artists, writers, nature-lovers, composers or simply as a quiet, serene getaway gathering house on 66 stunningly beautiful acres with stone walls, gardens, patios, open lawns, a beautiful swimming pond, in-ground heated saltwater pool with stone patio, and a breathtakingly beautiful outdoor screened pergola. The residence was constructed using reclaimed frames

  John Snyder Snyder Donegan Real Estate Group

  719 Walker Hill Rd, Barnard, VT 05068
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  /28

  $219,000

  • 1 Bed
  • 1 Bath
  • 744 Sq Ft

  16 Hemlock Ridge Dr Unit 101, White River Junction, VT 05001

  Charming 1-Bedroom Condo conveniently located just 3 miles to Dartmouth College and surrounding area with easy interstate access as well. This inviting one bedroom condo at the Barn at Hemlock Ridge offers the perfect blend of comfort and utility. The layout features an additional versatile room ideal for a dedicated home office or study space. Association dues cover both heat and hot water.

  Dorothy Griswold The Clerkin Agency, P.C.

  16 Hemlock Ridge Dr Unit 101, White River Junction, VT 05001
• 

  

  /17

  $225,000

  • Land
  • 27.2 Acres
  • $8,272 per Acre

  0 E Hill Rd, Andover, VT 05143

  Nestled in the heart of Vermont’s scenic countryside, this beautiful 27.2-acre parcel offers the perfect setting to build your dream home or mountain retreat. Mostly wooded with over 800 feet of road frontage, the property combines privacy, natural beauty, and easy access to some of Southern Vermont’s most desirable destinations.Enjoy mountain and scenic views that provide ideal building

  Gary Coger Four Seasons Sotheby's Int'l Realty

  0 E Hill Rd, Andover, VT 05143
• 

  

  /19

  $529,000

  $50K PRICE DROP

  • Land
  • 60.57 Acres
  • $8,734 per Acre

  0 Noah Wood Rd, Woodstock, VT 05071

  Incredible location! 60+ acres situated on the corner of South Rd. (106) and Noah Wood Rd. in beautiful South Woodstock. The land rises from the roads to the crest of the hilltop with amazing view potential looking to the Northeast. Multiple building sites can be found throughout the property which offers great recreational opportunities including direct access to the VAST trail on the lower

  Dan Noble Snyder Donegan Real Estate Group

  0 Noah Wood Rd, Woodstock, VT 05071
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  /39

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 3,308 Sq Ft

  76 Goldthwaite Rd, Chester, VT 05143

  Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting

  Gary Coger Four Seasons Sotheby's Int'l Realty

  76 Goldthwaite Rd, Chester, VT 05143
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  /39

  $649,000

  $46K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,288 Sq Ft

  11 Maple St, Woodstock, VT 05091

  A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is conveniently nearby! For children in Maple Street's Neighborhood, Woodstock Elementary School is just a short walk away. Currently the residence is configured as home to 2 generations of occupants. A ground floor apartment conveniently

  John Wetmore Wetmore Real Estate

  11 Maple St, Woodstock, VT 05091
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  /9

  $300,000

  • Land
  • 9.8 Acres
  • $30,612 per Acre

  00 Stagecoach Rd, Norwich, VT 05055

  Discover peace and privacy on this 9-acre wooded lot situated near the end of a quiet private road. This natural haven offers excellent seclusion while remaining just 10 minutes from town amenities. With a mix of hardwood and softwood, the property features a significant stand of hemlock and oak —potentially providing enough timber to build your own custom timber-frame home right from the

  Linda White EXP Realty

  00 Stagecoach Rd, Norwich, VT 05055
• 

  

  /43

  $1,299,000

  • 4 Beds
  • 3 Baths
  • 4,372 Sq Ft

  278 Lawrence Hill Rd, Weston, VT 05161

  OPEN HOUSE Saturday 6/13 12 - 2 PM!! Set in the heart of Vermont’s four season playground, this impeccably maintained 4 bedroom, 3 bath home with a private swimming pond offers the perfect balance of comfort, space and outdoor living. Thoughtfully built by the previous owners and meticulously maintained by the current owners, the property reflects care, pride, and attention to detail, with many

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  278 Lawrence Hill Rd, Weston, VT 05161
• 

  

  /40

  $479,000

  $21K PRICE DROP

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

  7429 US Route 4, Bridgewater, VT 05034

  THE SUGAR HOUSE — Beautifully renovated in 2007, this light-filled Vermont home is ideally located in the heart of historic Bridgewater, just 10 minutes from the charm, dining, and culture of the village of Woodstock. Offering the perfect balance of four-season recreation and classic New England character, the property is equally suited as a primary residence, weekend retreat, or investment

  Keri Cole Williamson Group Sothebys Intl. Realty

  7429 US Route 4, Bridgewater, VT 05034
• 

  

  /53

  $1,490,000

  $200K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 5,400 Sq Ft

  1302 Popple Dungeon Rd, Chester, VT 05143

  Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. Owned by one family and designed and built by its owner, the Williamsburg style reproduction Saltbox reflects a deep appreciation for traditional craftsmanship and enduring design.Inside, the home is defined by warm, handcrafted details wide plank wood floors, paneled walls,

  Gary Coger Four Seasons Sotheby's Int'l Realty

  1302 Popple Dungeon Rd, Chester, VT 05143
• 

  

  /56

  $724,500

  $26K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  228 Leonard Rd, Sharon, VT 05065

  Welcome home to this serene piece of Vermont paradise! The property offers an escape to a privately sited cape home featuring 3 bedrooms, 2.5 bathrooms with covered and open outdoor entertaining spaces both overlooking an exclusively-owned, spring-fed, swimming pond and long range pasture views - all enveloped by mixed forest land of hard- and softwoods. Inside the home gleaming hardwood floors

  Terry Davis Williamson Group Sothebys Intl. Realty

  228 Leonard Rd, Sharon, VT 05065

Showing Results 161 - 200, Page 5 of 13