Windsor County VT Homes for Sale

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  /60

  $880,000

  • 3 Beds
  • 3 Baths
  • 3,000 Sq Ft

  330 Spruce Dr, Andover, VT 05143

  Mountain View Timber Frame Retreat on 25+ Acres in Andover – This exceptional timber-frame home is true perfection and offers long-range mountain views, sunny southeastern exposure, and complete privacy and access to everything that makes you want to call Vermont home. The authentic post-and-beam retreat blends timeless craftsmanship with modern comfort and is offered fully furnished, making it

  Claudia Harris Mary Mitchell Miller Real Estate

  330 Spruce Dr, Andover, VT 05143
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  /60

  $299,000

  • 2 Beds
  • 1 Bath
  • 1,152 Sq Ft

  466 Estey Ln, Windsor, VT 05089

  Embrace the ultimate Vermont lifestyle with this 1950s ranch, perfectly situated on 6.8 sprawling acres of versatile land at 466 Esty Lane in Windsor. Combining nostalgic mid-century charm with extraordinary future potential, this property is an absolute dream for investors, developers, or anyone looking to build their ideal country homestead. The existing home offers 1,152 square feet of

  Francis Duffy

  466 Estey Ln, Windsor, VT 05089
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  /35

  $530,000

  $31K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,207 Sq Ft

  807 Murphys Rd Unit 4C, Quechee, VT 05059

  Welcome to a bright and serene retreat in Fairway Village, a highly sought-after enclave within the Quechee Lakes Community. This exceptional 3-bedroom condominium offers a rare combination of scenic tranquility and immediate access to resort-style amenities. The deck off the Living room is a great spot for entertaining or just relaxing. A first floor primary bedroom and full bath and on the

  Linda Hicks Quechee Lakes Real Estate Center

  807 Murphys Rd Unit 4C, Quechee, VT 05059
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  /58

  $579,000

  • 3 Beds
  • 2 Baths
  • 1,924 Sq Ft

  530 West Rd, Barnard, VT 05031

  Set just up West Road in Barnard, this inviting Cape-style home offers a classic Vermont setting: a peaceful wooded backdrop, warm interior character, and easy access to village life, Silver Lake, and the outdoors. The Barnard General Store and Silver Lake, with the town hall, town library, and newly constructed fire station, are nearby. West Road also serves as a way to head toward the

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  530 West Rd, Barnard, VT 05031
• 

  

  

  /31

  $465,000

  • 2 Beds
  • 3 Baths
  • 2,268 Sq Ft

  121 20 Townhouse Way, Woodstock, VT 05091

  Spacious, immaculate, and beautifully maintained Federal-style brick townhouse located in the prestigious village of Woodstock, often recognized as one of America’s most beautiful small towns. Three finished levels, the larger size residence of 24 homes. Surrounded by mature woods, perennial gardens, & maple trees. A peaceful setting just minutes from Woodstock Village. The Woodstock Farmers’

  Dorothea Mongulla High End Realty

  121 20 Townhouse Way, Woodstock, VT 05091
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  /24

  $425,000

  • 3 Beds
  • 1 Bath
  • 1,239 Sq Ft

  10 W Hill St, Ludlow, VT 05149

  Opportunities like this are rare. Tucked into one of the most desirable locations near Okemo Mountain, this property offers exceptional access to year-round recreation, dining, shopping, and entertainment while avoiding the congestion of the main Access Road. Just under a half mile away, Witalec Road provides a convenient cut-through directly to the Access Road and mountain parking, helping you

  Mendi Michael Engel & Völkers Okemo

  10 W Hill St, Ludlow, VT 05149
• 

  

  /12

  $699,000

  • Land
  • 52.3 Acres
  • $13,365 per Acre

  00 Granite Ledge, Pomfret, VT 05059

  Pristine Pomfret land with views of Mount Ascutney. Build your dream home on this exceptional parcel in one of Pomfret’s most scenic and well-preserved settings. Surrounded by large landholdings and conserved farmland, yet just 10 minutes from Woodstock with easy access to Quechee and Route 4, this property offers a rare combination of privacy and convenience. Historic stone walls, mature

  Keri Cole Williamson Group Sothebys Intl. Realty

  00 Granite Ledge, Pomfret, VT 05059
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  /43

  $309,000

  • 3 Beds
  • 2.5 Baths
  • 2,174 Sq Ft

  147 Park St, Springfield, VT 05156

  Welcome to 147 Park Street! Situated on a 0.31-acre lot with a fully fenced yard, perennial flower gardens, and attractive landscaping, this home offers plenty of space both inside and out.Full of character and style, this spacious home features a thoughtful floor plan designed for everyday living. The large kitchen includes updated appliances, a generous dining area, and plenty of room for

  Mary Paino Coldwell Banker LIFESTYLES - Quechee

  147 Park St, Springfield, VT 05156
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  /59

  $4,999,000

  • 5 Beds
  • 4.5 Baths
  • 9,170 Sq Ft

  62 Moon Shadow Dr, Ludlow, VT 05149

  Welcome to one of Okemo’s most distinctive properites, an iconic SKI-ON, SKI-OFF Tennessee log-style home set directly on the Moon Shadow ski trail within Solitude Village. This home offers the ultimate slopeside lifestyle with panoramic mountain views stretching across the Okemo Valley. Crafted with authentic log construction, showcasing broad hewn timbers, wide chinking, reclaimed wood floors,

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  62 Moon Shadow Dr, Ludlow, VT 05149
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  /30

  $3,500,000

  • 4 Beds
  • 3 Baths
  • 2,571 Sq Ft

  58 Lakeshore Dr, Ludlow, VT 05149

  One-of-a-kind Lake Rescue sanctuary with 179 feet of shoreline, stone walls, perennial gardens, apple trees, and a sprawling flat lawn perfect for games and gatherings. Offering exceptional flexibility, this special setting on 4.35 acres has the potential to become a family compound, multi-generational retreat, or income-producing investment. A 3-bedroom septic permit is already in place,

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  58 Lakeshore Dr, Ludlow, VT 05149
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  /4

  $169,000

  • Land
  • 15.4 Acres
  • $10,974 per Acre

  0 Iver Johnson Way Unit 5095630, Woodstock, VT 05091

  Instant equity in Woodstock! Bring your vision to life on this exceptional parcel of raw land, nestled in one of Vermont’s most coveted and quintessential communities. Offered below its current town-assessed value and backed by a recent independent appraisal valuation, this property delivers significant instant equity from day one. Whether you envision a private, tucked-away country estate or a

  Chelsea Bevis KW Vermont Woodstock

  0 Iver Johnson Way Unit 5095630, Woodstock, VT 05091
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  /56

  $3,650,000

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

  348 Turtle Hill Rd, Ludlow, VT 05149

  Set high with vistas of southern Vermont's valleys and mountains, "The Barn" is a remarkable custom timber frame retreat where exceptional craftsmanship meets breathtaking natural beauty. Completed in 2023 after two years of thoughtful design and construction, this residence was created to be a place of gathering, connection, and lasting memories for generations to come.Privately situated on

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  348 Turtle Hill Rd, Ludlow, VT 05149
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  /60

  $2,225,000

  • 4 Beds
  • 3 Baths
  • 3,867 Sq Ft

  473 Kendall Rd, Woodstock, VT 05091

  Nestled in amongst flowering lilacs, ancient apple trees, and terraced English perennial gardens, this lovingly restored classic antique stone cape has all the conveniences of modern living, while honoring and preserving the charming period detail. Built in 1860, the home is an impressive example of snecked ashlar stone construction, which was introduced to this region by Scottish immigrants in

  Danny Kogut Williamson Group Sothebys Intl. Realty

  473 Kendall Rd, Woodstock, VT 05091
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  /58

  $475,000

  • 5 Beds
  • 4 Baths
  • 3,865 Sq Ft

  81 Main St, Chester, VT 05143

  Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning

  Betsy Adamovich Real Broker LLC

  81 Main St, Chester, VT 05143
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  /58

  $795,000

  • 3 Beds
  • 2.5 Baths
  • 2,416 Sq Ft

  934 Heald Rd, Proctorsville, VT 05153

  Enjoy the best of Vermont living in this recently built 3-bedroom, 2.5 -bathroom country home in Cavendish. Designed with comfort and functionality in mind, this home welcomes you through a convenient mudroom with storage—perfect for all your year-round gear. Step into the open-concept living area featuring vaulted ceilings, a wood-burning fireplace, and a seamless flow between the kitchen,

  Joseph Karl William Raveis Real Estate Vermont Properties

  934 Heald Rd, Proctorsville, VT 05153
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  /60

  $1,350,000

  • 4 Beds
  • 3 Baths
  • 2,311 Sq Ft

  323 Turnpike Rd, Norwich, VT 05055

  Where to begin, this property has so many special facets: Antique Cape that has been sensitively updated consistent with the style of the house; a guest house (Cape) built in 2004; an amazing renovated barn ready to host gatherings of all sorts and plenty of storage under the main level;stonewalls, stone patio, raised stone patio, fenced garden space, large openlawn area at the back of

  Berna Rexford Four Seasons Sotheby's Int'l Realty

  323 Turnpike Rd, Norwich, VT 05055
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  /37

  $685,000

  • 4 Beds
  • 3 Baths
  • 2,428 Sq Ft

  1834 Tyson Rd, Reading, VT 05062

  Nestled in the heart of the Vermont countryside, this charming stone and clapboard home offers the perfect blend of classic New England character and modern comfort. Set on an expansive 37-acre parcel, the property provides exceptional privacy, open space, and endless opportunities for recreation or relaxation.The home features 4 spacious bedrooms and 3 well-appointed bathrooms, with warm

  Daniel Preston KW Vermont Woodstock

  1834 Tyson Rd, Reading, VT 05062
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  /34

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,626 Sq Ft

  3208 Green Mountain Turnpike, Chester, VT 05143

  Located in the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 home combines modern minimalist style with artisan craftsmanship. Set on .33± acres, this light-filled property features wide-pine floors, exposed beams, and a Vermont Castings woodstove anchoring an inviting open-concept living space. The kitchen/dining area showcases country cabinets with

  Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  3208 Green Mountain Turnpike, Chester, VT 05143
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  /60

  $2,250,000

  • 4 Beds
  • 3.5 Baths
  • 5,079 Sq Ft

  254 Town Line Rd, Plymouth, VT 05056

  Town Line Estate is a once-in-a-generation offering. This extraordinary 22-acre private estate is a testament to master builder craftsmanship and refined living. From the moment you arrive, every detail speaks to an uncompromising standard — classic beams, rich cherry cabinetry, and two Rumford fireplaces create warmth and character throughout. The heart of the home is a restaurant-quality

  Kevin Barnes William Raveis Real Estate Vermont Properties

  254 Town Line Rd, Plymouth, VT 05056
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  /13

  $215,000

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft

  122 Quechee Hollow Ln Unit 4E, Hartford, VT 05059

  Welcome to easy living in Quechee Lakes! This charming 2-bedroom condo offers a cozy, traditional style that feels warm and inviting from the moment you arrive. Neat, tidy, and well-maintained, it's the perfect retreat for year-round enjoyment or a convenient getaway. As part of the Quechee Lakes community, you'll have access to an outstanding array of amenities, including championship golf,

  Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

  122 Quechee Hollow Ln Unit 4E, Hartford, VT 05059
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  /51

  $595,000

  • 2 Beds
  • 2 Baths
  • 1,771 Sq Ft

  106 Scott Terrace, Plymouth, VT 05149

  Beautifully updated cape in the Okemo lakes region with shared lake frontage on Echo Lake. An inviting walkway from the driveway to the wrap around deck and entry leads to an open living design that embraces entertaining and lake living. Wood floors accentuate the wonderful main level spaces including living room, sitting room, dining room, and updated kitchen and bath. Kitchen updates include

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

  106 Scott Terrace, Plymouth, VT 05149
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  /48

  $319,000

  • 4 Beds
  • 3 Baths
  • 3,548 Sq Ft

  16 Furnace St, Springfield, VT 05156

  Wonderfully renovated home with incredible income potential! This property features a fully updated, separate entrance 1-bedroom, 1-bathroom unit with its own electrical meter (shared baseboard heat between both sides). Market data suggests similar units in the area can command around $750/month in rent. For an owner-occupant, leveraging this 1-bed unit could significantly lower your net monthly

  Franchesca Collins Hall Collins Real Estate Group

  16 Furnace St, Springfield, VT 05156
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  /50

  $1,399,000

  $49K PRICE INCREASE

  • 4 Beds
  • 3.5 Baths
  • 4,000 Sq Ft

  145 the Plateau, Windsor, VT 05089

  "The Plateau", originally part of the Kennedy Biscuit Co. (Nabisco) family estate, is nestled on a plateau at the end of a private road which greets you with open fields, mature trees, beautiful gardens, and a protected front-and-center view of Mt. Ascutney to the West and the Connecticut River to the East. This private peaceful setting includes an inground pool for those hot summer days, and two

  Dan Noble Snyder Donegan Real Estate Group

  145 the Plateau, Windsor, VT 05089
• 

  

  /22

  $650,000

  • 3 Beds
  • 3.5 Baths
  • 2,674 Sq Ft

  5863 Vermont Route 14, Royalton, VT 05068

  Dunrovin Manor is located at probably the most active area intersection, just off Exit 3, Royalton, Vt. Overlooking both the White River and Second Branch, this attractive older home is convenient to Vermont Law School and the quaint village of S. Royalton. Let the tenants pay your mortgage, while you livie in the main central area and open up the attached two apartments. Owner/Broker has

  Dean Goulet Dunrovin Real Estate

  5863 Vermont Route 14, Royalton, VT 05068
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  /53

  $675,000

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

  46 Davenport Ln, Hartford, VT 05047

  Welcome to this immaculate and lovingly maintained Quechee Lakes home, where comfort, privacy, and beautiful southern views come together in a truly special setting.Gorgeously landscaped with easy-care perennials, the outdoor spaces are designed to be enjoyed throughout the seasons. A generous stone patio and attractive stone wall provide the perfect backdrop for morning coffee, relaxing

  Mary Paino Coldwell Banker LIFESTYLES - Quechee

  46 Davenport Ln, Hartford, VT 05047
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  /58

  $2,950,000

  • 8 Beds
  • 8 Baths
  • 6,200 Sq Ft

  5798 South Rd, Woodstock, VT 05071

  Kedron Valley Farm c1850: A classic beauty, perched on a knoll overlooking the idyllic hills and lush meadows of the valley with approx 32 acres. This stunning extended antique post and beam cape is complete with a large traditional 4 story barn with 6 horse stables and equipment sheds offers everything one could wish for in a country property. The grounds include gracious old maples, beautiful

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  5798 South Rd, Woodstock, VT 05071
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  /40

  $325,000

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,474 Sq Ft

  58 Reservoir Rd, Springfield, VT 05156

  Move-in ready and lovingly maintained, this charming Cape-style home offers 3 bedrooms, an office/laundry room, 1 full bathroom, a spacious eat-in kitchen, a 2-car garage, and a large back deck perfect for relaxing or entertaining. The backyard abuts the Springfield Dam, providing beautiful views of Hawks Mountain and Mount Ascutney while offering close access to nearby nature preserves and

  Chelsea Richardson Barrett and Valley Associates Inc.

  58 Reservoir Rd, Springfield, VT 05156
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  /52

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,308 Sq Ft

  366 Crimson Hawk Rd Unit S1-24, Plymouth, VT 05056

  Tucked within the Hawk community, this charming mountain retreat offers the perfect blend of privacy, recreation, and convenience. Set within a private 1.09-acre wooded lot, owners are also able to enjoy access to Hawk's common land with room to explore, including trails ideal for snowshoeing, hiking, and cross-country skiing. Perfectly positioned between Killington and Okemo Mountain, and just

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  366 Crimson Hawk Rd Unit S1-24, Plymouth, VT 05056
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  /20

  $85,000

  • Land
  • 3.99 Acres
  • $21,303 per Acre

  00 Simonsville Rd, Andover, VT 05143

  ANDOVER 3.99 Acres on the Williams River that was once a part of the Historic Jaquith Homestead. Walk the old mowing road that winds through the property, leading to three meadow areas along the river. The central meadow has a designated home site for a 4 bedroom state approved septic. The owners have just had the house location resighted to make sure it is out of the flood zone. A great spot for

  Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  00 Simonsville Rd, Andover, VT 05143
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  /60

  $1,150,000

  $50K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,352 Sq Ft

  884 Bridgewater Center Rd, Bridgewater Corners, VT 05035

  Tucked on 13.68 private acres near the north branch of the Ottauquechee River, this one-owner Bridgewater estate was built from the ground up with uncommon care — and it shows in every detail. With 4,300 square feet of living space (6,700 total), the home is heated by radiant flooring throughout and served by a new furnace/boiler, a private septic system, and a private well known for its

  Tucker Adirondack Lange Lange & Lange

  884 Bridgewater Center Rd, Bridgewater Corners, VT 05035
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  /46

  $965,000

  • 3 Beds
  • 2.5 Baths
  • 2,638 Sq Ft

  358 Cowdrey Path, South Woodstock, VT 05071

  This beautifully renovated, truly move-in-ready home has been thoughtfully updated throughout — including a brand-new kitchen, refreshed flooring, modernized bathrooms, fresh interior paint, a new garage door, an automatic full-house generator, and more. The property is offered FULLY TURNKEY, with nearly all furniture and furnishings conveying with the sale (artwork excluded). Privately sited in

  John Snyder Snyder Donegan Real Estate Group

  358 Cowdrey Path, South Woodstock, VT 05071
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  /14

  $87,500

  • Land
  • 10.4 Acres
  • $8,413 per Acre

  00 Snell Rd, Chester, VT 05143

  CHESTER 10.4+/- acre parcel of land offers offers 180 degree ridgeline views with clearing from an elevated plateau for either a house site or a camp site with a home closer to the town maintained road. A nice stream meanders through the property which is dotted with large rocks and stone walls. There is 245 ft. of frontage on Snell Road and utility pole at the road. Close to Okemo and Magic

  Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  00 Snell Rd, Chester, VT 05143
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  /24

  $365,000

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft

  500 Chandler Rd, Hartford, VT 05001

  Charming and full of potential, this adorable 3-bedroom home offers comfortable living inside and out! The main level features an inviting eat-in kitchen, a wonderful living room, and three bedrooms, providing convenient one-level living. Downstairs, you'll find a spacious family room with daylight windows, a 3/4 bath, and a dedicated laundry room, creating the perfect space for relaxing,

  Jenna Luce RE/MAX Upper Valley

  500 Chandler Rd, Hartford, VT 05001
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  /32

  $379,000

  $16K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 884 Sq Ft

  145 Okemo Trailside Extension Unit 23 B-L, Ludlow, VT 05149

  Recently updated large one-bedroom condominium at Trailside Village within easy walking distance to ski on / ski off access to the Sachem Trail.The open kitchen flows seamlessly into a separate dining area, creating a comfortable space for everyday living or entertaining. A sunken living room features a newly replaced wood-burning fireplace and new carpeting, offering a warm and inviting

  McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

  145 Okemo Trailside Extension Unit 23 B-L, Ludlow, VT 05149
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  /46

  $589,000

  • 4 Beds
  • 2 Baths
  • 2,528 Sq Ft

  164 Pine View Ln, Cavendish, VT 05142

  This beautiful, spacious country home is just four miles from Okemo Mountain. Privately sited on more than an acre, it’s perfect for primary or vacation living. Sleeps 12+, close to town but a world away. The open meadow is a safe place for dogs and everyone to play. Enjoy the 8ft deep x 40ft farmers porch, deck, patio and fire ring. The private setting includes only two other homes and two other

  Jason Saphire www.HomeZu.com

  164 Pine View Ln, Cavendish, VT 05142
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  /36

  $75,000

  • 1 Bed
  • 1 Bath
  • 342 Sq Ft

  111 Acton Place, Royalton, VT 05068

  Delightful and well maintained, this charming home sits on a secluded, quiet lot offering comfort, privacy and easy living. Start your mornings on the covered porch with a cup of coffee while listening to the birds sing. Even on rainy days, the extended overhang provides plenty of shelter, so you can stay dry and enjoy the fresh air. The yard welcomes you to cultivate a green thumb with garden

  Amanda Gravel Birch and Maple Realty

  111 Acton Place, Royalton, VT 05068
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  /52

  $724,900

  $25K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 2,049 Sq Ft

  65 Steele Hill Rd, Weathersfield, VT 05030

  Nestled among mature trees with sweeping mountain views, this beautifully maintained 2-bedroom, 3 bath Cape is the perfect blend of classic New England character and modern convenience. From the moment you arrive, the lush, professionally landscaped grounds set the tone featuring ornamental plantings, natural boulder accents, a fire pit area, and manicured gardens that provide year-round curb

  Katie Ladue Gilbert BHHS Verani Upper Valley

  65 Steele Hill Rd, Weathersfield, VT 05030
• 

  

  /22

  $85,000

  • Land
  • 5 Acres
  • $17,000 per Acre

  0 Linden Way Unit 5093908, Chester, VT 05143

  Privacy doesn't have to mean isolation!!Wooded acreage, village convenience, and modern connectivity are rarely found in the same package. This newly approved 5 acre parcel in Chester, Vermont offers a private setting surrounded by mature forest while remaining just minutes from the historic village center. Accessed via a private right-of-way, the property provides a peaceful location for a

  Daire Gibney Barrett and Valley Associates Inc.

  0 Linden Way Unit 5093908, Chester, VT 05143
• 

  

  /60

  $770,000

  • 4 Beds
  • 3 Baths
  • 2,811 Sq Ft

  624 Baker Turn Rd Unit N/A, Hartford, VT 05059

  Experience the charm and beauty of Vermont living in this meticulously maintained, single-owner home nestled within the sought-after Quechee Lakes community off Baker Turn Road.Property Highlights:Wonderful screened on porch for those rainy or buggy nights. 4 bedrooms with potential for a 5th bedroom and/or main-level primary suite.Spacious layout — ideal for entertaining family and

  Lyndsey Freeman Quechee Lakes Real Estate Center

  624 Baker Turn Rd Unit N/A, Hartford, VT 05059
• 

  

  /40

  $1,400,000

  • Land
  • 250.7 Acres
  • $5,584 per Acre

  00 Route 100, Plymouth, VT 05056

  Imagine owning 250 acres of unspoiled land in Vermont's coveted Lake Region, featuring five separate access points to the crystal-clear waters of Echo Lake. Whether you're envisioning a private family retreat, a recreational paradise, a conservation property, or a future development opportunity, this remarkable offering offers endless possibilities. Miles of established trails wind through the

  Kevin Barnes William Raveis Real Estate Vermont Properties

  00 Route 100, Plymouth, VT 05056

Showing Results 81 - 120, Page 3 of 13