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Windsor County VT Homes for Sale

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  • /58

    $1,400,000

    • 6 Beds
    • 5 Baths
    • 4,571 Sq Ft

    505 Deweys Mills Rd, Hartford, VT 05047

    The Dewey House joins timeless elegance with contemporary convenience. Situated on a quiet road adjacent to the Quechee Gorge waterfall in the charming town of Quechee, this property offers easy access to I-89, I-91, and Route 4. Nearby walking trails and direct water access lend themselves to outdoor pursuits, while the views from the house and its decks over the mill pond and hills create the

    Agent Photo

    Jennifer Falvey

    KW Vermont Woodstock

    (877) 419-4767

    505 Deweys Mills Rd, Hartford, VT 05047
  • /4

    $160,000

    • Land
    • 6 Acres
    • $26,667 per Acre

    1901 Royalton Hill Rd, South Royalton, VT 05068

    Great opportunity to turn this private lot into your dream Vermont retreat. Just 10 minutes from the highway. Current owner has started some clearing and land prep.

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    Steve Swanson

    EXP Realty

    (802) 215-3062

    1901 Royalton Hill Rd, South Royalton, VT 05068
  • /43

    $425,000

    • 5 Beds
    • 2 Baths
    • 1,982 Sq Ft

    176 Meadow Rd, Chester, VT 05143

    The Best of Both Worlds: Modern Comfort Meets Village Charm!Discover the perfect blend of contemporary upgrades and serene neighborhood. This meticulously updated raised ranch offers an expansive layout designed for both effortless entertaining and comfortable daily living.Step inside to find a light-filled open-concept living and dining area, anchored by stunning hickory hardwood floors

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    Lauren Behm

    Berkshire Hathaway HomeServices Stratton Home

    (802) 416-3199

    176 Meadow Rd, Chester, VT 05143
  • /29

    $349,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    447 Elm St, Chester, VT 05143

    Welcome to your dream home – This meticulously maintained and efficient New England-style gem is bursting with charm and modern convenience. Extra insulation, new windows and new hot water heater make this home as energy-efficient as it is beautiful. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by

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    Lisa Kelley

    Cummings & Co

    (802) 200-2452

    447 Elm St, Chester, VT 05143
  • /2

    $169,000

    • 1,662 Sq Ft

    32 Reed St, Springfield, VT 05156

    Nice, neat 2-unit property with good rental history. Each unit has 2 bedrooms, 1 bath. Separate parking for both units and back yard for outdoor enjoyment. Property has been well maintained and could be converted into a one family if desired. Great income opportunity or great starter home if you are looking to get part of your mortgage paid by rental income.

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    Julie Buffum

    Buffum Realty

    (802) 471-3386

    32 Reed St, Springfield, VT 05156
  • /5

    $139,000

    • 2,144 Sq Ft

    73 Union St, Springfield, VT 05156

    Nice sized in-town home and yard with large 2 car garage and shed. Lots of room for your toys. The home is currently a 2-unit home but was originally a single-family home and could be changed back into a one family without a lot of effort. Home does need some work so cash buyers only please. This could be your chance to get into rental business. Lots of possibilities for this home.Home is

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    Julie Buffum

    Buffum Realty

    (802) 423-2965

    73 Union St, Springfield, VT 05156
  • /47

    $1,895,000

    • 3 Beds
    • 1 Bath
    • 1,708 Sq Ft

    196 Cowdrey Outlook, Bethel, VT 05032

    For the first time in over half a century, this extraordinary 100+ acre estate-level property in Barnard is being offered for sale. Cherished by the same family for generations, the property presents a rare opportunity to own one of Vermont’s most scenic and versatile landscapes. Commanding long-range mountain views define the setting, while several picturesque spring-fed ponds, rolling meadows,

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    Susan Hickey

    Snyder Donegan Real Estate Group

    (802) 284-4197

    196 Cowdrey Outlook, Bethel, VT 05032
  • /50

    $1,189,000

    • 5 Beds
    • 2.5 Baths
    • 2,662 Sq Ft

    63 Shiloh Ln, Norwich, VT 05055

    Tucked away on quiet Shiloh Lane in Norwich, VT, this exceptional 21.5-acre property offers a rare blend of privacy, usable land, and convenience—just minutes from Hanover and Dartmouth. The park-like setting features landscaped grounds, walking trails, garden areas, a greenhouse, a five-stall horse barn, and two potential pond sites—ideal for equestrian use, hobby farming, or enjoying Vermont’s

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    Melissa Robinson

    Coldwell Banker LIFESTYLES - Hanover

    (802) 200-2465

    63 Shiloh Ln, Norwich, VT 05055
  • /33

    $399,000

    • 3 Beds
    • 2 Baths
    • 2,446 Sq Ft

    158 MacIntosh Hill Rd, Randolph, VT 05060

    Charming 1820's antique farmhouse with handcrafted cabinets and wide board floors. The home has updated systems including Viessmann on demand water heater, holding tank, pressure tank, newer electrical. Fabulous upgraded bathroom. There is a space of many uses that could be a studio, master suite, in law/guest suite. Also the most lovely screened in back sitting porch overlooking the pastures.

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    Sherri McPhetres

    Vermont Heritage Real Estate

    (802) 499-2434

    158 MacIntosh Hill Rd, Randolph, VT 05060
  • /3

    $170,000

    • Land
    • 10.04 Acres
    • $16,932 per Acre

    00 Will Dean Rd, Springfield, VT 05156

    Nice piece of land with some selected clearing done but more could be done with the potential of views. Land is both clear and wooded, level and sloping. Located on a quiet gravel road with a mix of single-family homes and small farms it is the perfect reflection of rural Vermont. Just minutes to I91and downtown Springfield makes this a great spot to set down roots.

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    Julie Buffum

    Buffum Realty

    (802) 327-7566

    00 Will Dean Rd, Springfield, VT 05156
  • /17

    $239,000

    • 4 Beds
    • 2 Baths
    • 2,111 Sq Ft

    135 Wall St, Springfield, VT 05156

    Large, in town family home. Lots of room to spread out, 1st floor laundry, formal dining room, first floor bedroom, open second floor landing makes for a great space for a workspace, tv space or reading nook. All rooms are generous in size; large covered front porch makes for great place to hang out in rain or shine. Covered side entry into the home for convenience right off the driveway. Please

    Agent Photo

    Julie Buffum

    Buffum Realty

    (802) 613-9305

    135 Wall St, Springfield, VT 05156
  • /21

    $75,000

    • 1,440 Sq Ft

    178 Church St, Bethel, VT 05032

    Looking for a Summer Project? Put your ambition and skills to work in this unfinished, single-story 30' x 24'+ wood framed shell constructed with beefy rough-cut lumber. Electric service provided by Green Mountain Power (meter on building). Public water service to, and public sewage disposal from, are available on site. Currently, there is no electrical wiring, plumbing pipes, nor fixtures, but

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    Lori Holt

    BHHS Vermont Realty Group/Montpelier

    (802) 330-8205

    178 Church St, Bethel, VT 05032
  • /54

    $2,599,000

    • 9 Beds
    • 11 Baths
    • 5,993 Sq Ft

    41 Pleasant St, Woodstock, VT 05091

    This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont’s most beloved communities. Woodstock is often hailed as “the prettiest small town in America,” and for good reason. The village is a vibrant resort town with

    Agent Photo

    Jennifer Falvey

    KW Vermont Woodstock

    (802) 347-9544

    41 Pleasant St, Woodstock, VT 05091
  • /38

    $329,000

    • 2 Beds
    • 3.5 Baths
    • 1,984 Sq Ft

    974 Hard Rd Unit D6, Hartford, VT 05001

    This 2BR, 3.5BA end unit condo offers fantastic meadow views from the back deck, living room and dining room. Located in a private, quiet and serene country setting yet within close proximity to all Quechee Club and Upper Valley amenities. The condo has been lovingly cared for and updated throughout. It offers ample size with three separate levels of living space. Upstairs are two good size

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    Herb Hart

    Quechee Lakes Real Estate Center

    (802) 392-0255

    974 Hard Rd Unit D6, Hartford, VT 05001
  • /32

    $1,195,000

    • 3 Beds
    • 3.5 Baths
    • 2,592 Sq Ft

    26 Mount Peg Rd Unit A, Woodstock, VT 05091

    Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit A, Woodstock, VT 05091
  • /31

    $995,000

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

    26 Mount Peg Rd Unit B, Woodstock, VT 05091

    Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit B, Woodstock, VT 05091
  • /28

    $995,000

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

    26 Mount Peg Rd Unit C, Woodstock, VT 05091

    Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit C, Woodstock, VT 05091
  • /60

    $899,000

    • 6 Beds
    • 6 Baths
    • 5,497 Sq Ft

    31 Huntington Place Unit 1,2 & 3, Rochester, VT 05767

    Charming 1900s Village Building, Three Condo Units, One Incredible Opportunity! In the heart of Rochesters picturesque village, this beautifully restored early 1900s building is a rare investment opportunity, offered as a single property with three fully furnished condo units. Perfect for an owner-occupant, a multi-generational retreat, or a savvy investor, this historic gem blends classic New

    Kate Cassidy Four Seasons Sotheby's Int'l Realty

    31 Huntington Place Unit 1,2 & 3, Rochester, VT 05767
  • /31

    $1,195,000

    • 3 Beds
    • 3.5 Baths
    • 2,385 Sq Ft

    26 Mount Peg Rd Unit D, Woodstock, VT 05091

    Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit D, Woodstock, VT 05091
  • /41

    $1,495,000

    • 4 Beds
    • 1.5 Baths

    7 Slayton Terrace, Woodstock, VT 05091

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

    Keri Cole Williamson Group Sotheby's International Realty

    7 Slayton Terrace, Woodstock, VT 05091
  • /60

    $2,450,000

    • 5 Beds
    • 6 Baths
    • 5,625 Sq Ft

    16 Olcott Rd, Norwich, VT 05055

    16 OLCOTT ROAD- Elegant, spacious, and immaculate reproduction colonial constructed by premier builder Douglas Gest in an idyllic location minutes to Norwich Village yet privately set with lovely westerly views. This gorgeous home is well-appointed, bright, and has fine finish work at every turn. The main level flows effortlessly from a spacious kitchen and pantry to open concept dining and

    David Donegan Snyder Donegan Real Estate Group

    16 Olcott Rd, Norwich, VT 05055
  • /44

    $849,900

    • 3 Beds
    • 3 Baths
    • 3,392 Sq Ft

    117 Horseshoe Dr, Brownsville, VT 05037

    Experience Vermont living at its finest in this custom-built home, thoughtfully designed by the builder for exceptional energy efficiency and year-round comfort. Perfect as a relaxing getaway, this property offers expansive sleeping spaces ideal for hosting family and friends. Spend your days exploring the nearby VAST Trail system or Ascutney Mountain, and your evenings unwinding by the

    Katie Ladue Gilbert BHHS Verani Upper Valley

    117 Horseshoe Dr, Brownsville, VT 05037
  • /8

    $590,000

    • Land
    • 61.49 Acres
    • $9,595 per Acre

    0 Wild Apple Rd, Pomfret, VT 05067

    One of the most sought-after locations in the Woodstock area, this 61-acre property is accessed off of Wild Apple Road with a building site oriented to the south and east. At 1,600 feet in elevation, it enjoys sweeping views of Killington, Mount Ascutney, and the surrounding hills. The land offers complete privacy with a blend of woodlands, open fields, a stream, and a pond site. Bordering the

    Story Jenks LANDVEST

    0 Wild Apple Rd, Pomfret, VT 05067
  • /16

    $3,150,000

    • Land
    • 506 Acres
    • $6,225 per Acre

    Markham Mountain, Andover, VT 05143

    Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence.This land's historical roots run deep, originally belonging to the Marsh

    Story Jenks LANDVEST

    Markham Mountain, Andover, VT 05143
  • /41

    $795,000

    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft

    115 Prior Rd, Cavendish, VT 05142

    Living and working in the country with privacy, wildlife, snowmobiling from your front door, skiing at Okemo, and the overall beauty of Vermont would be a dream come true, right? Well, here's your opportunity with this pretty log home on 19 acres on a dead-end town-maintained road. Inside the house, you will love the open concept of the living room, and the kitchen and dining room with cathedral

    Glenn Olney Barrett and Valley Associates Inc.

    115 Prior Rd, Cavendish, VT 05142
  • /60

    $699,000

    • 4 Beds
    • 4 Baths
    • 2,578 Sq Ft

    78 Coopers Trace, Plymouth, VT 05056

    Set in Hawk Resort, conveniently located between Killington and Okemo, this well-kept four-bedroom, four-bath home offers privacy, space, and easy access to Vermont’s best outdoor recreation. The main level features an open layout with cathedral ceilings, wide pine floors, and excellent natural light from large windows and skylights. A renovated kitchen and fresh interior paint give the home a

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    78 Coopers Trace, Plymouth, VT 05056
  • /44

    $749,000

    • 5 Beds
    • 2.5 Baths
    • 2,018 Sq Ft

    51 High St, Ludlow, VT 05149

    Welcome to 51 High Street — an immaculate, turnkey village home just steps from the Okemo shuttle stop, offering effortless access to Okemo Mountain Resort and all that Ludlow has to offer. This inviting residence features five bedrooms and 2.5 baths, thoughtfully updated for comfortable year-round living. The renovated kitchen shines with classic soapstone countertops and a charming Jøtul

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

    51 High St, Ludlow, VT 05149
  • /38

    $614,000

    • 3 Beds
    • 2 Baths
    • 1,250 Sq Ft

    62 Okemo Trailside Extension Unit 9-C, Ludlow, VT 05149

    Welcome to a place where comfort meets mountain lifestyle. This beautifully updated 3-bedroom, 2-bath condo offers the perfect blend of warmth, space, and convenience—just a short walk to the ski trail for effortless days on the mountain. Inside, you’ll find wood floors, a thoughtful open layout, and a cozy fireplace that anchors the living space, making it ideal for both quiet evenings and

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

    62 Okemo Trailside Extension Unit 9-C, Ludlow, VT 05149
  • /31

    $795,000

    • 3 Beds
    • 3.5 Baths
    • 2,282 Sq Ft

    3755 Quechee Main St Unit 9A, Quechee, VT 05059

    The perfect combination of feeling like a single family home but with the convenience and ease of townhouse living! Enjoy a park like setting with wonderful landscaping and stone walls throughout. Walk, bike or golf cart to the Quechee Club and Lake Pineo. Located adjacent to the 13th fairway of the Highland golf course. On site there is a beautiful in ground pool and two tennis courts for that

    Barbara Ruel Coldwell Banker LIFESTYLES - Quechee

    3755 Quechee Main St Unit 9A, Quechee, VT 05059
  • /20

    $460,000

    • 2 Beds
    • 2 Baths
    • 1,228 Sq Ft

    145 Okemo Trailside Extension Unit 23C, upper, Ludlow, VT 05149

    Walk to the Sachem Trail from this recently remodeled, warm and charming, 2 bedroom, 2 bath, 2 level condominium. Easy maintenance with an open floor plan (kitchen, dining and living room with wood burning fireplace and slider to the deck). Updates include: new kitchen cabinets, granite countertops, wood plank flooring, carpet, and paint. The new bathrooms have large format tiling and frameless

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

    145 Okemo Trailside Extension Unit 23C, upper, Ludlow, VT 05149
  • /13

    $1,525,500 New Construction

    • 4 Beds
    • 4 Baths
    • 2,752 Sq Ft

    5677 Hendee Way Unit 5677, Hartford, VT 05001

    The Jasper at Mountain Stream — To be built by Mountain Stream at Quechee Lakes, the Jasper offers 2,752 square feet of refined single-level living, paired with a detached two-car garage. A long, low silhouette under a sweeping shed roof, vertical board-and-batten siding, and a dramatic central chimney give the home a distinctly modern presence — clean architectural lines softened by the

    Richard Higgerson Higgerson & Company

    5677 Hendee Way Unit 5677, Hartford, VT 05001
  • /36

    $845,000

    • 3 Beds
    • 3.5 Baths
    • 1,840 Sq Ft

    49 Vt Rt 12, Pomfret, VT 05053

    Discover the possibilities with this beautifully crafted three bedroom, three and one half bath home and versatile Post and Beam barn/studio, set between Woodstock and Silver Lake in scenic Barnard. The main residence features an airy great room with vaulted ceilings, warm wood accents, and expansive windows that invite natural light and frame peaceful views. Thoughtful design and quality

    Eric Johnston Four Seasons Sotheby's Int'l Realty

    49 Vt Rt 12, Pomfret, VT 05053
  • /21

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,134 Sq Ft

    32 Route 103 S Unit C5, Ludlow, VT 05149

    Outstanding views of Okemo Mountain from this well maintained, 3 bedroom, 2 full-bathroom condo with upgrades throughout. Living space is open and centered on a woodburning fireplace. Great mudroom with space to store all your gear. Located on the second level, this unit is bright with a private deck to enjoy sunsets and unobstructed views of ski trails, Black River, and pool. Primary bedroom has

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

    32 Route 103 S Unit C5, Ludlow, VT 05149
  • /54

    $685,000

    • 4 Beds
    • 3.5 Baths
    • 2,828 Sq Ft

    119 Pine Hill Rd, Ludlow, VT 05149

    Nestled in the desirable Okemo Pines community, this 4-bedroom, 3.5-bath home offers the perfect blend of comfort, charm, and convenience, only minutes from Okemo Mountain Resort. Thoughtfully designed for year-round enjoyment, the home features multiple seasonal living areas, including a large deck with Okemo views, a sunroom, and a covered porch with mountain views. The house offers privacy

    Joseph Karl William Raveis Real Estate Vermont Properties

    119 Pine Hill Rd, Ludlow, VT 05149
  • /23

    $369,000

    • 2 Beds
    • 1.5 Baths
    • 835 Sq Ft

    105 Williams Ln Unit 6C, Hartford, VT 05001

    Kingswood Village. Unit 6C is just a short walk to the Quechee Ski Hill—step into your bindings and you’re on the slopes. This three-level condominium offers a thoughtful sense of space, with a vaulted ceiling and a living and dining area that opens to the second floor. Hardwood floors run throughout, grounding the interior with warmth and continuity. Two bedrooms on the lower level provide

    Richard Higgerson Higgerson & Company

    105 Williams Ln Unit 6C, Hartford, VT 05001
  • /45

    $739,000

    • 4 Beds
    • 2.5 Baths
    • 2,663 Sq Ft

    490 W Hill Rd, Ludlow, VT 05149

    From mountain views to après-ski soaks in the hot tub, this home delivers the full Vermont lifestyle with ease. Located on one of Ludlow’s most coveted roads, this custom-built mountain retreat offers the perfect blend of quality, comfort, and convenience. Skip the village traffic and drive straight to the base of Okemo in just minutes! Thoughtfully designed and with so much to love, this

    Frank Provance Diamond Realty

    490 W Hill Rd, Ludlow, VT 05149
  • /51

    $399,800

    • 3 Beds
    • 2 Baths
    • 1,428 Sq Ft

    107 Blueberry Ledge Ridge Unit 45, Plymouth, VT 05056

    Perched at 1,600 feet elevation between Okemo and Killington, this beautifully furnished 3-bedroom, 2-bath condo at Hawk Resort offers the perfect mountain escape--complete with everything you need to move right in.Step into an open-concept living and dining area that flows onto a private deck through glass sliders--perfect for enjoying the sunsets. The living room features soaring cathedral

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    107 Blueberry Ledge Ridge Unit 45, Plymouth, VT 05056
  • /60

    $1,499,000

    • 4 Beds
    • 3.5 Baths
    • 3,560 Sq Ft

    652 Tierney Rd, Cavendish, VT 05142

    Tucked discretely off a meandering country road you will find this charming 4 bedroom, 3 and 1/2 bath contemporary home sited on 40 acres of land with miles of groomed trails that include a picnic area on Twenty Mile Stream. The grand living room , anchored by a wood-burning fireplace and lined by a wall of windows , frames views of the giant swimming pond and long range mountain views that

    Carol Wood Williamson Group Sothebys Intl. Realty

    652 Tierney Rd, Cavendish, VT 05142
  • /14

    $1,560,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 3,120 Sq Ft

    7034 Hiram Atkins Byway Rd Unit 7043, Hartford, VT 05059

    The Thistle at Mountain Stream — To be built by Mountain Stream at Quechee Lakes, the Thistle offers 3,120 square feet of contemporary living across two levels, paired with a single-bay tuck-under garage, separate heated storage with optional rec-room conversion, and a detached two-car garage. A long, low silhouette under a sweeping shed roof, vertical board-and-batten siding, and a dramatic

    Richard Higgerson Higgerson & Company

    7034 Hiram Atkins Byway Rd Unit 7043, Hartford, VT 05059
  • /51

    $719,000 Open Sat 10AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 2,019 Sq Ft

    455 Hawk Pine Rd, Norwich, VT 05055

    Well cared for energy efficient three bedroom two+ bath cape in a wonderful country setting! Set on 1.38 acres of gorgeously landscaped grounds, this home is a six minute drive to Marion Cross School and Norwich’s favorite store, Dan & Whit’s. Ten minutes to Dartmouth College. Norwich is part of the Dresden interstate School District and students attend Hanover for middle and high school. The

    Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

    455 Hawk Pine Rd, Norwich, VT 05055

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