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Windsor County VT Homes for Sale

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  • /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

    $339,000

    • 2 Beds
    • 1.5 Baths
    • 835 Sq Ft

    105 Williams Ln Unit 6C, Hartford, VT 05001

    Unit 6C is a well-positioned, three-level condominium in Kingswood Village at the top of Quechee Ski Hill, offering the convenience of immediate access to the slopes less than 500 ft away! This turnkey, fully furnished home provides a seamless entry into the Quechee Lakes lifestyle. Two bedrooms on the lower level provide privacy, while a large 17’ x 15’ loft on the third floor offers additional

    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
  • /51

    $625,000

    • 3 Beds
    • 2.5 Baths
    • 2,755 Sq Ft

    2371 Sanders Rd, Bethel, VT 05032

    Tucked away on 24 pristine acres, this beautifully custom-built home offers an exceptional blend of privacy, natural beauty, and comfortable country living — all just two miles from the heart of downtown Bethel. Step outside onto the expansive deck and take in sweeping mountain views and serene pond vistas, where the only sounds are birdsong and the rustle of leaves. Whether you're starting your

    Katie Ladue Gilbert BHHS Verani Upper Valley

    2371 Sanders Rd, Bethel, VT 05032
  • /56

    $750,000 Open Sun 11AM - 1PM

    • 3 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
  • /60

    $649,000

    • 3 Beds
    • 2 Baths
    • 2,205 Sq Ft

    688 Hidden Heights Rd, Chester, VT 05143

    Classic New England Salt Box - This charming home is nestled in a hillside neighborhood with wonderful western views and sunsets. Indoors you'll find a tidy mudroom entry with space for all your year round gear. Tiled heated floors lead you to the kitchen featuring newer stainless steel appliances. Vaulted ceilings draw you towards the open dining/living room where you'll be bathed in end of the

    Joseph Karl William Raveis Real Estate Vermont Properties

    688 Hidden Heights Rd, Chester, VT 05143
  • /51

    $799,900

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    1209 Wildlife Rd, White River Junction, VT 05001

    Privately set on 10.2 acres in Hartford, VT, this well-crafted log home offers a refined balance of natural beauty, thoughtful design, and modern infrastructure. The setting is a blend of open lawn and mature woodland, creating a sense of seclusion while remaining convenient to area amenities. Extensively renovated in recent years, the home features a dramatic vaulted living space anchored by a

    Grant Tyler BHHS Verani Upper Valley

    1209 Wildlife Rd, White River Junction, VT 05001
  • /49

    $715,000

    • 4 Beds
    • 3.5 Baths
    • 2,654 Sq Ft

    760 E Ash Rd, Plymouth, VT 05056

    Spacious Hawk Resort Home with Scenic Views Enjoy the perfect blend of comfort, space, and mountain charm in this inviting Hawk home. Designed for family gatherings and entertaining, the generous open-concept living area features a beautiful fieldstone fireplace and updated greenhouse windows that bring in natural light and picturesque views. The primary suite offers a cozy fireplace, private

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    760 E Ash Rd, Plymouth, VT 05056
  • /45

    $450,000

    • 3 Beds
    • 2.5 Baths
    • 1,919 Sq Ft

    824 Hard Rd Unit A5, Hartford, VT 05059

    Birchwood Condo in Quechee Lakes! This beautifully maintained end-unit condo offers a functional and inviting layout with tasteful updates throughout. The main level features an open dining and living area with a cozy gas fireplace, an updated kitchen, convenient half bath, and an essential mudroom entry.The upper level includes a spacious primary ensuite bedroom with updated bath, along with

    Heather Ashline BHHS Verani Upper Valley

    824 Hard Rd Unit A5, Hartford, VT 05059
  • /33

    $750,000

    • 3 Beds
    • 2 Baths
    • 2,616 Sq Ft

    28 Plumley Ridge, Ludlow, VT 05149

    Designed both as a peaceful retreat and a comfortable home for entertaining, 28 Plumley Ridge offers the best of both worlds. The location is private yet central. Ludlow Village is within walking distance and Okemo Mountain is just over a mile away. This quality constructed home is thoughtfully designed for both contentment and convenience. The wide wrap-around deck provides year round vistas of

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    28 Plumley Ridge, Ludlow, VT 05149
  • /37

    $349,000

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

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

    PRICED TO SELL - Come take a look at these amazing view. There is still plenty of time to enjoy the wood burning Fireplace after some time on the slopes or in the chilly spring nights. 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

    Katie McFadden RE/MAX North Professionals

    1226 E Ash Rd Unit L-34, Plymouth, VT 05056
  • /47

    $625,000

    • 4 Beds
    • 4 Baths
    • 2,904 Sq Ft

    5 Malagash Rd, South Reading, VT 05153

    Tucked within the peaceful hamlet of South Reading, this inviting property offers a lifestyle where the pace slows, and everyday living feels a bit more enjoyable. Set on over three acres, this spacious four-bedroom, four-bath home combines comfort, functionality, and natural beauty. The true highlight is the backyard oasis—featuring a tranquil pond, a generous deck ideal for entertaining, a

    Kevin Barnes William Raveis Real Estate Vermont Properties

    5 Malagash Rd, South Reading, VT 05153
  • /58

    $599,000

    • 4 Beds
    • 3 Baths
    • 3,200 Sq Ft

    84 Old Barn Ln, West Windsor, VT 05089

    Open House Saturday 5/9/26 10-12n. Breathtaking Views of Mt. Ascutney & the Valley Beyond!Welcome to this stunning custom-built 4-bedroom, 3-bath home where every window frames a masterpiece. Sweeping, panoramic views of majestic Mt. Ascutney and the rolling hillsides create an awe-inspiring backdrop you'll never tire of — whether sipping morning coffee or watching the sunset paint the peaks

    Katie Ladue Gilbert BHHS Verani Upper Valley

    84 Old Barn Ln, West Windsor, VT 05089
  • /39

    $749,000

    • 3 Beds
    • 2 Baths
    • 1,660 Sq Ft

    37 South St, Woodstock, VT 05091

    Welcome to this beautifully renovated residence in the vibrant heart of Woodstock Village. Enjoy unparalleled convenience with a short stroll to the Elementary School, Woodstock Inn, the picturesque Green, and an array of charming shops, restaurants, and bakeries that define village living. Nestled directly across from Vail Field, this home offers easy access to playgrounds, ball fields, and

    Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

    37 South St, Woodstock, VT 05091
  • /12

    $245,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    891 Vermont Route 100, Weston, VT 05161

    Charming and efficient, this 2-bedroom, 1-bath home offers a cozy retreat in the heart of Weston, Vermont. Designed for single-level living and low maintenance, the layout makes the most of its space. The main living area features an open flow between the living room and eat-in kitchen, leading to a deck that is perfect for morning coffee or outdoor grilling. Two bedrooms and a full bath complete

    Andie Fusco Four Seasons Sotheby's Int'l Realty

    891 Vermont Route 100, Weston, VT 05161
  • /24

    $217,500

    • Land
    • 94 Acres
    • $2,314 per Acre

    6416 Vermont 107, Stockbridge, VT 05772

    Nestled among natural streams in the rolling hills of Vermont’s Green Mountains, this remarkable 94-acre parcel offers sweeping views overlooking the White River. Rich with potential for residential use or future development, the property includes a private septic system and a drilled well already in place. With 670 feet of frontage along VT Route 107, the land provides convenient access while

    Kate Jarvis Williamson Group Sothebys Intl. Realty

    6416 Vermont 107, Stockbridge, VT 05772
  • /17

    $53,000

    • Land
    • 1.5 Acres
    • $35,333 per Acre

    2-66 Goshawk Dr, Plymouth, VT 05056

    Dreaming of building your own Vermont-style home but hoping to find an affordable parcel? This lot at Hawk Resort is the perfect opportunity. With power and other utilities already on site and the ability to connect to the community septic system, you’ll be well on your way to breaking ground on your dream home. Tucked among the trees in a peaceful natural setting, this property offers privacy

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    2-66 Goshawk Dr, Plymouth, VT 05056
  • /25

    $115,000

    • Land
    • 10 Acres
    • $11,500 per Acre

    S-1C Great Roaring Brook Rd, Plymouth, VT 05056

    Ten-acre wooded parcel with potential views located near the top of Great Roaring Brook Rd. The topography is rolling too steep with multiple buildings sites, rock crop outs, and streams throughout. A wonderful opportunity to design and build your Vermont dream home. Located between Ludlow and Woodstock with equal distance to Killington and Okemo Ski areas. Close to Lake Rescue and Echo Lake for

    Terry Davis Williamson Group Sothebys Intl. Realty

    S-1C Great Roaring Brook Rd, Plymouth, VT 05056
  • /36

    $95,000

    • 2 Beds
    • 2 Baths
    • 1,025 Sq Ft

    224 QIV Jackson Gore Inn Unit 224 QIV, Ludlow, VT 05149

    Experience Vermont's Premier Mountain Living Without Full Ownership Costs. Step directly onto Okemo's slopes from your slopeside retreat at Jackson Gore. This condo-tel quarter-share gives you deeded ownership of 13 weeks annually (25% of the year)—at a fraction of the cost of whole ownership. You own one of four deeded interests in this unit. You receive every fourth week on a rotating schedule,

    Rachael Lange Lange & Lange

    224 QIV Jackson Gore Inn Unit 224 QIV, Ludlow, VT 05149
  • /3

    $199,000

    • Land
    • 29 Acres
    • $6,862 per Acre

    00 Vermont 12, Barnard, VT 05031

    A beautiful and private 29 acre building lot on a mountainside in an area of Barnard populated by estate properties. A road to the potential building site is in and soil testing for septic will be completed as soon as snow clears. Views of the valley and local mountains currently cleared and can be expanded with additional clearing. The location is a short drive to Woodstock, a shorter drive to

    Stan Butler Four Seasons Sotheby's Int'l Realty

    00 Vermont 12, Barnard, VT 05031
  • /43

    $79,000

    • 1 Bed
    • 2 Baths
    • 775 Sq Ft

    211/213 Qtr I Jackson Gore Inn, Ludlow, VT 05149

    Welcome to effortless mountain living in this spacious 1-bedroom, 2-bathroom unit at the premier Jackson Gore Inn at Okemo Mountain Resort. Boasting slope views, a lockout design, and room to comfortably sleep up to 8 guests, this is the perfect blend of personal getaway with rental opportunities.The well-designed floor plan features a full kitchen, dining area, and cozy living room with a gas

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

    211/213 Qtr I Jackson Gore Inn, Ludlow, VT 05149
  • /3

    $175,000

    • Land
    • 12.51 Acres
    • $13,989 per Acre

    377 Coach Rd, Chester, VT 05143

    Minutes to the Village Green, yet peaceful and private, this rare parcel offers the perfect balance of convenience and Vermont tranquility. The property features beautiful long-range views and a small pond with potential for expansion, creating a picturesque setting for your future home.Located in an area identified for development, it offers both a wonderful building site and long-term

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

    377 Coach Rd, Chester, VT 05143
  • /29

    $530,000

    • 3 Beds
    • 2.5 Baths
    • 4,020 Sq Ft

    28 Fairview Terrace, Royalton, VT 05068

    This 3-bedroom, 2.5-bath home is full of potential, with the option to create an auxiliary dwelling for added flexibility. The current owner saw the promise in this gem and has already invested in the important updates: fresh exterior paint, a brand-new septic system, a new roof, upgraded electrical, and other quality improvements. With much of the essential work complete, the next owner has the

    Wendie Wright Coldwell Banker LIFESTYLES - Hanover

    28 Fairview Terrace, Royalton, VT 05068
  • /31

    $299,000

    • 2 Beds
    • 1 Bath
    • 750 Sq Ft

    29 Markham Ln, Weston, VT 05161

    This delightful 2-bedroom, 1-bath cottage located in the heart of the picturesque village of Weston is waiting for a new owner that is looking for a sweet little Vermont retreat. Built in 1947, this home offers timeless character with cozy living spaces and classic Vermont charm. Perfectly situated within walking distance to the Weston Playhouse, the iconic Vermont Country Store, and locally

    Catherine Cairns Maple Leaf Realty

    29 Markham Ln, Weston, VT 05161
  • /37

    $55,000

    • 1 Bath
    • 390 Sq Ft

    212 QIII Jackson Gore Inn Unit 212 QIII, Ludlow, VT 05149

    Jackson Gore Inn at Okemo Mountain Resort. Quarter Share Ownership, Unit 212 Quarter III is a true four-season destination offering a rare combination of slope-side convenience, year-round recreation, and resort-style amenities. With quarter-share ownership, you can enjoy the benefits of mountain living without the full-time commitment. This studio condominium is located in the Jackson Gore Inn

    Kevin Barnes William Raveis Real Estate Vermont Properties

    212 QIII Jackson Gore Inn Unit 212 QIII, Ludlow, VT 05149
  • /20

    $169,000

    • Land
    • 22,651 Sq Ft
    • $325,000 per Acre

    71 S Windsor St, Royalton, VT 05068

    Centrally located, in the picturesque village of South Royalton, is a building lot with multifaceted potential! The desirable attributes of both the ability for connection to the municipal sewer and connection to the municipal water system could present the opportunity for multi-unit residential construction! An extensive level lawn area makes visualizing prospective building sites a simple

    John Wetmore Wetmore Real Estate

    71 S Windsor St, Royalton, VT 05068
  • /12

    $79,000

    • Land
    • 2.53 Acres
    • $31,225 per Acre

    Lot #4 Meadow Rd, Ludlow, VT 05149

    Private 2.53+/- acre state approved building lot located at the end of a dead-end, private road. Positioned at the south end of Ludlow off East Hill Road, this lot offers easy access to town amenities and the Okemo Ski Area. Possible views of Okemo with clearing.

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

    Lot #4 Meadow Rd, Ludlow, VT 05149
  • /6

    $195,000

    • Land
    • 1 Acre
    • $195,000 per Acre

    Lot 48 Partridge Rd, Ludlow, VT 05149

    1.01+/- acres. Lot 48. Ready to build. Prestigious neighborhood, some lots with views of Okemo Slopes with clearing. Very convenient to the village and Okemo Mountain Resort. This property is owned by a Vermont licensed real estate agent.

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

    Lot 48 Partridge Rd, Ludlow, VT 05149
  • /41

    $1,576,000

    • 9,455 Sq Ft

    14 Summarsell Dr Unit 16, Hartland, VT 05048

    This charming converted farmstead features two primary buildings on one parcel, combining classic Vermont character with solid investment returns. The property offers a diverse mix of one-, two-, and four-bedroom apartments, plus one commercial unit currently leased to a local bath and body company. Additional income comes from a three-bay garage, a shed, and a storage container — all fully

    Loren Wehmeyer Tesla Realty Group, LLC

    14 Summarsell Dr Unit 16, Hartland, VT 05048
  • /20

    $599,000

    • Land
    • 33 Acres
    • $18,152 per Acre

    00 Olcott Rd Unit 189, Norwich, VT 05055

    This 33-acre estate quality parcel is offered with conceptual drawings and a fully permitted four-bedroom wastewater system design, presenting an exceptional opportunity to build in a prime Upper Valley location. Overlooking and bordering conserved land, the property is located just 1.5 miles from the center of Norwich, Vermont. Its close proximity to downtown Hanover, NH, and Dartmouth College,

    Richard Higgerson Higgerson & Company

    00 Olcott Rd Unit 189, Norwich, VT 05055
  • /48

    $2,500,000

    • 6 Beds
    • 6 Baths
    • 7,019 Sq Ft

    5518 Vermont 12, Barnard, VT 05031

    This gracious 1796 Brick Federal homestead was transformed into a popular gathering spot more than 60 years ago. The Barnard Inn has long been considered among the finest dining and hospitality venues in Vermont. It is currently operated as an event destination by the chef-owner and his family. Now, with children grown and off on their own paths, it is time to pass stewardship of the historic

    Laird Bradley Williamson Group Sothebys Intl. Realty

    5518 Vermont 12, Barnard, VT 05031
  • /13

    $199,000

    • Land
    • 4.1 Acres
    • $48,537 per Acre

    398 Valley View Rd, White River Junction, VT 05001

    Opportunity meets convenience on this versatile 4.10-acre property with both residential and commercial zoning, offering endless potential for your future plans. The lot includes an existing foundation along with utilities already in place, including power, spring well, and septic, giving buyers a valuable head start. Set adjacent to the highway for quick and easy access, the property enjoys

    Grayson VanHendrick Flex Realty

    398 Valley View Rd, White River Junction, VT 05001
  • /58

    $485,000

    • 8 Beds
    • 1 Bath
    • 3,500 Sq Ft

    1254 U S 5, Springfield, VT 05156

    Welcome to the former Danforth Inn! Take a trip back in time to 1780 as you look at this extremely original old building that was built in Weathersfield Bow in 1780 by Gideon Lyman. In 1789 Joseph Danforth moved to the Bow and he leased and then bought the Inn, changing the name to the Danforth Inn. This property will need some love, but it has never been spoiled in its originality, and it's just

    Glenn Olney Barrett and Valley Associates Inc.

    1254 U S 5, Springfield, VT 05156
  • /13

    $229,000

    • Land
    • 46.06 Acres
    • $4,972 per Acre

    0 French Meadow Rd, Springfield, VT 05156

    Just over 46 acres of rural wooded and rolling pastureland in southeastern Vermont. There are two access points to this lot, and both are off of publicly maintained roads. Substantial road frontage on both Spoonerville and French Meadow Roads. Historically used to graze cattle, the property features perimeter stone walls. Recently perc tested in 2 potential building areas. This lot was formerly

    Jessica Landers Barrett and Valley Associates Inc.

    0 French Meadow Rd, Springfield, VT 05156

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