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Windsor County VT Homes for Sale

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  • /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
  • /43

    $279,000

    • 3 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    436 Mount View Loop, Rochester, VT 05767

    Located on the back side of Mt View Loop is this comfy home, furnished and ready to move right in. Very open concept living space on top floor with woodstove and large dining room set up to enjoy gatherings of any size. Lower floor bedrooms and full bath. Community swim or fishing pond is a deeded right with garden space available and cross country skiing terrain. North Hollow is a desirable area

    Patricia Harvey Xsell Realty LLC

    436 Mount View Loop, Rochester, VT 05767
  • /14

    $69,000

    • Land
    • 1.05 Acres
    • $65,714 per Acre

    Lot 49 Spring St, Stockbridge, VT 05772

    Attractive building lot in the desirable Highwood community. This lot offers potential long-range views and includes sewer rights in the Highwood community sewer system, sufficient for a three-bedroom residence. Architectural review and protective covenants ensure that the quality of life in this small community is always preserved. Highwood is adjacent to the Green Mountain Trail network for

    Kyle Kershner Killington Pico Realty

    Lot 49 Spring St, Stockbridge, VT 05772
  • /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
  • /22

    $290,000

    • Land
    • 75 Acres
    • $3,867 per Acre

    1175 Quarry Rd, Chester, VT 05143

    An extraordinary potential homesite set in the hills of southern Vermont. This expansive 75-acre parcel offers the perfect blend of privacy, natural beauty, and endless potential. Whether you dream of building a secluded hilltop retreat or preserving land for recreation and conservation, this property invites endless possibilties. Improvements include a septic system, dug well, electricity and a

    Jessica Samples BHG Masiello Keene

    1175 Quarry Rd, Chester, VT 05143
  • /19

    $125,000

    • Land
    • 10.24 Acres
    • $12,207 per Acre

    0 Hoey Rd, Cavendish, VT 05142

    This is a special property. Ten acres of woodland with a mix of hardwood and softwood. There appear to be many harvestable trees. There are a couple of different building sites...one on the flat spot on the lower side of the property overlooking the stonewall and the brook. The other is on the uphill side where you also have a flat spot and a gorgeous view of the neighboring field. The property

    Betty McEnaney Diamond Realty

    0 Hoey Rd, Cavendish, VT 05142
  • /60

    $200,000

    • 3 Beds
    • 3 Baths
    • 2,011 Sq Ft

    625/627 Q3 Jackson Gore Adams House Unit 625/627 Q3, Ludlow, VT 05149

    Jackson Gore area of Okemo– Adams House Quarter Share Ownership, Unit 625/627 Quarter III (includes Christmas weeks for 2026). Enjoy slopeside living with mountain views in this three-bedroom, three-bathroom condominium with just over 2000 square feet of living space. Located within The Adams House at Jackson Gore on Okemo, offering direct slope access. Enjoy luxury living with full access to The

    Kevin Barnes William Raveis Real Estate Vermont Properties

    625/627 Q3 Jackson Gore Adams House Unit 625/627 Q3, Ludlow, VT 05149
  • /37

    $1,995,000

    • 4 Beds
    • 2.5 Baths
    • 3,839 Sq Ft

    198 Piper Hill Rd, Weston, VT 05161

    Uplands is a gracious 105-acre hill farm on the south-facing slope of Markham Mountain, located just outside the historic village of Weston. Anchored by an 1800s farmhouse, the main residence has been thoughtfully added on to and renovated over the years and offers over 3,839 square feet of living space, including four bedrooms, three fireplaces and an attached two bay garage. The guest house

    Story Jenks LandVest, Inc/Woodstock

    198 Piper Hill Rd, Weston, VT 05161
  • /38

    $1,499,000

    • 4 Beds
    • 5 Baths
    • 3,500 Sq Ft

    2391 Music Mountain Rd, Stockbridge, VT 05772

    OVER $496,000 PRICE ADJUSTMENT AND OVER $120,000 RENTAL INCOME, THIS ONE YOU SHOULD CONSIDER OWNING. LUXURY FURNISHINGS TOO. TIMBERS IN THE SKY – Featured in Log and Timber Home Living magazine, this one-of-a-kind Vermont timber frame retreat, built in 2022, blends dramatic architecture with refined comfort. Fully furnished with luxury pieces, the open floor plan showcases a soaring great room

    Freddie Ann Bohlig Four Seasons Sotheby's Int'l Realty

    2391 Music Mountain Rd, Stockbridge, VT 05772
  • /60

    $2,499,000

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

    254 Town Line Rd, Plymouth, VT 05056

    First time offered on market! Stunning VT private estate on over 22 +/- acres w/mountain views, gorgeous gardens & 2 ponds one of which is a 7-feet-deep spring fed glacial pond. This exquisite property has been meticulously designed & custom crafted by the owner who is a well-known respected master builder. As you enter this gem you will experience the thoughtful care everywhere you look.

    Marni Rieger KW Vermont-Killington

    254 Town Line Rd, Plymouth, VT 05056
  • /5

    $75,000

    • Land
    • 0.5 Acre
    • $150,000 per Acre

    1015 Maple St, White River Junction, VT 05001

    Nice IN-town building lot! Don't miss this opportunity to build a home, business or garage / storage space along Route 14 / Maple Street. Situated just above the White River and Watson Park in Hartford village! This .50+/- acre in town lot has town water, sewer and power available at the street. Just minutes to I 89 & I 91, Dartmouth College, Dartmouth Hitchcock Medical Center, the VA Hospital,

    Alex DeFelice The Clerkin Agency, P.C.

    1015 Maple St, White River Junction, VT 05001
  • /30

    $375,000

    • 1 Bed
    • 1 Bath
    • 884 Sq Ft

    162 Okemo Trailside Extension Unit 22C-L, Ludlow, VT 05149

    Okemo Trailside 22-CL is a spacious one-bedroom with a bunk room, ideally located just a minute's walk from the Upper Sachem Trail. This ski-in/ski-out condo, which has seen significant renovations, offers flat, easy access to the slopes and community amenities. Inside, you'll find an open 884-square-foot layout. The entry features a mudroom with rustic pine accents, perfect for storing gear. The

    Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

    162 Okemo Trailside Extension Unit 22C-L, Ludlow, VT 05149
  • /50

    $425,000

    • 3 Beds
    • 3 Baths
    • 1,918 Sq Ft

    11 Blueberry Ledge Ridge Unit L3, Plymouth, VT 05056

    Ledges 3--This updated 3-bedroom, 3-bath townhouse offers a welcoming retreat in the lakes region, midway between Killington and Okemo. Renovated in 2013, the home features a stylish kitchen with new cabinetry, quartz countertops, tiled backsplash, cork flooring, and quality appliances including a gas range. The main level is warm and inviting with random-width pine floors and a wood-burning

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    11 Blueberry Ledge Ridge Unit L3, Plymouth, VT 05056
  • /59

    $99,000

    • 2 Beds
    • 3 Baths
    • 1,369 Sq Ft

    510/512 Qiii Jackson Gore Adams House Unit 510/512 QIII, Ludlow, VT 05149

    Jackson Gore Village at Okemo – Adams House Condominium. Welcome to slopeside living at its finest in the Adams House at Jackson Gore Village, located at the heart of Okemo Mountain Resort. This spacious and beautifully appointed condominium offers effortless access to the slopes and a full suite of resort amenities. The open-concept living area features a comfortable space to gather, complete

    Joseph Karl William Raveis Real Estate Vermont Properties

    510/512 Qiii Jackson Gore Adams House Unit 510/512 QIII, Ludlow, VT 05149
  • /45

    $795,000

    • 2 Beds
    • 2.5 Baths
    • 1,248 Sq Ft

    144 Lodge Rd Unit 6, Ludlow, VT 05149

    SouthFace Village Tamarack #6Ski-on, ski-off access, luxury amenities, and stunning views await at this beautiful, two-level condominium. This two-bedroom, three-bath unit is steps away from the brand-new recreation building, making it the perfect spot for après-ski relaxation.Inside, you'll find a bright and sunny open-concept living space. A gas fireplace creates a cozy ambiance, while

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

    144 Lodge Rd Unit 6, Ludlow, VT 05149
  • /60

    $475,000

    • 4 Beds
    • 5 Baths
    • 3,036 Sq Ft

    7868 Pomfret Rd, North Pomfret, VT 05053

    CASH FLOW POSITIVE - PRICE REDUCTION! A rare opportunity to own a piece of Vermont history - The North Pomfret Store & Post Office, c.1830. This 3-story New Englander offers charm, character, and a solid income stream on 1.84 picturesque acres. With 5 total units, the property includes 3 residential apartments (one 2-bedroom, one 1-bedroom, and an Efficiency), a ground-floor commercial office

    John Bassette Bassette Real Estate Group

    7868 Pomfret Rd, North Pomfret, VT 05053
  • /38

    $795,000

    • 4 Beds
    • 3 Baths
    • 2,099 Sq Ft

    6077 Vt Route 12, Barnard, VT 05031

    BARNARD VILLAGE CAPE- This elegant Cape sits in an ideal location in the idyllic village of Barnard, just a short walk to the Barnard General Store and Silver Lake. The perfect blend of original charm, sophistication, and modern amenities, the house is bright and welcoming with lovely natural woodwork and plenty of space for social gatherings or quiet privacy. A large central living room features

    David Donegan Snyder Donegan Real Estate Group

    6077 Vt Route 12, Barnard, VT 05031
  • /10

    $388,888

    • 1 Bed
    • 2 Baths
    • 884 Sq Ft

    807 Murphys Rd Unit 7D, Quechee, VT 05059

    Beautifully updated one-bedroom plus loft condo located in Fairway Village. Recent improvements include new AC mini-splits, updated bathrooms, new flooring, a redesigned staircase with banister, loft safety windows, wood shelving, new shades, and toilets. The condo is part of the Quechee Club, which offers a wide range of amenities (additional club fee applies along with HOA dues). Fairway

    Kris Lippi Get Listed Realty

    807 Murphys Rd Unit 7D, Quechee, VT 05059
  • /50

    $100,000

    • 2 Beds
    • 3 Baths
    • 1,367 Sq Ft

    606/608 QII Jackson Gore Adams House Unit 606/608 QII, Ludlow, VT 05149

    Jackson Gore Village at Okemo Mountain Resort - Welcome to the Adams House at Jackson Gore, where mountainside living meets year-round adventure. This spacious, well-appointed condominium offers comfort and convenience in one of Okemo’s most sought-after slopeside communities. Step inside to find a generous open-concept living space with a cozy gas fireplace, ideal for relaxing after a day on the

    Katherine Burns William Raveis Real Estate Vermont Properties

    606/608 QII Jackson Gore Adams House Unit 606/608 QII, Ludlow, VT 05149
  • /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
  • /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
  • /29

    $179,000

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    9 Stryhas Trailer Ct, Ludlow, VT 05149

    Charming and well-maintained 3-bedroom, 2-bathroom manufactured home on leased lot in a peaceful 55+ community. This inviting home features an open concept layout, high ceilings, and is filled with natural light pouring in through multiple skylights, creating a bright and airy atmosphere. Step outside to a new deck with an awning—perfect for enjoying warm summer days. The fenced yard is great for

    Gabrielle Turco Kelley Real Estate, Inc.

    9 Stryhas Trailer Ct, Ludlow, VT 05149
  • /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.

    Agent Photo

    Julie Buffum

    Buffum Realty

    (802) 471-3386

    32 Reed St, Springfield, VT 05156
  • /32

    $2,300,000

    • 4 Beds
    • 4.5 Baths
    • 3,524 Sq Ft

    134 Chester Arthur Rd, Hartford, VT 05047

    A quality residence with 4.69 landscaped acres beautifully complimenting the estate! Entering into the grounds a graceful drive meanders through landscaped lawns to arrive at a stone patio and an appealing New England style residence. Conveniently, there is option to enter an attached garage with direct entrance to the residence. After crossing the stone patio, passing through the front door

    John Wetmore Wetmore Real Estate

    134 Chester Arthur Rd, Hartford, VT 05047
  • /60

    $200,000

    • Land
    • 6.63 Acres
    • $30,166 per Acre

    00 Vermont 103, Andover, VT 05143

    Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With aproposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offersample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

    Rachael Rogala Lange & Lange

    00 Vermont 103, Andover, VT 05143
  • /34

    $449,000

    • 3 Beds
    • 2 Baths
    • 1,489 Sq Ft

    6852 Us Route 4, Bridgewater, VT 05034

    This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont

    Laird Bradley Williamson Group Sothebys Intl. Realty

    6852 Us Route 4, Bridgewater, VT 05034
  • /60

    $115,000

    • Land
    • 3.28 Acres
    • $35,061 per Acre

    00 Vt Route 103 N, Chester, VT 05143

    Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With a proposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offers ample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

    Rachael Rogala Lange & Lange

    00 Vt Route 103 N, Chester, VT 05143
  • /37

    $985,000

    • 4 Beds
    • 3 Baths
    • 2,785 Sq Ft

    1782 Randall Rd, Woodstock, VT 05091

    This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide

    Wade Treadway Wade I Treadway Real Estate

    1782 Randall Rd, Woodstock, VT 05091
  • /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
  • /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
  • /16

    $250,000

    • 5 Beds
    • 2 Baths
    • 1,728 Sq Ft

    101 Mount Vernon St, Springfield, VT 05156

    Built as a duplex, this and last owner have used it as a single family. Therefore there are no traditional figures for income and expenses. Easy to transform into the duplex for income by adding appliances to the upstairs apartment. This home has many upgrades including siding, windows, decks/railings/stairway (outside). Drive is paved and there looks to be room to replace the shed. Perfect one

    Christine Lewis Brattleboro Area Realty

    101 Mount Vernon St, Springfield, VT 05156
  • /6

    $172,000

    • Land
    • 4.3 Acres
    • $40,000 per Acre

    51 Loveland Rd, Norwich, VT 05055

    Fantastic opportunity to build your dream home on this 4.3 -acre lot in Norwich, Vermont, complete with full architectural plans for the exact home the sellers were planning to build, as shown in the photos and renderings. The property has already undergone significant preparation, including completed building designs and preliminary plans for the water and septic system along with other

    Agent Photo

    Spenser Molloy

    Nexthome Modern Realty

    (802) 214-8650

    51 Loveland Rd, Norwich, VT 05055
  • /2

    $450,000

    • Land
    • 119 Acres
    • $3,782 per Acre

    00 Bradley Hill Rd Unit 121, Norwich, VT 05055

    Unusually large parcel of land in Norwich. 119 +/- ac with over 2500' of road frontage on delightful Bradley Hill Road. Close to town yet calm and quiet. The land abuts conservation land and the "Bradley Hill Loop" - a maintained trail. Not yet in Current Use though the forestry plan is ready to be implemented. A great opportunity to build in the Dresden School District.

    Jane Darrach Martha E. Diebold/Hanover

    00 Bradley Hill Rd Unit 121, Norwich, VT 05055
  • /14

    $199,000

    • Land
    • 27.1 Acres
    • $7,343 per Acre

    00 Albin Hill Rd, Braintree, VT 05060

    Imagine waking up to sweeping vistas of Vermont’s Green Mountains, surrounded by 27.1 acres of pure tranquility. This rare parcel offers the perfect canvas for your dream estate, luxury retreat, or off-the-grid sanctuary. Perched at an impressive 1,800 feet in elevation, the property offers stunning panoramic views and unparalleled privacy, while still being just minutes from amenities, shopping

    Will Spanos KW Vermont-Killington

    00 Albin Hill Rd, Braintree, VT 05060
  • /32

    $875,000

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

    233 Brothers Rd, Hartland, VT 05048

    The idyllic Hartland countryside is the setting for this handsome cape. A delightful three season porch is entered by way of the attached two car garage or directly by a lovely landscaped pathway. Once inside you will be greeted by a warm and inviting kitchen detailed with cherry cabinetry, the dining room with a bay window view of the gardens,a living room with fireplace, and a spacious

    Mary Mayhew Snyder Donegan Real Estate Group

    233 Brothers Rd, Hartland, VT 05048
  • /60

    $3,100,000

    • 5 Beds
    • 4.5 Baths
    • 7,634 Sq Ft

    165 Moonshadow Dr Unit M-15, Ludlow, VT 05149

    Welcome to your mountain sanctuary in the heart of Solitude Village—Okemo’s premier slopeside community. This luxurious 5-bedroom, 3-bathroom retreat offers true ski-on/ski-off access, allowing you to hit the Rising Star Trail or Moon Shadow right from your doorstep. Step inside to a warm, elegant interior featuring radiant-heated tile and rich hardwood floors throughout. The expansive great

    Joseph Karl William Raveis Real Estate Vermont Properties

    165 Moonshadow Dr Unit M-15, Ludlow, VT 05149
  • /46

    $540,000

    • 1 Bed
    • 2 Baths
    • 1,112 Sq Ft

    193 Jackson Gore Unit 639/641, Ludlow, VT 05149

    Escape to mountain luxury with this fully furnished 1-bedroom, 2-bathroom condo located in the heart of the premier Okemo ski resort at Jackson Gore. Perfectly positioned just steps from the slopes, this stylish retreat offers the ultimate blend of comfort, convenience and year round adventure. The open-concept living space features a cozy gas fireplace and large windows with mountains views. The

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

    193 Jackson Gore Unit 639/641, Ludlow, VT 05149
  • /19

    $325,000

    • Land
    • 18 Acres
    • $18,056 per Acre

    00 Turtle Hill Rd, Ludlow, VT 05149

    Build Your Dream Home on a Private 18-Acre Estate in South HillDiscover the perfect setting for your custom-designed residence on this expansive 18-acre parcel, ideally situated at the secluded end of a cul-de-sac within South Hill's exclusive community. This exceptional property offers a rare blend of privacy and convenience, surrounded by other custom-built homes. Imagine your new home

    Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

    00 Turtle Hill Rd, Ludlow, VT 05149
  • /34

    $289,000

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    842 Main St, Proctorsville, VT 05153

    This property must be seen in person to be appreciated. Very clean and move-in ready Vermont 3-bedroom, 2-bath home just minutes from Okemo Mountain Resort in Proctorsville Village. Ideal as a low-maintenance vacation retreat or full-time residence, this well-kept home on .26± acres features a new roof and combines comfort and convenience in one of the most desirable areas of the Okemo Valley.

    Geralyn Donohue Engel & Völkers Okemo

    842 Main St, Proctorsville, VT 05153
  • /16

    $96,232 New Construction

    • 2 Beds
    • 2 Baths
    • 777 Sq Ft

    517 Back Mountain Rd, Windsor, VT 05089

    Welcome to 517 Back Mountain Rd., Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

    Kate Barry EXP Realty

    517 Back Mountain Rd, Windsor, VT 05089

Showing Results 281 - 320, Page 8 of 10

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