158

Windham County VT Homes under $300,000

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  • /27

    $17,500

    $7K PRICE DROP
    • 1 Bed
    • 2 Baths
    • 941 Sq Ft

    230, Qtr. 4 89 Grand Summit Way, Dover, VT 05356

    PRICE IMPROVEMENT! This one-of-a-kind unit-style is on one level and includes one bedroom, two full bathrooms, and an open-concept kitchen, living, and dining area. The living room area features a queen Murphy bed and a queen pull-out sleeper sofa, comfortably sleeping six people. The spacious bedroom includes a king-size bed and a balcony with beautiful ridgeline views. The benefits of Grand

    Patricia Fitzpatrick Skihome Realty

    230, Qtr. 4 89 Grand Summit Way, Dover, VT 05356
  • /3

    $125,000

    • Land
    • 1.77 Acres
    • $70,621 per Acre

    997 Stratton Arlington Rd, Stratton, VT 05360

    STRATTON & MOUNT SNOW - Build your dream ski home on this newly subdivided lot with 103' of road frontage and 1.77 private acres located only 10 minutes from both Stratton Mountain Ski Resort and Mount Snow Ski Resort. All the hard work has been done! Survey, septic design, site plan, state of VT wastewater and well approval, and driveway permit have all been approved and filed with the town.

    Derek Greene Derek Greene

    997 Stratton Arlington Rd, Stratton, VT 05360
  • /22

    $19,500

    $3K PRICE DROP
    • 1 Bath
    • 407 Sq Ft

    121 Qtr 4 89 Grand Summit Way Unit 121, Dover, VT 05356

    Quarter share (deeded interval 4) ownership at the Grand Summit offers 13 weeks of vacation per year on a rotating schedule that can be used, rented, or traded as you desire. Experience the mountain resort lifestyle affordably!! This first floor (Unit 121) with a sleep four studio is 407 sq ft and has a Murphy bed in the living area, a kitchen/dining area, and a full bath. This unit is located on

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    121 Qtr 4 89 Grand Summit Way Unit 121, Dover, VT 05356
  • /48

    $28,000

    $4K PRICE DROP
    • 1 Bed
    • 2 Baths
    • 846 Sq Ft

    226/228, Qtr 2 Grand Summit Way Unit 226/228, Qtr 2, Dover, VT 05356

    Experience the ultimate in flexibility and mountain living with this deeded quartershare at the Grand Summit Hotel. Enjoy 13 weeks of vacation annually—one week every 28 days—on a rotating basis. Use it, rent it, or trade it for other destinations! This spacious valley-side lockout unit comfortably sleeps 8 and features 2 full baths, a kitchen/dining area, and stunning valley views. Unit 226 is a

    Donna Brown Skihome Realty

    226/228, Qtr 2 Grand Summit Way Unit 226/228, Qtr 2, Dover, VT 05356
  • /60

    $225,000

    Open Sun 11AM - 2PM
    • 2,619 Sq Ft

    6 Tuttle St, Bellows Falls, VT 05101

    JUNE 21ST OPEN HOUSE CANCELLED DUE TO MULTIPLE OFFERS RECEIVED, OFFER DEADLINE OF 12PM MONDAY. In the village of Bellows Falls, overlooking the Connecticut River, sits this lovely Colonial 2-unit. With a vacant first floor, excellent tenants on the second where a porch commands river views, and an unfinished third floor leaving room for added value, this property is an exciting prospect for

    Zachary Zupan EXP Realty

    6 Tuttle St, Bellows Falls, VT 05101
  • /16

    $23,000

    • 1 Bath
    • 407 Sq Ft

    354 Qtr. 2, 89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Benefits of Grand Summit ownership include the best ski in/out mountain location available. Use of the Grand Summit amenities all year round including valet parking, owners private lounge, private owners library, full service spa with saunas hot tubs and outdoor heated pool, private owners only ski/golf locker rooms for year

    Kelly Agrillo Southern Vermont Realty Group

    354 Qtr. 2, 89 Grand Summit Way, Dover, VT 05356
  • /28

    $235,000

    • 2 Beds
    • 1 Bath
    • 970 Sq Ft

    3153 Vermont Route 100, Wardsboro, VT 05355

    Charming 2-bedroom, 1-bath rustic cottage featuring a versatile 14x9 mudroom and plenty of recent upgrades. The spacious kitchen flows into a generous dining area, while the cozy living room offers a VT Castings woodstove, a side bar with stools, and warm, inviting finishes. Both bedrooms are nicely sized, with one offering sliding doors that open directly to the backyard—perfect for easy outdoor

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    3153 Vermont Route 100, Wardsboro, VT 05355
  • /2

    $59,900

    • Land
    • 1 Acre
    • $59,900 per Acre

    Lot 35 Woodsman Rd, Dover, VT 05356

    Super building lots up near the Dover Elementary School. Gentle sloping lots, with municipal sewer and underground telephone & electric. Prices reflect the quality of the view(s). Some with ski area(s) to the west and others with local ridgelines to south. Only moments from West Dover dining, shopping, and skiing. The Elementary School provides a fun campus for younger recreational fun. How many

    Michael Purcell Berkley & Veller Greenwood/Dover

    Lot 35 Woodsman Rd, Dover, VT 05356
  • /10

    $165,000

    $60K PRICE DROP
    • Land
    • 9.45 Acres
    • $17,460 per Acre

    0 Higley Hill, Dover, VT 05356

    Fantastic eastern views of New Hampshire mountains & valleys. A roadway, power & phone already exists for 4 dramatic view lots. Pick the one you want! Family & friends will enjoy ski area resort & local amenities nearby, while Brattleboro & CT River Valley resources are just down the hill. Truly majestic sites! Package lot offers considered. Appointment is required to walk the property.

    Michael Purcell Berkley & Veller Greenwood/Dover

    0 Higley Hill, Dover, VT 05356
  • /22

    $110,000

    • Land
    • 2.5 Acres
    • $44,000 per Acre

    69 Old Haven Ln, Putney, VT 05346

    Nestled in an idyllic setting at 69 Old Haven Lane, this exceptional building lot offers a rare opportunity to bypass the typical hurdles of new construction and start bringing your vision to life immediately. Located in a sought-after and peaceful pocket of Putney, this property perfectly balances the privacy of a country retreat with the convenience of an excellent location. Much of the

    Kate Barry EXP Realty

    69 Old Haven Ln, Putney, VT 05346
  • /28

    $52,000

    • 2 Beds
    • 2 Baths
    • 1,098 Sq Ft

    274/76Qtr. 1 Grand Summit Way, Dover, VT 05356

    Wake up to the Grand Summit Express and the Bluebird lifts right outside your room. Sleep 10 condo comprises of two units. Unit 276 has a private bedroom with a queen bed, queen sleeper sofa and queen murphy bed in the living area. Kitchenet and a full bath with an extra large covered balcony. Adjoining room 274 has 2 king beds and a full bath. Units are located on the base area side of the

    Kelly Agrillo Southern Vermont Realty Group

    274/76Qtr. 1 Grand Summit Way, Dover, VT 05356
  • /31

    $20,000

    $5K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 673 Sq Ft

    222 Qtr 3 Grand Summit Way Unit 222, Qtr 3, Dover, VT 05356

    Trailside! Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Own this deeded quartershare property for 1 week every 28 days, on a rotating basis. This valley side 1 bedroom, 1 full bath unit has sleeping space for 6, plus a balcony off the bedroom with a valley view. Open concept kitchen/dining room, and a large living room with a queen sleeper sofa, and a queen murphy bed.

    Donna Brown Skihome Realty

    222 Qtr 3 Grand Summit Way Unit 222, Qtr 3, Dover, VT 05356
  • /4

    $125,000

    $15K PRICE DROP
    • Land
    • 1.3 Acres
    • $96,154 per Acre

    00 Creamery Rd, Guilford, VT 05301

    Just in time for Spring building! This incredibly beautiful high meadow is perfect for your new home, be it a get away or primary. Wake up to the views of the local hills and rolling countryside...enjoy gardening, a pool, decks or covered porches ..or just install oversized windows to take advantage while you putter about! Soils tests are done...drive is into the lot...consult GMP for power...Get

    Christine Lewis Brattleboro Area Realty

    00 Creamery Rd, Guilford, VT 05301
  • /8

    $199,000

    $200K PRICE DROP
    • Land
    • 13,939 Sq Ft
    • $621,875 per Acre

    8 A Freestyle Cir, Dover, VT 05356

    Ski in and out at Mount Snow from one of the last two buildable lots. In other words, if you like the convenience of slopeside living this could be the location for you to build your dream home with easy access to the mountain. This building site is part of the TrailsEdge PUD, sharing in their utilities and ski access to/from Mount Snow through the Snowdance Village ski trails. Note that this is

    John Redd Skihome Realty

    8 A Freestyle Cir, Dover, VT 05356
  • /10

    $250,000

    • 2 Beds
    • 2 Baths
    • 1,139 Sq Ft

    108 Morningside Commons, Brattleboro, VT 05301

    Take a deep breath...enjoy your free time...sit back and wait for the walks to be clear, the lawn mowed and the flowers to bloom...without lifting a finger! Take a dip in the clear waters of the fenced, private pool or have a game of friendly tennis or pickleball! No clean up there either! The best of the best! Top floor, end unit 2nd floor deck for looking down at the world, and windows

    Christine Lewis Brattleboro Area Realty

    108 Morningside Commons, Brattleboro, VT 05301
  • /43

    $299,000

    • 3,942 Sq Ft

    2072 N Main St, Londonderry, VT 05148

    This is your chance to own in downtown Londonderry! You have the option of commercial, residential or BOTH. One unit is currently set up for residential use with living area and 3/4 bath on the first level and three bedrooms and full bath on the second floor. The second unit has been used for commercial use in the past with open space and 1/2 bath on the first floor with 3 rooms and 2 full baths

    Catherine Cairns Maple Leaf Real Estate

    2072 N Main St, Londonderry, VT 05148
  • /2

    $80,000

    $10K PRICE DROP
    • Land
    • 1.97 Acres
    • $40,609 per Acre

    24 Summit Cir, West Brattleboro, VT 05301

    Gorgeous building lot nestled into a prime development on a wooded hillside in Southern Vermont. The 1.97 wooded lot is minutes to downtown Brattleboro, yet private and rural!

    Claire Renaud Berkley & Veller Greenwood Country

    24 Summit Cir, West Brattleboro, VT 05301
  • /24

    $20,000

    $5K PRICE DROP
    • 1 Bed
    • 2 Baths
    • 754 Sq Ft

    250/252 Q4, 89 Grand Summit Way Unit 250/252, Dover, VT 05356

    Enjoy the ski-on, ski-off lifestyle, while also experiencing the luxuries of hotel amenities with this spacious valley facing quarter share unit at the beautiful Grand Summit Hotel, directly at the base of Mount Snow! This sleep 6 condo is comprised of a studio unit (unit 252) with a queen murphy bed, kitchenette, sitting area and a full bathroom. This unit adjoins a hotel unit (unit 250) with 2

    Prema Fitzpatrick Real Broker LLC

    250/252 Q4, 89 Grand Summit Way Unit 250/252, Dover, VT 05356
  • /20

    $90,100

    • Land
    • 21,780 Sq Ft
    • $180,200 per Acre

    LOT 3 158/160 High Peak Way, Wilmington, VT 05363

    A opportunity to own this .50-acre double lot in the High Peak Development, offering a double lot for your Vermont getaway. Ideally situated adjacent to the Haystack Golf Course, this parcel provides the perfect mountain convenience. Just a short drive to Mount Snow**, The Hermitage Club, and all the year-round recreation the Deerfield Valley is known for, this property also offers direct access

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    LOT 3 158/160 High Peak Way, Wilmington, VT 05363
  • /2

    $195,000

    • Land
    • 4.86 Acres
    • $40,123 per Acre

    1036 Dalewood Rd, Jamaica, VT 05343

    This is a town sale property. There is a 30-day waiting period after a fully executed contract. The 30 days is a window for public feedback. Under the statute, if Town residents object to the sale, they have 30 days from the date of the notice to submit a petition to the Town. If a petition is signed by at least 5% of the town's registered voters, the Select Board cannot just sell the property.

    Carrie Mathews Winhall Real Estate

    1036 Dalewood Rd, Jamaica, VT 05343
  • /4

    $55,000

    • Land
    • 1.05 Acres
    • $52,381 per Acre

    31 Woodsman Rd, West Dover, VT 05356

    Lovely wooded building site not far from the Mount Snow ski resort, nearby lakes, villages, shopping, and dining. The Woodsman development features large private home sites affording great privacy with thick tree buffers, public sewer hookups, easy access of a paved road nearby and tremendous site potential. This lot has been priced to sell!

    Adam Palmiter Berkley & Veller Greenwood/Dover

    31 Woodsman Rd, West Dover, VT 05356
  • /26

    $32,000

    • 1 Bed
    • 2 Baths
    • 791 Sq Ft

    249/251 Qtr 3 Grand Summit Way Unit 249/251 Qtr 3, Dover, VT 05356

    Trailside, best ski in/out mountain location. A really comfortable unit sleep 8. Unit 251 includes a kitchenette, comfortable living room setting, a sleep sofa a Murphy bed and full bath. Unit 249 boasts 2 queen size beds a full bathroom, and a deck with views of the mountain to enjoy skiers on the slope and fireworks. Just imagine entertaining family and friends! Benefits of ownership include

    Sheila Joyce-Albano Skihome Realty

    249/251 Qtr 3 Grand Summit Way Unit 249/251 Qtr 3, Dover, VT 05356
  • /2

    $150,000

    • Land
    • 2.05 Acres
    • $73,171 per Acre

    00 Fort Dummer Heights, Brattleboro, VT 05301

    Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation.

    Christine Lewis Brattleboro Area Realty

    00 Fort Dummer Heights, Brattleboro, VT 05301
  • /26

    $75,000

    • Land
    • 1 Acre
    • $75,000 per Acre

    170 Maple Dr, Wardsboro, VT 05355

    Are you looking for a beautiful, build-ready lot in Southern Vermont? This one-acre parcel at 170 Maple Drive in the Snow Mountain Farms community offers the perfect opportunity to start your Vermont dream home. The property already has a state-issued 4-bedroom wastewater permit in place, making it ready for your 2026 build. Located on a town-maintained road with a quiet cul-de-sac setting, this

    Chris Lowe Lowe's Real Estate, LLC

    170 Maple Dr, Wardsboro, VT 05355
  • /30

    $137,000

    $2K PRICE DROP
    • Land
    • 20.1 Acres
    • $6,816 per Acre

    251 Phillips Hill Rd, West Halifax, VT 05358

    Discover 20.10 acres of land in Halifax, Vermont, just a short drive to Greenfield, MA, and from skiing at Mount Snow and The Hermitage Club. This property consists of two separately deeded building lots, offering flexibility for two homes or a single retreat. Enjoy seasonal mountain views, peaceful surroundings, and direct access from a quiet country road. In the warmer months, take advantage of

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    251 Phillips Hill Rd, West Halifax, VT 05358
  • /13

    $195,000

    Open Sun 11AM - 1PM
    • 3 Beds
    • 2.5 Baths
    • 1,591 Sq Ft

    3 Gove St, Bellows Falls, VT 05101

    This property has been used for family only for many years. Three years ago the first floor was was converted to short term housing primarily for traveling medical professionals which has been very successful, never vacant. Second floor is a two level apartment and has been owner occupied. It consists of living room, office, dining room, full bath and kitchen on the first level and 2 spacious

    Oona Madden Berkley & Veller Greenwood Country

    3 Gove St, Bellows Falls, VT 05101
  • /43

    $110,000

    $15K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,040 Sq Ft

    1940 Vermont 30, Jamaica, VT 05343

    YES this is a FULL time Residence ... Charming two-bedroom, two-bathroom mobile home situated along the scenic West River. The property includes two small storage buildings, a fruit tree screened enclosure, and a carport. Inside, there is ample space for comfort with two living rooms, one of which opens to a deck with picturesque views of the river. Located just 30 minutes from Stratton, Mount

    Mike England Michael England Real Estate

    1940 Vermont 30, Jamaica, VT 05343
  • /2

    $45,000

    • Land
    • 10,890 Sq Ft
    • $180,000 per Acre

    45 Mowing Way, Wilmington, VT 05363

    Level building lot with public sewer and water at the street. Across from the Haystack Golf Course for easy year round enjoyment. Direct snowmobile access from the lot. A short drive to the public boat launch at Lake Whitingham or Mount Snow ski resort.

    Adam Palmiter Berkley & Veller Greenwood/Dover

    45 Mowing Way, Wilmington, VT 05363
  • /24

    $140,000

    • Land
    • 1.4 Acres
    • $100,000 per Acre

    0 Scattered Timber Rd Unit 5094122, Wilmington, VT 05363

    Build your dream mountain retreat on this exceptional 1.4-acre double lot (Lots 494 & 495) in the highly desirable Chimney Hill community. Gently sloping and situated at approximately 2,400 feet in elevation, this unique parcel offers outstanding privacy with seasonal winter valley views while directly abutting Green Mountain National Forest and HOA common land, helping preserve the peaceful

    Grayson VanHendrick Flex Realty

    0 Scattered Timber Rd Unit 5094122, Wilmington, VT 05363
  • /23

    $78,000

    • 2 Beds
    • 1 Bath
    • 728 Sq Ft

    4 Reservoir Rd, Brattleboro, VT 05301

    In a very private area of the Park. Right out your door is the walking path to Pleasant Valley Reservoir! This 2 bedroom home has an updated bathroom. There's a concrete grilling/patio pad, lovely flower beds line the front yard and the front and back entryway are covered.

    Victoria Woods Brattleboro Area Realty

    4 Reservoir Rd, Brattleboro, VT 05301
  • /14

    $55,000

    • 3 Beds
    • 1.5 Baths
    • 924 Sq Ft

    78 Shady Pines Park, Westminster, VT 05158

    Looking for an affordable home you can truly call your own? This could be the one! This 1989 mobile home is nestled on a large rented lot in the highly convenient Shady Pines Park in Westminster, VT. Just minutes from I-91, it offers easy access to Bellows Falls, Saxtons River, Walpole, and surrounding communities. The home features a spacious eat-in kitchen, three bedrooms, one and a half

    Derek Winchester ACORN REAL ESTATE GROUP LLC

    78 Shady Pines Park, Westminster, VT 05158
  • /22

    $86,000

    • Land
    • 6.2 Acres
    • $13,871 per Acre

    1297 River Rd, Jamaica, VT 05343

    Unique! Do you love to camp? swim? fish?.....this may be it for you....Over2000 feet of West River frontage with electric on site and just offpavement and at the intersection of 2 major access road to skiing andrecreation! Much of the frontage is in flood plain and it is subject to flowage rights of the dam, but an amazing site! The current owner has had a Jamaica cottage for camping

    Christine Lewis Brattleboro Area Realty

    1297 River Rd, Jamaica, VT 05343
  • /3

    $299,000

    $100K PRICE DROP
    • Land
    • 36,590 Sq Ft
    • $355,952 per Acre

    8 B Freestyle Cir, Dover, VT 05356

    Ski in and out at Mount Snow from one of the last two buildable lots on the mountain. If you understand the convenience of slopeside living this could be the location for you to build your dream home. This building site is part of the TrailsEdge PUD, sharing in their utilities and ski access to/from Mount Snow through the Snowdance Village ski trails. Note that this is the larger of 2 lots

    John Redd Skihome Realty

    8 B Freestyle Cir, Dover, VT 05356
  • /7

    $279,000

    • Land
    • 45 Acres
    • $6,200 per Acre

    Lot 0 Saddada Rd, Whitingham, VT 05361

    Lovely pastoral parcel of land in Whitingham Vermont with mountain views. This parcel sits conveniently on the MA border for easy access into the Deerfield Valley or Heath area. The 45 acre parcel is about half pasture and half mature woodlands, with easy access of the quiet country road, old stone walls, views of the mountains to the west, and a serene setting.

    Michael Purcell Berkley & Veller Greenwood/Dover

    Lot 0 Saddada Rd, Whitingham, VT 05361
  • /31

    $33,500

    • 1 Bed
    • 2 Baths
    • 709 Sq Ft

    145/47 Qtr.1,89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 6 unit consists of two adjoining units; Studio unit (145) Queen murphy bed, kitchenette, full bathroom and a balcony. Hotel unit (147) Two queen beds, full bathroom and balcony. Units are located the mountain side of the hotel just down the hallway from the Spa, ski locker, health club and pool.. Lock out units

    Kelly Agrillo Southern Vermont Realty Group

    145/47 Qtr.1,89 Grand Summit Way, Dover, VT 05356
  • /20

    $39,900

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 530 Sq Ft

    8 Dorf Auf Radar Rd, Wilmington, VT 05363

    Delightful, affordable! Be right in the heart of ski country with access to hiking, boating, fishing and biking! This tidy 2 bedroom home has a 10x16 storage shed for your gear! Big enough for a weekend of fun but small enough to keep the costs reasonable. This is better than renting, and always available when you are! This is an exciting find! The property can only be a vacation/second home only.

    Christine Lewis Brattleboro Area Realty

    8 Dorf Auf Radar Rd, Wilmington, VT 05363
  • /37

    $36,500

    • 2 Beds
    • 2 Baths
    • 878 Sq Ft

    313 Qtr.1, 89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Mountainside two bedroom sleep 6 unit with a covered balcony. Kitchen, living room and queen sleeper sofa as well as a king bed in private bedroom on the first floor. Full bath with double sink vanity on the first floor. Lofted bedroom also has a king bed and a 3/4 bath . Benefits of Grand Summit ownership include the best

    Kelly Agrillo Southern Vermont Realty Group

    313 Qtr.1, 89 Grand Summit Way, Dover, VT 05356
  • /2

    $59,900

    • Land
    • 1 Acre
    • $59,900 per Acre

    Lot 37 Woodsman Rd, Dover, VT 05356

    Super building lots up near the Dover Elementary School. Gentle sloping lots, with municipal sewer and underground telephone & electric. Prices reflect the quality of the view(s). Some with ski area(s) to the west and others with local ridgelines to south. Only moments from West Dover dining, shopping, and skiing. The Elementary School provides a fun campus for younger recreational fun. How many

    Michael Purcell Berkley & Veller Greenwood/Dover

    Lot 37 Woodsman Rd, Dover, VT 05356
  • /10

    $80,000

    $15K PRICE DROP
    • Land
    • 10.05 Acres
    • $7,960 per Acre

    Lot 3 North St, Dover, VT 05431

    Discover the perfect Vermont retreat on this 10.15 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape. Whether you envision a

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 3 North St, Dover, VT 05431
  • /23

    $189,000

    • Land
    • 3.6 Acres
    • $52,500 per Acre

    00 Lake Hill Rd, Whitingham, VT 05361

    Rare opportunity to own the “Spring Lot,” a beautiful 3.6-acre building site overlooking private Laurel Lake in Southern Vermont. This peaceful 17-acre lake is reserved exclusively for landowners—no motorboats allowed—perfect for kayaking, canoeing, fishing, and swimming, with the ability to add your own private dock. With preliminary soil testing & septic design showing positive results,

    Chad Lackey Deerfield Valley Real Estate

    00 Lake Hill Rd, Whitingham, VT 05361

Showing Results 41 - 80, Page 2 of 4

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