Windham County VT Homes under $300,000

• 

  

  

  /19

  $165,000

  $20K PRICE DROP

  • Land
  • 16.05 Acres
  • $10,280 per Acre

  00 E Hill Rd, Wardsboro, VT 05355

  Discover the perfect setting for your Vermont dream on 00 East Hill Road in Wardsboro. This impressive 16.05-acre parcel captures the essence of the Green Mountains, offering a blend of absolute privacy and breathtaking mountain views. Whether you envision a contemporary mountain escape or a classic timber-frame homestead, this expansive acreage provides an incredible canvas characterized by its

  Steve Lawrence KW Vermont-Stowe

  00 E Hill Rd, Wardsboro, VT 05355
• 

  

  

  /31

  $35,000

  $3K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 914 Sq Ft

  311 Qtr 3 Grand Summit Way, Dover, VT 05356

  Beautiful mountain view from this two-level, two-bedroom loft quartershare in the Grand Summit Resort Hotel! This trailside condo can be used, rented, or traded for stays at other vacation destinations! 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 mountain-side unit features an open-concept kitchen/dining

  Patricia Fitzpatrick Skihome Realty

  311 Qtr 3 Grand Summit Way, Dover, VT 05356
• 

  

  /2

  $45,000

  • Land
  • 1 Acre
  • $45,000 per Acre

  0 W Hill 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 residence 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 towns registered voters, the select, Board cannot just sell the property,

  Carrie Mathews Winhall Real Estate

  0 W Hill Rd, Jamaica, VT 05343
• 

  

  

  /51

  $284,000

  $15K PRICE DROP

  • 2,360 Sq Ft

  5 Reynolds Dr, Brattleboro, VT 05301

  Turn-Key Investment in the Heart of Brattleboro! This versatile three-unit multifamily property offers an excellent opportunity for both investors and owner-occupants. Two of the three units have been recently and extensively renovated, featuring brand-new flooring, fresh paint, modern baseboards, and updated plumbing and light fixtures. One of these renovated units is currently occupied, while

  Kate Barry EXP Realty

  5 Reynolds Dr, Brattleboro, VT 05301
• 

  

  

  /10

  $299,000

  $51K PRICE DROP

  • Land
  • 7.08 Acres
  • $42,232 per Acre

  103 Schoolbus Depot Rd, Town of Rockingham, VT 05101

  Located between Chester and Bellows Falls, just a mile from exit 6 off I-91, the opportunity for development awaits your ideas. Easy access, level parcel for either commercial ventures, gardens, or home. Land consists of two parcels separated by School Bus Depot Road totaling 7.08 acres. The island parcel gives excellent exposure to Route 103 for terrific signage. 103 is a high traffic corridor

  Heidi Bernier Berkley & Veller Greenwood Country

  103 Schoolbus Depot Rd, Town of Rockingham, VT 05101
• 

  

  /12

  $199,000

  $116K PRICE DROP

  • Land
  • 18.93 Acres
  • $10,512 per Acre

  0 Forest Heights Rd, West Dover, VT 05356

  Are you ready to turn your dream home into a reality? This expansive parcel of land, located just 2 miles from the slopes of Mount Snow, is waiting for your vision. The property offers an ideal combination of privacy and seclusion and with some clearing, you can unveil extraordinary views of the Mount Snow ski slopes, creating the perfect backdrop for your dream home. The property boasts

  Michelle O'Neil Deerfield Valley Real Estate

  0 Forest Heights Rd, West Dover, VT 05356
• 

  

  /23

  $20,000

  • 1 Bath
  • 407 Sq Ft

  152 - Qtr 3 89 Grand Summit Way Unit 152, Dover, VT 05356

  Quarter share (deeded interval 3) 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 152) 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

  152 - Qtr 3 89 Grand Summit Way Unit 152, Dover, VT 05356
• 

  

  /49

  $295,000

  $55K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,500 Sq Ft

  106 Main St Unit 5, Putney, VT 05346

  Bright, airy, and full of personality, this charming two-bedroom, one-bathroom condo in the Village of Putney offers comfort, style, and convenience. Ideally located just minutes from I-91 and close to Putney’s vibrant downtown shops, cafés, and everyday amenities, this condo offers easy access to village life. Inside, natural light fills the thoughtfully designed space, highlighting dreamy

  Rebecca Hiam Southern Vermont Realty Group

  106 Main St Unit 5, Putney, VT 05346
• 

  

  /49

  $259,000

  • 3 Beds
  • 1.5 Baths
  • 1,655 Sq Ft

  373 Vt Route 30, Newfane, VT 05345

  A great fixer-upper find! Solid feeling cape home set on 2 level acres just outside the village of Newfane with long frontage on the Smith Brook. Once a loved local primary home - now it's your opportunity. If you are handy and have cash or pre-qualified for a construction loan this may be your chance to break into the Newfane area at a fraction of what a renovated home will cost. Seller has

  Jessica Landers Barrett and Valley Associates Inc.

  373 Vt Route 30, Newfane, VT 05345
• 

  

  /9

  $195,000

  • Land
  • 1.2 Acres
  • $162,500 per Acre

  4769 Pikes Falls Rd, Jamaica, VT 05143

  This 1.2-acre parcel offers what few properties in Southern Vermont can—a front-row seat to one of the region’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this land enjoys immediate proximity to a setting protected by the Conservation Society of Southern Vermont. Glamping has become one of Vermont’s most sought-after experiences, and this

  Rachel Febbie EXP Realty

  4769 Pikes Falls Rd, Jamaica, VT 05143
• 

  

  /5

  $185,000

  • Land
  • 36,590 Sq Ft
  • $220,238 per Acre

  1 Pinnacle View Ln, Dover, VT 05356

  If it's close proximity you want to skiing Mt. Snow then this is your place to build your dream home. Just off a paved road in a small 5 lot subdivision. Underground utilities and sewer hookup available. Convenient to lakes, golf and restaurants, a diamond in the rough. Winter views of Mt. Snow (says owner)

  Regina Perrotto Skihome Realty

  1 Pinnacle View Ln, Dover, VT 05356
• 

  

  /28

  $52,000

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

  274/76Qtr. 2 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 two units. Unit 276 has a private bedroom with a queen bed, a queen sleeper sofa, and a queen Murphy bed in the living area, a kitchenette, and a full bath with an extra-large covered balcony. The adjoining room, 274, has 2 king beds and a full bath. Units are located on the base area side

  Kelly Agrillo Southern Vermont Realty Group

  274/76Qtr. 2 Grand Summit Way, Dover, VT 05356
• 

  

  /25

  $270,000

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  111 Central St, Brattleboro, VT 05301

  This adorable single-level home offers easy living with a functional layout and comfortable living spaces. The warm and inviting interior is designed for everyday living. The home features a large living and dining area, a convenient laundry nook, a spacious primary bedroom, and two additional bedrooms that can accommodate guests, a home office, or other multi-purpose needs. Outside, you'll find

  Desiree Stango Berkley & Veller Greenwood Country

  111 Central St, Brattleboro, VT 05301
• 

  

  /36

  $279,000

  $10K PRICE DROP

  • 1 Bed
  • 2 Baths
  • 895 Sq Ft

  13 Snowtree Ln Unit Willows K, West Dover, VT 05356

  Just a short walk over bridge by Maples Building to the lifts at Mount Snow via the magic carpet, this stunning loft-style, fully remodeled Snowtree condo offers modern comfort and undeniable charm. The open-concept living area features vaulted ceilings, gleaming bamboo floors, and a cozy wood-burning fireplace. A glass slider leads to a private balcony overlooking a babbling brook and peaceful

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  13 Snowtree Ln Unit Willows K, West Dover, VT 05356
• 

  /2

  $59,900

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

  Lot 36 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 36 Woodsman Rd, Dover, VT 05356
• 

  

  /24

  $275,000

  • 1 Bed
  • 1 Bath
  • 664 Sq Ft

  9 Mountain Village Unit 141, West Dover, VT 05356

  One of a kind 1 bedroom, 1 bath condo at Snow Mountain Village near the base of the Mount Snow ski resort. This gorgeous remodeled unit has all the style you would expect in a mountain retreat, with none of the headaches. Open concept space with a vaulted living room and kitchen, a wood burning fireplace, updated kitchen with ample storage and breakfast bar, updated furnishings, paint, and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  9 Mountain Village Unit 141, West Dover, VT 05356
• 

  

  /3

  $169,900

  • Land
  • 35.4 Acres
  • $4,799 per Acre

  0 Minard Rd, Westminster, VT 05346

  Over 35 wooded acres to call your own. Drive up the winding country road edged with meadows, views and a sense of peace to your own little haven. Spend some time on the land, scouting the views, finding the right site and falling in love with all the potential. Owned by the same family for over 30 years, it has finally come to market in just the right season to experience the golden glow of

  Christine Lewis Brattleboro Area Realty

  0 Minard Rd, Westminster, VT 05346
• 

  

  /27

  $199,595

  • Land
  • 4.2 Acres
  • $47,523 per Acre

  19 Stone Ridge Loop, Dover, VT 05356

  Located within the prestigious Village at Sawmill Farm, this exceptional homesite presents a rare opportunity to own in one of the Mount Snow Valley’s most sought-after communities. The extremely private property enjoys desirable southeasterly exposure with potential views of surrounding ridgelines, beautifully framed by timeless stone walls and majestic pines. A gentle slope makes it ideally

  Monique White Deerfield Valley Real Estate

  19 Stone Ridge Loop, Dover, VT 05356
• 

  

  /9

  $85,000

  $30K PRICE INCREASE

  • Land
  • 1 Acre
  • $85,000 per Acre

  000F-320 Bourbon Run Rd, Jamaica, VT 05343

  This 1-acre wooded lot in Jamaica permitted for a 3 bedroom , Vermont offers a unique opportunity for peaceful living in a quiet town with no zoning restrictions. Jamaica maintains its own roads and is home to a State Park that provides excellent camping and summer recreational activities. The property is conveniently located near major ski resorts including Stratton, Bromley, Magic Mountain, and

  Mike England Michael England Real Estate

  000F-320 Bourbon Run Rd, Jamaica, VT 05343
• 

  

  /12

  $125,000

  • Land
  • 15.6 Acres
  • $8,013 per Acre

  0 Thayer Rd, Westminster, VT 05158

  Rural 15.6 acre lot located at the end of Thayer Rd off Davidson Hill Rd in Westminster. This land is located in a quiet rural community on a gravel road about 10 minutes drive from Saxtons River Village and Bellows Falls Village. The lot consist of 3 lots of record all serviced by a common Right of Way. The ROW is also shared with a abutter to the north. The ROW provides ready to use access to

  Steve Schoppmeyer BHG Masiello Brattleboro

  0 Thayer Rd, Westminster, VT 05158
• 

  

  /20

  $99,500

  • Land
  • 10.27 Acres
  • $9,688 per Acre

  0 Theresa Ln, Wilmington, VT 05363

  This is a rare 10.27 acre offering located in the pastoral town of Wilmington, Vermont. Featuring approximately 8 acres open field, stone walls, cherry trees, potential views of the windmills with clearing, and the Beaver Brook running through the lower section, this property offers privacy and beauty. In addition, the land is close to Mount Snow and the Hermitage Club, plus provides easy access

  Lisa Mirando Deerfield Valley Real Estate

  0 Theresa Ln, Wilmington, VT 05363
• 

  /2

  $300,000

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft

  109 Central St, Brattleboro, VT 05301

  Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard to

  Christine Lewis Brattleboro Area Realty

  109 Central St, Brattleboro, VT 05301
• 

  

  /11

  $174,000

  • Land
  • 15 Acres
  • $11,600 per Acre

  491 Whitneyville Rd, Halifax, VT 05358

  Tucked away along a quiet, town-maintained dead-end road, this private 15-acre parcel offers a rare combination of seclusion, character, and natural beauty. Set high on a peaceful knoll, the property features an old homesite's stone foundation, open meadow areas, and several mature apple trees that hint at the land’s past, also a drilled well.A gentle babbling brook traces one boundary,

  Leslie Fraser Four Seasons Sotheby's Int'l Realty

  491 Whitneyville Rd, Halifax, VT 05358
• 

  

  /43

  $75,000

  $20K PRICE DROP

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

  169 Sun and Ski Rd, Wilmington, VT 05363

  Dreaming of building a home in Vermont but not sure where to start? With several significant steps in the preparation process already done, this one-acre lot is truly ready for your vision. A three-bedroom septic design by a Vermont engineer has been completed, with permits filed and approved by the state of Vermont. Plus, the land has already been partially cleared for a driveway and building

  Kim Meeker Southern Vermont Realty Group

  169 Sun and Ski Rd, Wilmington, VT 05363
• 

  

  /14

  $235,000

  • Land
  • 33.48 Acres
  • $7,019 per Acre

  0 Vt Route 100 Unit 5072614, Londonderry, VT 05155

  Beautiful 33.48 acre building lot in Londonderry. Some views possible and some clearing has been done. There are some wetlands on property but various choices for building sites exist. South East Facing

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  0 Vt Route 100 Unit 5072614, Londonderry, VT 05155
• 

  

  /24

  $210,000

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft

  40 Brookside Dr Unit 6, Brattleboro, VT 05301

  Rare to find an in-town condo with a waterfront view like this! Desirable 2 bedroom, 1 bath low maintenance, affordable home. Your spacious living/dining area has sliders looking out to the tranquil Whetstone Brook. Upstairs are 2 large bedrooms and a full bath. The lower level is a 465 square foot basement with washer/dryer hookup and extra storage. The entire interior has been freshly painted,

  Angela Sherman Brattleboro Area Realty

  40 Brookside Dr Unit 6, Brattleboro, VT 05301
• 

  

  /58

  $32,000

  • 1 Bed
  • 2 Baths
  • 771 Sq Ft

  123/125 Qtr 4 Grand Summit Way Unit 123/125, Qtr 4, 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 mountain-side lockout unit, the closest unit to the back door to the slopes, comfortably sleeps 8. Unit 123 is a hotel room with 2

  Donna Brown Skihome Realty

  123/125 Qtr 4 Grand Summit Way Unit 123/125, Qtr 4, Dover, VT 05356
• 

  

  /27

  $33,900

  • 1 Bed
  • 2 Baths
  • 771 Sq Ft

  235/237, QTR 2 89 Grand Summit Way, Dover, VT 05356

  Own Where You Play! One-of-a-kind sleep eight quartershare, featuring a gas fireplace, updated decor and furnishings, plus gorgeous mountain views, this is a rare find in the Grand Summit Resort Hotel! This comfortable condo has two full baths and a lockout feature, with an adjoining door within the unit, so you can use it, rent it, or trade it for a timeshare vacation simultaneously! Overlooking

  Patricia Fitzpatrick Skihome Realty

  235/237, QTR 2 89 Grand Summit Way, Dover, VT 05356
• 

  /2

  $249,000

  • Land
  • 1.29 Acres
  • $193,023 per Acre

  350 Route 100, Dover, VT 05356

  Amazing opportunity to have a building lot near Mount Snow with huge view potential, no HOA restrictions, and easy access off a main paved road. This unique site is being offered for the first time in a long time and could be the ideal spot to build your dream Vermont home.

  Adam Palmiter Berkley & Veller Greenwood/Dover

  350 Route 100, Dover, VT 05356
• 

  

  /44

  $65,000

  • Land
  • 36,154 Sq Ft
  • $78,313 per Acre

  123 High Top Rd, Wilmington, VT 05363

  Section B - new to market! Oversized building lot with new perc tests show it is suitable for a 3-bedroom single family home. Lot may support a larger home; buyer would have to pursue this option at their own cost. As an owner of an undeveloped lot in CHOA, you are entitled to all the recreation amenities in the Resort, including year-round swimming at the exclusive member-only clubhouse, located

  Sigrid Pickering Chimney Hill Realty

  123 High Top Rd, Wilmington, VT 05363
• 

  

  /39

  $25,000

  • Land
  • 21,780 Sq Ft
  • $50,000 per Acre

  30 Upper Howes Way, Wilmington, VT 05363

  Affordable Single Lot with favorable soil tests for a 3-bedroom single family home in Chimney Hill. Surrounded on two sides by common land, this lot is in a quiet section of the Main Hill. Buyer is responsible or securing a septic permit. Join a community of over 560 homes sited on 1,200-Acres adjoining the Green Mt. National Forest, with 550-Acres owned in common by the membership of the HOA.

  Sigrid Pickering Chimney Hill Realty

  30 Upper Howes Way, Wilmington, VT 05363
• 

  

  /5

  $250,000

  $20K PRICE DROP

  • 2,112 Sq Ft

  556 S Main St, Brattleboro, VT 05301

  New beginnings! Just right to live in one side, fix the other and have the tenant pay for your new lifestyle or have a family duplex and lie with extended family. the north side is vacant, needs renovation, and the south side has a tenant that will transfer with the building. Corner lot, yard, off street parking. Easy to see north unit, but otherwise a 48 hour notice to show.

  Christine Lewis Brattleboro Area Realty

  556 S Main St, Brattleboro, VT 05301
• 

  /2

  $2,500

  $13K PRICE DROP

  • Land
  • 7,840 Sq Ft
  • $13,889 per Acre

  0 Clayton Ln Unit 5094564, 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 residence 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 towns registered voters, the select, Board cannot just sell the property,

  Carrie Mathews Winhall Real Estate

  0 Clayton Ln Unit 5094564, Jamaica, VT 05343
• 

  

  /16

  $259,900

  • Land
  • 29.2 Acres
  • $8,901 per Acre

  1270 Melendy Hill Rd, Guilford, VT 05301

  A rare find! This amazing land has long range views, privacy and close to everything! There is a right of way for egress, and will be perfect for an off grid tuck away cabin or primary. A small meadow is part of the 2 acre exemption for house site, just at the end of the existing drive...easy to get to and just the beginning of the land. Mostly Black Birch, Sugar Maple and Hemlock, there is a

  Christine Lewis Brattleboro Area Realty

  1270 Melendy Hill Rd, Guilford, VT 05301
• 

  /2

  $95,000

  $30K PRICE DROP

  • Land
  • 14.7 Acres
  • $6,463 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
• 

  

  /32

  $24,500

  • 1 Bed
  • 2 Baths
  • 869 Sq Ft

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

  This unique style, a sleep six condo, is located on the top floor of the hotel and features two levels, including a loft bedroom, two full bathrooms, and an open-concept kitchen, living, and dining area. The living room area has a queen Murphy bed and a queen pull-out sleeper sofa, comfortably sleeping four people. The spacious loft bedroom features a king-size bed, a large walk-in closet, and an

  Patricia Fitzpatrick Skihome Realty

  328, Qtr. 4 89 Grand Summit Way, Dover, VT 05356
• 

  

  /13

  $49,900

  $29K PRICE DROP

  • Land
  • 3.69 Acres
  • $13,523 per Acre

  0 Honeycomb Hill, Marlboro, VT 05301

  On the privately maintained road of Honeycomb Hill sits this 3.69 acre lot. The wooded parcel has young tree growth and slopes gently. There are three areas that are fairly level and open and may be suitable building sites. Just 30 minutes to Mt. Snow, 25 minutes to Brattleboro and 15 minutes to Harriman Reservoir, this conveniently located parcel offers easy access to all of Southern Vermont's

  Laura D'Angelo Berkley & Veller Greenwood Country

  0 Honeycomb Hill, Marlboro, VT 05301
• 

  

  /16

  $260,000

  • 1 Bed
  • 1 Bath
  • 512 Sq Ft

  319 River Rd S, Putney, VT 05346

  Looking for the simple life in tiny home living, or maybe just a good basecamp to explore the outdoors? Look no further! This unique property is conveniently located just a couple miles outside the bucolic village of Putney off a main road, with easy access to I-91. With 33 acres of rolling woods and local valley views there's plenty of land to explore and play with, while the cozy little home

  Courtney Doubleday EXP Realty

  319 River Rd S, Putney, VT 05346
• 

  

  /19

  $170,000

  $79K PRICE DROP

  • Land
  • 20.09 Acres
  • $8,462 per Acre

  189 North St, Dover, VT 05356

  Discover the perfect Vermont retreat on this 20.09 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

  189 North St, Dover, VT 05356
• 

  

  /45

  $28,500

  • 1 Bed
  • 2 Baths
  • 771 Sq Ft

  204/206 Qtr 2 Grand Summit Way Unit 204/206 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. Unit 204 is a hotel room with 2 king-size beds, a full bath, & a deck. The adjoining

  Donna Brown Skihome Realty

  204/206 Qtr 2 Grand Summit Way Unit 204/206 Qtr 2, Dover, VT 05356

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