39

Windham County VT Homes under $300,000

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  • /31

    $259,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    51 Golding Rd, Windham, VT 05359

    Tucked away on a quiet dead end dirt road in the heart of Windham, this cute Vermont log home offers the kind of peace and privacy that is getting harder to find. Set in a clearing of four acres of wooded land, this property feels like a private retreat, surrounded by conservation land and abundant wildlife. The log home blends rustic charm with comfortable living. The warm wood finishes on the

    Agent Photo

    Alison Cummings

    Cummings & Co

    (802) 802-9554

    51 Golding Rd, Windham, VT 05359
  • /29

    $290,000

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft

    18 Ripple Ln, Bellows Falls, VT 05101

    Welcome to peaceful country living with room to breathe. Nestled on a private road, this well-maintained 3-bedroom, 13⁄4-bath ranch offers privacy, comfort, and over 13 acres of beautiful land to enjoy. The home's single-level layout provides convenient living with spacious bedrooms, functional living areas, and a comfortable flow for everyday life and entertaining. A two-car garage offers plenty

    Rob Weltz Barrett and Valley Associates Inc.

    18 Ripple Ln, Bellows Falls, VT 05101
  • /18

    $285,000

    $35K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,323 Sq Ft

    164 Chestnut St, Brattleboro, VT 05301

    Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with sliders

    Christine Lewis Brattleboro Area Realty

    164 Chestnut St, Brattleboro, 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
  • /57

    $259,900

    $40K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 1,248 Sq Ft

    552 - 554 Hinesburg Rd, Brattleboro, VT 05301

    Unique opportunity to own a nearly 40 acre tract and 2 homes on Hinesburg Road in a great West Brattleboro location. The homes sit unseen approximately 500 feet back on a private driveway from the public road. The houses need a fair amount of repair and remodeling to get them in good condition. The main house is a cape style home with open concept kitchen/dining/living room, full bath, and 2

    Steve Schoppmeyer BHG Masiello Brattleboro

    552 - 554 Hinesburg Rd, Brattleboro, VT 05301
  • /23

    $260,000

    • 2 Beds
    • 1 Bath
    • 1,010 Sq Ft

    429 Vt Route 30, Newfane, VT 05345

    Discover the perfect blend of charm and tranquility in this delightful 2-bedroom bungalow nestled in the heart of Newfane Village. Fresh paint throughout, this home is move-in ready and awaiting its next owner. You can sit on the side deck and enjoy a spacious, yard ideal for gardening, entertaining, or simply soaking in the sounds of nature with direct access to a picturesque stream. You can

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    429 Vt Route 30, Newfane, VT 05345
  • /44

    $274,900

    $25K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    10 King St, Bellows Falls, VT 05101

    Discover the ideal balance of privacy and convenience in this welcoming 4-bedroom, 2-bath home in the heart of Bellows Falls. Set on a spacious 1-acre lot, the 1,800-sq-ft interior provides generous room for comfortable everyday living. A private garage and secluded yard offer both practicality and serenity, while the large covered porch invites year-round enjoyment of the outdoors. With

    Floyd Amidon Maple Leaf Realty

    10 King St, Bellows Falls, VT 05101
  • /16

    $275,000

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft

    10 Riverfront Dr, Bellows Falls, VT 05101

    This recently renovated home is located on and with gorgeous views of the Connecticut River, frontage suitable for a wharf. Two bedrooms, two full baths and a beautifully crafted stone and brick fireplace. A large, private backyard, inviting family gatherings, just minutes to I91 and Okemo Mountain. Motivated Seller

    Gale Alger

    10 Riverfront Dr, Bellows Falls, VT 05101
  • /3

    $275,000

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft

    2173 Vermont 8a, Whitingham, VT 05361

    4 bedroom 2 bath home located on 4.7 acres. Has a ground level access. Level parking and garden spots. There are huge White Pine trees surrounding this home. Showings delayed until September 29, 2025 to allow for cleaning. License to Sell is needed and in progress, Expected in October.

    Mark Yule BHG Masiello Brattleboro

    2173 Vermont 8a, Whitingham, VT 05361
  • /6

    $295,000

    • 4 Beds
    • 2 Baths
    • 1,744 Sq Ft

    48 Pleasant St, Brattleboro, VT 05301

    This handsome two unit home is located on desirable Pleasant Street and includes a large yard with plenty of parking. Each unit is 2 bedrooms, bath, living room and kitchen and they feature softwood flooring, bulls eye molding, replacement windows, decking and a covered front porch. Tenant pays for Electric and Heat and each unit has new Buderus boilers. W&D hookup up and Coin washer and dryer in

    Robert Doyle Berkley & Veller Greenwood Country

    48 Pleasant St, Brattleboro, VT 05301
  • /2

    $245,000

    • 4 Beds
    • 2 Baths
    • 2,148 Sq Ft

    69 Grove St, Brattleboro, VT 05301

    69 Grove Street is a pleasant 2 unit home just a short walk from vibrant downtown. Each unit features 2 bedrooms, bath, living room and kitchen with wide board flooring and replacement windows. The first floor unit has a covered front porch, pantry and W&D hookups in the basement. The second floor apartment has an additional room (office), W&D hookups, decking and a rear staircase. Recent

    Robert Doyle Berkley & Veller Greenwood Country

    69 Grove St, Brattleboro, VT 05301
  • /8

    $250,000

    $230K PRICE DROP
    • Land
    • 5.08 Acres
    • $49,213 per Acre

    10 Overlook Dr, Dover, VT 05356

    A rare opportunity to own one of the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 5.08 acres of land and features full panoramic mountain and woodland views to the south, including mountain views to undeveloped national forest land. This property is one of the most private lots in The Peaks community, providing a full immersion in the woods

    Patricia Fitzpatrick Skihome Realty

    10 Overlook Dr, Dover, VT 05356
  • /33

    $249,000

    • 2 Beds
    • 1 Bath
    • 1,004 Sq Ft

    662 Vt Route 30, Newfane, VT 05345

    Whether you’re just starting out with your first home or looking to downsize and simplify, this sweet home is just the right size. It features two bedrooms plus bonus room upstairs, with a full bathroom conveniently located on the first floor. The kitchen is charming, complete with a dishwasher, newer refrigerator and stove, opens to a dining area, and a spacious living room with beautiful wood

    Rebecca Seymour Brattleboro Area Realty

    662 Vt Route 30, Newfane, VT 05345
  • /9

    $250,000

    $230K PRICE DROP
    • Land
    • 7.8 Acres
    • $32,051 per Acre

    16 Overlook Dr, Dover, VT 05356

    A rare opportunity to own one of the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 7.8 acres of land with a home site featuring full panoramic mountain and woodland views to the north and east, including mountain views to undeveloped national forest land. This property is the largest and most private lot in The Peaks community, providing a

    Patricia Fitzpatrick Skihome Realty

    16 Overlook Dr, Dover, VT 05356
  • /18

    $299,000

    • Land
    • 1.06 Acres
    • $282,075 per Acre

    12 Someday Rd, Dover, VT 05356

    Located in the prestigious Someday neighborhood of West Dover,VT this 1.06-acre building lot offers a unique opportunity to create your dream home with breathtaking views of Mount Snow ski resort. The lot, which once housed the original Someday homestead as your footprint, it is now ready for its next chapter. With a permit for sewer in place for a 6-bedroom home, the property provides a head

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    12 Someday Rd, Dover, VT 05356
  • /11

    $250,000

    • Land
    • 18 Acres
    • $13,889 per Acre

    0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301

    Tucked in the gently rolling hills of Vermont, this is a sweet spot to build your new home. Located on a class 3 privately maintained road, there are power poles the length of the road with fiber optics ready for the streamers or work at home folks. Build on the road for a short drive and utility ease, or take the secluded route and tuck away in the forest. The acreage is an educated guess and

    Christine Lewis Brattleboro Area Realty

    0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301
  • /19

    $229,000

    $56K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 960 Sq Ft

    3095 Thompsonburg Rd Unit B/2, Londonderry, VT 05155

    Close to Magic, Bromley and Stratton! This two-bedroom, one bath condo with woodburning fireplace overlooks a beautiful brook and tennis court area. Private deck out back to enjoy some sun. Eat in kitchen with pass through countertop area opens into the living room. Manageable and spacious for a nice weekend getaway or make this your fulltime home. Just minutes to downtown with shopping, fuel,

    Julie Lowe Lowe's Real Estate, LLC

    3095 Thompsonburg Rd Unit B/2, Londonderry, VT 05155
  • /37

    $250,000

    $40K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 1,521 Sq Ft

    134 Washington St, Brattleboro, VT 05301

    Tucked away on a quiet corner just off Washington Street in Brattleboro, VT, this charming 4-bedroom, 1-bath home offers a peaceful setting with beautiful views overlooking town. Enjoy the best of both privacy and convenience, with ample parking and a generous backyard space perfect for relaxing, gardening, or entertaining. Inside, you’ll find spacious living areas filled with character,

    Kate Barry EXP Realty

    134 Washington St, Brattleboro, VT 05301
  • /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
  • /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

    • 6 Beds
    • 5 Baths
    • 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 Realty

    2072 N Main St, Londonderry, VT 05148
  • /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
  • /48

    $294,000

    $5K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 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 a rare "move-in ready" opportunity for both savvy 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. With new toilets and stainless/modern

    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
  • /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
  • /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
  • /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
  • /29

    $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
  • /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
  • /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
  • /29

    $205,000

    • 3 Beds
    • 2 Baths
    • 1,183 Sq Ft

    18 Lindy Rd, Vernon, VT 05354

    Welcome to this charming and well-maintained 3-bedroom, 13⁄4-bath single-level home, offering the ease and comfort of first-floor living. Tucked at the end of Lindy Road, the property provides a peaceful setting on a spacious, level 0.58-acre lot, surrounded by mature trees that offer both natural shade and privacy. Inside, the home is bright, open, and thoughtfully designed, creating an inviting

    Kerry Mulverhill

    18 Lindy Rd, Vernon, VT 05354
  • /9

    $250,000

    • Land
    • 3.79 Acres
    • $65,963 per Acre

    000 Fort Dummer Heights, Brattleboro, VT 05301

    Easy to build!!! The land is open, so no fuss with a lot of prep. Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? 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

    000 Fort Dummer Heights, Brattleboro, VT 05301
  • /14

    $210,000

    • Land
    • 35 Acres
    • $6,000 per Acre

    00 Vermont Route 100, Jamaica, VT 05343

    Discover the beauty and tranquility of this picturesque wooded parcel—approximately 35 acres—nestled along the serene Deerfield River and spanning the border of Jamaica and Wardsboro. Perfectly situated within easy reach of Mount Snow, Stratton, and Bromley, the property offers convenient access to year-round recreation while preserving the sense of peace and privacy that only a large forested

    Patrice Schneider Southern Vermont Realty Group

    00 Vermont Route 100, Jamaica, VT 05343
  • /15

    $215,000

    • 2 Beds
    • 1 Bath
    • 691 Sq Ft

    8581 Vermont 30 Unit B, Jamaica, VT 05343

    Escape to the mountains in this charming 2-bedroom/1 bath condominium conveniently located near premier ski areas and year-round outdoor recreation. It's only 15 minutes to Stratton, 20 minutes to Bromley, and 10 to the Jamaica State Park. Enjoy easy access to skiing, hiking, biking, golf, and snowmobile trails, all just minutes from your door, and Manchester's shopping and dining are 30 minutes

    Deborah Hanst

    8581 Vermont 30 Unit B, Jamaica, VT 05343
  • /33

    $229,000

    • 1 Bath
    • 475 Sq Ft

    11C Snow Tree Ln Unit Birches 11C, Dover, VT 05356

    Discover effortless mountain living in this beautifully updated studio condominium that is walking distance to the slopes and in the desirable Snow Tree community. Perfect for weekend getaways, seasonal escapes, or as a high performing rental investment. This home boasts an extremely strong rental history supported by a documented 3 year history of over $25,000 annually and is being offered fully

    Melissa Ellis Southern Vermont Realty Group

    11C Snow Tree Ln Unit Birches 11C, Dover, VT 05356
  • /9

    $249,000

    $46K PRICE DROP
    • Land
    • 54.8 Acres
    • $4,544 per Acre

    0 Townshend Dam Rd Unit 5066172, Wardsboro, VT 05355

    Explore the potential of this beautiful 53.8-acre parcel just 3.5 miles from the scenic Townshend Dam. This expansive property offers a peaceful, wooded setting with ample privacy—ideal for recreation, a possible future homesite, or continued forest management. Currently enrolled in Vermont’s Current Use Program, the land offers significant tax savings and can remain in the program under new

    Carrie Mathews Winhall Real Estate

    0 Townshend Dam Rd Unit 5066172, Wardsboro, VT 05355
  • /18

    $250,000

    $30K PRICE INCREASE
    • 3 Beds
    • 1 Bath
    • 1,050 Sq Ft

    5362 Us Route 5, Westminster, VT 05158

    BRAND NEW SEPTIC SYSTEM!! Move-in ready home, ideally situated in the heart of picturesque Westminster. This 3-bedroom, 1-bath home offers the perfect blend of charm, comfort and convenience. Step inside from the sunny, porch into a bright and functional kitchen featuring new countertops and easy access to the first-floor laundry area and recently renovated full bath. The layout flows seamlessly

    Karen Hoppe Berkley & Veller Greenwood Country

    5362 Us Route 5, Westminster, VT 05158
  • /53

    $200,000

    • 384 Sq Ft

    91 Vermont 35, Athens, VT 05143

    A little piece of heaven awaits you at this charming camp set on 44 acres. The cabin sits high on a knoll overlooking a beautiful view of the expansive lower field and the distant hills. The wrap-around porch afford a birds-eye view of the changing seasons and the perfect perch to observe wildlife. The land – a great mix of fields, hills and woods – is an oasis for year-round outdoor recreation.

    Laura D'Angelo Berkley & Veller Greenwood Country

    91 Vermont 35, Athens, VT 05143
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