Windham County VT Homes under $300,000

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.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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