Brattleboro Real Estate

Welcome to Brattleboro, Vermont – a charming town nestled in the picturesque Windham County, where the beauty of nature meets a rich tapestry of culture and community. Known for its vibrant arts scene and stunning landscapes, Brattleboro is a hidden gem that offers a unique blend of small-town charm and modern amenities.

As you stroll through the historic downtown area, you'll be captivated by the eclectic mix of shops, galleries, and eateries that line the streets. Whether you're indulging in a locally brewed coffee or exploring the works of talented artisans, Brattleboro's creative spirit is palpable. The town is also home to the renowned Brattleboro Museum & Art Center, showcasing contemporary art and engaging exhibitions that reflect the community’s artistic flair.

Nature enthusiasts will find themselves in paradise, with the Connecticut River and the surrounding Green Mountains providing endless opportunities for outdoor adventures. From hiking and biking in the warmer months to skiing and snowshoeing in winter, Brattleboro's natural beauty is a year-round playground for all ages.

In addition to its cultural and recreational offerings, Brattleboro boasts a strong sense of community, with numerous festivals and events that bring residents together. The annual Brattleboro Literary Festival and the vibrant farmers market are just a couple of highlights that showcase the town's commitment to fostering connections among its residents.

With its welcoming atmosphere, rich history, and breathtaking scenery, Brattleboro is not just a place to live – it's a place to thrive. Discover your dream home in this enchanting town and become a part of its wonderful community!

Newest Listings in Brattleboro

$499,000

2 Beds ⋅ 2 Baths ⋅ 5106916 MLS

Celebrate! You have earned it! A gentle neighborhood for 55 and more, mowing, plowing and shoveling included in the HOA.. Leave the tough stuff for the young at heart! Sit snug as a bug in the sun room and watch it snow, without a care or worry, or run off to play pickle ball in the warm seasons....Want to be snow birding? Perfect set up as the home is easy care inside and out. Park a car in the garage for the winter and forget about it till spring. Comfort is what you deserve and have earned. This is it.

171 Buttonwood Dr, Brattleboro

$525,000

3 Beds ⋅ 3 Baths ⋅ 5106903 MLS

Just what you have been waiting for! The perfect spot in the perfect neighborhood! Watch the moon rise over Wantastiquet and the seasons change from your back yard! Listen for spring...when the ice cracks on the river and lets go...and watch the shoots pop to greet a new warm and beautiful summer season. This contemporary raised ranch has a wall of windows to the garden, a lovely little wood stove for chilly evenings and a cook's kitchen. The Star Trek elevator allows you to age in place, drive in to the garage, step on the elevator and zoom to the main floor so every inch of the house is accessible. Recently renovated, this is worth seeing. Possession on 11/6/26. Join us at the Open House 8/30/26, 11-1.

205 Wantastiquet Dr, Brattleboro

$479,000

2 Beds ⋅ 2 Baths ⋅ 5106580 MLS

It has all you wanted! Shiny wood floors to celebrate New England building, plenty of windows to capture every inch of light possible, granite tops on a multitude of cabinets, a step in shower but also a tub for long soaks or the little ones who visit....total one floor living, so rare locally, even no stairs to the direct entry garage. A service that plows, shovels and mows.....a playground for adults with pickle ball, dedicated exercise room, meeting room and kitchen, and a cozy place by the fire to sit and visit. If you are at an age when you can appreciate an easier lifestyle, come take a look and see if this is your next adventure. This property is being subdivided from a larger parcel.

162 Buttonwood Dr, Brattleboro

$439,000

2 Beds ⋅ 2 Baths ⋅ 5106541 MLS

You've earned it.....the right to easy living.....have someone to do the heavy lifting...This community has become a much needed addition to the housing community. All are designed for the 55 and over who are looking for an easy way to settle in. Just think, the snowplowing, shoveling and salting are all taken care of, as well as the summer mowing and hedge trimming. One level living with no steps, a step in shower...no hopping over the tub rim...no cleaning off the car when you park in the garage...Besides all this there is a community center featuring exercise equipment, a function room, cozy fireplace and kitchen. A great place for walking, meeting the neighbors and making friends. Pickle Ball anyone? Located right off I91, you CAN get there from here. No mud season, no fuss. You have earned it! This property is being subdivided from a larger parcel.

77 Buttonwood Dr, Brattleboro

$615,000

4 Beds ⋅ 3 Baths ⋅ 5106451 MLS

You don't have to wear pearls to live here! This home oozes classic charm, memories of Thanksgivings and every holiday celebrated. The first step in has a welcoming wood stove for winter chill and glass french doors to fling open the first day of spring....Bring them home to the heart of the house with a dining room big enough for a feast...living room with a fireplace....warm hardwood floors, a lovely staircase and windows everywhere. Inside or out... every season will capture your heart....you will find them on the patio surrounded by blooms and summer sounds, tucked in reading a book while the snow swirls, taking in a game while the snacks flow. There is room for it all, and they will come home.

354 Orchard St, Brattleboro

$299,000

5106434 MLS

On offer is this tidy, three-unit multi-family home, located in a tranquil residential neighborhood on Moreland Avenue. Originally designed as a multi-family, the three units have identical floor plans with good layout flow. Each 2-bedroom unit has a large eat-in kitchen with pantry, a dining room with French doors opening to the living room and the bonus of a generous, three-season, enclosed front-porch. Each unit features the original handsome wood trim and doors, gleaming hard wood floors, good closet space, and many huge windows filling the place with glorious natural light. There are separate electric meters and boilers for each unit. Additional bonuses are the two-car garage, a small but sweet yard with trees including two pear trees, and a good basement. Great investment opportunity or owner occupied income property. Currently, the first floor is rented with a lease while the second and third floor units are vacant. Great location near high school, hospital, shopping and I-91. Property is being sold "as is". Please Note: Unit 3's pantry is unfinished. Showings begin Saturday 8/29. OPEN HOUSES Saturday 12pm-2pm and Sunday 10am-12pm.

75 Moreland Ave, Brattleboro

$290,000

5 Beds ⋅ 2 Baths ⋅ 5105369 MLS

Offered to the public for the first time in nearly 60 years, this majestic Colonial-style home is located in one of Brattleboro’s oldest neighborhoods. The property showcases exquisite original details, including maple floors and fine hardwood trim throughout both levels. Many of the original plaster walls and ceilings have been professionally restored and await your personal color choices. The first floor provides an expansive layout designed for gathering. Enter through a generous mudroom into a functional kitchen - ready to be customized into a chef's dream or kept simple - complete with a large walk-in pantry. The kitchen flows seamlessly into the dining room, which features a built-in cabinet. Across the foyer, a bright living room opens into a cozy den or parlor with a quarter bath. Upstairs, you will find five bedrooms and a full bath, with the added potential to finish the full attic for even more living space. Situated on two combined lots, this in-town gem includes off-street parking for multiple vehicles and plenty of room for gardening. Are you ready to become the next steward of this stately property?

207 Elliot St, Brattleboro

$439,000

3 Beds ⋅ 2 Baths ⋅ 5105327 MLS

Elegant and charming cape with an enchanting, exceptional garden that will impress even the seasoned green thumb. This magnificent home is solar equipped; the owner has had no electric bills for 3 years and the solar agreement may be transferred to the new buyer. Classic Vermont timeless style throughout features gorgeous archways, built-ins, and oak flooring. The kitchen is spacious with a traditional counter and views out to the tranquil gardens. The circular first floor plan graciously leads you into the long living room with a woodstove and pretty mantel. A second dining space, a bedroom, and a full bath complete the circle, allowing for easy single-floor living. Upstairs are two more bedrooms, a full bath, and an impressively large sitting room/den. The two mini-splits provide both heating and air conditioning for year-round comfort. In addition, there is an attached two-car garage and a full basement with space for your workshop. Visit this gem that has beauty and functionality.

1137 Upper Dummerston, Brattleboro

$390,000

2 Beds ⋅ 3 Baths ⋅ 5104900 MLS

Welcome to 116 Green Meadow Road, where a unique shared-meadow setting offers the feel of country living with the convenience of Brattleboro nearby. Built in 1981 and situated on a manageable .25-acre lot, this home overlooks a beautiful 22-acre meadow. The current owner holds 20 shares in the meadow, providing shared ownership, recreational use and a voice in its stewardship. Purchase of the 20 shares by the buyer is a condition of sale ($6,800). Step inside to a freshly painted interior with all-new flooring and new appliances. The flexible floor plan currently offers two bedrooms, including an exceptionally spacious bedroom with potential to be divided to create additional sleeping or living space. Three 3/4 baths provide convenience throughout the home, with one offering space to accommodate a future bathtub. The walk-out basement already has a 3/4 bath and offers wonderful potential for additional finished living space. Enjoy your morning coffee or unwind at the end of the day on the back deck under the awning while taking in the peaceful meadow views. Inside, a propane stove in the living room adds warmth and coziness during the cooler Vermont months. Energy-conscious and practical features include solar panels, a standing seam metal roof, 3 heat pumps, mini-splits and a whole-house propane generator. A one-car garage with additional storage, fully fenced backyard, garden shed and space for gardening complete the property. A special opportunity to enjoy the privacy, views and open feeling of a much larger country property without having to maintain 22 acres yourself. Open House Saturday, August 22: 10am to 12 Noon.

116 Green Meadow Rd, Brattleboro

$250,000

2 Beds ⋅ 2 Baths ⋅ 5104720 MLS

Easy living. This move-in-ready townhouse comes with snow removal; trash, recycling and compost removal; landscaping; a swimming pool; tennis and pickleball courts; a hiking trail and little libraries included. The seller has refurbished the entire unit by installing beautiful flooring on the first floor and in bathrooms, refinishing cabinets, painting, and cleaning carpeting in order to get the condo ready for you. It is fresh, clean and ready for you! The convenient second floor laundry has a newer energy efficient all-in-one washer/dryer unit. You can sit on your private patio and enjoy nature. Or, escape the heat with a dip in the pool. Morningside Commons is within walking distance of downtown Brattleboro with its many shops and restaurants. Your condo awaits you!

147 Morningside Commons, Brattleboro

$190,000

2 Beds ⋅ 1 Baths ⋅ 5104626 MLS

Move-in ready and easy to maintain, this 2-bedroom, 1-bath townhouse-style condo offers comfortable living in a convenient Brattleboro location. The main level features a bright, open living and dining area with sliding doors that lead to a private patio and a peaceful, wooded backdrop. An inviting spot to relax or enjoy the outdoors. The kitchen offers plenty of cabinetry and workspace and flows easily into the main living area. Upstairs, you’ll find two generously sized bedrooms and a full bath. With 930 square feet of finished living space plus a full 465-square-foot unfinished basement, there’s excellent additional room for storage, hobbies, or everyday necessities. Conveniently located near shopping, public transportation, I-91, the Farmers Market, Living Memorial Park, and all that downtown Brattleboro has to offer. Association fees include heat, water/sewer, landscaping, and more, helping make this an appealing low-maintenance home at an accessible price point.

39 Brookside Dr Unit 4, Brattleboro

$245,000

2 Beds ⋅ 2 Baths ⋅ 5104214 MLS

**Open House Sunday 8/23/26 from 1-3pm** Welcome to Brookside Condominiums! This 2-bedroom, 1.5-bath end-unit townhome offers a comfortable, low-maintenance lifestyle in a convenient Brattleboro location. Natural light fills the living areas throughout, while the thoughtfully designed galley kitchen offers ample cabinet and counter space, a breakfast bar, and an easy flow into the dining area. Upstairs, two spacious bedrooms feature generous closet space, and the full bathroom is easily accessible from both bedrooms. There is even a surprise bonus room, perfect for additional storage or for extra daily use! The first level includes an attached one-car garage with automatic opener, laundry and utility room off the garage, and foyer area for coats and shoes. As an end unit, the home enjoys added privacy along with both a welcoming side deck off the living room and a peaceful rear brick patio, providing inviting outdoor spaces to relax or entertain. Conveniently located near shopping, dining, parks, recreation, downtown Brattleboro, and major commuter routes, this home offers easy access to many local amenities while providing a comfortable place to call home.

9 Evergreen Ln, Brattleboro

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