By Tony Walton, Principal Broker, New England Landmark Realty
Brattleboro is a Windham County town of about 12,000 people in the southeast corner of Vermont, where the West River and Whetstone Brook meet the Connecticut River. It has a walkable downtown with a strong arts scene, its own hospital, and easy access to Interstate 91 and Amtrak's Vermonter. Homes range from downtown and village houses to condos and rural properties in the hills. Current Brattleboro homes for sale appear at the bottom of this page, and our Brattleboro market report shows recent sales and prices.
Brattleboro's downtown is known for independent shops, restaurants, galleries, and music, with the Brattleboro Museum & Art Center and galleries around town taking part in the regular Gallery Walk. Main Street's brick blocks overlook the Connecticut River.
The town's history runs deep. Fort Dummer, built in 1724 just south of today's downtown, is often described as the first permanent European settlement in what became Vermont. From 1852, Brattleboro was home for about a century to the Estey Organ Company, once the largest organ manufacturer in the United States.
Brattleboro is also a regional center for southern Vermont, with Brattleboro Memorial Hospital, the SIT Graduate Institute, and Community College of Vermont and Vermont State University locations.
Buyers in Brattleboro find Victorian and older homes in and around downtown, condominiums, neighborhoods in West Brattleboro, and rural homes with land in the hills west of town. See what's for sale now in the listings below, and check recent sale prices in the Brattleboro market report, which updates as homes sell.
For homes near the Connecticut River, the West River, or Whetstone Brook, read the seller's flood disclosure and check the property's flood zone before you buy.
Vermont's property transfer tax, paid by the buyer at closing, is 0.5% on the first $200,000 of a primary residence and 1.47% above that; 3.62% for a second home; and a VHFA-financed primary residence is exempt on the first $250,000. Estimate your payment, transfer tax, and cash to close with our Vermont Home Cost Calculator. Downtown homes are often on town water and sewer, while rural homes usually have private wells and septic systems; see our Vermont home inspection guide.
Windham County, in the southeast corner of Vermont on the Connecticut River.
05301 through 05304.
Brattleboro's public schools are part of the Windham Southeast Supervisory Union, including Brattleboro Union High School.
By Interstate 91, which has three exits in Brattleboro, or by Amtrak's Vermonter, which stops in Brattleboro daily.
Our Brattleboro market report lists recent sales, prices, and days on market, and updates automatically.
Call our office at 802-253-4711, reach Tony Walton directly at 802-233-4107, or contact us.
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This sweet home eagerly awaits new owners wanting to put their personal stamp on a cute home with an incredibly convenient location! With 3 nicely sized bedrooms plus an ...
Well maintained 4-bedroom, 2 full bath In-town cape on a large open and sunny lot in a sought after West Brattleboro neighborhood. The house features a large bright livin...
OPEN HOUSE SUNDAY 10/25 12-2:00PM. Welcome to Evergreen Lane. Enjoy comfortable, low-maintenance living in this beautifully renovated three-level condo! Featuring 2 bed...
Just right! All spiffed up, shinny and ready to move right in. Sweet aging in place home on one level, level back yard, and minutes from grocery stores, hospital and Me...
Located in the desirable Black Mountain Road area, this cozy log home includes an attached two-car garage with a workshop area, a three-season porch, and a wraparound dec...
This cozy condo faces a hillside, landscaped with beautiful mature hydrangeas. Besides beauty, the hillside offers privacy and quiet. And no headlights will shine in your...
In this second floor condo you will not be bothered by steps overhead. You can relax on the back deck overlooking nature. You can spread out in the comfort of a living ro...
This is an estate sale. Entry into the property is forbidden. While the land is beautiful and in a very pastoral rural setting, the dwelling is considered to be a tear do...
Tiny-home ready for the next owner to make their own! The property offers a solid start to creating a comfortable, 2-bedroom tiny-home. The original log cabin sugarhouse ...
Quite simply, one of the finest units ever offered at Morningside Commons. This beautifully updated 2nd-FL condominium combines thoughtful design, quality upgrades, and t...
Don't wait to come view this newly remodeled, low maintenance, affordable and desirable ground floor end unit. Inviting circular flow, the spacious living room has a bran...
In the heart of it all! Just minutes to everything Brattleboro...Day or night, there is something fun to do....movies, eats, hiking and so may other choices....3 generat...
Welcome to this classic in-town gem, where timeless architectural character meets thoughtful updates and beautifully cultivated outdoor spaces. Offering approximately 1,7...
A Home Filled With Possibilities! For the first time in 43 years, this charming and comfortable Organ Street home is ready to welcome its next owner. Offering a spacious,...
Sited at the top of the hill in one of Brattleboro's desirable, close to town, neighborhoods, this mini victorian home is arguably one of the coolest houses in town! Offe...
Welcome to the last building lot on the desirable Meetinghouse Lane! This property offers a blank slate to bring your vision to life; small efficient home? Forever family...
Whether you are a first time home buyer or looking for an investment property, this is a home you will not want to miss. This property’s location, which abuts Brattlebor...
Sunny and inviting, this classic ranch offers easy single-level living with 3 bedrooms, 1 full bath, and a spacious living/dining area. Classic wainscoting adds charm and...
This beautiful, elevated, and sparsely wooded in-town lot features an established shared driveway with power nearby, as well as a woods road running throughout the proper...
Desirable 2 bedroom, 1 bath low maintenance, affordable home. Your spacious living/dining area has sliders looking out to the woods and a small yard space. Upstairs are 2...
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 a...
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 showc...
PRICE IMPROVEMENT! MOTIVATED SELLER! Welcome to this brand NEW, beautiful home, professionally blower-door tested at an exceptional 1.7 providing outstanding airtightness...
Looking for your first home, ready to downsize, or seeking single level living? This one is for you. Set in a peaceful rural location near the end of a quiet dead end roa...
This in town 4 bedroom, 2 bath home offers the perfect blend of comfort, convenience and versatility. Ideally located close to town amenities, this property provides easy...
Nestled in a highly desirable West Brattleboro neighborhood, this well-cared-for home offers a wonderful community lifestyle and the ease of main-level living. The first ...
It doesn't get better than this! Stunning! Over 3.25 acres in a neighborhood with a wait list, well known hiking trails, near cross country skiing, country club and min...
This inviting 2 bedroom, 2-bathroom townhouse is located with privacy but close to Brattleboro amenities. Drive into your one car garage, in addition there is a storage a...
Nestled just behind 117 Fuller Drive, with privacy and easy access from the street, this property is the perfect spot for the tiny home you have been longing for. Water, ...
Tucked in near schools, hospital, shopping and a short walk to fishing and a canoe ride. Room enough for a garden, play space and just the right size for new beginnings....
Motivated Seller, Make an offer! Move in ready and full of potential, this charming Brattleboro home is ready for its next chapter. The main level features a bright, ope...
Rare opportunity to enjoy single-level living with all modern conveniences on the main floor in this magnificent condo unit. Featuring a spacious primary bedroom with a w...
Lovely level lot, close to schools, hospital, shopping, State park and downtown. The best of everything, and BRAND NEW!!! Be the the envy of all your friends, with this...
Simple but elegant! Historic posts and wonderful beams define the magnificent open concept, giving visual shape and creating traditional options or whimsical uses for yo...
Welcome to the effortless existence of condominium life with the rare addition of uniqueness. How nice to own a home while splitting the expenses with two other condo own...
Welcome to this beautifully refurbished one-bedroom, one-bath condominium in desirable West Brattleboro. Freshly updated with new flooring, fresh interior paint, vanity, ...
First time offered, EVER... built and loved by the current family, it is time to pass the keys to a new generation of owners ready to put their own love and dreams into t...
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 y...
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...
Manicured into a beautiful high meadow, in a nice little neighborhood....sunny with views, what more could you want? Easy to build!!! The land is open, so no fuss with ...
Major price reduction! This price reduction involves the seller staying on as a tenant for up to a year after closing. Ask for details! Fabulous potential with this in-to...
Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking O...
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 ...
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 r...
Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .
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