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Brattleboro VT Real Estate: Homes for Sale in Southern Vermont

By Tony Walton, Principal Broker, New England Landmark Realty

Quick Answer

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 at a Glance

  • County: Windham
  • ZIP codes: 05301-05304
  • Population: 12,184 (2020 Census)
  • Area: about 32 square miles
  • Villages: Brattleboro and West Brattleboro
  • Neighbors: Guilford, Dummerston, and Vernon, with New Hampshire across the Connecticut River
  • Schools: Windham Southeast Supervisory Union, including Brattleboro Union High School
  • Health care: Brattleboro Memorial Hospital and the Brattleboro Retreat

Living in Brattleboro

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.

Homes in Brattleboro

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.

Getting Around

  • Interstate 91 has three Brattleboro exits: Exit 1 (south), Exit 2 (west), and Exit 3 (north). It's the main route south to Massachusetts and north toward White River Junction.
  • Vermont Route 9 runs west over the Green Mountains toward Bennington, and east across the river into New Hampshire.
  • Vermont Route 30 follows the West River northwest toward Newfane and Manchester.
  • US Route 5 runs north-south through town along the Connecticut River.
  • Amtrak's Vermonter stops in Brattleboro daily.

Costs to Plan For

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.

Frequently Asked Questions

What county is Brattleboro, VT in?

Windham County, in the southeast corner of Vermont on the Connecticut River.

What are the ZIP codes for Brattleboro, VT?

05301 through 05304.

What schools serve Brattleboro?

Brattleboro's public schools are part of the Windham Southeast Supervisory Union, including Brattleboro Union High School.

How do you get to Brattleboro?

By Interstate 91, which has three exits in Brattleboro, or by Amtrak's Vermonter, which stops in Brattleboro daily.

How do I see recent home prices in Brattleboro?

Our Brattleboro market report lists recent sales, prices, and days on market, and updates automatically.

What to Do Next

Call our office at 802-253-4711, reach Tony Walton directly at 802-233-4107, or contact us.

Want Vermont market updates and homeowner tips in your inbox? Sign up for Tony's newsletter. You can unsubscribe at any time.

  • Vermont Home Buying Guide
  • Moving to Vermont
  • Best Places to Buy in Vermont

Sources

  • Brattleboro, Vermont (county, population, area, ZIP codes, highways, rivers, Fort Dummer, Estey Organ, schools, hospitals, Amtrak)
  • Vermont Department of Taxes, Property Transfer Tax

Brattleboro Homes & Land For Sale

35 Fairground Rd, Brattleboro image
35 Fairground Rd, Brattleboro $280,000

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 ...

  • 3 Beds
  • 1 Baths
  • 5115217 MLS
  • 0.23 Acres
311 Guilford St, Brattleboro image
311 Guilford St, Brattleboro $349,900

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...

  • 4 Beds
  • 2 Baths
  • 5115066 MLS
  • 0.48 Acres
9 Evergreen Ln, Brattleboro image
9 Evergreen Ln, Brattleboro $230,000

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...

  • 2 Beds
  • 2 Baths
  • 5114878 MLS
43 Winter St, Brattleboro image
43 Winter St, Brattleboro $275,000

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...

  • 3 Beds
  • 1 Baths
  • 5114102 MLS
  • 0.23 Acres
625 Black Mountain Rd, Brattleboro image
625 Black Mountain Rd, Brattleboro $339,000

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...

  • 3 Beds
  • 2 Baths
  • 5113538 MLS
  • 1.7 Acres
29 Morningside Commons, Brattleboro image
29 Morningside Commons, Brattleboro $189,500

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...

  • 2 Beds
  • 2 Baths
  • 5112756 MLS
164 Morningside Commons, Brattleboro image
164 Morningside Commons, Brattleboro $229,000

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...

  • 2 Beds
  • 2 Baths
  • 5111836 MLS
627 Abbott Rd, Brattleboro image
627 Abbott Rd, Brattleboro $310,000

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...

  • 3 Beds
  • 2 Baths
  • 5111605 MLS
  • 1.9 Acres
50 Lawton Dr, Brattleboro image
50 Lawton Dr, Brattleboro $129,000

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 ...

  • 2 Beds
  • 1 Baths
  • 5111023 MLS
  • 0.14 Acres
104 Morningside Commons, Brattleboro image
104 Morningside Commons, Brattleboro $279,000 ▼

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...

  • 2 Beds
  • 2 Baths
  • 5110840 MLS
40 Brookside Dr Unit 2, Brattleboro image
40 Brookside Dr Unit 2, Brattleboro $179,000

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...

  • 1 Beds
  • 1 Baths
  • 5110478 MLS
36 Pine St, Brattleboro image
36 Pine St, Brattleboro $289,000 ▼

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...

  • 3 Beds
  • 2 Baths
  • 5110381 MLS
  • 0.19 Acres
19 Blakeslee St, Brattleboro image
19 Blakeslee St, Brattleboro $379,000

Welcome to this classic in-town gem, where timeless architectural character meets thoughtful updates and beautifully cultivated outdoor spaces. Offering approximately 1,7...

  • 4 Beds
  • 2 Baths
  • 5109984 MLS
  • 0.22 Acres
41 Organ St, Brattleboro image
41 Organ St, Brattleboro $270,000

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,...

  • 2 Beds
  • 1 Baths
  • 5109722 MLS
  • 0.08 Acres
59 Highland St, Brattleboro image
59 Highland St, Brattleboro $319,000

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...

  • 2 Beds
  • 2 Baths
  • 5109553 MLS
  • 0.29 Acres
Meetinghouse Ln, Brattleboro image
Meetinghouse Ln, Brattleboro $135,000

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...

  • 5109235 MLS
  • 1.5 Acres
145 Belmont Ave, Brattleboro image
145 Belmont Ave, Brattleboro $289,000

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...

  • 3 Beds
  • 1 Baths
  • 5108845 MLS
  • 0.3 Acres
48 Wilsons Woods Rd, Brattleboro image
48 Wilsons Woods Rd, Brattleboro $269,900 ▼

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...

  • 3 Beds
  • 1 Baths
  • 5108647 MLS
  • 0.29 Acres
Marlboro Rd, Brattleboro image
Marlboro Rd, Brattleboro $139,000

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...

  • 5107996 MLS
  • 3.8 Acres
39 Brookside Dr Unit 5, Brattleboro image
39 Brookside Dr Unit 5, Brattleboro $190,000

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...

  • 2 Beds
  • 1 Baths
  • 5107706 MLS
77 Buttonwood Dr, Brattleboro image
77 Buttonwood Dr, Brattleboro $439,000

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...

  • 2 Beds
  • 2 Baths
  • 5106541 MLS
  • 0.18 Acres
207 Elliot St, Brattleboro image
207 Elliot St, Brattleboro $290,000

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...

  • 5 Beds
  • 2 Baths
  • 5105369 MLS
  • 0.37 Acres
203 Fairview St, Brattleboro image
203 Fairview St, Brattleboro $305,000 ▼

PRICE IMPROVEMENT! MOTIVATED SELLER! Welcome to this brand NEW, beautiful home, professionally blower-door tested at an exceptional 1.7 providing outstanding airtightness...

  • 2 Beds
  • 1 Baths
  • 5103959 MLS
  • 0.25 Acres
68 E Bonnyvale Ln, Brattleboro image
68 E Bonnyvale Ln, Brattleboro $299,000

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...

  • 3 Beds
  • 2 Baths
  • 5103897 MLS
  • 6.5 Acres
110 Western Ave, Brattleboro image
110 Western Ave, Brattleboro $289,000

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...

  • 4 Beds
  • 2 Baths
  • 5103506 MLS
  • 0.13 Acres
72 Green Mdw, Brattleboro image
72 Green Mdw, Brattleboro $450,000

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 ...

  • 3 Beds
  • 2 Baths
  • 5103012 MLS
  • 0.23 Acres
Pleasant Valley Rd, Brattleboro image
Pleasant Valley Rd, Brattleboro $198,000

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...

  • 5102764 MLS
  • 3.27 Acres
11 Evergreen Ln, Brattleboro image
11 Evergreen Ln, Brattleboro $230,000 ▼

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...

  • 2 Beds
  • 2 Baths
  • 5099302 MLS
117 Fuller Dr, Brattleboro image
117 Fuller Dr, Brattleboro $90,000 ▼

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, ...

  • 5099250 MLS
  • 0.12 Acres
455 S Main St, Brattleboro image
455 S Main St, Brattleboro $269,000 ▼

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....

  • 3 Beds
  • 1 Baths
  • 5097858 MLS
  • 0.15 Acres
412 Western Ave, Brattleboro image
412 Western Ave, Brattleboro $249,000 ▼

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...

  • 3 Beds
  • 3 Baths
  • 5094671 MLS
  • 0.22 Acres
136 Morningside Commons, Brattleboro image
136 Morningside Commons, Brattleboro $289,000 ▼

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...

  • 2 Beds
  • 3 Baths
  • 5093917 MLS
550 S Main St, Brattleboro image
550 S Main St, Brattleboro $305,000 ▼

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...

  • 3 Beds
  • 2 Baths
  • 5086341 MLS
  • 0.15 Acres
116 Birge St Unit 2, Brattleboro image
116 Birge St Unit 2, Brattleboro $239,000 ▼

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...

  • 1 Beds
  • 1 Baths
  • 5081546 MLS
219 High St Unit 3, Brattleboro image
219 High St Unit 3, Brattleboro $139,000 ▼

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...

  • 1 Beds
  • 1 Baths
  • 5081405 MLS
  • 0.17 Acres
39 Brookside Dr Unit 7, Brattleboro image
39 Brookside Dr Unit 7, Brattleboro $135,000 ▼

Welcome to this beautifully refurbished one-bedroom, one-bath condominium in desirable West Brattleboro. Freshly updated with new flooring, fresh interior paint, vanity, ...

  • 1 Beds
  • 1 Baths
  • 5081287 MLS
39 Atwood St, Brattleboro image
39 Atwood St, Brattleboro $320,000 ▼

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...

  • 3 Beds
  • 2 Baths
  • 5075506 MLS
  • 0.23 Acres
000 Fort Dummer Hts, Brattleboro image
000 Fort Dummer Hts, Brattleboro $250,000

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...

  • 4934983 MLS
  • 3.79 Acres
00 Fort Dummer Hts, Brattleboro image
00 Fort Dummer Hts, Brattleboro $150,000

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...

  • 4934978 MLS
  • 2.05 Acres
Fort Dummer Hts, Brattleboro image
Fort Dummer Hts, Brattleboro $125,000

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 ...

  • 4934976 MLS
  • 1.75 Acres
16 Washington St, Brattleboro image
16 Washington St, Brattleboro $225,000 ▼

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...

  • 5 Beds
  • 3 Baths
  • 5024828 MLS
  • 0.21 Acres
925 Hinesburg Rd, Brattleboro image
925 Hinesburg Rd, Brattleboro $899,800

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...

  • 5 Beds
  • 8 Baths
  • 5045909 MLS
  • 18.11 Acres
109 Central St, Brattleboro image
109 Central St, Brattleboro $350,000 ▲

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 ...

  • 4 Beds
  • 2 Baths
  • 5054419 MLS
  • 0.12 Acres
24 Summit Cir, Brattleboro image
24 Summit Cir, Brattleboro $80,000

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...

  • 5009351 MLS
  • 1.97 Acres

board logoCopyright 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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