Brattleboro VT Homes for Sale

Brattleboro is a small Vermont city with alot of personality. Brattleboro offers residents the perfect balance between outdoor adventure and shop-lined streets.

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Condos | Multi-Family | Commercial | Land

60-62 Brook Street Brattleboro VT 05301

Brattleboro, VT60-62 Brook Street

Price$399,000

Est. Mortgage: $/month

MLS Number 4945998

  • Residential Single Family
  • Square Feet 2,993
  • Bedrooms 4
  • Construction Existing
  • Bathroom 2

A beautifully maintained home with lots of vintage charm. Situated on a nice street with very low traffic flow. Located just minutes to downtown, the famous Brattleboro Food Coop, and a short distance to Brattleboro Memorial Hospital and the high school. You will fall in love with the special details of this home. Covered wrap-around front porch and upstairs portico. Handsome quarter-sawn oak hardwood floors, artfully laid out. High ceilings, many built-ins, and original Kohler clawfoot bathtubs stamped 1898! The current owner has invested in smart energy upgrades such as Farnum Insulation in the attic and basement, an efficient hybrid heat pump, a new oil tank, and updated electrical and heating systems. Three bedrooms downstairs, and two bedrooms up. You will find a vintage stained glass window in the upstairs hallway. This house is filled with sunlight! A sweet backyard & gorgeous (always organic), garden space on the southeast side, and many special plantings, like Japanese Maple, blueberries and raspberries, and many pollinator plants, will give the sense of country living right in the middle of town. Keep one unit for yourself and have tenants pay for most of the mortgage, or maybe use it as a multigeneration home, where everyone has their own space but can have that sense of communal living as well. All in all, a great property that must be seen to be appreciated. Delayed showings until March 24, 2023.

Listed by Thom Dahlin of Berkley & Veller Greenwood Country

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$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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475 Upper Dummerston Road Brattleboro VT 05301

MLS Number 4945883

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,860

Rare opportunity to own an elegant 1880's farmhouse with attached 2-car garage & 21+ protected acres just minutes from downtown Brattleboro & with quick access to I91 where you're 2.5 hours from Boston & 3.5 from NY. This gorgeous home sits across the street from the Country Club with 18 holes of golf, a restaurant, & groomed nordic trails in the winter, if you prefer alpine skiing you're only 30 minutes from Mt Snow. This gracious home offers 4 bedrooms, an office, 2 1/2 baths, a kitchen open to a spacious family room that is ideal for entertaining & cozy with a woodstove or use the heat pump to cool in the warmer months, if you prefer a more intimate space adjourn to the dining room with a vintage tin ceiling, the living room is spacious & overlooks the kitchen garden & the wrap around extra wide country porch. The refinished wood floors throughout the house gleam in the sun from the oversized windows which overlook the barn, tunnel greenhouse, & the many established gardens. If homesteading is your dream then you'll be all ready to farm and garden with an expansive meadow, currently being hayed by a neighbor, 6 stall barn, 50' caterpillar tunnel, 18 established beds for low till gardening complete with drip irrigation system. Special option to purchase farm LLC separately. If you'd rather not, then consider leasing to an appreciative local farmer! This home has been repainted inside & out, insulated, & is ready for the next owner. Showings start w/open house on 3/25 11-1

Listed by Brattleboro Area Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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83 Brattle Street Brattleboro VT 05301

Brattleboro, VT83 Brattle Street

Price$289,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4944710

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,799

The welcoming warmth of this cottage-style home greets you with vintage flair the moment you arrive at its doorstep. Enter to find gorgeous cherry & oak floors, huge living room, formal dining, library, kitchen, & a half bath. A stream of windows in the living room fills the room with natural light & the converted gas fireplace & mantle add to the charm. You will fall in love with the classic library with its French doors & an abundance of built-in shelves. The most charming of all is the renovated kitchen with its iconic style & retro feel. Beautiful ceramic tile floor & custom granite counters have been added while retaining the home's original personality. There are many period features throughout such as built-ins, beautiful lattice windows, a built-in bread box, & the old fashion telephone nook. On the second floor, there are three good-sized bedrooms with walk-in closets, a full bath, & a full-size attic. The bonus of an enclosed back porch overlooks the spacious 20x30 open deck. Wishing for an additional workshop or sweet studio? The 2-car garage/barn with a second floor lends the opportunity for developable space. This property is complete with a sunny yard & the spring blossoms of your apple tree. New roof 2020. Easy access to the Brattleboro Country Club trails which connect at the end of the dead-end street. This special home is looking for a new owner to continue the legacy of appreciating its character. Delayed showings until 3/10/23.

Listed by Brattleboro Area Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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11 Robin Way Brattleboro VT 05301
Active With Contract

MLS Number 4943326

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,248

Sweet and beautiful two bedroom condo in Brattleboro! Located a stone's throw from the Summer Farmer's Market and Memorial Park, nestled up on the hill in the Brookside apartments lies this gem of a home. This home has some exquisite features including bamboo flooring, cathedral ceilings, and spacious bedrooms. With a direct-entry garage and laundry room, back-deck outdoor space, and on-site property management included this property provides ease of living at an affordable price. The kitchen and dining areas are airy and bright and sunny. The bedrooms are spacious and comfortable. The home has some recent upgrades including interior painting and electric upgrades, as well as a nice deep clean. Ready for its new owners, come and check it out at the open house this Saturday from 11am-1pm!

Listed by Kate Barry of EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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103 New England Drive Brattleboro VT 05301
Active With Contract

MLS Number 4942824

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,119

Your mid century dream awaits! For the first time on the market in over 30 years this three bed two bath home is full of natural light & ready for new life! Close to 91 for easy commuting. About an hour to ski at either Okemo or Stratton. Covered parking - you'll never have to clean snow off your car again! The main floor boasts a giant primary suite with bathroom and walk in closet - and even a sunken jacuzzi tub! Up next it's time to cozy up in front of the pellet stove in the sunken living room. Downstairs you will find a large bonus room, two bedrooms, and a full bath! Outside all your recreation dreams come true! There is an in-ground pool perfect for hosting large or intimate gatherings! Behind the pool is a small basketball court perfect for working on your layup. Come see all this great space has to offer!

Listed by Courtney White of Greenwald Realty Associates

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$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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49 Marlboro Avenue Brattleboro VT 05301

Brattleboro, VT49 Marlboro Avenue

Price$329,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4942456

  • Residential Single Family
  • Bathroom 2
  • Construction Existing
  • Bedrooms 3
  • Square Feet 1,929

Located in one of Brattleboro's treasured neighborhoods, you'll find this home a true gem! The spacious two-car garage brings you through a mud room and private office into a beautiful open-concept Kitchen/Dining/Living area boasting hardwood oak flooring. First-floor bedroom and full bath offer one-floor living with the luxury of aging-in-place. Adjacent there is a wonderfully bright sitting room/playroom/office, perfect for keeping cozy on those snowy winter days. Two additional bedrooms with another full bath are located on the second floor, one of which spans the length of the Kitchen/Dining/Living area below. This home affords space and opportunities galore, limited only by your own creativity. The large, partially-finished basement adds a fourth bedroom, laundry room, storage area, and workshop to the home's footprint. Another heated workshop is off the garage with the layout of private stairs leading to an unfinished attic, replete with a cedar storage closet. Your possibilities are endless. Could a rented room, another office or studio be in your future? This picture perfect home is superbly completed by a deck overlooking the luxury of an in-town, private, fenced-in backyard, perfect for child's play, entertaining, or gardening. This is an ideal location so close to I91, shopping, restaurants, schools, and the hospital. Contingent upon Sellers securing housing. Delayed showings until Friday, Feb 10th

Listed by Brattleboro Area Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1149 Western Avenue Brattleboro VT 05301

Brattleboro, VT1149 Western Avenue

Price$156,500

Est. Mortgage: $/month

MLS Number 4942095

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Square Feet 1,873
  • Bedrooms 4

A Single-family home on an intown lot that is in need of some rehabilitation to bring it back to its original glory. Located on Western Avenue with a corner lot. This home features 4 bedrooms and 2 full bathrooms and a detached garage. This home is a handyman's project! Being sold "AS IS". Will need to be a cash buyer

Listed by Peggy Winchester of Brattleboro Area Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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28 Blakeslee Street Brattleboro VT 05301

Brattleboro, VT28 Blakeslee Street

Price$269,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4933724

  • Residential Single Family
  • Construction Existing
  • Square Feet 1,840
  • Bathroom 2
  • Bedrooms 4

This classic four bedroom home is tucked away in privacy while also located right in the middle of all the conveniences of Brattleboro. This neighborhood is perfect for new families or folks looking to quiet down on a slow road while still benefitting from a good location. This New Englander has the original hardwood floors throughout the whole house giving it classic charm. The main floor includes a large bedroom with views of the neighborhood and a full bathroom making this a perfect option for first floor living. All four bedrooms in this home are large and feature a closet. Both the attic and basement have potential to be finished areas to maximize living space in the home. A large deck off the side of the house is perfect to sit out during the warm seasons. A second floor balcony is perfect to relax and watch the neighborhood pass. Located under a mile from Brattleboro Union High School, grocery stores, pharmacies, and restaurants make this home convenient to all your immediate necessities.

Listed by Teddy Kramer of Berkley & Veller Greenwood Country

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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35 Fairground Road Brattleboro VT 05301

Brattleboro, VT35 Fairground Road

Price$265,000

Est. Mortgage: $/month

MLS Number 4925668

  • Residential Single Family
  • Bedrooms 3
  • Square Feet 1,008
  • Bathroom 1
  • Construction Existing

Looking for a starter-home, wishing to downsize or planning to age-in-place? Then look no further. The answer is this compact but surprisingly roomy, in-town Cape home with a large 0.43 acres lot. This sunny and cheery home's ground floor has a kitchen, a living room, a bedroom and a bonus small office/study. The ground floor's ¾ bath has been recently updated with a newly tiled shower and floor. There's new vinyl flooring in the kitchen and hallway. All the other ground floor rooms have hardwood floors. The upper level has two bedrooms with pine wood floors (one has part vinyl covering). The home has a full, dry basement with laundry and dryer hook-up. The basement has both interior and exterior access (the basement's bulkhead is new!). The level, open and sunny yard is a generous 0.43 acres - a surveyed, two lot parcel (see survey). Great for fun, gardening or whatever your favorite outdoor activities may be. Minutes away from all that Brattleboro has to offer, this well cared for home is ready for it's next owners to make it their own and bring it to the next level. Contingent on Sellers finding suitable housing.

Listed by Laura D'Angelo and Thom Dahlin of Berkley & Veller Greenwood Country

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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204 Williams Street Brattleboro VT 05301

Brattleboro, VT204 Williams Street

Price$198,900

Est. Mortgage: $/month

MLS Number 4922763

  • Residential Single Family
  • Bedrooms 3
  • Construction Existing
  • Square Feet 1,611
  • Bathroom 2

Built in 1840, this two story home offers approximately 1611 finished square feet, three bedrooms, one full and one half bath, hardwood, unfinished basement and detached one car garage. This home sits on an approximate 15682 sqft lot.

Listed by Sherry Price of REALHome Services and Solutions,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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750 Upper Dummerston Road Brattleboro VT 05301
Active With Contract

MLS Number 4916437

  • Residential Single Family
  • Square Feet 1,989
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1

This gorgeous circa 1800's Cape Cod style home is an eye catcher for sure. Located in a most desirable neighborhood, just around the corner from the Brattleboro Country Club. Holding onto its classic charm, this sweet home has retained much of its original character. An impressive large kitchen with a center island, wall oven, walk-in-in pantry and a gorgeous formal dining room. The 1st floor has a relaxed feel of spaciousness with an office or potential ground floor bedroom, a generous living room, den, full bath and washer/dryer hookup. Take the classic staircase upstairs to the three bedrooms. The oversized detached 2 car garage has an expansive second floor that offers a storage area as well as potential for an office or studio. Capturing natures beauty from you back stone patio, you overlook 2 acres of open land and mature trees or waive to your neighbors on your covered front porch. This is a fabulous home for entertaining, all just minutes to downtown Brattleboro, the Retreat Farm, hiking and biking trails, kayaking etc. This gem checks all the boxes if you are looking for a classic Vermont home in a superb setting.

Listed by Brattleboro Area Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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67 Pine Street Brattleboro VT 05301

Brattleboro, VT67 Pine Street

Price$350,000

Est. Mortgage: $/month

MLS Number 4606363

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 2,584

Great set up for family groups who would love to share expenses and have great living space. Lovely mother in-law apartment with great room and two first floor bedrooms and bath, screened porch. Or, occupy with single family and have a music/entertainment/studio. In-town lot close to schools, hospital, downtown and services. Easily handicapped accessible. Subject to seller finding suitable housing.

Listed by Brattleboro Area Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2023 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, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated March 28, 2023 10:54 PM EDT