Homes for Sale near Brattleboro Area Middle School

• 

  

  

  /32

  $475,000

  $75K PRICE DROP

  • 4,116 Sq Ft

  33 Oak St, Brattleboro, VT 05301

  This is a rare opportunity to take over a multi-family redevelopment project in the heart of Brattleboro. Situated on a 0.40-acre site, the property features a vacant three-story building that has already been gutted and fully remediated for lead paint. With municipal zoning approvals already in place to expand from 8 to 13 units and full architectural plans included with the sale, the

  Kate Barry EXP Realty

  33 Oak St, Brattleboro, VT 05301
• 

  

  

  /34

  $149,900

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  14 Deepwood Park, Brattleboro, VT 05301

  Fully remodeled in 2018, this double wide manufactured home looks far newer and nicer than its 1994 age might show. The home is nicely situated on a wide lot well back from the road and it backs up to a nice forest. The kitchen had lots of cabinetry, a center peninsula, wood countertops and a newer stainless side by side refrigerator, microwave, and propane stove. The large dining area abuts the

  Steve Schoppmeyer BHG Masiello Brattleboro

  14 Deepwood Park, Brattleboro, VT 05301
• 

  

  

  /16

  $139,000

  • Land
  • 3.8 Acres
  • $36,579 per Acre

  0 Marlboro Rd Unit 5107996, Brattleboro, VT 05301

  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 property. Significant clearing has already been completed, and a substantial amount of firewood remains on the lot.The property will require a septic system and well; however, the neighboring lot has perc'd for an inground

  Victoria Woods Brattleboro Area Realty

  0 Marlboro Rd Unit 5107996, Brattleboro, VT 05301
• 

  

  

  /26

  $1,350,000

  • 7,660 Sq Ft

  131,133,141 Green St, Brattleboro, VT 05301

  What an opportunity to own 11 units in 3 separate buildings with a fantastic rental history. Close to downtown, schools, shopping and bus routes. Very well maintained properties with 3 - two bedroom units and 8 one bedroom units. On site laundry for the convenience of tenants. Wonderful features including hardwood floors and large windows for exceptional natural light. Great porches and very

  Susan Bellville Bellville Realty

  131,133,141 Green St, Brattleboro, VT 05301
• 

  

  

  /22

  $399,000

  • 3,286 Sq Ft

  19 Canal St, Brattleboro, VT 05301

  Located in the heart of Brattleboro, this fully occupied and consistently high-performing investment property offers an outstanding opportunity for investors seeking strong cash flow and steady rental demand. Currently configured with 9 individual rentable rooms, the property has been successfully exclusively rented to The New England Center for Circus Arts students for years and maintains an

  Karen Hoppe Berkley & Veller Greenwood Country

  19 Canal St, Brattleboro, VT 05301
• 

  /2

  $350,000

  $30K PRICE DROP

  • 3,312 Sq Ft

  573 S Main St, Brattleboro, VT 05301

  Just around the corner! From the middle and high school, Oak groveelementary! Pop around the corner for all the high school games,exercise at the track. Interstate is minutes away for easy access towork or play! One apartment is over 1,000 square feet so tons of roomfor owner occupancy! 2 nice front porches. Worth looking at for eitheryour own home or as an investment. Masks

  Christine Lewis Brattleboro Area Realty

  573 S Main St, Brattleboro, VT 05301
• 

  

  /19

  $479,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  162 Buttonwood Dr, Brattleboro, VT 05301

  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

  Christine Lewis Brattleboro Area Realty

  162 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  /42

  $340,000

  $10K PRICE DROP

  • 2,745 Sq Ft

  120 Western Ave, Brattleboro, VT 05301

  Discover this lovingly cared-for two-unit multi-family property, ideally located in town with convenient access to shopping, restaurants, public transportation, and everyday amenities. Each unit offers a comfortable layout featuring 2 bedrooms and 1 bathroom, making this property an excellent opportunity for owner-occupants, investors, or those seeking rental income. Pride of ownership is evident

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  120 Western Ave, Brattleboro, VT 05301
• 

  /2

  $350,000

  $20K PRICE DROP

  • 3,002 Sq Ft

  10 Birge St, Brattleboro, VT 05301

  Invest in your own home town! Full tenant roster with the easy access to laundry across the street, grocery stores, train and The Moover. Right in the heart of things with little yard to maintain! Consider as an investment in your portfolio or decide to live in one unit and have the others pay your mortgage! Good way to start, retire or increase your portfolio! Owner is a licensed appraiser.

  Christine Lewis Brattleboro Area Realty

  10 Birge St, Brattleboro, VT 05301
• 

  

  /51

  $899,800

  $49K PRICE DROP

  • 5 Beds
  • 8 Baths
  • 7,430 Sq Ft

  925 Hinesburg Rd, Brattleboro, VT 05301

  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 Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

  Christine Lewis Brattleboro Area Realty

  925 Hinesburg Rd, Brattleboro, VT 05301
• 

  

  /37

  $595,000

  • 3 Beds
  • 3 Baths
  • 2,172 Sq Ft

  171 Green Meadow, Brattleboro, VT 05301

  Immaculate! Lovingly reimagined over two decades, this impeccable residence blends thoughtful design with modern sustainability. The heart of the home is a chef’s kitchen with ample counter space and a spacious pantry with an integrated dining area - perfect for entertaining. Relax in the stunning living room, anchored by a gas insert fireplace crafted by a very talented local mason. Outdoor

  Thomas Dahlin Berkley & Veller Greenwood Country

  171 Green Meadow, Brattleboro, VT 05301
• 

  

  /3

  $125,000

  $50K PRICE DROP

  • Land
  • 1.75 Acres
  • $71,429 per Acre

  0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301

  Manicured into a beautiful high meadow, in a nice little neighborhood....sunny with views, what morecould you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor

  Christine Lewis Brattleboro Area Realty

  0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301
• 

  

  /17

  $255,000

  $30K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 1,320 Sq Ft

  116 Birge St Unit 2, Guilford, VT 05301

  Simple but elegant! Historic posts and wonderful beams define the magnificent open concept, giving visual shape and creating traditional options or whimsical uses for your new lifestyle. High ceilings and huge windows create a celebration of light, complementing the glowing antique floors magical in combination and truly beautiful. A home, an artist loft...so many uses, so unique, so

  Christine Lewis Brattleboro Area Realty

  116 Birge St Unit 2, Guilford, VT 05301
• 

  

  /17

  $439,000

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  77 Buttonwood Dr, Brattleboro, VT 05301

  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

  Christine Lewis Brattleboro Area Realty

  77 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  /27

  $450,000

  • 3 Beds
  • 2 Baths
  • 2,530 Sq Ft

  72 Green Meadow Rd, West Brattleboro, VT 05301

  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 floor features three bright bedrooms and a full bath - perfect for aging in place. Inside, you'll find classic hardwood floors and a cozy fireplace warming the living room. Step outside to an incredible, private backyard deck

  Thomas Dahlin Berkley & Veller Greenwood Country

  72 Green Meadow Rd, West Brattleboro, VT 05301
• 

  

  /31

  $299,000

  $16K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,607 Sq Ft

  136 Morningside Dr, Brattleboro, VT 05301

  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 walk-in closet and full en-suite bathroom, this home offers comfort and functionality throughout. A second bedroom provides flexibility for guests, a home office, or additional living space. The open-concept kitchen and dining

  Desiree Stango Berkley & Veller Greenwood Country

  136 Morningside Dr, Brattleboro, VT 05301
• 

  

  /12

  $285,000

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  455 S Main St, Brattleboro, VT 05301

  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. Nice sun porch doubles a a mud room, kitchen is huge with room enough for an island, a sweet spot with lots of potential.

  Christine Lewis Brattleboro Area Realty

  455 S Main St, Brattleboro, VT 05301
• 

  /2

  $80,000

  $10K PRICE DROP

  • Land
  • 1.97 Acres
  • $40,609 per Acre

  24 Summit Cir, West Brattleboro, VT 05301

  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 rural!

  Claire Renaud Berkley & Veller Greenwood Country

  24 Summit Cir, West Brattleboro, VT 05301
• 

  

  /29

  $289,000

  • 4 Beds
  • 2 Baths
  • 1,860 Sq Ft

  110 Western Ave, Brattleboro, VT 05301

  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 access to shopping, dining, services, schools, parks and everyday essentials while offering a spacious place to call home. Inside you’ll find beautiful wood flooring, inviting living spaces and a layout that provides flexibility

  Wilma Skovinski Berkley & Veller Greenwood Country

  110 Western Ave, Brattleboro, VT 05301
• 

  

  /33

  $225,000

  $75K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,209 Sq Ft

  16 Washington St, Brattleboro, VT 05301

  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-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt

  Rebecca Seymour Brattleboro Area Realty

  16 Washington St, Brattleboro, VT 05301
• 

  

  /9

  $198,000

  • Land
  • 3.27 Acres
  • $60,550 per Acre

  0 Pleasant Valley Rd, Brattleboro, VT 05301

  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 minutes to downtown. There are 2 lots, the front being mostly wooded with some clearing started and the rear lot with an old horse meadow, stone wall and a bit of height for potential views. Not only is there road frontage on Pleasant

  Christine Lewis Brattleboro Area Realty

  0 Pleasant Valley Rd, Brattleboro, VT 05301
• 

  

  /23

  $499,000

  $41K PRICE DROP

  • 6,000 Sq Ft

  16 School St, Brattleboro, VT 05301

  Attention Investors & 1031 Exchange Buyers! A premier, turn-key investment opportunity is now available in the high-demand Brattleboro rental market. Offered at $540,000, this massive, stately 6-unit multifamily building delivers immediate, fully stabilized cash flow from day one. With a robust gross monthly income of $7,675 and an outstanding gross annual income of $92,100, this property is a

  Kate Barry EXP Realty

  16 School St, Brattleboro, VT 05301
• 

  

  /5

  $380,000

  • 3,264 Sq Ft

  25 Cottage St, Brattleboro, VT 05301

  Sweet neighborhood. This would be a great location for an owner to live in one unit and rent the other 3. Lots of character! Great investment possibility. Close to Hospital, nursing homes, shopping, interstate for travel. Plenty of off street parking

  Christine Lewis Brattleboro Area Realty

  25 Cottage St, Brattleboro, VT 05301
• 

  

  /27

  $240,000

  $10K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  11 Evergreen Ln, Brattleboro, VT 05301

  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 area and laundry room. The second floor has a spacious living room and galley kitchen with eating nook which flows into a dining room and outdoor deck. The third level of this cozy condominium has a full sectional bathroom and 2

  Janet Lucier Barrett & Valley Assoc. Inc

  11 Evergreen Ln, Brattleboro, VT 05301
• 

  

  /4

  $182,000

  • 3 Beds
  • 1.5 Baths
  • 1,114 Sq Ft

  23 Williams St, Brattleboro, VT 05301

  Cute as a button! Everyone knows this home painted as pretty as a picture, on the corner lot at the foot of Union Hill. The owners over the years have landscaped and created a magical setting........walk to downtown, coop and the MOOVER! Previous owners did a amazing renovation after Irene. An intown, affordable, vintage home with lots of character. 48 hour notice please in respect of the

  Christine Lewis Brattleboro Area Realty

  23 Williams St, Brattleboro, VT 05301
• 

  

  /35

  $315,000

  New Construction $35K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 640 Sq Ft

  203 Fairview St, Brattleboro, VT 05301

  PRICE IMPROVEMENT! MOTIVATED SELLER! Welcome to this brand NEW, beautiful home, professionally blower-door tested at an exceptional 1.7 providing outstanding airtightness, energy efficiency, & year-round comfort. Completed in July 2026 & designed for low-maintenance living, the home benefits from net-metered solar credits that have offset the owner’s electrical needs, including heating & cooling.

  Kristen Ziter Taylor Brattleboro Area Realty

  203 Fairview St, Brattleboro, VT 05301
• 

  

  /32

  $299,000

  Open Sat 11AM - 1PM Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft

  48 Wilsons Woods Rd, Brattleboro, VT 05301

  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 character to the hallway and bathroom. Recent updates include a roof replaced in 2019 and water heater replaced in 2022. The back deck overlooks a large yard with plenty of room for gardening, pets, and entertaining, plus a shed

  Cassandra Ehrlich BHG Masiello Brattleboro

  48 Wilsons Woods Rd, Brattleboro, VT 05301
• 

  

  /20

  $320,000

  $34K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  39 Atwood St, Brattleboro, VT 05301

  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 this sweet home. Just across from the high and middle schools, around the corner from Oak Grove grade school, and down the street from the hospital and shopping. There is a first floor bed and bath for aging in place, but 2 big

  Christine Lewis Brattleboro Area Realty

  39 Atwood St, Brattleboro, VT 05301
• 

  

  /51

  $284,000

  $15K PRICE DROP

  • 2,360 Sq Ft

  5 Reynolds Dr, Brattleboro, VT 05301

  Turn-Key Investment in the Heart of Brattleboro! This versatile three-unit multifamily property offers an excellent opportunity for investors. 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. All three units are currently occupied, providing immediate cash flow. Unit 2 also

  Kate Barry EXP Realty

  5 Reynolds Dr, Brattleboro, VT 05301
• 

  

  /35

  $230,000

  $15K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  9 Evergreen Ln, Brattleboro, VT 05301

  **Motivated seller -- offering $5,000 concession to buyers for closing costs** 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

  Ayden Hardy BHG Masiello Keene

  9 Evergreen Ln, Brattleboro, VT 05301
• 

  

  /19

  $804,650

  • 7,120 Sq Ft

  820 & 28 Western Ave, Brattleboro, VT 05301

  Exceptional cash flow, a desirable unit mix, and future potential come together in this well-maintained 8-unit investment package in vibrant Brattleboro. Offered together, the two 4-unit properties feature six spacious 2-bedroom, 1-bath apartments and two 1-bedroom, 1-bath apartments, appealing to a broad range of tenants. Pride of ownership is evident throughout, with recent improvements

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  820 & 28 Western Ave, Brattleboro, VT 05301
• 

  /2

  $350,000

  $50K PRICE INCREASE

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft

  109 Central St, Brattleboro, VT 05301

  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

  109 Central St, Brattleboro, VT 05301
• 

  

  /21

  $190,000

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft

  39 Brookside Dr Unit 5, Brattleboro, VT 05301

  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 large bedrooms and a full bath. The lower level is a 465 square foot basement for extra storage with washer/dryer. Newer kitchen cabinets, countertop, flooring, bathroom vanity, vinyl windows and front door. This condo is

  Angela Sherman Brattleboro Area Realty

  39 Brookside Dr Unit 5, Brattleboro, VT 05301
• 

  

  /5

  $250,000

  $20K PRICE DROP

  • 2,112 Sq Ft

  556 S Main St, Brattleboro, VT 05301

  New beginnings! Just right to live in one side, fix the other and have the tenant pay for your new lifestyle or have a family duplex and lie with extended family. the north side is vacant, needs renovation, and the south side has a tenant that will transfer with the building. Corner lot, yard, off street parking. Easy to see north unit, but otherwise a 48 hour notice to show.

  Christine Lewis Brattleboro Area Realty

  556 S Main St, Brattleboro, VT 05301
• 

  

  /35

  $68,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft

  22 Valley St, Brattleboro, VT 05301

  Welcome to 22 Valley Road, an affordable and easy-to-maintain 2-bedroom, 1-bath mobile home located in Brattleboro’s Tri-Park Cooperative Housing Corporation. This cozy single-level home offers a bright and refreshed interior with natural light, LED lighting, first-floor laundry hookups, and a functional layout that makes great use of the space. The kitchen features an electric range,

  Grayson VanHendrick Flex Realty

  22 Valley St, Brattleboro, VT 05301
• 

  

  /24

  $59,000

  • 2 Beds
  • 1 Bath
  • 744 Sq Ft

  9 Village Dr, Brattleboro, VT 05301

  Sweet little mobile home! Large mudroom or multi purpose sun room, eat in kitchen separated from the living room with open shelving. Two bedrooms, the larger used to be two smaller bedrooms which could become that again if you need 3 bedrooms, otherwise a great bedroom with a sitting area, and a second bedroom at the end! Stackable washer/dryer in the bathroom. A large shed is great for storage,

  Rebecca Seymour Brattleboro Area Realty

  9 Village Dr, Brattleboro, VT 05301
• 

  

  /37

  $615,000

  • 4 Beds
  • 2.5 Baths
  • 2,212 Sq Ft

  354 Orchard St, Brattleboro, VT 05301

  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

  Christine Lewis Brattleboro Area Realty

  354 Orchard St, Brattleboro, VT 05301
• 

  

  /50

  $250,000

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  147 Morningside Dr, Brattleboro, VT 05301

  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

  Sally Fegley BHG Masiello Brattleboro

  147 Morningside Dr, Brattleboro, VT 05301
• 

  

  /37

  $265,000

  $34K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  412 Western Ave, Brattleboro, VT 05301

  Move in ready and full of potential, this charming Brattleboro home is ready for its next chapter. The main level features a bright, open concept layout with a spacious kitchen and comfortable living area, creating an ideal space for everyday living and entertaining. Filled with natural light, the living room opens directly onto a private rear deck overlooking a manageable backyard perfect for

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  412 Western Ave, Brattleboro, VT 05301
• 

  

  /20

  $319,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft

  550 S Main St, Brattleboro, VT 05301

  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 wonderful, open concept, one level home. Primary bedroom on one end with an ensuite for privacy! New, shiny appliances, good sized island for cooking or hanging out and both a tub and a walk in shower. Special in so many ways,

  Christine Lewis Brattleboro Area Realty

  550 S Main St, Brattleboro, VT 05301

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