Homes for Sale near Academy School

• 

  

  

  /32

  $495,000

  • 3,882 Sq Ft

  1309 Putney Rd, Brattleboro, VT 05301

  Exceptional investment opportunity! This well maintained six-unit property is in outstanding condition and has seen numerous recent improvements, making it an attractive addition to any investment portfolio. Exterior updates include fresh paint completed last year, newer windows (approximately three years old), a newer rubber membrane roof, buried power, updated electrical, a newer hot water

  Kerry Mulverhill

  1309 Putney Rd, Brattleboro, VT 05301
• 

  

  

  /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 project in the heart of Brattleboro. The 0.40-acre site features a vacant three-story building that has already been gutted and fully remediated for lead paint. With town zoning already approved to expand from 8 to 13 units and full architect plans included, the heavy lifting and permitting phase is already behind you. Upon completion, the

  Kate Barry EXP Realty

  33 Oak St, Brattleboro, VT 05301
• 

  

  

  /8

  $95,000

  $25K PRICE DROP

  • Land
  • 15 Acres
  • $6,333 per Acre

  0 Carpenter Hill Rd Unit 5090787, Guilford, VT 05301

  Hillside building lot deeded for one beautiful home, with a straight-ahead view of inspiring mountains and valleys to the south. The property is moderately sloped near the road but more flat at the highest elevation, with benches of level ground at intervals up and down the land. A network of hiking trails is blazed across the property, but the easiest way to view the high ground is what remains

  David White OwnerEntry.com

  0 Carpenter Hill Rd Unit 5090787, Guilford, 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
• 

  

  

  /19

  $295,000

  $30K PRICE DROP

  • Land
  • 2.11 Acres
  • $139,810 per Acre

  00 Mountain Rd Unit 2.43, West Chesterfld, NH 03466

  Enjoy the sights and sound of the Connecticut River. 2.11 Acres with over 392 feet of water frontage. The land comes with private access to the River making a great site to plan your dream home. When you drive up Mountain Road the lot is on the left with the river on the right. The road dead ends with the access to the trailhead containing a 520 acre trail system that leads to the summit of

  Sandy Cormier Greenwald Realty Group

  00 Mountain Rd Unit 2.43, West Chesterfld, NH 03466
• 

  

  /22

  $399,000

  • 9 Beds
  • 4 Baths
  • 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
• 

  

  /42

  $325,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  205 Route 9, West Chesterfield, NH 03466

  Welcome to 205 Route 9 in Chesterfield, NH, a home designed for easy living. This inviting ranch combines the convenience of a single-level floor plan with valuable updates, including a newer metal roof (2020), Harmon pellet stove, and updated appliances. Downstairs, the finished bonus room provides flexibility that's hard to find. Use it as a playroom, home office, workout space, game room, or

  Kelsey Malloy Keller Williams Realty Metro-Keene

  205 Route 9, West Chesterfield, NH 03466
• 

  /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
• 

  

  /45

  $1,165,000

  • 4 Beds
  • 2.5 Baths
  • 3,338 Sq Ft

  1472 Carpenter Hill Rd, Guilford, VT 05301

  The Governor Carpenter Homestead, a pivotal piece of American history in Guilford, VT, is now accepting applications for its next Steward. This remarkable property was constructed in 1772 by Benjamin Carpenter, Vermont's first Lieutenant Governor. Lovingly maintained for decades, the residence combines historic integrity with modern functionality. Key features include: Architectural Significance:

  Thomas Dahlin Berkley & Veller Greenwood Country

  1472 Carpenter Hill Rd, Guilford, 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
• 

  

  /30

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  68 E Bonnyvale Ln, Brattleboro, VT 05301

  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 road, this single level ranch offers comfort, privacy, and great potential on 6.5+ acres just outside the village of West Brattleboro. Enjoy an in ground swimming pool with a pool house and bathroom - perfect for summer relaxation.

  Dan Normandeau Berkley & Veller Greenwood Country

  68 E Bonnyvale Ln, 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
• 

  

  /10

  $199,000

  $51K PRICE DROP

  • Land
  • 23.1 Acres
  • $8,615 per Acre

  184 Dupre Dr, Guilford, VT 05301

  Here's a large 23.10 +/- acre parcel that's mostly wooded but with a little bit of open field and possible short range local views. Conveniently located within a few minutes of town, here's an opportunity to enjoy country living while having access to modern amenities. There's a lot of potential for the right buyer! Please respect the privacy of the other houses on the road past this land.

  A.J. Bellville Bellville Realty

  184 Dupre Dr, Guilford, VT 05301
• 

  

  /44

  $450,000

  $25K PRICE DROP

  • 6 Beds
  • 2.5 Baths
  • 3,682 Sq Ft

  4303 Hinesburg Rd, Brattleboro, VT 05301

  Private! Guilford! This unusual combination of a true log home with an incredible center double sided chimney....a fireplace facing the kitchen/dining and wood stove in the living room, bringing the best of both worlds:... ambiance and warmth. There is a surprise of one more fireplace on the 2nd floor in the charming primary bedroom...use the ensuite for a huge walk in closet. The other half of

  Christine Lewis Brattleboro Area Realty

  4303 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 living

  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
• 

  

  /38

  $769,900

  $25K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,600 Sq Ft

  5 Hillwinds N, Brattleboro, VT 05301

  New updates: roof replacement with 30 year architectural shingles completed and six new skylights with remote control shades installed. Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls & gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails in the desirable Hillwinds community.

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, 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
• 

  

  /23

  $115,000

  • 2 Beds
  • 2 Baths
  • 1,222 Sq Ft

  13 Winding Hill, Brattleboro, VT 05301

  This Park home has so much to offer! There are 2 bedroom and 2 full baths, with a large living area and a mudroom. Upgrades include new vinyl plank flooring, some new windows and a new mini split. There are solid Oak cabinets.The one car garage is attached and behind it there is a 3-season screened porch. From the back you can also access the 2 additional sheds. The grassy yard wraps around

  Victoria Woods Brattleboro Area Realty

  13 Winding Hill, Brattleboro, VT 05301
• 

  

  /14

  $680,000

  • 5,540 Sq Ft

  50 Terrace St, Brattleboro, VT 05301

  SUPERB OPPORTUNITY to acquire one of Brattleboro’s nicest multi-family, investment properties!! Situated in one of THE BEST neighborhoods in Brattleboro, Vermont, this sweet, money-maker offers 7 units on a quiet street that is SOOO close to downtown Brattleboro. What every investor dreams of!!! Location, quality condition and build, spacious unit size, superb level, off-street parking, and

  Dan Normandeau Berkley & Veller Greenwood Country

  50 Terrace St, Brattleboro, VT 05301
• 

  

  /40

  $190,000

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft

  39 Brookside Dr Unit 4, Brattleboro, VT 05301

  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

  Grayson VanHendrick Flex Realty

  39 Brookside Dr Unit 4, 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
• 

  

  /30

  $305,000

  $10K 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
• 

  

  /4

  $125,000

  $15K PRICE DROP

  • Land
  • 1.3 Acres
  • $96,154 per Acre

  00 Creamery Rd, Guilford, VT 05301

  Just in time for Spring building! This incredibly beautiful high meadow is perfect for your new home, be it a get away or primary. Wake up to the views of the local hills and rolling countryside...enjoy gardening, a pool, decks or covered porches ..or just install oversized windows to take advantage while you putter about! Soils tests are done...drive is into the lot...consult GMP for power...Get

  Christine Lewis Brattleboro Area Realty

  00 Creamery Rd, Guilford, 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
• 

  /2

  $150,000

  • Land
  • 2.05 Acres
  • $73,171 per Acre

  00 Fort Dummer Heights, Brattleboro, VT 05301

  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 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 cooperation.

  Christine Lewis Brattleboro Area Realty

  00 Fort Dummer Heights, 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
• 

  

  /35

  $239,000

  $50K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 2,000 Sq Ft

  116 Birge St Unit 3, Brattleboro, VT 05301

  Price Improvement! Welcome to Esteyville! Here, history, location, and distinctiveness excel. This rare, NYC loft-style condo on the 3rd and 4th floors was formerly home to Estey Organ, the world's largest pipe organ manufacturer, circa 1870. Listed in the National Registry of Historic Places, you will find original pine wide-plank floors, exposed post-and-beam construction, soaring ceilings,

  Liz LaVorgna Brattleboro Area Realty

  116 Birge St Unit 3, Brattleboro, VT 05301
• 

  

  /27

  $245,000

  $5K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 2,496 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

  $350,000

  New Construction

  • 2 Beds
  • 1 Bath
  • 640 Sq Ft

  203 Fairview St, Brattleboro, VT 05301

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

  Kristen Ziter Taylor Brattleboro Area Realty

  203 Fairview St, Brattleboro, VT 05301
• 

  

  /37

  $679,000

  • 3 Beds
  • 3.5 Baths
  • 2,476 Sq Ft

  15 Skyline Dr, Vernon, VT 05354

  Open House 8/2, 1:00–3:00 PM Nestled on approximately 4 private acres, this custom-built timber frame home offers an exceptional blend of craftsmanship, comfort, and privacy. Tucked away on a quiet, dead-end road, this is one of only four sites, providing a peaceful setting with the perfect balance of seclusion and convenience. Inside, exposed timber framing, soaring vaulted ceilings, and walls

  Morriah Adams BHG Masiello Brattleboro

  15 Skyline Dr, Vernon, VT 05354
• 

  

  /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

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