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Brattleboro VT Real Estate

Brattleboro is a charming town in Windham County, Vermont. Situated along the Connecticut River, Brattleboro’s historic downtown is thriving with local shops and eateries. The town is an oasis for the arts and is even home to the New England Center for Circus Arts. Whether enjoying all that the town has to offer or simply strolling by the beautiful landscape in the foothills of the Green Mountains, Brattleboro has something for everyone. 

Search the latest real estate in Brattleboro, VT with Maple Sweet Real Estate. Find the right property for you from a variety of listings. To save your favorites, register with us and you can get email notifications when similar properties are posted. Already have an account with us? Log in here.

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925 Hinesburg Road Brattleboro VT 05301

Brattleboro, VT925 Hinesburg Road

Price$795,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4904241

  • Residential Single Family
  • Bathroom 7
  • Construction Existing
  • Bedrooms 5
  • Square Feet 7,430

Tucked into a quiet neighborhood minutes from downtown Brattleboro, this spacious home seamlessly blends clean contemporary lines with rustic charm. Situated on 18 acres, the house immediately beckons with its tastefully designed clapboard-style exterior. As you enter the foyer, you are met with attractive terra-cotta tile, practical for VT's ever-changing weather. Continuing into the large living room, you'll find a fully functional gray stone fireplace. As you pass through the formal dining room to the kitchen, you'll find your chef's dream has come true with a 6-burner brushed chrome professional Viking gas range. The ample-sized (14' X 11') pantry is perfect for all your cooking equipment. On the other side of the kitchen is the family room, featuring a Hearthstone soapstone woodstove. Upstairs are 5 large bedrooms, 4 en-suite, all with lots of closet space. The finished attic area is perfect as a reading nook or fun spot for a ping-pong table. The equally finished basement, which now includes a pool table, could easily be converted into a large studio apt. A whole house generator is wired to come on automatically if the power goes out. During Vermont's beautiful summers you will love the in-ground 20' X 40' pool, set next to a 200 sf. pool house, which features a kitchen, outdoor shower, & even a hidden TV to watch while you do your laps. A must see! Delayed showings until 4/24/2022.

Listed by Thom Dahlin of Berkley & Veller Greenwood Country

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

239 Old Ferry Road Brattleboro VT 05301

Brattleboro, VT239 Old Ferry Road

Price$750,000The price has recently decreased

MLS Number 4908636

  • Commercial
  • Year Built 1955
  • Acreage 4.04

20,000 sq. ft. commercial/industrial/warehouse building ideal for any business in need of office/manufacturing and distribution in one location. The property consists of over 4 acres and can be divided, or an additional building built on the large open gravel pad adjacent to the existing structure. Easy access from I-91 at Exit 3 and Route 9 toward Keene. Building has 12' plus clear span spaces, 5 drive in doors and 3 loading dock doors into the multi-level warehouse space, high capacity 3 Phase electrical service, a freight elevator, 4 offices on two levels and 3 bathrooms. The versatility of the building will adapt to many business options and uses. 48 hours' notice required for showings.

Listed by Chris Long of BHG Masiello Brattleboro

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

51 & 61 Grove Street Brattleboro VT 05301

Brattleboro, VT51 & 61 Grove Street

Price$749,900The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 4900601

  • Multifamily
  • Bathroom 11
  • Units 11
  • Square Feet 9,639
  • Acreage 0.33

Investment opportunity! Two large multi-family dwellings (one 6 unit and one 5 unit) offered as a package due to the fact they are abutting properties and share off street parking. An ideal location on Grove Street adjacent to the town municipal office building and walking distance to downtown. 51 Grove Street was originally built as a 6-unit apartment building and has six 2- bedroom units on 3 levels. 61 Grove is a converted single family with 5 total units (one 2-bedroom and four 1-bedroom units). There is shared off street parking behind the buildings and also an old barn that could be fixed up as a garage or possibly an additional dwelling unit. The longtime owner has not increased rents in many years so the actual rents at present are well below market value. At the current NET income, the CAP rate is 9.5 but with an increase to market rents the CAP rate would be a solid 12 CAP. Income & Expense and Proforma is available. All utilities of 61 Grove are paid by the tenants which make it an easy building to operate. Heat and HW are included in the rents at 51 Grove but everything else are separated and paid by tenants. Both buildings are up to date on EMP certifications and have had many recent energy efficiency upgrades including new heating systems in 2016, basements weatherized with high density foam sprayed on insulation, attics have had cellulose blown in. If you are looking for a solid income producing asset, this is a very good option.

Listed by Chris Long of BHG Masiello Brattleboro

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

25 Estey Street Brattleboro VT 05301

Brattleboro, VT25 Estey Street

Price$700,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 4905374

  • Multifamily
  • Bathroom 7
  • Square Feet 8,080
  • Units 7
  • Acreage 0.15

A behemoth of a building! This property is a stunner in more ways than one. Large apartment units with great layouts, additional fire escape/porches off the back, tons of tenant parking, additional storage units for tenants or for additional income, solar system arrays, and additionally a huge industrial sized workshop for the owner or managers to have. The solar array generates 11.28kW and pays for $2,000 in electricity annually. SO many great bonuses on top of this building being a stabilized cash flowing investment property in an excellent location. Can be sold as a packaged deal with any or all of the following properties MLS#4905365, 4905368, 4905373

Listed by Kate Barry of EXP Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

155 Summit Circle Brattleboro VT 05301

Brattleboro, VT155 Summit Circle

Price$675,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4903580

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Square Feet 2,500
  • Bathroom 3

Offering spectacular long-range views of the Connecticut River Valley & the New Hampshire mountain ridge-line, this striking, maximum, energy efficiency home was built in 2019. Cutting edge in its contemporary design, the numerous over-sized windows bath the home in natural light. Wide-plank, hickory flooring, maple cabinetry, and marble counter tops add a richness and warmth. The home's main floor is an open-concept design with an inviting flow of kitchen, dining and living spaces. This floor features the primary en-suite bedroom with full-bath. There is also a second room to be used as bedroom or office with a half bath. The entry level has 3 bedrooms, one of which has a private deck with valley views. This newer addition has expanded this living area, also adding an attached, over-sized, 2 car, well insulated garage with direct entry into the home. There is an ERV ventilation system and this home is 5-star energy rated and could readily achieve net-zero rating, as stated by the builder. This magnificent home is on 2.58 +/- acres hidden in the midst of Brattleboro. How rare to enjoy luxurious evenings and sunsets on your glass railing deck, over-looking woods, ledges and fields of wild flowers, yet being so close to Brattleboro's vibrancy. Come visit this very impressive home. Delayed showings until April 8, 2022

Listed by Kristen Ziter Taylor of Brattleboro Area Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

16 School Street Brattleboro VT 05301

Brattleboro, VT16 School Street

Price$600,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4905082

  • Multifamily
  • Square Feet 6,000
  • Bathroom 6
  • Units 6
  • Acreage 0.13

Fantastic rental opportunity available for the first time in over 30 years! All well maintained two bedroom units in this sturdy apartment building. Located in close proximity to shops, schools, downtown parking and hospitals. Currently operating at a 8.5% cap rate with only room for improvements. This cash cow is a great investment in a great location!

Listed by Kate Barry of EXP Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

60 Bittersweet Lane Brattleboro VT 05301

Brattleboro, VT60 Bittersweet Lane

Price$595,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4849623

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,834

Sweet! If you have been struggling to find just the right home, this is it! Designed by the owner for easy retirement living with low exterior maintenance, easy rolling landscape (bordering the golf course) and a delightful wrap-around deck overlooking the expansive back yard! Inside is just as special with the ability to live on one floor if you want with open concept, vaulted ceilings for light and air, 3 bedrooms and 2 baths on the main floor AND SURPRISE!!! Pop down to the lower level and there is another bedroom, bath and amazing living room. Perfect for live in help, the child that's not quite ready to leave the nest, office or guest space. All nicely finished and a view to the back yard. Perfect for the growing family. Add the loop to your daily exercise and meet your neighbors, cross country ski from your yard...all 5 minutes from downtown. A perfect match for any time in your life...any lifestyle.

Listed by Christine Lewis of Brattleboro Area Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

11 Pleasant Street Brattleboro VT 05301

Brattleboro, VT11 Pleasant Street

Price$575,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4903029

  • Multifamily
  • Units 6
  • Square Feet 5,592
  • Bathroom 6
  • Acreage 0.23

Large and in-charge 6 unit multi family on the corner of Pleasant and Chestnut in Brattleboro. Well maintained for decades with lots of opportunity for improvement, finish off the top level for additional living spaces. Tons of parking and easy commute to shops, schools, hospitals and grocery stores. The property has One 3BR apartment, four 2BR apartments and one 1BR apartment.Apartments are spacious and well-maintained. Both floors boast high ceilings, hardwood flooring, and beautiful original crown moulding. At one time this property belonged to the director of the Estey Organ Company. Truly a gem! Also can be found as Commercial listing under MLS#4901840

Listed by Kate Barry of EXP Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

11 Pleasant Street Brattleboro VT 05301

Brattleboro, VT11 Pleasant Street

Price$575,000The price has recently decreased

MLS Number 4901840

  • Commercial
  • Year Built 1894
  • Acreage 0.23
  • NOI 46700

Large and in-charge 6 unit multi family on the corner of Pleasant and Chestnut in Brattleboro. Well maintained for decades with lots of opportunity for improvement, finish off the top level for additional living spaces. Tons of parking and easy commute to shops, schools, hospitals and grocery stores. The property has One 3BR apartment, four 2BR apartments and one 1BR apartment. Apartments are spacious and well-maintained. Both floors boast high ceilings, hardwood flooring, and beautiful original crown moulding. At one time this property belonged to the director of the Estey Organ Company. Truly a gem!

Listed by Kate Barry of EXP Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

480 Pleasant Valley Road Brattleboro VT 05301

Brattleboro, VT480 Pleasant Valley Road

Price$575,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 4906597

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Square Feet 2,164
  • Bathroom 3

Distinctive in its authenticity, this captivating 1790s farmhouse is fully updated to combine historic, classic character and charm with 21st century modernization. Located in one of the area's most pastoral settings, you are only moments away from Brattleboro's downtown vibrancy. The property is situated on 9.8 spectacularly beautiful acres abutting the Pleasant Valley Reservoir and is surrounded by protective lands with extensive trail systems. You are close to the Brattleboro Country Club and ease of access to VT's major ski mountains. Original, exposed beams, 3 stunning mantel fireplaces, classic built-ins, elegant wainscoting and wide plank flooring maintain historic elegance and warmth. With a formal dining room, stunning kitchen renovation offers views of pure tranquility. This home provides the comfort of first floor living with a first floor primary en-suite and potential for a second-floor expansion. You have direct entry from the 2-car garage into a spacious mudroom. This home and its location are special, in a way that few are. The 9.8 acres is divided into 3 separate lots: house 3.2 acres, south field 4.0 acres and across the road 2.6 acres. Not only does this ensure privacy but could have great potential. This homestead is in a league of its own, prepare to be wowed! Please click on the unbranded tour link above the remarks to watch a short video. Delayed showings until Friday, April 29th. Sellers would appreciate a July 1st closing.

Listed by Kristen Ziter Taylor of Brattleboro Area Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

45 Linden Street Brattleboro VT 05301

Brattleboro, VT45 Linden Street

Price$535,000The price has recently decreased

Active With Contract

MLS Number 4904352

  • Commercial
  • Acreage 0.24

SUPERB IN-TOWN OPPORTUNITY!! Originally a single-family residence, this circa 1820 Federal has been used as professional office space since approximately 1986. Extremely convenient location at the immediate edge of downtown Brattleboro. MOVE-IN READY for your business! More space than required?? Lease remaining offices to help pay your property taxes, etc.! LOOKING FOR AN IN-TOWN HOME?? Easy conversion back to residential use. ARE YOU AN ENTREPRENEUR?? Perfect layout for conversion to four 1-bedroom apartments to rent on Airbnb, use as corporate housing, or rent long-term. Maybe convert into mixed use - office and residential! The potential is huge for THIS building in THIS location! Additional details… 13 dedicated, marked parking spaces. Adjacent to the Courthouse and a short walk to the Post Office, Municipal Center, and many other businesses. This two-story gem offers 16 rooms with just over 4,000 SF. There is a full kitchen, a full bath and two half-baths. Up-dated systems offering 200-amp electrical service and central air throughout. Heat is off an oil-fired boiler and delivered via hot water baseboard, as well as forced hot air. Basement sill and upper foundation is insulated. Many original features remain - four panel interior doors, six over six sash, period molding, and the grand six panel parlor doors. LOCATION AND OPPORTUNITY!!! Brattleboro, VT is where you want to be! Private showings on request. Also listed in Residential MLS #4904354.

Listed by Dan Normandeau of Berkley & Veller Greenwood Country

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

45 Linden Street Brattleboro VT 05301

Brattleboro, VT45 Linden Street

Price$535,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4904354

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Square Feet 4,054
  • Acreage 0.24

LOOKING FOR AN IN-TOWN HOME?? SUPERB IN-TOWN OPPORTUNITY!! Originally a single-family residence, this circa 1820 Federal has been used as professional office space since approximately 1986. Extremely convenient location at the immediate edge of downtown Brattleboro. Easy conversion back to residential use. ARE YOU AN ENTREPRENEUR?? Perfect layout for conversion to four 1-bedroom apartments to rent on Airbnb, use as corporate housing, or rent long-term. Maybe convert into mixed use - office and residential! The potential is huge for THIS building in THIS location! Additional details… 13 dedicated, marked parking spaces. Adjacent to the Courthouse and a short walk to the Post Office, Municipal Center, shopping, and many other businesses. This two-story gem offers 16 rooms with just over 4,000 SF. There is a full kitchen, a full bath and two half-baths. Up-dated systems offering 200-amp electrical service and central air throughout. Heat is off an oil-fired boiler and delivered via hot water baseboard, as well as forced hot air. Basement sill and upper foundation is insulated. Many original features remain - four panel interior doors, six over six sash, period molding, and the grand six panel parlor doors. LOCATION AND OPPORTUNITY!!! Brattleboro, Vermont is where you want to be! Private showings on request. Also listed in commercial MLS #4904352.

Listed by Dan Normandeau of Berkley & Veller Greenwood Country

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

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 2022 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. 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 May 24, 2022.

 

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