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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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423 and 435 Marlboro Road Brattleboro VT 05301

Brattleboro, VT423 and 435 Marlboro Road

Price$950,000The price has recently decreased

MLS Number 4923673

  • Commercial
  • Year Built 2016
  • Acreage 3.3

Tremendous Investment/Business Opportunity. Three businesses in one property: Deli/Restaurant with all pertinent equipment included (stoves, ovens, mixers, fryers, etc.); Self -Storage with 61 units inside the 423 building; and Multi-Family Residential 3 units currently occupied with stable tenancy. Property is situated on the North side of VT Route 9 which is a major East/West thoroughfare. Excellent exposure. Deli/Restaurant building constructed in 2016 and in superb condition. Lot has 3.3 level grassy acres with potential for other enterprises.

Listed by Vincent Dolan of RE/MAX Town & 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: 6.29% last updated on 2022-09-22

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

817 Putney Road Brattleboro VT 05301

Brattleboro, VT817 Putney Road

Price$850,000The price has recently decreased

MLS Number 4915924

  • Commercial
  • Acreage 1.75

One of the last undeveloped highly visible/ high traffic count commercial lots left in the town of Brattleboro. Located on Route 5 (Putney Road) and situated in the midst of all the major commercial strip development in the town. The parcel is actually 2 separate lots (Parcel 47 & 48 on the tax map) totaling 1.75 acres of level and open land both with access to town water and sewer and easy access. The lots are located only 1 mile south of Exit 3 off I-91 and Route 9 East toward Keene NH. If you have a use that requires a commercial location to have outstanding visibility and plenty of off-street parking, this one will be very hard to duplicate.

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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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: 6.29% last updated on 2022-09-22

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

773 Guilford Street Brattleboro VT 05301

Brattleboro, VT773 Guilford Street

Price$765,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4920372

  • Residential Single Family
  • Bedrooms 4
  • Construction Existing
  • Square Feet 4,858
  • Bathroom 4

All the things you come to Vermont for in one simply amazing property! Blue Heron Pond, small enough to be all yours, but big enough for the famous blue heron to display herself, in all her beauty on the pond's natural rock perch. Big enough for skating under the crisp Vermont starry skies, taking a cool dip from the dock in the high summer heat or just holding hands at the very edge of a dream while the peeps, crickets and birds sing your lullaby. Friends will flock for sleepovers in the sweet screened gazebo by the pond with it own outdoor shower! So versatile and so loved by the owners who have created a lifestyle of creativity and peace in our ever changing world. Artists and other creators will love the look and design of the Quonset hut for large or small work..as they become a part of the local art world. Designed with modern world needs, there is a walk out lower level with full living quarters, but accessible to the main level for older relatives who need care, our x generation of young adults, at home office or a great extra space for larger families. Survey all that is yours, with an inner giggle that is is all yours, from the high deck while you ponder what this home can become for you and plan your first steps in a new lifestyle. Come home to Vermont and bring your dreams, fall in love for the rest of your life! Masks up please.

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: 6.29% last updated on 2022-09-22

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

37 Bittersweet Lane Brattleboro VT 05301

Brattleboro, VT37 Bittersweet Lane

Price$725,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4920577

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 3,472

Designed by well-known local architect Chip Greenberg and built by local craftsman Jonathan Klein, this is a recently-constructed, high-performing, super-insulated house on 3.42 acres, abutting the Brattleboro Country Club golf course. Primary en suite bedroom and laundry on the first floor. Elevator to the walk-out basement level, which has two bedrooms and a full bathroom. Both levels have a full sprinkler setup. The house is built to the high levels of the Vermont Energy code. It has an elegant, open stairway tying together living and working spaces on both floors that give it a three-dimensional character. You couldn't recreate this building for the list price!

Listed by John Hatton of Berkley & Veller Greenwood Country

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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: 6.29% last updated on 2022-09-22

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

80 Linden Street Brattleboro VT 05301

Brattleboro, VT80 Linden Street

Price$699,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4919600

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Square Feet 5,768
  • Acreage 0.44

In town property with RESIDENTIAL, OFFICE, OR MIXED USE OPPORTUNITY. Steeped in history, this building is known as Deacon John Holbrook House. It is one of the village's finer Federal Style houses facing the Common. The interior detail and craftsmanship are notable as Holbrook built it for himself circa 1825 after a successful career in local business ventures. Two story main building was converted to be used as office space with 14+ offices, a kitchen, and 4 bathrooms. On the first floor, 4 offices and 2 bathrooms are ADA accessible. There is separate newly renovated "carriage house" with two office spaces and a bathroom. The property is on a corner lot with frontage on Linden and Chapin St and has 19 dedicated parking spots. It is one block from the Town Hall and the Court House. Brattleboro is located along the Connecticut River Valley with easy access to Interstate 91, Vermont Route 5 and 9. Several ski areas are within an hour drive. Owner is licensed real estate agent with Lake Point Properties. Also listed Commercial MLS#4919541.

Listed by Yana Walder of Lake Point Properties,LLC

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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: 6.29% last updated on 2022-09-22

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

80 Linden Street Brattleboro VT 05301

Brattleboro, VT80 Linden Street

Price$699,000The price has recently decreased

MLS Number 4919541

  • Commercial
  • Square Feet 5,768
  • Year Built 1825
  • Acreage 0.44
  • Area In Town

In town property with RESIDENTIAL, OFFICE, OR MIXED USE OPPORTUNITY. Steeped in history, this building is known as Deacon John Holbrook House. It is one of the village's finer Federal Style houses facing the Common. The interior detail and craftsmanship are notable as Holbrook built it for himself circa 1825 after a successful career in local business ventures. Two story main building was converted to be used as office space with 14+ offices, a kitchen, and 4 bathrooms. On the first floor, 4 offices and 2 bathrooms are ADA accessible. There is separate newly renovated "carriage house" with two office spaces and a bathroom. The property is on a corner lot with frontage on Linden and Chapin St and has 19 dedicated parking spots. It is one block from the Town Hall and the Court House. Brattleboro is located along the the Connecticut River Valley with easy access to Interstate 91, Vermont Route 5 and 9. Several ski areas are within an hour drive. Owner is licensed real estate agent with Lake Point Properties. Also listed Residential MLS.

Listed by Yana Walder of Lake Point Properties,LLC

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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: 6.29% last updated on 2022-09-22

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

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: 6.29% last updated on 2022-09-22

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$570,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4905082

  • Multifamily
  • Square Feet 6,000
  • Units 6
  • Bathroom 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: 6.29% last updated on 2022-09-22

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$550,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4903029

  • Multifamily
  • Square Feet 5,592
  • Units 6
  • 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: 6.29% last updated on 2022-09-22

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$550,000The price has recently decreased

MLS Number 4901840

  • Commercial
  • Square Feet 8,000
  • Year Built 1894
  • Acreage 0.23
  • NOI 51384

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

{$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: 6.29% last updated on 2022-09-22

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

287 Marlboro Road Brattleboro VT 05301

Brattleboro, VT287 Marlboro Road

Price$499,000The price has recently decreased

MLS Number 4902679

  • Commercial
  • Year Built 1955
  • Square Feet 7,519
  • Acreage 2

Over 7,500 sq. ft. commercial/retail building originally built and operated as a very popular area restaurant with high visibility and easy access off Route 9 in West Brattleboro only 2 miles west of exit 2 off I-91. Situated on one of the most heavily traveled tourism routes in southern VT it is ideal for a variety of commercial/retail uses. Route 9 connects I-91 to the resort towns of Wilmington, Dover and Stratton which are home to Mount Snow and Stratton ski areas and also the lakes and mountains of the Green Mountain National Forest and the thousands of acres of year-round recreational opportunities it offers. An absolutely ideal location for any use in need of easy access, visibility on a highly traveled main state highway. New roof in 2021 but the building does need renovations and systems repair. The 2-acre lot is level and prepped for new pavement providing tons of off-street parking.

Listed by Chris Long of BHG Masiello Brattleboro

{$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: 6.29% last updated on 2022-09-22

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

12-14 Elliot Street Brattleboro VT 05301

Brattleboro, VT12-14 Elliot Street

Price$499,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4916192

  • Residential Single Family
  • Square Feet 8,000
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4

Listed by Richard Caplan of Deerfield Valley Real Estate

{$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: 6.29% last updated on 2022-09-22

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

Broker Reciprocity

Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. 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 September 29, 2022 3:53 AM EDT.

 

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