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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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373 Summit Circle Brattleboro VT 05301-4489

Brattleboro, VT373 Summit Circle

Price$895,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5000685

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4

Enjoy year-round comfort in this stunning Net Zero home, built in 2012 to meet the rigorous Passive House standard. You won't pay a cent to heat and cool this all-electric house or even charge your EV. Gorgeous woodwork, soaring ceilings, and premium finishes make this light-filled sustainable home a rare find. With superinsulated walls, triple-glazed tilt-turn windows, ducted air exchange with heat recovery, two mini-split heat pumps, a huge solar array, and two Tesla Powerwalls for multiple days of backup power, you'll wonder why every house isn't built this way. Spacious kitchen with cherry cabinets, granite counters, Bosch induction cooktop, and a Miele dishwasher, plus a breakfast bar and pass-thru window. The newly-built 1st-floor bedroom suite boasts a walk-in closet and private bathroom with double vanity, curbless shower, quartz countertop, and marble accents. Three more bedrooms upstairs (including another en-suite), plus office space and a sunny indoor garden deck. Surrounded by trees in the perfect Vermont location, near the top of a quiet cul-de-sac but less than 10 min from downtown Brattleboro--home to a vibrant arts community and one of the region's best farmers' markets. A short distance to Hilltop Montessori School and mere steps to wooded trails for hiking, snowshoeing, and backcountry skiing. Downhill skiers can reach Mt. Snow in 40 min or Stratton and Okemo in under an hour. Make an offer before this one-of-a-kind home slips away!

Listed by Patrice Schneider of Four Seasons Sotheby's Int'l Realty

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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: 6.12% last updated on 2024-10-03

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

23 South Main Street Brattleboro VT 05301

Brattleboro, VT23 South Main Street

Price$850,000The price has recently decreased

Pending

MLS Number 5010643

  • Commercial
  • Year Built 1890
  • Square Feet 8,032
  • Acreage 0.23
  • PricePerSqFt 105.83

We are pleased to present the exclusive opportunity to purchase the multi-family investment property located at 23 S Main Street in Brattleboro, Vermont (the “Property”). The Property is a three story multi-family building containing ten (10) residential units comprised of one (1) Studio/1-Bathroom unit, four (4), 1-Bedroom/1-Bathroom units, and five (5), 2-Bedroom/1-Bathroom units with 8,032 square feet of living area in 8,578 square feet of gross area on a 0.23-acre parcel. 23 S Main Street is located on a quiet street in a residential neighborhood in the center of Brattleboro, Vermont. The Property is positioned along Main Street and is one block from Canal Street, one of the area's primary commercial and commuter corridors and enjoys convenient access to the town's restaurants, schools, and numerous parks and recreation areas. Additionally, the Property is close to area highways (VT Route 9 and Interstate 91) and is 19-miles from Keene, New Hampshire and Greenfield, Massachusetts, the area's largest cities which provide access to more restaurants and shopping as well as larger retailers, several grocery stores, and higher education centers.

Listed by Brian Brockmann of Bang Realty

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

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.12% last updated on 2024-10-03

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

207 Ursa Ridge Brattleboro VT 05301

Brattleboro, VT207 Ursa Ridge

Price$799,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5006233

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2

This custom home on 27+ acres is one of the most stunning properties in the area. Built in 2011 with meticulous attention to detail, this turnkey home offers unparalleled privacy just minutes from downtown Brattleboro and 3 miles from I-91. The house is high-end, superior quality construction with an open floor plan featuring a large open-loft primary suite. A soaring stone center chimney highlights the interior. Floors are a mix of slate tile, maple and golden pine. Multiple efficient heating sources include propane fired subfloor radiant & electric under-tile mats, complemented by a Jotul wood stove that will comfortably heat the entire house. In the kitchen, hickory cabinets & granite countertops surround a 6-burner Viking gas range. A full, heated and dry walkout basement and four bedroom septic system offer expansion potential. The basement has built in storage & a root cellar. Roof-mounted solar panels offset the electric bill. Fiber optic internet is on site. Expansive open acreage with outbuildings including a 3-stall barn with carport & spacious dormered loft built in 2012 as well as a substantial shed/chicken coop. Vegetable gardens, a cultivated blueberry lot, strawberry patch, Christmas trees, firewood forever and pasture make for exceptional homestead sustainability. Walk or snowshoe on the woodland trails & never leave your own property. Long, private drive- no drive-bys please. Delayed showings until Sunday, July 28th by appointment only.

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: 6.12% last updated on 2024-10-03

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

30 Crosby Street Brattleboro VT 05301

Brattleboro, VT30 Crosby Street

Price$775,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5011829

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5

Available for the first time in over thirty years, this stunning colonial property offers a peaceful escape from city life while being just minutes from downtown amenities. With its timeless elegance and classic charm, this home features abundant natural light that fills the sun porch, providing a perfect spot to relax and enjoy views of the lush, private gardens. Cozy up by the fireplace during winter evenings for added warmth and comfort. The expansive first floor boasts a seamless flow and includes a private office and a beautifully appointed library, ideal for both work and leisure. Upstairs, discover four spacious bedrooms, two of which are en-suite, each exuding its unique character. With an attached two-car garage, convenience is key, and for added flexibility, a separate, inviting guest house/ADU at the rear of the property presents excellent options for extended family living or rental income. Combining privacy with accessibility, this exceptional property is conveniently located just 2 hours from Boston and 3.5 hours from NYC, making it the perfect retreat that offers tranquility and urban proximity. Don't miss this rare opportunity!

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

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: 6.12% last updated on 2024-10-03

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

423 and 435 Marlboro Road Brattleboro VT 05301

Brattleboro, VT423 and 435 Marlboro Road

Price$750,000The price has recently decreased

MLS Number 4991094

  • 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

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: 6.12% last updated on 2024-10-03

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

50 Terrace Street Brattleboro VT 05301

Brattleboro, VT50 Terrace Street

Price$680,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5016387

  • Multifamily
  • Units 7
  • Acreage 0.48
  • Square Feet 5,540
  • PricePerSqFt 122.74

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 public water and sewer. Many units have private entrances - wow! On-site laundry, too! It's time to diversify, and acquiring a steady income stream is the best way forward!!! Excellent investment with superb ROI potential. LOCATION & OPPORTUNITY. This is THE ONE for you. Do NOT miss out! Private showings on request. Delayed Showings begin on October 11, 2024.

Listed by Dan Normandeau 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: 6.12% last updated on 2024-10-03

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

147 Country Hill Brattleboro VT 05301

Brattleboro, VT147 Country Hill

Price$649,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5000860

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3

Close to town, located on a residential cul de sac, in a country-like setting, this handsome colonial gambrel home offers a spacious interior, with numerous upgrades, including a fabulous kitchen renovation! Features include 2 fireplaces, a den, study, 4 bedrooms, 3 full baths, media room (over 2-car garage), dining and living room, mahogany, oak and tile floors and numerous built in bookcases. The inviting backyard is accessed from the kitchen leading to a vine covered pergola and stone patio, perfect for outdoor dining. The large lot is thoughtfully landscaped and enhanced by a delightful variety of flowering trees and shrubs with views overlooking the peaceful private Meadow Corp land, owned by the neighboring shareholders, in Current Use, appreciated by neighbors for walking and cross-country skiing! See packet for more information, including Meadow Corp Share offer.

Listed by Heidi Bernier 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: 6.12% last updated on 2024-10-03

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

135 Upper Dummerston Road Brattleboro VT 05301

Brattleboro, VT135 Upper Dummerston Road

Price$599,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4993919

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4

An ideal location from which to enjoy the countless in-town and country activities available in the Brattleboro area! This circa 1910 arts and crafts style cedar shingle house was one of Brattleboro's historic downtown homes and was moved to its current enviable location in 1996. The house sits 1/8th of a mile off of Route 30, within one mile of downtown Brattleboro and even closer to the active Retreat Farm (with its seasonal music and food truck roundups), the Meadows (water related activities) and the extensive Retreat trail system. The house is under 1/4 mile from the Brattleboro Country Club for golf, cross-country skiing and dining. The home offers an exceptional combination of country living and accessibility and features wood floors with radiant heat, a wood burning fireplace with built-in bookcase surrounds, high ceilings throughout, a formal dining room, office, and a kitchen with informal kitchen dining area with abundant natural light. The second floor is home to four spacious bedrooms and a full bathroom. The primary bedroom includes another private ensuite bath. There is ample outdoor common area including a 440 square foot deck above the home's two-bay garage and a covered entry porch which looks to the property's yard and surrounding woods. The walkout level basement is currently utilized as a rented apartment with one bedroom, an office space, and an open plan kitchen and living/dining space. Showings Begin 5/4! Contact us to discuss this special offering!

Listed by Eben Viens and Susan LeCours of Barrett & Valley Assoc. Inc

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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: 6.12% last updated on 2024-10-03

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

7 Chase Street Brattleboro VT 05301

Brattleboro, VT7 Chase Street

Price$579,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4996622

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 5
  • Bathroom 3

This 3-bedroom/2-bathroom home with attached 2-bedroom/1-bathroom in-law is situated on a corner lot in a quiet neighborhood steps to downtown Brattleboro. This recently renovated antique home offers the best of both worlds: With the convenient location, you'll enjoy easy access to local amenities including shops, restaurants, parks, and more. Escape the hustle and bustle of downtown in the peaceful, professionally landscaped backyard or explore the Retreat Trails, steps from the front door. While retaining its antique charm, the home has undergone extensive updates to offer all of the contemporary comforts. Enjoy the spacious layout of the main residence with ample natural light and modern amenities, including stainless appliances, wide pine plank flooring, central A/C, and an inviting covered porch entry. The attached apartment, built in 2011 offers endless possibilities. The two units can easily be reconnected to enlarge your living space, or keep them separate and rent one for supplemental income. Don't miss your chance to own this exceptional property offering endless possibilities for comfortable in-town living and potential rental income.

Listed by Rebecca Hiam of Southern Vermont Realty Group

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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: 6.12% last updated on 2024-10-03

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

10 Strawberry Hill Brattleboro VT 05301

Brattleboro, VT10 Strawberry Hill

Price$579,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5016885

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5

This extraordinary home was built in 1940 by a couple who sailed to England on the Queen Mary for their honeymoon. Inspired by the elegance and modernity of the ship, they sought to infuse their home with the same glamour, resulting in a striking blend of nautical design and Modernist architecture. The sunken living room boasts large glass windows, gleaming hardwood floors, and an exquisite fireplace adorned with a large mirror. The library features a round porthole-inspired fireplace, built-ins, blonde wood paneling, and glass brick accents. The expansive kitchen includes a breakfast bar, cozy dining nook, and both a butler's pantry and cook's pantry leading to the formal dining room with outdoor views. Upstairs, the red staircase leads to the ensuite primary bedroom, three additional bedrooms, and a dramatic sun porch that spans the full width of the house, offering tree-top views. On the ground floor, discover a whimsical wet bar complete with brass portholes, a ship's bell, a heated garage, utility area, half bath, and laundry. Ideally located on a side private street in a wonderful sought after neighborhood yet close to downtown Brattleboro, known for its thriving arts scene, great restaurants, and eclectic shops, this home offers easy access to year-round attractions. Just a short drive from top ski resorts and outdoor recreation, it's also conveniently located within hours of both New York City and Boston, making it perfect for a weekend escape or full-time residence.

Listed by Erica Reynolds of Southern Vermont Realty Group

{$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: 6.12% last updated on 2024-10-03

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

60 Moonlight Lane Brattleboro VT 05301

Brattleboro, VT60 Moonlight Lane

Price$550,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5016868

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

Moonlight Lane...could there ever be a better address? Moonlight in Vermont....just what you dream of when you see the big night sky and the full moon rising, such a Vermont attitude that slides right into morning! Only 2 homes claim this address, this cozy corner of the world. Nestled on 10 acres and surrounded by even larger parcels, this home has the perfect setting at the edge of a lovely, level meadow...mow as much yard as you like...sporting a much loved inground pool, fruit trees, berry bushes, and 2 sets of solar panels.....a small barn for storage, and lots more! Built for the owners 23 years ago, they made great choices in the huge main bedroom, farmer's porch and an open concept perfect for entertaining. The location is a bonus! A blink to Hilltop Montessori, downtown, hospital, shopping but totally country! First time ever on the market...picture this as your last home, your forever home.

Listed by Christine Lewis 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: 6.12% last updated on 2024-10-03

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

31 Red Tail Lane Brattleboro VT 05301

Brattleboro, VT31 Red Tail Lane

Price$525,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 4999433

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,120

This wonderfully unique home was designed and built for the owner, by the owner, in 2022. The house is close to downtown but is privately nestled in a new neighborhood just off the beaten path. The beautiful rear porch is surrounded by professionally maintained gardens, a meadow view, and a lovely secluded rear lawn. The interior open-concept layout shows a U-shaped kitchen with a long center island at one end and the living room with huge windows to the gardens at the other. One-level living is hard to find and this is a perfect fit with an attached garage so no raindrops will ever fall on your head. The energy efficiency of this home is 5-Star +. This is a house of the future - all-electric, no fossil fuels, an impressive HERS rating, an induction range, a heat pump dryer, and a heat pump water heater. The energy usage for the calendar year 2023 totaled $1188. (with daytime thermostat at 69, nighttime at 66). The addition of a modestly sized photovoltaic roof system would bring the annual energy usage down to zero.

Listed by Christine Lewis 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: 6.12% last updated on 2024-10-03

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

Broker Reciprocity 

Copyright 2024 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 October 8, 2024 5:24 PM EDT

 

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