Brattleboro VT Homes $350k to $500k

Browse all homes between $350,000 and $500,000 for sale in Brattleboro, VT. Contact us if you have questions or would like to schedule a tour.

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148 Hillwinds North Brattleboro VT 05301

Price$365,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4753603

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 3,040

There is a lot to love with this comfortable contemporary located in the desirable Hillwinds community. The open concept kitchen with a butcher block island, large pantry, cherry cabinets and sitting area is perfect for entertaining. Large dining area overlooks the sunny living room with wood burning fireplace will be a perfect place to dine and watch the seasons go by. Oak hardwood floors throughout the main floor. There are three bedrooms upstairs with a spacious master bedroom en-suite complete with whirlpool soaking tub and walk in closet and sitting area. In the basement, there is a large finished walk out basement with a Waterford wood stove and another finished room for an office or guest room. There is another space that would be perfect for a shop or craft space. Spacious two car garage with lots of space above for storage or another finished work space. The basement and the first floor have radiant heat and second floor is kept warm with baseboard hot water. Surrounded by conserved land complete with trails for biking hiking and walking, this stress free sanctuary is only a short drive to town. You will fall in love with this home.

Listed by Thom Dahlin of Berkley & Veller Greenwood Country

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$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1013 South Street Brattleboro VT 05301

Price$479,000

Est. Mortgage: $/month

MLS Number 4778068

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 3,000

Impeccable, upscale, open-concept home with income potential, in desirable West Brattleboro location. Lovely quiet, country setting yet just 8 minutes from RT 91 and 10 minutes from Brattleboro and Marlboro. New kitchen with honed granite counters, slate floor, Fisher-Paykel frig, Bosch dishwasher, stainless professional range, farmers sink and large island, perfect for entertaining. All new baths with granite vanity tops, slate floors and marble showers. Large living room with beautiful wood stove insert in fireplace with large windows overlooking manicured lawns and stunning gardens. In-law suite, office or guest ensuite with kitchen, LR, bedroom, bath, electric heat and separate entrance. Radiant heat (with liquid propane) throughout main house, hot tub, privacy and more. Only a short distance to Mt Snow and Stratton Mountain for skiing fun. Two hours to Boston and New Haven, 3.5 to NYC and the Cape. Don't miss this stunner!

Listed by Patti Long and Arlene Palmiter of Four Seasons Sotheby's Int'l Realty

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$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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81 Olson Drive Brattleboro VT 05301

Price$449,000

Est. Mortgage: $/month

MLS Number 4748648

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 4,000

This beautiful home is set on a knoll providing lovely easterly view (exquisite sunrises) and is only 15 easy minutes to Brattleboro. Sited on 3 acres of landscaped grounds, the exterior is reminiscent of a rustic lodge with large front deck via blue stone steps, rear circular stone patio and charming gazebo overlooking the view. The interior is simply stunning and provides exceptional living space with large principal rooms and superb custom features and amenities throughout. Little was spared to create a unique and exquisite living environment. Large living room with fireplace, extraordinary custom & gourmet kitchen with adjacent dining room, family room/gym, master suite with bath (granite heated flooring, black nickel faucets & oversized shower with double Kohler rain shower heads), two additional bedrooms and another 1.5 baths. Central A/C, central vac, self testing Kohler generator, heated garage with openers, separate car port, many rooms with speakers, exceptional hand forged lighting throughout created by Hubbardton Forge and SO MUCH MORE!!

Listed by Robert Doyle of Berkley & Veller Greenwood Country

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$
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$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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111 Hillcrest Terrace Brattleboro VT 05301
Active With Contract

MLS Number 4721243

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 4,282

Enjoy a rare combination of proximity and privacy from this well built 1999 home on Hillcrest Terrace with 2.99 acres and spectacular mountain views. This home is being offered by the original owners who have lovingly maintained and updated the home to stay functional and charming for the new owners. Features include open concept living spaces, spacious kitchen with breakfast bar and walk-in pantry, large dining room, vaulted living room with great natural light and large windows to the views, sitting room with wood burning fireplace and brick hearth, main floor guest suite, second floor master suite with soaking tub, double vanity, toilet closet, stand up shower, and walk-in closet, 2 upstairs bedrooms with shared updated bathroom, and office/bonus room great for overflow. The full finished walk out basement is wide open for family room, exercise, or game space, and has tremendous storage. Head out to the stone patio and custom stone work, enjoy the beautiful Vermont scenery from the expansive screened in porch with room for dining and seating, or bask in the sun on the double decks with room for hot tub. There is an attached 2 car garage, another oversize detached 2 car, 3 story barn for tremendous extra storage, and piping for future additional potential. The 3 acre lot includes a paved driveway, ample lawn space, perennial gardens, mature maple trees, and privacy from neighbors.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

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$
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$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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40 High Street Brattleboro VT 05301

Price$357,000

Est. Mortgage: $/month

MLS Number 4766805

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 7
  • Square Feet 3,606

A classic Victorian, built in 1895 during a period of prosperity in Brattleboro, by a banker for his family. This became the primary residence for Oates & Bredfeldt, and the primary office space for their B&B and Inns consulting firm. The dining room has been the location for many small conferences, as well as gathering place for family & friends to celebrate holidays & special occasions, as well as gala business events utilizing the well-equipped kitchen. Currently, the 1st floor is dedicated for social events, 2nd floor is office space, and the 3rd floor is an apartment. The back of the house is spacious; an octagonal winterized porch leads to attached garage with own attic. Special features include a unique wood/gas stove in kitchen, cherry woodwork throughout 1st floor, chestnut flooring in kitchen; all fireplaces were built by Estey Organ craftspeople. Full, dry basement w/ wine cellar, 2 storage rooms.

Listed by John Hatton and John McPherson of Berkley & Veller Greenwood Country

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$
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$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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92 Canal Brattleboro VT 05301

Price$425,000

Est. Mortgage: $/month

MLS Number 4745044

  • Multifamily Multi-Family
  • Square Feet 7,068
  • Units 4
  • Acreage 0.28

MONEY MAKING INVESTMENT$$ In prime location, close enough to capture that downtown excitement! It's time to invest locally! With over 5000 square feet of multi use space...6 units: 2+ storefronts, 1 2-bed, 2 1-bed, 1 studio, 2 garages, 12+ parking spots, loading dock, and storage. Updated electric and plumbing, new Buderus heat and hot water system 2014, new vinyl roof 2015. Incredible visibility...great signage possibilities! Turnkey investment! Keep the current format with 2 large commercial rentals on the first floor and residential above, creating a great income stream. Or...boutique the first floor and renovate for owners quarters on 2nd floor and become low carbon footprint. Walk to downtown, Coop, Hospital and other great services. Think about how you can reinvest in your own home town or look to the future and bring your new business to a thriving small town with great heart and many, many possibilities.

Listed by Chris Lewis of Brattleboro Area Realty

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$
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$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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375 Orchard Street Brattleboro VT 05301

Price$499,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4750542

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,280

ORCHARD HILL FARM - Country charm meets in-town convenience with this classic, circa 1865 Vermont farmhouse. In a country setting minutes from downtown Brattleboro, this spectacular home has been tastefully & meticulously renovated to retain antique charm & maximize comfort & energy efficiency. The spacious, country kitchen includes a cozy dining area & a sunny corner nook near the wood stove. There's also a formal dining room, an office, ½ bath & living room with fireplace & built-in bookcases. Three bedrooms share a full bath while the master bedroom has an en suite bathroom. A gorgeous back yard with heirloom apple trees and a private patio are only three reasons to look at this stunning home. Very convenient to Retreat and Windham Foundation trail systems! Summer or Winter access is right in your own back yard! Along with the wood-pellet boiler, upgraded windows, insulation & extensive structural upgrades it even offers a plug-in for an electric car. The large barn, the beneficiary of considerable renovation, provides plenty of space for your hobbies & passions, like boats, bikes, art, woodworking or animals. This one of a kind property is listed on the National Register of Historic Places. Subject to subdivision. House on 2.5+/- acres will be divided off the 16.1+/- acres. Additional land may be purchased with the house. Lot 1 5.5+/- acres for $49,000. Lot 2 7.5+/- acres for $69,000. Lots themselves cannot be purchased prior to house sale.

Listed by Thom Dahlin of Berkley & Veller Greenwood Country

$
$
%
$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

81 Laurel Street Brattleboro VT 05301

Price$420,000

Est. Mortgage: $/month

MLS Number 4759079

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 4,394

MOTIVATED SELLER! Come take a look at this fantastically priced exposed beam timbre frame on 18 acres. As you turn up the driveway you are whisked away to a natural retreat yet are only 1 mile from downtown Brattleboro. With Windham Foundation trail access you are surrounded by a beautiful woodland setting. When you enter the home the natural beauty outdoors is let in with vaulted ceilings and skylights. There is room for everyone with over 4000 Sq/ft of living space, a large open Kitchen, formal dining room, living room, and a large 4th bedroom that could be the library. A large Ipe deck on the front of the house overlooks where your future gardens can be planted. Upstairs are two matching bedrooms with lofts and large private Master suite with 2 walk in closets and a sauna! The retreat trails are accessible right from the driveway and the famous Harris Hill ski jump is right next door. A truly unique home that has a lot to offer. Come see this wonderful spot.

Listed by Keith Nowak of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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236 Barrows Road Brattleboro VT 05301

Price$400,000

Est. Mortgage: $/month

MLS Number 4753481

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 960

Gorgeous long-range views of Vermont and New Hampshire from this hillside farm! 88 acres of pasture and woodland straddling both sides of a very quiet dirt road within 15 minutes from I-91 and downtown Brattleboro. Two ponds, a 4,000+ sf barn, 2 hoop houses (60'x30' and 48'x30') AND a newer construction, single-level house with radiant heat and hardwood floors. This farm is currently used for raising beef and was previously used as a dairy farm. What is your passion? Beef? Horses? Alpaca? Goats? How about hemp for CBD oil? The barn and hoop houses are perfect for these and many other uses. It's not very often a sweet property like this comes along. Own your personal view of Mount Monadnock and let the sun greet you every morning. Spectacular opportunity!

Listed by Dan Normandeau of Berkley & Veller Greenwood Country

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$
%
$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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41 Juniper Ridge Road Brattleboro VT 05301

MLS Number 4705098

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 3,741

Something Special! If you're looking for country casual with a refined touch, this is it! A gentle stone wall, lined by colorful trees in the fall and gardens emphasized by stone walkways greet you every time you come home. The ever important southern exposure with lovely local long range views will draw you out to the tranquil deck. The gym may become the master bedroom, the family room or an in law suite...or, work out and hit the hot tub under the moonlight. You will love the open concept kitchen dining, (great for entertaining) the light filled living room to the view and the casual family room in the daylight lower level! Let us tell you about the amazing new heating system and all the other perks. Just off pavement for the practical minded, a must see for all.

Listed by Chris Lewis of Brattleboro Area Realty

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$
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$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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108 East Orchard Street Brattleboro VT 05301

MLS Number 4751478

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 3,235

This impressive country home was renovated in 2004 with an eye towards simple elegance and livability. The setting is beautiful with views over farmlands and distant mountains, yet only minutes to vibrant downtown. The interior is stunning with large principal rooms, hardwood flooring, crown molding, two fireplaces, exceptional gourmet Kitchen, Sun Room, formal Living and Dining rooms, 1st floor Master with en suite Bath, 2 guest Bedrooms, 3.5 Baths, lower Family Room with 2nd Kitchen & pool access and so much more. An exquisite one of a kind property not to be missed!!!

Listed by Robert Doyle and John Hatton of Berkley & Veller Greenwood Country

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$
%
$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1017 Marlboro Brattleboro VT 05301

Price$485,000

Est. Mortgage: $/month

MLS Number 4755930

  • Multifamily Multi-Family
  • Square Feet 7,209
  • Units 7
  • Bathroom 7
  • Acreage 4.7

7 unit rental property offers 3 separate buildings with different character to accomodate nearly every type of tenant. The main building is a 3 story house with units on each floor. Possible owner occupy situation as the main floor has access to a private fenced area with inground pool and covered porch. Spacious 2 bedroom units with a great rental history. Main house also includes a large 2 story barn for storage and possible additional rental opportunities. Second building began life as a motel which has been converted into three 1-bedroom units. The building was reconstructed about 20 years ago and the units are all in nice shape. The third building is a 2005 double wide mobile home and this 3 bedroom / 2 bath unit stands alone and has nice privacy. All the buildings are on a park like 4.7 acre lot. The area along the road, aka as Route 9, has a permit for the owners to hold a weekend flea market. Excellent numbers with room for improvement make for an excellent return on your investment. Excellent rental history and many long term tenants.

Listed by Steve Schoppmeyer of BHG Masiello Brattleboro

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$
%
$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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23 South Main Brattleboro VT 01503

Price$500,000

Est. Mortgage: $/month

MLS Number 4754733

  • Multifamily Multi-Family
  • Square Feet 7,556
  • Units 10
  • Bathroom 10
  • Acreage 0.23

10 unit apartment building with plenty of parking. Stove, refrigerator and all utilities included. Space for an additional building.

Listed by Susan Wylie of Vermont Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
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 2019 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 October 14, 2019.