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.

Search Smarter - Create an account to save your favorite listings and we'll notify you when similar properties hit the market.

111 Hillcrest Terrace Brattleboro VT 05301

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

165 Barred Owl Lane Brattleboro VT 05301

Price$385,000

Est. Mortgage: $/month

MLS Number 4747901

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,500

Very comfortable contemporary 3 bedroom, 3 bathroom house on peaceful 3+/- acres off of Bonnyvale Road. Standing seam roof. Large, well-designed kitchen opens to a sunny dining room. Living room is warm & relaxing, heated by Vermont Castings woodstove; walk out onto a wide deck and have your quiet time. First-floor laundry room. Office has large, double-pane windows that let you gaze out into the trees. Custom ceramic tile at entrance, maple flooring. Master bedroom sliders open onto a cozy balcony, offering a private view to the land and woods in back; large, walk-in closet, generous master bathroom. Walk-out basement with two finished rooms for exercise, recreation, or time-out.

Listed by John Hatton of Berkley & Veller Greenwood Country

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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

352 Orchard Street Brattleboro VT 05301

Price$389,000

Est. Mortgage: $/month

MLS Number 4751795

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,416

Meticulously maintained contemporary cape in one of Brattleboro's most coveted locations. 3 bedroom, 2.5 bath home with lovely features including hardwood flooring, brick fireplace, attractive open concept kitchen with granite countertops and stainless steel appliances, attached two car garage. Currently the master bedroom suite with walk-in closet is on the second floor, but there is incredible potential and (finished) space for a ground-bedroom suite (currently used for family room and office). Nice back deck, southern exposure...large basement for lots of dry storage. This property is in very good condition on a level one acre lot, less than two miles to the entrance of the golf course, right up the road from the Brattleboro Country Deli, Brattleboro Memorial Park, and on a popular road for a 2 mile walking loop. Make your appointment today!

Listed by Stephanie Peduzzi-Baker of Berkley & Veller Greenwood Country

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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

169 Akley Road Brattleboro VT 05301

Price$429,000

Est. Mortgage: $/month

MLS Number 4751814

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,800

This charming late 18th Century cape, the Thomas Akley House, home to one of Brattleboro's early settlers is located on an exquisite parcel of land providing a country location just minutes from downtown. The land is stunning with 5.7 acres of verdant field, mixed woodland, formal gardens, stone walls, walkways and patios and a large swimming pond with year round stream. The interior is lovely with wonderful period features, two fireplaces, wood flooring, master suite and numerous upgrades throughout. Light filled rooms, intimate spaces and a sense of history prevail throughout this fine offering.

Listed by Robert Doyle of Berkley & Veller Greenwood Country

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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!!! Showings to begin May 31, 2019.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

375 Orchard Street Brattleboro VT 05301

Price$499,000

Est. Mortgage: $/month

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: 4.07% last updated on May 16, 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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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

711 Black Mountain Road Brattleboro VT 05301

MLS Number 4745671

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,840

Perched high on a hill with total privacy and lovely westerly views sits this handsome contemporary colonial. Sited on 16+/- acres, the location is choice on desirable Black Mountain Road and is country in feel, yet only a short ride to Brattleboro's downtown. The interior is bright and inviting with large principal rooms loaded with special features including cherry flooring, granite counter tops, over sized windows, soaring spaces, brick Rumsford fireplace, master suite and much more.With an eye towards energy independence,the Owners have installed Solar Panels on the roof,and now have no electric bill! The large basement is insulated and semi finished and the high efficiency Buderus Boiler is a thing of beauty! This is a very special offering.

Listed by Thom Dahlin of Berkley & Veller Greenwood Country

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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

673 South Street Brattleboro VT 05301

Price$460,000

Est. Mortgage: $/month

MLS Number 4715159

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 6
  • Square Feet 3,970

Here is your chance to own a classic Vermont colonial in the beautiful town of Brattleboro. This classic Vermont farmhouse has it all! A quiet country location with southern exposure and mountain views, yet only minutes to downtown Brattleboro shopping and restaurants. This very traditional home has many modern updates. The heart of this home is the kitchen, which was recently renovated with granite counter tops, custom cabinets, pantry and a large island - also comes with top of the line appliances. The dining area has a large bay window that fills the room with light. The expansive family room boasts a wood burning fireplace and wet bar, with its own ¾ bathroom. With six bedrooms and four bathrooms there is plenty of space for family and friends. The large second floor family room or fully finished third floor could be your work from home office - the possibilities are endless. The eight acres of land include woods with walking trails, pastureland, a pond and stream. There are berry bushes and fruit trees and lots of space to breathe. The barn is in great condition with running water and electricity. The yard also has a gorgeous stone patio with propane hookups for your gas grill. Huge attached garage has tons of additional storage space and original work bench. This is a very special home in a very special location. Do not miss this one!

Listed by Claire Renaud and Thom Dahlin of Berkley & Veller Greenwood Country

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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

40 High Street Brattleboro VT 05301

Price$450,000

Est. Mortgage: $/month

MLS Number 4663587

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 6
  • Square Feet 3,606

This elegant 1895 Victorian is offered for purchase for the first time in 40 years. It is located in the heart of downtown just up the High Street hill to provide a panoramic view of downtown Brattleboro. The current owners have maintained an apartment in the upper floors while operating an active small business in the lower levels. Because of its urban center zoning, uses are almost unlimited. Whatever you use, this is one of Brattleboro's finest examples of the Victorian era showplace homes! The home has been maintained without disturbing the fine features of the age and boasts three hand carved fireplace fronts, sweeping staircase with pedestal light globe, gleaming wood floors, beautiful wrap porch with wonderful detail and original front door! The huge kitchen includes two pantries with lots of built-ins. Amazing high ceilings, and tall windows let in the light and air. Two sets of original cherry pocket doors allow the front of the two parlors to be separated. The original cherry woodwork abounds in the parlors and formal dining room. Walk to downtown, or sit on the porch and enjoy the rooftops and a view of the mountain. This is a very, very special property! Please give courtesy to the business and give lots of notice for viewing. Qualified buyers only please.

Listed by Chris Lewis of Brattleboro Area Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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

1211 Ames Hill Road Brattleboro VT 05301

Price$359,000

Est. Mortgage: $/month

MLS Number 4745878

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,450

This well built spacious Contemporary is privately located on desirable Ames Hill, country in feel yet only minutes to vibrant downtown Brattleboro. The setting is lovely and the house is perched high above the road allowing for gorgeous views of Mt. Monadnock---there is a deeded easement to maintain and expand the views. Close to shopping, skiing and the world famous Marlboro Music Festival. Light filled with open concept, the house is a delight providing large principal rooms including Formal Entry w/wood stove, massive Living Room w/ cathedral ceiling, stunning brick fireplace and lots of glass capturing distant vistas, Kitchen/Dining with island, pantry area and tile flooring, 3 amply sized Bedrooms---the Master w/ en suite Bath, 2 additional Baths, Loft/Game Room, huge Family/Studio room and SO much more-----passive solar gain, lots of closet and storage space, wired for a generator, full Basement with Buderus Boiler and washer/dryer. ****Priced $90,000 below the current town assessment****. No showings until April 24, 2019

Listed by Robert Doyle of Berkley & Veller Greenwood Country

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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

181 Quails Hill Road Brattleboro VT 05301

Price$475,000

Est. Mortgage: $/month

MLS Number 4740342

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,341

PRIME LOCATION! Meticulously maintained, updated, and lovingly cared for 4 bedroom, 4 bath, cape with 2 car attached garage. Graciously situated on 4.8 acres offering beautiful perennial gardens, level lawn, woods, views, and a pond. A complete feel of a country setting, yet a just a few short paved miles to downtown Brattleboro. Take a walk or bicycle ride 1.2 miles to the organic farm stand or 1.5 miles to the Round Mnt trailhead for hiking. First floor: Light and bright open floor plan of kitchen/dining and living rooms ideal for entertaining. An attractive gourmet kitchen- fully equipped with cherry cabinets, stainless appliances, double ovens, breakfast bar with wine rack. Off the kitchen, a half bath, an office (that could be used as bedroom). Take the slider to the back deck to admire your view in complete privacy. Second floor: Master suite is striking with new oak flooring, an over-sized walk-in closet with custom shelving. Master bath: double vanity and travertine flooring, stand up tile shower, and backsplash surrounding the deep soaking tub. 3 additional bedrooms, full bath with marble flooring, and laundry on the upper level. Lowest level is newly finished! Perfect for in-laws featuring a large family/rec room, an additional room for a gym or possible bedroom, 3/4 bath with Grecian white marble flooring and stand up tile shower, lots of closets for storage, slider and door to exterior, walk-up/ walk-out. Welcome home! Owner is a licensed Real Estate Agent.

Listed by Tracy Marino of Brattleboro Area Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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

Broker Reciprocity

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 May 19, 2019.