Brattleboro Vermont homes for sale starting at Fifty Thousand Dollars

$995,000 - Brattleboro, VT

266 Ursa Ridge Road Brattleboro, VT - Homes surrounded by nature's tranquility are plentiful. However, this fabulous, 51+/- acre property is enveloped within an additional 100 acres of deeded building-restricted land. Serenity, never to be threatened, is your guarantee. Cedar, pine, maple, walnut, beech, hickory, birch and oak are featured throughout this home. The owner-builder inter-laced timbers from the land to create a masterful, interior display of nature. Floors of varying woods and all windows framed in sugar maple are some details of owners craftsmanship. Walls of windows allow natural light to fill the rooms & bring outdoor beauty within. Enjoy views from this hilltop retreat whether inside or from the spacious deck. All floors have radiant heat from the basement mechanical room to the over-sized garage and framed-in, plumbed & wired space above it. Anticipating future needs, the 3 bedroom, 3 bath home has a septic permit for four bedrooms. The two independent heating systems of propane & wood create the opportunity for an almost ‘off-the-grid” independence. And yet, the most distinctive quality of this unique property is the assurance of quietude & land conservation with neither the costly purchase of 100s of acres nor the tax cost of additional land ownership. Craft a world with the calm of streams, rock formations and towering trees that is unbelievably only 5 minutes from Brattleboro's eclectic main street. Seize this rare opportunity to redefine life & your legacy for the generations that follow.

$859,000 - Brattleboro, VT

104 Juniper Ridge Road Brattleboro, VT - Welcome to Juniper Ridge! Where you will find superior craftsmanship, a private haven, and neighbors only one can dream of. As you enter the foyer of this custom built home, you'll feel its character & elegance with vaulted ceilings, arched doorways, terracotta tile and balconies lined with bookshelves. The home was built with attention to the flow, energy and natural light. The kitchen has Italian ceramic countertops & butcher block, including a dinette with southern light. With an open concept living/dining arrangement, the living room has lovely radiant wood stove heat. The adjacent dining area is drenched in sunlight. The home affords views of the West River Valley and Green Mountain vistas as far as Hogback Mountain. The first floor offers a fabulous great room, 2 fireplaces, an office, a sun room with hot tub, a laundry room and decks for admiring the sunrises and sunsets. The second floor is exceptional with three expansive primary en suites and two more rooms perfect for study, meditation, or extra bedrooms if needed. The two car garage has plenty of room for a workshop and the landscape features stone walking paths, wildflowers, perennials, pear trees as well as an in-ground pool. Brattleboro offers that small town charm with culture everywhere, from our music center, the Brattleboro Museum and Art Center, galleries, cafes, and more. Convenient to ski mountains & easy access to Boston and NYC. The next owner will truly be fortunate! Delayed showings until 6/12/25.

$650,000 - Brattleboro, VT

301 Maple Street Brattleboro, VT - How sweet it is! It is the perfect time to own this home, as the season turns to spring all the extraordinary effort in design and creating the hardscape and gardens come to life in bursts of bloom, enchanting ribbons of perfume and delightful fragrant nooks. Perfect set up for home office on first floor or tuck away in a sweet 2nd floor option with lots of room to work in private. Out back, in the private, personal space is the 24x50 salt water pool....once a swim school pool....now an oasis waiting for you to kick back and relax. The home...rich in history.....dates to 1819.....has been lovingly updated, keeping as much character as possible, but with the eye to modern standards of comfort. The main floor has an option for a lovely main bedroom with....just around the corner... a tiled walk in shower and laundry to allow for one floor, aging in place option. The light filled 2nd floor is classic colonial big bedrooms, big windows and 2 huge walk in closets. You will never wonder where to store the linens again! Plan a bit of time for this one. Please be respectful and be prequalified before making showing arrangements.

$599,000 - Brattleboro, VT

135 Upper Dummerston Road Brattleboro, VT - 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!

$550,000 - Brattleboro, VT

441 Guilford Street Brattleboro, VT - Perched proudly on a knoll, this mid-19th-century colonial was one of two farmsteads in this neighborhood of Brattleboro, VT. This stunning, 4-BR, 2-BA hip roof colonial & spacious, 2-story barn have been lovingly cared for by the same owner for 56 years! Now is your opportunity to own a New England classic in a neighborhood setting, but country feel - all w/in very close proximity to town amenities – hospital, town park & ski hill, schools, and downtown. ONLY 1 mile to I-91. A sweeping driveway off the town road brings you up to the home & barn, culminating w/ an elegant loop for convenient entry & exit. A charming, covered porch leads you into the home’s center hall w/ a stunning 2nd-floor staircase. Turn left into the spacious kitchen, or right, into the expansive full-width living room w/ center fireplace. Completing the 1st FL are a formal DR, 3/4-BA, OFC or FR w/ priv entr, & a sweet, screened porch from which to look over the flat back yard & watch the colorful summer sunsets. Upstairs are 4 BR’s and a large full BA. A nice mix of hardwood & softwood flooring adds to the aesthetic appeal of the home. Newer windows throughout. Durable slate & metal roofing. Views up the Connecticut River valley, increase after the leaves fall. The nearly 2,000 SF barn offers a multitude of options, w/ approx. half of the space being clear span w/ 20+ ft of headroom; the other half offers 2 full stories. You will want to see this gem! Delayed Showings Begin June 6, 2025.

$547,000 - Brattleboro, VT

628 South Main Street Brattleboro, VT - Absolutely Gorgeous In-Town Home with Exceptional Attention to Detail. This stunning residence offers over 5,000 square feet of meticulously designed living space in the main house, plus a fully separate accessory dwelling with two independent living areas—ideal for extended family, guests, or producing income. Additionally there is a two-car garage with an integrated service pit for convenient vehicle maintenance. Originally built around 1860, the home was completely renovated down to the frame in 2000, combining timeless character with modern upgrades and superior craftsmanship. The remarkably clean basement offers a multi-zone heating system for customizable comfort, foamed sills for added insulation and a separate electric hot water heater for energy efficiency in summer. Throughout the home you will find hard-wired ethernet for seamless high-speed steaming, central vacuum plus an outdoor spigot with hot water and a retractable hose to prevent freezing during the winter. The 3 story, 5 bedroom home offers a spacious updated kitchen on the main floor, a formal dining room, living room, plus a den with a wet bar. The 2nd floor offers spacious bedrooms and an office. The 3rd floor offers a kitchenette with 3 more bedrooms—perfect for guests. The in-town oasis backs up to a spacious ball field, just minutes from downtown, schools, shopping, the hospital, and public transportation. This is a rare opportunity to own a thoughtfully upgraded home in a prime location.

$525,000 - Brattleboro, VT

1073 Upper Dummerston Road Brattleboro, VT - This very Vermont country home is nestled on a peaceful, beautifully landscaped 1.5 acre lot along Upper Dummerston Road. Built with unparalleled craftsmanship by some of the region’s finest artisans, the home exudes exceptional quality throughout. At the heart of the residence is a large chef's kitchen, complete with a gas fireplace, granite countertops, solid maple cabinetry, and premium Wolf and Jenn-Air side-by-side ovens and range & walk-in pantry. The home features three bedrooms, one located on the first floor, and one upstairs with a soaring cathedral ceiling. Additional spaces include a formal dining room, a spacious living room, two beautifully tiled bathrooms, and a finished basement designed for both relaxation and entertaining. The interior is thoughtfully crafted with warm tones, hardwood cherry and oak floors, and solid wood doors. Energy-efficient windows and a newly installed boiler system, and heat pumps for both floors ensure year-round comfort. A generous 2-car garage offers ample storage space above, while a tiled mudroom provides added convenience. The maintained grounds include perennial and raised vegetable gardens, flowering trees and shrubs, stone walls, and a custom-built outdoor craft/sitting area. A professionally designed Ashfield Stone Patio, complete with a wood-fired oven (Pizza!!) crafted by a local mason, offers the perfect setting for outdoor entertaining.

$495,000 - Brattleboro, VT

21 Howard Street Brattleboro, VT - This beautiful Victorian home is just a short stroll from vibrant Brattleboro and has access to a huge town trail network. Nicely landscaped and has a partially fenced yard for pets or children. The house has lovely Victorian detailing and includes 3 covered porches. The formal entry has hardwood flooring, period staircase, stained glass window and a 3/4 bath. The adjacent front parlor includes oak flooring, ceiling fan and double French doors opening onto a cozy living room w/ornate fireplace w/gas stove, ceiling fan and hardwood floors. There is a formal dining room w/built-in hutch and Southern pine flooring. Then kitchen is delightful boasting elegant wainscoting, spacious center island and a walk-in pantry/mud room. The 2nd level offers a blend of comfort and style w/3 bedrooms, 2 of which share a full tiled bath. The primary bedroom is a serene retreat w/direct access to a 2nd floor covered porch, a private dressing room and an en suite tiled bath. The 3rd level unveils even more versatility with a large finished storage room that opens onto a "Summer Bedroom" w/colored glass windows, perfect for additional living space or creative pursuits (artist studio?). This charming home celebrates period Victorian features and a sense of elegance. There is a 2-Car garage, central air conditioning and the residence is located in a highly sought after neighborhood. A special spot offering comfort, beauty and a unique sense of place. Delayed showings 4/28/25.

$450,000 - Brattleboro, VT

36 Spruce Street Brattleboro, VT - You choose! This amazing property can be used as one of the grand ladies of the neighborhood...just open a door or two and repurpose the kitchen...what a nice laundry room it would make...or use as is with 2 flats, live in 1 and have a bit of income from the other...What else, you might ask! There is a rear section of the house ready to be reclaimed, and a barn attached that could also be built out as living space!. So...a nice big rambling home or maybe 2 more apartments! And there is more! In the back, out of the way...there is a beautiful 40x40 building for all sorts of uses...storage, workshop,....perhaps create a bonus room! There is so much to consider you will need to take a bit of extra time to look at this one. Please, respect the tenants, a 48 hour notice and be prepared for shoe removal for the apartments!

$450,000 - Brattleboro, VT

1142 Western Avenue Brattleboro, VT - You choose! Such a versatile property...invest in 2 rentals...live in either unit and rent the other...maybe develop the barn into another unit, home business, workshop..(check with Zoning). Just short of an acre (.86) the land is the big, big seller....the huge, mostly level back yard is already lush with flourishing fruit trees and blueberry bushes. There is a garage/gardening shed for your lawn tractor and gardening equipment, or tune it up and give your collectable car a new home. Age in place! Everything you need on the first floor with bed, bath and laundry. Newly renovated, this one sparkles and shines. There are still some touches for the new owner in the warmer weather to complete, but you can move right in, start collecting rent from the 4 room apartment in the rear, range, fridge, w/d included. $850 a month and they pay their utilities. Great for income or generation x interim housing! Apartment shown on 2nd showing and with 48 hour notice. Shoes off, so wear those slip ons.

Brattleboro, Vermont listings for sale

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