Brattleboro, VT Homes for Sale

Step back in time and discover the enchanting potential of this distinguished 1940 Colonial, perfectly positioned to capture the spirit of Brattleboro. Perched on a generous 0.79-acre level lot, this home offers a rare blend of expansive personal space and convenient in-town living. From the moment you arrive, the classic lines, wood siding, and enduring slate roof hint at the craftsmanship of a

Keith Nowak Four Seasons Sotheby's Int'l Realty

Welcome to 23 Wilsons Woods Road, a meticulously maintained Colonial-style home that offers the perfect Vermont balance: total wooded privacy combined with absolute convenience. Nestled at the end of a quiet road, this property feels like a secluded retreat tucked into the forest, yet you are literally moments away from Brattleboro’s vibrant restaurants, local shops, the hospital, and a thriving

Kate Barry EXP Realty

Built in 2004 in this much-loved neighborhood, on a desirable one-way cul-de-sac, beautifully maintained, sits this 3-bedroom, 3-bath home. The first floor has a beautiful, large, eat-in kitchen, dining room, 1/2 bath, and access to a very spacious and inviting 16x16 deck ideal for family gatherings or entertaining, and a real sense of privacy. On the second floor, there is a primary bedroom with

Neil Goldberg Brattleboro Area Realty

Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

Christine Lewis Brattleboro Area Realty

Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on 11 acres of landscaped grounds with lawns, stone walls, gardens, and woodland in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered porch that opens into a marble floored foyer

Robert Doyle Berkley & Veller Greenwood Country

BLACK MOUNTAIN ESTATES - where your next chapter begins! Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

Dan Normandeau Berkley & Veller Greenwood Country

Welcome to the effortless existence of condominium life with the rare addition of uniqueness. How nice to own a home while splitting the expenses with two other condo owners. Park in your driveway and follow a pretty stone path to your first-floor sanctuary. This efficient 592 sq ft space offers an open kitchen, dining area with a washer and dryer, living room, one bedroom, and a full bath. Share

Kristen Ziter Taylor Brattleboro Area Realty

Just around the corner! From the middle and high school, Oak groveelementary! Pop around the corner for all the high school games,exercise at the track. Interstate is minutes away for easy access towork or play! One apartment is over 1,000 square feet so tons of roomfor owner occupancy! 2 nice front porches. Worth looking at for eitheryour own home or as an investment. Masks

Christine Lewis Brattleboro Area Realty

Invest in your own home town! Full tenant roster with the easy access to laundry across the street, grocery stores, train and The Moover. Right in the heart of things with little yard to maintain! Consider as an investment in your portfolio or decide to live in one unit and have the others pay your mortgage! Good way to start, retire or increase your portfolio! Owner is a licensed appraiser.

Christine Lewis Brattleboro Area Realty

Simple but elegant! Historic posts and wonderful beams define the magnificent open concept, giving visual shape and creating traditional options or whimsical uses for your new lifestyle. High ceilings and huge windows create a celebration of light, complementing the glowing antique floors—magical in combination and truly beautiful. A home, an artist loft...so many uses, so unique, so

Christine Lewis Brattleboro Area Realty

Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with sliders

Christine Lewis Brattleboro Area Realty

Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass

Rebecca Seymour Brattleboro Area Realty

Sweet neighborhood. This would be a great location for an owner to live in one unit and rent the other 3. Lots of character! Great investment possibility. Close to Hospital, nursing homes, shopping, interstate for travel. Plenty of off street parking

Christine Lewis Brattleboro Area Realty

Huge price reduction! Welcome to Esteyville! Here, history, location, and distinctiveness excel. This rare, NYC loft-style condo on the 3rd and 4th floors was formerly home to Estey Organ, the world's largest pipe organ manufacturer, circa 1870. Listed in the National Registry of Historic Places, you will find original pine wide-plank floors, exposed post-and-beam construction, soaring ceilings,

Liz LaVorgna Brattleboro Area Realty

Prime commercial opportunity in the heart of downtown Brattleboro. This mixed-use property features seven residential apartments on the upper levels and five ground-floor commercial units. Two retail spaces have direct frontage on Elliot Street, offering strong visibility, while three others open onto the Harmony Lot pedestrian area, a centrally located public parking and business zone. The

Erica Reynolds Southern Vermont Realty Group

Conveniently located in Brattleboro Center, this historic three-family home offers the perfect blend of Historic charm, and modern convenience. It is an ideal opportunity for an investor seeking profitable rental income or an owner-occupant looking to live on the main level while offsetting their mortgage with two additional rental units. The first-floor unit features high ceilings, French doors,

Matt Waddington Hoffman Real Estate

First time offered, EVER... built and loved by the current family, it is time to pass the keys to a new generation of owners ready to put their own love and dreams into this sweet home. Just across from the high and middle schools, around the corner from Oak Grove grade school, and down the street from the hospital and shopping. There is a first floor bed and bath for aging in place, but 2 big

Christine Lewis Brattleboro Area Realty

Turn-Key Investment in the Heart of Brattleboro! This versatile three-unit multifamily property offers a rare "move-in ready" opportunity for both savvy investors and owner-occupants. Two of the three units have been recently and extensively renovated, featuring brand-new flooring, fresh paint, modern baseboards, and updated plumbing and light fixtures. With new toilets and stainless/modern

Kate Barry EXP Realty

Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard to

Christine Lewis Brattleboro Area Realty

Move up to a designer condo! Impeccable detailing by an IKEA design team raised this unit to a high level of quality. From the marble floor entrance to the architectural ceiling over the dining area to the custom kitchen and bathroom installations to the decorator lighting to the PAX closet wardrobe systems... it all speaks "beautiful". Newer features include a propane boiler and hot water heater

Sally Fegley BHG Masiello Brattleboro

The one you have been waiting for! This traditional New England cape with a twist checks all the boxes! Remodeled in the 90's, it has a cook's delight for a kitchen with tons of cabinets and lots of countertops for baking prep...cookies and breads are a must!. The first floor was expanded to almost double the size of the living room, adding a fireplace and a main bedroom. Aging in place is easy

Christine Lewis Brattleboro Area Realty

What a great way to start your home ownership! A tenant can help with the monthly expenses letting you build your own reserves and take a bit ofpressure off the cost of home ownership! This 2 family has two-3 bedroom units, a nice yard and off street parking. Check it out and see for yourself...please respect the 48 hour notice for tenants, mask up! No interior photos due to tenant privacy.

Christine Lewis Brattleboro Area Realty

Don't wait to come view this newly remodeled, low maintenance, affordable and desirable ground floor end unit. Inviting circular flow, the spacious living room has a brand new slider with a view of the rear yard and the Whetstone brook. Plus, you have a brand new kitchen and appliances. The large bedroom with double closet has direct access to the newly renovated bath. This condo is located in a

Angela Sherman Brattleboro Area Realty

An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please, only

Christine Lewis Brattleboro Area Realty

Unique opportunity to own a nearly 40 acre tract and 2 homes on Hinesburg Road in a great West Brattleboro location. The homes sit unseen approximately 500 feet back on a private driveway from the public road. The houses need a fair amount of repair and remodeling to get them in good condition. The main house is a cape style home with open concept kitchen/dining/living room, full bath, and 2

Steve Schoppmeyer BHG Masiello Brattleboro

Move right in! This condo has had some updates to include new scratch resistant vinyl plank flooring, new bathroom vanity, new kitchen range and freshly painted interior. Located in a prime location with quick, easy access to I91 and a stones throw to the Whetstone Brook, Farmers Market and Living Memorial Park. Shared basement with assigned storage space. Association fees include heat,

Angela Sherman Brattleboro Area Realty

Great opportunity for starting or expanding your investment portfolio. Good rental income and affordable property. Nice location. Good parking for tenants and private porches. Minimal yard maintenance.

Susan Bellville Bellville Realty

What will the next life be for this iconic property? From popular and innovative hair salon to successful dental practice to a 4 unit family complex....pick your use!!! Owner occupied business...roomy apartments...small business complex...this multi use property has been renovated in the last few years with nice kitchens and baths..and has been used essentially as a single family with a huge

Christine Lewis Brattleboro Area Realty