You are viewing all listings Homes between $250000 and $500000 dollars.
New Listing!
$289,000 $274 per sq.ft. Brattleboro VT Home »
3 Beds | 1 Baths | Total Sq. Ft. 1056 | Acres: 0.3Listed on Wednesday Sep 9, 2026
Description: Whether you are a first time home buyer or looking for an investment property, this is a home you will not want to miss. This property's location, which abuts Brattleboro Memorial Hospital, offers the best of both worlds as it sits atop a quiet road within a half mile of grocery stores, schools, pharmacies and shopping. The home's interior offers three bedrooms, a built in fireplace and hardwood floors. The basement features walk out access, a dedicated laundry space, ample dry storage with tons of potential to renovate into more living space. In the winter you'll love the pull-in garage with a sheltered breezeway leading inside your home, never having been exposed to the elements. The back yard is fenced in with a gate opening to a wooded area on your land with a walking trail to the hospital. With a bone dry basement, on town septic and sewer, and a new standing seam metal roof installed by the previous owner, this home is ready to be moved into and enjoyed with peace of mind for years to come! Please come to our open house at this property on Saturday, September 12 from 10 am to 1 pm! See Listing Details & 19 images.
Under Contract
$290,000 $134 per sq.ft. Brattleboro VT Home »
5 Beds | 2 Baths | Total Sq. Ft. 2167 | Acres: 0.37Listed on Monday Aug 17, 2026
Description: Offered to the public for the first time in nearly 60 years, this majestic Colonial-style home is located in one of Brattleboro's oldest neighborhoods. The property showcases exquisite original details, including maple floors and fine hardwood trim throughout both levels. Many of the original plaster walls and ceilings have been professionally restored and await your personal color choices. The first floor provides an expansive layout designed for gathering. Enter through a generous mudroom into a functional kitchen - ready to be customized into a chef's dream or kept simple - complete with a large walk-in pantry. The kitchen flows seamlessly into the dining room, which features a built-in cabinet. Across the foyer, a bright living room opens into a cozy den or parlor with a quarter bath. Upstairs, you will find five bedrooms and a full bath, with the added potential to finish the full attic for even more living space. Situated on two combined lots, this in-town gem includes off-street parking for multiple vehicles and plenty of room for gardening. Are you ready to become the next steward of this stately property? See Listing Details & 26 images.
Under Contract
$295,000 $270 per sq.ft. Brattleboro VT Home »
3 Beds | 1 Baths | Total Sq. Ft. 1092 | Acres: 0.28Listed on Monday Aug 3, 2026
Description: Welcome to this charming, well maintained ranch built with character, exceptional functionality, and comfort on a desirable dead end street. Classic curb appeal and the timeless design allow for first-floor living with spacious living and dining areas. It is flooded with natural light from the oversized windows and features original hardwood trim, solid wood doors, built-ins, and vintage light fixtures. Currently carpeted, but beautiful oak floors are underneath. The sunroom is welcoming and bright, offering the perfect space for an artist or an afternoon retreat while connecting with nature. The floor plan includes 3 bedrooms all of which look out to the expansive, level backyard. The vintage bathroom has warm accents, featuring original cream tiles with delicate pink surrounding the tub and shower, along with a laundry chute to the basement. The outside is impressive with a large open backyard offering endless possibilities for entertaining, gardening, recreation, or future outdoor additions. There is a charming rustic outbuilding that is the perfect garden shed or potential workshop. An oversized one-car garage connects to the home via a comfortable breezeway. There's an expansive full basement with cold storage room and flexibility for hobbies or a workshop. This home is rich in character yet full of opportunity for the next special owners to add their touches. Very close to the hospital, shopping, schools, bus route, and I-91. See Listing Details & 24 images.
New Listing!
![Brattleboro VT Home for sale $299,000 $271 per sq.ft.]()
$299,000 $271 per sq.ft. Brattleboro VT Home »
3 Beds | 1 Baths | Total Sq. Ft. 1104 | Acres: 0.29Listed on Tuesday Sep 8, 2026
Description: Sunny and inviting, this classic ranch offers easy single-level living with 3 bedrooms, 1 full bath, and a spacious living/dining area. Classic wainscoting adds charm and character to the hallway and bathroom. Recent updates include a roof replaced in 2019 and water heater replaced in 2022. The back deck overlooks a large yard with plenty of room for gardening, pets, and entertaining, plus a shed for additional storage. The full, unfinished basement offers versatile space for storage, a workshop, hobbies, or future living space, with a propane heating stove that provides supplemental warmth and an added measure of comfort and peace of mind during a power outage. Conveniently located near schools, shopping, and the hospital. See Listing Details & 32 images.
Under Contract
$299,000 $346 per sq.ft. Brattleboro VT Home »
Price Change! Reduced by $20,000 down 7% on July 29th 2026
3 Beds | 1 Baths | Total Sq. Ft. 1140 | Acres: 0.41
Listed on Monday Jun 22, 2026
Description: Welcome to a home where everyday living feels just a little more special. Offering three comfortable bedrooms and a functional, inviting layout, this property is designed for everything from quiet evenings at home to hosting family and friends. The true highlight is the incredible backyard, a rare, fully fenced, level oasis that's ready for every season of life. Fire up the grill on the spacious back deck, let the kids and pets roam freely, plant the garden you've always wanted, or gather around a fire pit under the Vermont stars. This is the kind of outdoor space buyers dream about and seldom find. In addition to the incredible yard. A fully paved driveway with room for multiple cars, space for RV's Boats and other recreational items is at your service. Located in one of Brattleboro's most convenient neighborhoods, you'll love being just minutes from vibrant downtown shops, local restaurants, schools, parks, and minutes from I-91 leaving you 30 minutes to major MA and NH Hubs. Enjoy year-round community events while still enjoying the peace and privacy of your own backyard retreat. Whether you're grabbing a morning coffee, exploring the local arts scene, or taking advantage of nearby hiking and recreation, everything you love about Brattleboro is right at your fingertips. This isn't just a place to live, it's a place to make memories. This home offers the lifestyle you've been waiting for. Don't miss your chance to experience everything this exceptional property has to offer. List Agent is related to the Sellers See Listing Details & 38 images.
Under Contract
$299,000 $214 per sq.ft. Brattleboro VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1400 | Acres: 6.5Listed on Friday Aug 7, 2026
Description: Looking for your first home, ready to downsize, or seeking single level living? This one is for you. Set in a peaceful rural location near the end of a quiet dead end road, this single level ranch offers comfort, privacy, and great potential on 6.5+ acres just outside the village of West Brattleboro. Enjoy an in ground swimming pool with a pool house and bathroom - perfect for summer relaxation. High speed internet keeps you connected, a reliable Buderus boiler provides heat and hot water, and most windows have been updated to double glazed vinyl for improved efficiency. Inside, the layout is practical and inviting. Enter from the attached 24x24 two car garage into a substantial mudroom/laundry room - a huge perk in Vermont. The kitchen offers ample workspace and storage, opening to the dining and living areas with a wall of west facing windows. The living room fireplace is an ideal candidate for a woodstove insert, offering efficient heat with the ambiance of a traditional hearth. Off the central living area are three bedrooms, including a primary bedroom with full bath. Two additional bedrooms - or office/studio/workout spaces - plus a second full bath complete the floor plan. Outside, there's room to garden, play, and enjoy the land. The price reflects the opportunity for a new owner to perform work and updates to build meaningful equity while enjoying a cozy home in a rural setting close to everyday necessities. Minutes from Memorial Park, trail networks, shopping, schools, the hospital, and I 91, this property delivers outstanding value at a competitive price. Don't let it get away. See Listing Details & 30 images.
$315,000 $492 per sq.ft. Brattleboro VT Home »
Price Change! Reduced by $35,000 down 11% on September 8th 2026
2 Beds | 1 Baths | Total Sq. Ft. 640 | Acres: 0.25
Listed on Friday Aug 7, 2026
Description: PRICE IMPROVEMENT! MOTIVATED SELLER! Welcome to this brand NEW, beautiful home, professionally blower-door tested at an exceptional 1.7 providing outstanding airtightness, energy efficiency, & year-round comfort. Completed in July 2026 & designed for low-maintenance living, the home benefits from net-metered solar credits that have offset the owner's electrical needs, including heating & cooling. Warrantied ENERGY STAR® appliances, two quiet high-efficiency mini-splits, & a continuous fresh-air ventilation system support healthy indoor air, low operating costs, & efficient climate control. Just minutes from Brattleboro Hospital, shopping, restaurants, downtown, & Interstate 91, the home also offers walking access to miles of peaceful forested hiking trails. Designed for one-level living, the first floor includes an inviting foyer, abundant natural light, an open-concept kitchen, dining, & living area, a primary bedroom & full bath, & a large pantry with a washer & dryer. The cozy loft offers flexible space for a second bedroom, office, studio, or guests. Southeast-facing windows & double glass doors open to a rear deck overlooking the Connecticut River Valley. Enjoy autumn foliage, mountain views, classic winter landscapes, colorful sunrises, & warm-weather privacy from mature maple, oak, & locust trees. The poured-concrete walk-out basement is plumbed for radiant heat & includes two windows & double glass doors, offering potential for a workshop, recreation room, studio, guest suite, or possible efficiency apartment, subject to local approvals. The backyard offers room for gardens & outdoor enjoyment. Solar credits are available for purchase separately, creating an exceptional opportunity for long-term energy savings. Every major design decision reflects quality, durability, energy performance, & ease of living. Whether as a year-round residence, Vermont retreat, or simplified one-level home, this home offers thoughtful design, modern comfort, & long-term value. See Listing Details & 35 images.
$319,000 $249 per sq.ft. Brattleboro VT Home »
Price Change! Reduced by $20,000 down 6% on August 13th 2026
3 Beds | 2 Baths | Total Sq. Ft. 1280 | Acres: 0.15
Listed on Thursday Apr 30, 2026
Description: Lovely level lot, close to schools, hospital, shopping, State park and downtown. The best of everything, and BRAND NEW!!! Be the the envy of all your friends, with this wonderful, open concept, one level home. Primary bedroom on one end with an ensuite for privacy! New, shiny appliances, good sized island for cooking or hanging out and both a tub and a walk in shower. Special in so many ways, easy to show. See Listing Details & 20 images.
New Listing!
![Brattleboro VT Home for sale $319,000 $169 per sq.ft.]()
$319,000 $169 per sq.ft. Brattleboro VT Home »
2 Beds | 2 Baths | Total Sq. Ft. 1883 | Acres: 0.29Listed on Saturday Sep 12, 2026
Description: Sited at the top of the hill in one of Brattleboros desirable, close to town, neighborhoods, this mini victorian home is arguably one of the coolest houses in town! Offering a perfect blend of character, comfort, and convenience. Located in a quiet, leafy area close to downtown, where you'll find a vibrant arts scene, great restaurants, shops, food coop, train station, and more. The space features high ceilings, original wood floors, and great light. Currently set up as a two family with a 1-2 bedroom on the first floor, a one bedroom on the second floor with unique arched windows, and a turret room encompassing the third floor. One could make this a single family just by removing the second stove, opening doors, and a change of use, plenty of room for everyone! If rental income would be welcome, the detached garage offers possibility for a tiny home. The established perennial gardens are lovely and provide a tranquil retreat. This house does need exterior maintenance but this would be an investment worth making, restore this magical home to its former beauty!! See Listing Details & 44 images.
$320,000 $278 per sq.ft. Brattleboro VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1152 | Acres: 0.23Listed on Monday Feb 2, 2026
Description: 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 bedrooms and full bath up! The full basement has room for a workshop, storage or game room. Drive and carport are paved for easy maintenance. Huge shed in the back for storage or lawn care tools. Just what you have been waiting for! See Listing Details & 20 images.
$350,000 $194 per sq.ft. Brattleboro VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 1808 | Acres: 0.12Listed on Thursday Jul 31, 2025
Description: 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 care for. Near down town,, MOOVER route, hospital and all the other good stuff. Quite, level short street, with easy access. Come join the neighborhood! Only the first floor is available to show on first showing. Please have all buyers qualified before requesting an appointment. See Listing Details & 2 images.
Under Contract
$369,000 $256 per sq.ft. Brattleboro VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 1882 | Acres: 0.37Listed on Wednesday Jun 17, 2026
Description: MAKE YOUR APPOINTMENT TODAY! A very sweet house in a desired West Brattleboro neighborhood on nice corner lot. Pull your car right into the 2-car oversized garage and enter through the enclosed porch which makes an excellent mudroom. First floor: beautifully updated kitchen with quartz countertops and cherry cabinets, a dining area that adjoins the light-filled large living room with lovely warm hardwood floors, exposed beam, an enormous picture window that allows for streaming sunshine throughout the morning. The centrally located Hearthstone woodstove adds to the appealing aesthetics of the home and provides for a secondary heat source that warms the entire home in the winter. Down the hall- a full bath and two good-sized bedrooms with wood floors. Upstairs, you will find an expansive primary bedroom, a half bath and a large office (or 4th bedroom). There is a full, poured concrete basement with bulkhead, where one of two rooms is finished and has served as a play/rec room through the years. The other room is used for storage with shelving, includes a washer and dryer, and an on-demand water heater and furnace that are only 6 years old. Outside you will enjoy a large back deck for summer grilling and relaxing. The yard provides areas for flowering trees, sun and natural shade, plantings and play. Garage roof is brand-new. Convenient location just minutes to downtown Brattleboro, or all of the West Brattleboro offerings such as hardware store. coffee shop, farm-stands, convenience store, restaurants and more. Make your appointment today! See Listing Details & 37 images.
Under Contract
$390,000 $246 per sq.ft. Brattleboro VT Home »
2 Beds | 3 Baths | Total Sq. Ft. 1614 | Acres: 0.25Listed on Wednesday Aug 12, 2026
Description: Welcome to 116 Green Meadow Road, where a unique shared-meadow setting offers the feel of country living with the convenience of Brattleboro nearby. Built in 1981 and situated on a manageable .25-acre lot, this home overlooks a beautiful 22-acre meadow. The current owner holds 20 shares in the meadow, providing shared ownership, recreational use and a voice in its stewardship. Purchase of the 20 shares by the buyer is a condition of sale ($6,800). Step inside to a freshly painted interior with all-new flooring and new appliances. The flexible floor plan currently offers two bedrooms, including an exceptionally spacious bedroom with potential to be divided to create additional sleeping or living space. Three 3/4 baths provide convenience throughout the home, with one offering space to accommodate a future bathtub. The walk-out basement already has a 3/4 bath and offers wonderful potential for additional finished living space. Enjoy your morning coffee or unwind at the end of the day on the back deck under the awning while taking in the peaceful meadow views. Inside, a propane stove in the living room adds warmth and coziness during the cooler Vermont months. Energy-conscious and practical features include solar panels, a standing seam metal roof, 3 heat pumps, mini-splits and a whole-house propane generator. A one-car garage with additional storage, fully fenced backyard, garden shed and space for gardening complete the property. A special opportunity to enjoy the privacy, views and open feeling of a much larger country property without having to maintain 22 acres yourself. Open House Saturday, August 22: 10am to 12 Noon. See Listing Details & 59 images.
Under Contract
$439,000 $274 per sq.ft. Brattleboro VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1600 | Acres: 3.6Listed on Monday Aug 17, 2026
Description: Elegant and charming cape with an enchanting, exceptional garden that will impress even the seasoned green thumb. This magnificent home is solar equipped; the owner has had no electric bills for 3 years and the solar agreement may be transferred to the new buyer. Classic Vermont timeless style throughout features gorgeous archways, built-ins, and oak flooring. The kitchen is spacious with a traditional counter and views out to the tranquil gardens. The circular first floor plan graciously leads you into the long living room with a woodstove and pretty mantel. A second dining space, a bedroom, and a full bath complete the circle, allowing for easy single-floor living. Upstairs are two more bedrooms, a full bath, and an impressively large sitting room/den. The two mini-splits provide both heating and air conditioning for year-round comfort. In addition, there is an attached two-car garage and a full basement with space for your workshop. Visit this gem that has beauty and functionality. See Listing Details & 41 images.
$439,000 $283 per sq.ft. Brattleboro VT Home »
2 Beds | 2 Baths | Total Sq. Ft. 1550 | Acres: 0.18Listed on Tuesday Aug 25, 2026
Description: You've earned it.....the right to easy living.....have someone to do the heavy lifting...This community has become a much needed addition to the housing community. All are designed for the 55 and over who are looking for an easy way to settle in. Just think, the snowplowing, shoveling and salting are all taken care of, as well as the summer mowing and hedge trimming. One level living with no steps, a step in shower...no hopping over the tub rim...no cleaning off the car when you park in the garage...Besides all this there is a community center featuring exercise equipment, a function room, cozy fireplace and kitchen. A great place for walking, meeting the neighbors and making friends. Pickle Ball anyone? Located right off I91, you CAN get there from here. No mud season, no fuss. You have earned it! This property is being subdivided from a larger parcel. See Listing Details & 17 images.
