You are viewing all listings Homes between $250000 and $500000 dollars.
$300,000 $166 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.
$325,000 $147 per sq.ft. Brattleboro VT Home »
5 Beds | 3 Baths | Total Sq. Ft. 2209 | Acres: 0.21Listed on Wednesday Dec 18, 2024
Description: 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 windows, and glowing wood floors. First floor has a bedroom option and a full bathroom, there's a full bathroom on each floor! Plenty of room for everyone with three more bedrooms and a bathroom on the second floor. There is an additional room on the second floor with separate entrance that would make a great office, and the third floor offers an in-law potential with a one bedroom studio apartment. There are two furnaces and two oil tanks, one for the first floor, one for the second floor, and a propane wall unit for the third floor. See Listing Details & 28 images.
$345,000 $299 per sq.ft. Brattleboro VT Home »
Price Change! Reduced by $8,900 down 3% on April 6th 2026
3 Beds | 2 Baths | Total Sq. Ft. 1152 | Acres: 0.23
Listed 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 & 16 images.
$350,000 $206 per sq.ft. Brattleboro VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1703 | Acres: 0.56Listed on Thursday Sep 11, 2025
Description: 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 here. Along with the bedroom, there is laundry and full bath on the first floor. The attached 2 car garage keeps you out of the weather, tidy and dry. An amazingly level lot is great for gardening or games. And, you are on pavement, no mud season here! Easy to get to the mountains or Brattleboro and beyond. This is a must see for those long in the market, looking for just the right home. See Listing Details & 30 images.
Under Contract
$395,000 $186 per sq.ft. Brattleboro VT Home »
3 Beds | 3 Baths | Total Sq. Ft. 2128 | Acres: 0.33Listed on Monday Mar 2, 2026
Description: 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 an ensuite bath, two more bedrooms, and another full bath. The basement is sure to impress, 22 x 19 and finished. This home has gorgeous hardwood flooring, tile, and carpet upstairs. There is a spacious two-car garage. Conveniently located, less than 10 minutes to vibrant downtown and 5 min to I-91. Enjoy country living with the convenience of town amenities minutes away. See Listing Details & 26 images.
Under Contract
$449,000 $270 per sq.ft. Brattleboro VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1660 | Acres: 4.81Listed on Monday Mar 9, 2026
Description: Enjoy privacy and nature just minutes from town! This well-cared for 3 bedroom, 2 bath home sits on 4.81 acres, offering space, tranquility, and convenience. Features include a first-floor bedroom, bright and comfortable living areas, a beautiful three-season porch perfect for relaxing and taking in the peaceful setting, and a two-car garage for added storage and functionality. A great opportunity to enjoy country living with easy access to town amenities. OPEN HOUSE SATURDAY 3/21 11AM - 1PM. See Listing Details & 32 images.
$475,000 $192 per sq.ft. Brattleboro VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 2480 | Acres: 0.27Listed on Tuesday Jan 13, 2026
Description: This well-maintained three-bedroom, two-bath single-family home is set on a level, fenced-in lot in a coveted neighborhood close to downtown, with convenient access to major highways. The home features radiant flooring, central air, and a finished basement offering flexible living or recreational space. A spacious kitchen provides ample cabinetry and storage, ideal for everyday living and entertaining. Two bedrooms are located on the main level, while the second-floor primary suite offers vaulted ceilings and added privacy. Outdoor highlights include a 16' x 20' Trex deck, a bluestone walkway, and a large driveway bordered by a stone wall. A detached one-car garage with a carport adds functionality. Enjoy proximity to the Retreat Trails and Harris Hill Ski Jump, combining comfort, convenience, and an exceptional location. See Listing Details & 35 images. Includes a Virtual Tour
Under Contract
$489,000 $212 per sq.ft. Brattleboro VT Home »
Price Change! Reduced by $10,000 down 2% on April 2nd 2026
4 Beds | 4 Baths | Total Sq. Ft. 2312 | Acres: 0.27
Listed on Saturday Feb 28, 2026
Description: 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 arts scene. The standout feature of this residence is the thoughtfully designed addition, which serves as a premier mother-in-law suite or guest wing. This expansive space offers flexible multi-generational living without compromise, featuring its own eat-in kitchen and sitting area, and the high-end luxury of radiant floor heating for year-round comfort. With direct access to a private deck and open patio, it is a seamless blend of indoor-outdoor living. The home's exceptional layout includes 4 bedrooms and 4 bathrooms, providing a natural flow that is perfect for both entertaining and quiet daily life. High standards of maintenance are evident throughout, including recent roof renovations and pristine mechanical systems. Whether you are relaxing on the classic covered wraparound porch or hosting a dinner on the beautiful rear deck, the serene surroundings provide a sense of total calm. This move-in-ready property offers the comfort and quality lifestyle Vermont is known for--quality construction, modern upgrades, and a location that puts the very best of Brattleboro right at your fingertips. Open House April 12th 12pm-2pm See Listing Details & 60 images.
Under Contract
$495,000 $180 per sq.ft. Brattleboro VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 2756 | Acres: 0.79Listed on Friday Feb 13, 2026
Description: 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 bygone era. Inside, the home spans a spacious 2,756 square feet, featuring four bedrooms plus bonus room and three bathrooms that provide ample room for family, guests, or creative pursuits. While the interiors are ready for a thoughtful restoration, the home's historic character serves as a beautiful canvas for your vision. This is a unique opportunity to breathe new life into a property with significant provenance, preserving its architectural soul while infusing it with modern comforts and your own personal style.The true magic of this property lies in its setting. Imagine waking up to sweeping, picturesque views of the West River Meadows, a daily reminder of Vermont's natural beauty right from your back yard. Despite this serene visual escape, you are just a short, pleasant walk from the vibrant heartbeat of downtown Brattleboro, where local shops, dining, and community events await. This residence offers the best of both worlds: a private, historic retreat with the convenience of a walkable, connected lifestyle. There are extensive berry bushes, a vegetable garden, and perennials growing on the property. Don't miss this rare opportunity. See Listing Details & 46 images.
New Listing!
$495,000 $397 per sq.ft. Brattleboro VT Home »
3 Beds | 3 Baths | Total Sq. Ft. 1246 | Acres: 0.08Listed on Wednesday Apr 8, 2026
Description: Step into an 1880s Victorian re-imagined for the 21st century. Located moments from downtown Brattleboro, this 3-bedroom, 3-bath home blends historic craftsmanship with a cutting-edge deep-energy retrofit. Enjoy easy access to shops, dining, the Amtrak station, and the Retreat Trails from a peaceful, residential setting. Unlike typical historic renovations, this property underwent a from-the-studs rebuild in 2018, serving as a pilot for high-performance building science. It is now fully electric and fossil-fuel free, featuring : Air-to-water heat pump for heating/cooling and an Energy Recovery Ventilation (ERV) system for superior indoor air quality. The home also has a super-insulated, airtight building envelope ensuring year-round comfort and efficiency, with a durable standing seam roof equipped with solar panels. The interior honors its heritage while embracing sustainable, modern design, using eco- friendly materials: copper countertops, natural linoleum flooring, and Energy Star appliances. Modern mechanical systems and smart features throughout, you get turn-key Peace of Mind.: Every major system-from insulation to infrastructure-is new, offering a rare level of durability in a vintage home. 81 Chapin Street is more than a renovation; it's a blueprint for the future. For those seeking environmental responsibility without sacrificing historic charm, this is a truly unique opportunity. Open House: Saturday, April 11, 11am-1pm. See Listing Details & 27 images.
$499,000 $322 per sq.ft. Brattleboro VT Home »
2 Beds | 2 Baths | Total Sq. Ft. 1550 | Acres: 0.18Listed on Tuesday Mar 31, 2026
Description: 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 mile from I-91, with ease of access to cultural & recreational opportunities, shopping, dining, & medical care. Nestled on 33 acres of pristine Vermont landscape, this premier neighborhood is thoughtfully designed, offering a vibrant community center w/ library, fireplace lounge, fitness center, full kitchen, & outdoor patio w/ fire pit. Outdoor recreational amenities incl. pickleball, bocce, shuffleboard, & horseshoes--perfect for staying active & social. Enjoy the ease of HOA-managed services & a lifestyle designed for freedom & fulfillment. Each home is single-story & ADA-compliant, offering ease, accessibility, & long-term comfort. Designed w/ energy efficiency in mind, these residences feature building materials & floor plans that minimize energy usage-providing a healthier, more affordable way to live. PRICED FROM $475,000 - $585,000. HOMES OFFER at least 5 rooms - kitchen, living, dining, primary BR w/ en-suite BA, & bonus room for office/study or guest BR - 2 BA's, & a 1-car garage. UPGRADED HOMES OFFER: 2-car garage, sunroom, expanded living & guest rms, & larger yard. Some special touches that make BME homes beautiful & comfortable: finished 1 or 2-car garage; marble & porcelain tile; radiant floor heat; porch, private backyard, patio; marble sunken-floor showers & vanities; multi-zone heat & A/C; cherry cabinetry; granite countertops; walk-in closets; high-efficiency appliances & lighting. DO NOT MISS THIS OPPORTUNITY. Even if you are not quite ready to commit, reach out right away and ask to have your name put on the waiting list! See Listing Details & 32 images.
$449,000 $302 per sq.ft. Bridgewater VT Home »
Waterfront on River Ottauquechee River3 Beds | 2 Baths | Total Sq. Ft. 1489 | Acres: 0.33
Listed on Thursday Jul 24, 2025
Description: This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont country kitchen-dining and family room flow into a south facing sunroom overlooking the Ottauquechee River with a terraced yard providing direct access to the water. The home is midway between the resort communities of Woodstock and Killington 5 and 9 miles away. A public park and the Bridgewater Mill showcasing nationally and internationally recognized handmade furniture and pottery of Charles Shackelton and Miranda Thomas, respectively, in addition to a popular restaurant with live entertainment all within walking distance. Ideally sited offering an array of amenities at an attractive price. See Listing Details & 34 images.
$485,000 $163 per sq.ft. Bridgewater VT Home »
4 Beds | 4 Baths | Total Sq. Ft. 2977 | Acres: 0.23Listed on Saturday Feb 28, 2026
Description: This property is conveniently located in Bridgewater Village, situated midway between Woodstock and the Killington Ski Area. While currently configured as three income-producing units, it offers an outstanding opportunity for a creative conversion back into a single-family residence, with the detached rear unit available to supplement the cost of ownership. Recent updates include a new roof, mini-splits, kitchen renovation and a new heating system. Additionally, the high-visibility location is ideal for an entrepreneur or service provider seeking a home occupation. Please come and see the possibilities for yourself. We require 48 hours' notice for all showings, furniture negotiable. See Listing Details & 27 images. Includes a Virtual Tour
$449,000 $180 per sq.ft. Bridport VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 2490 | Acres: 1.9Listed on Thursday Apr 2, 2026
Description: This charming 1850's Farmhouse set on 1.9 acres, offers a blend of classic character and thoughtful updates in a beautiful country setting. A versatile layout greets you with two rooms off the foyer - serving as a mudroom and a large storage room - perfect for outdoor gear. The first floor also has a home office, a formal dining room, wood floors in the living room, as well as an updated kitchen overlooking the backyard. The primary bedroom is bright and spacious with a full en suite bathroom as well as a walk-in closet. Upstairs, you'll find a large family room, two additional bedrooms, and a bonus room that share a ¾ bath. The second level also has storage space plus an unfinished workout room that is accessible through its own stairwell or through a bedroom closet. Outside, trees create a natural privacy border around the property. Relax on the new stone patio and take in the surrounding country views. Recent updates include a 3-bay garage, a new roof, re-graveled driveway, and some siding. Don't miss this classic Vermont country property! See Listing Details & 57 images.
$399,500 $225 per sq.ft. Bristol NH Home »
3 Beds | 2 Baths | Total Sq. Ft. 1773 | Acres: 0.44Listed on Saturday Jan 10, 2026
Description: In the tradition of a great Victorian structure, The home has great bones, lots of space and has all those charming features of it's time. Window seats, built in bureaus, curved walls and beautiful scalloped trim. Partial restoration in progress, bring your ideas to finish this beauty. Lots of the materials are there to finish projects. The home is in a commercially zoned location and offers that option. There is a large attic for storage or extra living area. The attached barn has 2.5 stories and is in decent shape and has potential as a business location. Property is close to downtown with many local amenities right out your front door. See Listing Details & 22 images.
