You are viewing all listings Homes between $250000 and $500000 dollars.
$435,000 $252 per sq.ft. Brandon VT Home »
3 Beds | 3 Baths | Total Sq. Ft. 2520 | Acres: 10.75Listed on Sunday Aug 24, 2025
Description: UPDATED LISTING with NEW PRICE! This well cared for property is close to downtown on 10.75 acres. Mountain and pasture views are amazing from the many sunny windows in the living room that leads to a private deck. This home offers a large kitchen, separate dining room, a split floor plan with the master bedroom and bath on one side of the home and the other two bedrooms, bathroom, office with private entry and bath on the other side. On the lower level is a family room with dry bar, patio door, an attached two car garage, workshop area, all with full walkout access. There is a 6 stall barn with a hay loft that holds approx 1,000 bales of hay. A back field has been used to produce hay and the back border of this long lot is Otter Creek. Brandon has a quaint downtown with shops and a town hall theater, as well as grocery store and pharmacy just moments away. Nearby are lakes and ski areas, as well as public trails and dirt roads for hiking or horseback riding. You can have a little farm or homestead and lots of outdoor recreation! This property is a one of a kind! See Listing Details & 27 images.
Under Contract
$494,000 $253 per sq.ft. Brandon VT Home »
3 Beds | 3 Baths | Total Sq. Ft. 2472 | Acres: 0.64Listed on Wednesday Dec 10, 2025
Description: This beautifully maintained 3-bedroom, 3-bathroom ranch is filled with natural light creating a bright and uplifting atmosphere from morning to evening. This home has been thoughtfully updated with solar panels, a new roof, a custom kitchen with stainless steel appliances and a paved driveway. The spacious primary suite offers a spa-like bathroom with double sinks, a jetted tub and an oversized walk-in shower. The lower level provides space for a family room, storage and an unfinished space that can be used as a large workshop or workout area. Outside you can relax on the large back deck and enjoy the mountain views. The backyard has established gardens, a raspberry patch and plenty of space for gardening. Ideally located this home offers convenient access to everything the town of Brandon has to offer while also providing an easy commute to Middlebury, Rutland or all points North and South. Move-in ready and ideally located, this home blends comfort, convenience and easy Vermont living. See Listing Details & 32 images.
$499,000 $208 per sq.ft. Brandon VT Home »
3 Beds | 4 Baths | Total Sq. Ft. 2400 | Acres: 6.3Listed on Friday Jul 17, 2026
Description: Completely renovated from top to bottom and set on 6.3 private acres, this exceptional Brandon property offers flexibility, space, and privacy. Whether you're looking for a spacious single-family home, a multigenerational living arrangement, or the opportunity to offset expenses by renting the attached in-law suite, this property delivers. The main home features 3 bedrooms, 3 bathrooms, a versatile bonus room, and a loft that is ideal for a home office, playroom, reading nook, or additional guest space. Sunlight pours through the home, highlighting the extensive renovations that include a brand new roof, all new cabinetry, countertops, appliances, flooring, bathroom fixtures, and countless other updates throughout. There is also a woodstove waiting to be hooked up and enjoyed! The attached 1-car garage adds everyday convenience. The attached 1-bedroom, 1-bathroom in-law suite offers excellent separation while remaining connected to the main home, creating endless possibilities for extended family, guests, rental income, or a private workspace. Outside, you'll enjoy the peace and privacy of 6.3 acres perched above Route 7, providing an ideal balance of seclusion and accessibility. Brandon continues to be one of Vermont's most desirable small towns, known for its vibrant downtown, locally owned shops, restaurants, cafés, breweries, galleries, and year-round community events. Outdoor enthusiasts will appreciate nearby hiking, biking, fishing, golf, and the stunning natural beauty of the region, while Middlebury, Rutland, and Lake Dunmore are all within an easy drive. Renovated homes with this level of flexibility, acreage, and move-in-ready condition are exceptionally difficult to find. If you've been searching for a property that offers modern finishes, abundant natural light, privacy, and multiple living options, this is one you won't want to miss. See Listing Details & 58 images.
Under Contract
$279,000 $279 per sq.ft. Brattleboro VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 1000 | Acres: 0.26Listed on Friday Jul 17, 2026
Description: Sweet ranch home with 2 car attached garage. A lovely and level lot for gardening or outdoor entertaining, this location provides a country feel but only minutes from vibrant West Brattleboro events and businesses and a short trip brings you into downtown Brattleboro with lots of opportunities. This home with a generous living/dining space, good sized kitchen, 2 bedrooms and 1 full bathroom is great for a starter home or people looking to down size. The attached two car garage has automatic garage doors and an attached breezeway provides direct entry into the house and makes a great mud room with storage. The full basement has storage, the washer and dryer, the pellet stove and an oil hot air furnace. There is also a place to install a bathroom if you want. Use some of the basement as a workshop for projects and fix-it shop. Recent upgrades include new windows and a standing seam metal roof and hot water heater. See Listing Details & 39 images.
$285,000 $271 per sq.ft. Brattleboro VT Home »
Price Change! Reduced by $15,000 down 5% on July 24th 2026
3 Beds | 1 Baths | Total Sq. Ft. 1050 | Acres: 0.15
Listed on Thursday Jul 2, 2026
Description: Tucked in near schools, hospital, shopping and a short walk to fishing and a canoe ride. Room enough for a garden, play space and just the right size for new beginnings. Nice sun porch doubles a a mud room, kitchen is huge with room enough for an island, a sweet spot with lots of potential. See Listing Details & 12 images.
Under Contract
$295,000 $219 per sq.ft. Brattleboro VT Home »
3 Beds | 1 Baths | Total Sq. Ft. 1350 | Acres: 0.14Listed on Wednesday Jul 15, 2026
Description: Timeless Character on Coveted Oak Grove Avenue! There's something special about an American Foursquare. Built for comfort and designed to stand the test of time, this quintessential early 20th-century home welcomes you with classic architecture, generous room sizes, and the warmth of original craftsmanship. Set on a desirable in-town lot along Oak Grove Avenue, this 3-bedroom home showcases beautiful hardwood floors, rich natural woodwork, and a cozy fireplace that anchors the inviting living room. The screened front porch is the perfect place to enjoy your morning coffee, greet neighbors, or unwind on warm summer evenings. Upstairs, you'll find three comfortable bedrooms and a full bath, while the unfinished attic offers exciting possibilities - whether you envision a studio, home office, playroom, or additional living space. Outside, there's room to garden, entertain, or simply enjoy the yard, along with the convenience of a one-car garage. Combining timeless character with everyday practicality, this home is just minutes from schools, the hospital, restaurants, shopping, and all the conveniences of in-town living. Come experience everything this Oak Grove Avenue gem has to offer. See Listing Details & 27 images.
$299,000 $160 per sq.ft. Brattleboro VT Home »
3 Beds | 3 Baths | Total Sq. Ft. 1872 | Acres: 0.22Listed on Sunday Jun 14, 2026
Description: Move-in ready and full of potential, this charming Brattleboro home is ready for its next chapter. The main level features a bright, open-concept layout with a spacious kitchen and comfortable living area, creating an ideal space for everyday living and entertaining. Filled with natural light, the living room opens directly onto a private rear deck overlooking a manageable backyard--perfect for relaxing, gardening, or outdoor gatherings. Upstairs, the bedrooms offer comfortable accommodations with the opportunity to add a full bathroom in the future, allowing the home to grow with your needs. The lower level includes a separate in-law suite complete with its own private entrance and laundry area, offering flexibility for guests, multi-generational living, a home office, or potential rental income. Conveniently located, the property is less than a block from the Vermont Country Deli and within walking distance of the Brattleboro Farmers' Market, Memorial Park, and recreation fields. Easy access to Interstate 91 makes commuting simple while keeping downtown Brattleboro's shops, restaurants, arts, and entertainment just minutes away. Whether you're searching for a primary residence, an investment property, or a home with income-producing potential, this well-priced property offers an excellent opportunity. See Listing Details & 37 images.
$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: ***Open House Sunday 7/19 from 11am-1pm** 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
$319,000 $245 per sq.ft. Brattleboro VT Home »
Price Change! Reduced by $20,000 down 6% on June 19th 2026
3 Beds | 1 Baths | Total Sq. Ft. 1300 | Acres: 0.13
Listed on Wednesday May 20, 2026
Description: Located in one of the area's most desirable and close-knit neighborhoods, this beautifully preserved 1929 home blends timeless character with thoughtful updates. Featuring hardwood floors, natural woodwork, custom built-ins, classic wainscoting, and a welcoming mudroom, the home retains the charm and craftsmanship buyers love. The open and inviting first floor offers generous living space and a formal dining room, complemented by a retro-inspired kitchen full of personality. Just off the living room, the enclosed south-facing porch with newer windows may become your favorite place to relax and unwind. Upstairs offers 3 bedrooms, a bright and cheerful bath, and access to an incredible attic space with exciting potential for a studio, yoga room, office, or expanded living area. Outside, the landscaping is a delightful surprise, featuring striking artistic bluestone details and a peaceful water feature that create a private, zen-like setting rarely found in town. This is a wonderful opportunity to own a character-filled home in a neighborhood known for its quality homes, strong sense of community, and convenient access to restaurants, shopping, and local amenities. See Listing Details & 27 images.
$320,000 $278 per sq.ft. Brattleboro VT Home »
Price Change! Reduced by $33,900 down 11% on June 29th 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 & 20 images.
$325,000 $267 per sq.ft. Brattleboro VT Home »
Price Change! Reduced by $10,000 down 3% on July 7th 2026
4 Beds | 1 Baths | Total Sq. Ft. 1216 | Acres: 0.18
Listed on Friday May 29, 2026
Description: Located in one of Brattleboro's desirable neighborhoods, this inviting 4-bedroom home offers a comfortable layout, great natural light, and convenient access to schools, parks, trails, shopping, and downtown amenities. The bright living room features a large bay window that fills the space with natural sunlight, while the kitchen offers ample cabinet space and overlooks the backyard. With two bedrooms and a full bathroom on the first floor, the layout offers flexibility for a variety of living needs. Outside, enjoy a spacious backyard with room to garden, gather, or simply relax. A warm and welcoming home ready for its next chapter. Open house Saturday, 5/30 from 1-3 and Sunday 5/31 from 11-1 See Listing Details & 36 images.
$329,000 $257 per sq.ft. Brattleboro VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1280 | Acres: 0.15Listed 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 & 17 images.
Under Contract
$339,000 $151 per sq.ft. Brattleboro VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 2250 | Acres: 0.2Listed on Monday Jun 8, 2026
Description: Step into a world of artistic whimsy and historic allure at 65 Cedar Street, a property overflowing with character, magic, and boundless potential. Nestled in an ideal location with an entrance to the beloved Retreat Trails, this unique home offers an enchanting escape from the everyday. Outside, the property is embraced by beautiful, mature gardens cultivated over time in a spirit of enchanting "benign neglect"--where nature and romance intertwine to create a storybook setting that will capture your heart from the moment you arrive. Inside, you will find a spacious layout featuring 4 bedrooms and 2 full baths spread across 2,250 square feet of versatile living space. The home has been thoroughly cleaned out and deep-cleaned, presenting a pristine, blank canvas with exceptional, rock-solid "bones" ready for its next chapter. Fine historic details anchor the home, from rich wood floors to timeless built-ins. At the heart of the home sits a magnificent centerpiece: a vintage Vermont Iron Stove Works stove, radiating authentic New England warmth and charm. The footprint continues to impress with a bright, beautiful sunroom perfect for morning coffee, a large attached 2-car garage providing excellent storage, and a expansive bonus space tucked away in the finished attic. This property is being offered in "as-is" condition and does not include appliances, making it the ultimate dream project for those looking to invest sweat equity into a truly remarkable historic home. Bring your vision to finish the cosmetic upgrades and unlock the true grandeur of this whimsical masterpiece. OPEN HOUSE SUNDAY, JUNE 14TH | 12:00 PM - 2:00 PM Come experience the magic and explore the incredible potential of this one-of-a-kind home in person! See Listing Details & 40 images.
Under Contract
$340,000 $267 per sq.ft. Brattleboro VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1272 | Acres: 0.32Listed on Wednesday May 27, 2026
Description: Perfectly situated at the top of the hill on highly desirable Carriage Hill in West Brattleboro, this delightful yellow ranch offers the perfect blend of neighborhood comfort and exceptional curb appeal, accented by a lovely stone pathway and beautiful exterior gardens. Step out back to discover your own private oasis featuring a spacious wooden deck with a gorgeous overhead pergola, custom built-in bench seating, and an attached screened-in porch that looks out over a lush green backyard complete with a handy storage shed. Inside, the home boasts a bright, expansive living room with durable flooring and a mini-split system for efficient year-round comfort. The generous eat-in kitchen features warm wood cabinetry with vibrant turquoise accent shelving, tile flooring, and a large window overlooking the serene backyard. Comfortable bedrooms with unique, colorful accent walls and a dedicated home office or study space under a cheerful blue ceiling provide a highly versatile layout. Complete with two functional bathrooms--including one full bath with a tub/shower combo and a second featuring a retro blue shower stall--this home is ready for its next chapter. Come see all this West Brattleboro gem has to offer at our upcoming open house on Sunday, May 31st from 2:00 PM to 4:00 PM! See Listing Details & 43 images.
$344,900 $223 per sq.ft. Brattleboro VT Home »
Price Change! Reduced by $4,100 down 1% on July 6th 2026
3 Beds | 2 Baths | Total Sq. Ft. 1550 | Acres: 0.41
Listed on Thursday May 28, 2026
Description: Enjoy the privacy of your own space secluded from the rest of the world. Enjoy the comfort of a country setting in town. Look through the tree tops over the roofs of houses below on one side, onto a garden on another side, and onto a wooded hillside on the rest. Nature surrounds this immaculate house on a hill. Amenities include stone walls, a dog cage, a fire pit, raised gardens, a convenient 2-car garage, a mudroom with a closet off the garage, a workshop on the basement level, a pantry with spice racks, a palladian window and ceiling fan in one bedroom, and privacy, privacy, privacy. The seller spent a lot of time and money preparing the house for sale; see the list of improvements in the Documents section of this listing. Includes a 1/34 share of common interest in the Wilsons Woods land. Near the middle school and high school, hospital and shopping. Showings begin on Friday 6/5/26. See Listing Details & 60 images.
