Properties Near 455 South Main Street Brattleboro, VT

Neighborhood home! Living in a sweet neighborhood is a lifestyle choice. Walk to schools, playgrounds, and shopping. This vintage home has an added features of roof top solar, 2 car direct entry garage, a fenced-in yard, and lots and lots of gardens. The classic front porch is on everyone's list of must haves. The neighborhood is perfect for long evening strolls or a brisk walk at dawn. Inside there is a huge living room for hanging out with friends, entertaining or movie night. Work at home? You will love the corner office, age in place with first floor bedroom and bath...So nice, just the right location and just the right home.

Sweet and charming from an era of wonderful wood work, polished floors and rooms with a purpose. This home has a lovely big kitchen with a peninsula for baking prep, formal dining with built in china cabinet, living room and an first floor bedroom with 1/2 bath. Since the basement is walk out, the back porch is 2nd level, above the bugs, and overlooking the private back yard. Fenced for a dog, the side yard pops off the kitchen deck for easy pet access. Gardens and a small rivulet in the back complete this special setting. In-town corner lot, ready to go!

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!

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.

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.

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!

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!

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.

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.

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

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!

Charming and conveniently located, this inviting home is situated less than one mile from the heart of Brattleboro Village. Offering 3–4 bedrooms, including a first-floor bedroom for added flexibility, the home features a practical mudroom entry and a bright, sun-filled dining porch just off the kitchen. The basement provides a dedicated workshop area, laundry space, and ample additional storage. Set on a manageable 0.09-acre lot, the property is bordered by mature trees along the rear for added privacy, while the open yard offers excellent potential for gardens and outdoor enjoyment. A cozy screened-in porch tucked behind the house creates the perfect retreat for relaxing during the warmer months.

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.

Rare opportunity to enjoy single-level living with all modern conveniences on the main floor in this magnificent condo unit. Featuring a spacious primary bedroom with a walk-in closet and full en-suite bathroom, this home offers comfort and functionality throughout. A second bedroom provides flexibility for guests, a home office, or additional living space. The open-concept kitchen and dining area features quality KitchenAid appliances and flows seamlessly into the inviting living room. An additional full bathroom, first-floor laundry, and a walkout patio complete the main level. Large windows provide an abundance of natural light throughout the home. The finished lower level offers a spacious family room with a walkout door, a convenient half bath, and an additional large unfinished area ideal for storage, a workshop, or hobby space. Only a handful of units at Morningside Commons offer this highly desirable floor plan. Enjoy all the amenities Morningside Commons has to offer, including an inground pool, tennis and pickleball courts, and beautifully maintained grounds. Leave the snow removal, lawn care, and landscaping to someone else and enjoy the ease of low-maintenance living.

***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

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.

**Includes 1-Year Home Warranty** Welcome to this lovingly maintained 3-bedroom, 1-bath ranch located in the sought-after Carriage Hill neighborhood of West Brattleboro. Where affordability & opportunity come together in this move-in ready home. Whether you're taking the exciting step into homeownership or searching for a home that lets you spend less time on upkeep and more time enjoying life. The open-concept, light filled living room and eat-in kitchen create a comfortable, welcoming space that feels like home the moment you walk in. South facing windows fill the living room with an abundance of natural light, creating a bright and inviting atmosphere throughout the day. Just off the kitchen, step onto the back deck overlooking the spacious, fenced-in backyard. Mature trees provide natural shade and privacy, while the property extends well into the woods with established walking trails, offering a setting to explore and enjoy nature right from your own backyard. Back inside, you'll find three comfortable bedrooms and a full bath, all conveniently located on the main level. The partially finished basement adds valuable living space with a versatile bonus room, a rec room or office space, and a spacious utility area, providing flexibility for hobbies, fitness space, or additional storage. Thoughtfully cared for over the years, this home offers peace of mind with a roof that's approximately seven years old and a hot water heater that's just two years old. Additional features include town water and sewer, a paved driveway, and a functional layout designed for today's lifestyle. Enjoy easy access to shopping, local restaurants, coffee shops, Brattleboro Memorial Hospital, Interstate 91, public transportation, schools, and countless everyday conveniences, all while coming home to the peaceful charm of an established neighborhood. ** OPEN HOUSE ** Sunday, July 19th 11AM to 1PM.

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.

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.

Nestled next to Brattleboro's favorite public park, this end unit is wrapped in coveted out door space ,wrapping from the coffee deck all the way around to the back brick patio It also features a private garage with auto open, and laundry and storage neatly behind, The parking is paved with plenty of room for guests. Inside the ample galley kitchen has everything you need including a large top doing double duty as prep space and an extension of the dining room with stools to sit and sip. Just the right size for entertaining or family time, the living room is bathed in light from the large windows and the slider to the deck. A refuge from every day life, the huge main bedroom has room for a cozy chair, lots of closets and direct access to the bath. So special in it's location, so close to I91 north and south and east/west travel on RT 9, you can easily access health care, shopping, and all the fun things Vermont has to offer. Worth a visit for affordability, location and ease of lifestyle.

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 inspiring...A Joy to own.

This adorable single-level home offers easy living with a functional layout and comfortable living spaces. The warm and inviting interior is designed for everyday living. The home features a large living and dining area, a convenient laundry nook, a spacious primary bedroom, and two additional bedrooms that can accommodate guests, a home office, or other multi-purpose needs. Outside, you'll find a nicely-sized, level yard that offers plenty of space to enjoy gardening, outdoor activities, or simply relaxing without the burden of extensive maintenance. Whether you're a first-time buyer, looking to downsize, or seeking a low-maintenance property, this charming home provides the perfect blend of comfort and convenience. Enjoy the simplicity of one-level living while being conveniently located near the hospital, pharmacy, shopping, dining, and other everyday amenities.

This inviting 2 bedroom, 2-bathroom townhouse is located with privacy but close to Brattleboro amenities. Drive into your one car garage, in addition there is a storage area and laundry room. The second floor has a spacious living room and galley kitchen with eating nook which flows into a dining room and outdoor deck. The third level of this cozy condominium has a full sectional bathroom and 2 bedrooms with vaulted ceilings. Just next door is the Living Memorial Park offering swimming, baseball games, pickleball, skiing, skating and annual events, The popular Farmer's Market is also close by. Close to 1-91 this convenient property can be your next ....home sweet home.

Price Improvement! 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, cool factory-style windows, slate siding, and 2,000 square feet of sunny living space. The second level has a bedroom and a full bath, and the third level has two spacious private rooms that have been used in the past as bedrooms or office space with a large common/recreation area in between. Beautiful double patio doors open to a private sun-filled deck for outdoor dining. Zoning allows for a multitude of uses. Whether it's a primary residence, an artist studio, or a second home, this is a must-see for those who appreciate in-town offerings with a vibe and the only condo-ized loft on the market. Centrally located you are a stones throw to our lively downtown, Co-op, Kikitta Ahki park, hospital and I91. Look for the building with the Estey clock and prepare to be enraptured.