Properties Near 111 Central Street Brattleboro, VT

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 Saturday 6/27 from 11am-2pm** Step into a home that offers the space, privacy, and outdoor lifestyle today's buyers are searching for. With three bedrooms and a comfortable layout, this property blends everyday functionality with room to relax and entertain. The real showstopper is the backyard. Fully fenced and remarkably level, it's a rare find that creates the perfect setting for summer cookouts, backyard games, pets, gardening, or simply enjoying Vermont's beautiful seasons. The spacious rear deck extends your living space outdoors, making it easy to host family and friends or unwind after a long day. Located just minutes from downtown Brattleboro, you'll enjoy convenient access to shopping, dining, schools, and local attractions while still having a private outdoor retreat to call your own. Whether you're gathering around the grill, watching the kids play, or enjoying a quiet evening under the stars, this home delivers the kind of lifestyle that's becoming harder to find. Come see for yourself why this property stands out from the crowd. 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.

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.

There is plenty of space to garden to your heart’s content! A place to sit under mature trees for the pleasant sound of a babbling brook, and peaceful views into a quiet woods bordered by a rambling old stone wall. With almost an acre of land, this 1941 five room, country cape has an open floor plan for kitchen, dining and living room, wood beams and a friendly wood stove. There is a first floor bedroom and full bathroom. The dormered upstairs has a bedroom with a large studio/workroom beyond. The breezeway connects the house to a two car garage with loft storage. A shed behind the garage offers handy space for wood, equipment and tools. This West Brattleboro location is just four miles from downtown Brattleboro on a paved town maintained road. Access to Interstate 91 is two miles away. Showings by appointment start on Thursday May 7, 2026.

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, 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.

What sets this unit apart is not just that it is an end unit, but it is an end unit with a private deck! You are also right next to the path to Memorial Park for swimming, skiing, skating, baseball games, summer theatre, and so much more! Or head to the popular Saturday Farmer's Market just around the corner. This unit features two bedrooms, one and a half bathrooms, single car garage with storage and laundry. The end units are bright with extra windows and this unit has wood floors in the dining room and hall, carpet for the living room and bedrooms, and has also had efficiency upgrades. There is a charming brick patio off the dining area, think summer potted plants and fairy lights! A previous owner had a stairlift installed which could stay or go. This unit is ready to go and could not be easier!

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.

DESIRABLE END UNIT! Why rent when you can buy- giving you peace of mind, an opportunity for stability and building equity. Maybe you are a first-time homebuyer? Or someone who wants to downsize from a bigger house and time-consuming yard chores and projects to a simpler life. An investor? Enjoy easy, affordable, and low-maintenance living in this sweet two-bedroom, 1.5 bath townhouse. Storage space in the attic! Conveniently located 1/2 mile to downtown Brattleboro's Main Street, the food Co-op, the new Brattleboro train station and museum, and lots of fun shops and diverse restaurants. Association amenities: a fabulous in-grown pool, pickleball/tennis court. HOA dues include lovely landscaping, master insurance policy, plowing, snow-removal, and trash. A delightful community of neighbors in a very pretty setting. Sale is contingent on Sellers finding suitable housing/closing within 90 days of contract.