Properties Near 161 Buttonwood Drive Brattleboro, VT

Come experience the elegance and charm of this stunning in-town retreat! Close to the town common and vibrant downtown Brattleboro—home to fine dining, galleries, quaint shops, and live music venues. Step inside the main house and be welcomed by a country kitchen featuring a large island, ideal for gatherings. The home exudes Victorian character with soaring ceilings, hardwood floors, and oversized wavy glass windows that bathe the interior in natural light. The 1st floor is bright and inviting, with a sun-filled dining room and a living room featuring a propane insert for warmth and ambiance. For accessibility, there is a 1st floor full bathroom and bedroom with historic curved wall. The gracious staircase brings you to a reading nook on the landing, 3 bedrooms, and a full bath with a clawfoot tub. The large laundry room offers flexibility to double as a studio, craft, or hobby space. The property also features two accessory apartments, offering excellent income potential or space for guests or extended family. A detached barn has storage above, and plenty off-street parking. The yard has been extensively and thoughtfully landscaped with lush, low-maintenance perennials, stone patios, and garden pathways. A private sauna nestled among the gardens creates a peaceful retreat a after a busy day.This exceptional property is a rare find—gracefully blending history, function, and opportunity in one of Brattleboro’s most coveted locations. Being offered as a single family home.

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. 2BR/2BA; finished 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.

Your Dream Home Awaits on Meetinghouse Lane! Nestled in the desirable and quiet neighborhood of Meetinghouse Lane, this contemporary home offers both privacy & charm. Surrounded by mature trees, the property feels like a peaceful retreat, while still being conveniently located. A paved driveway leads to an oversized two-car garage, connected to the house by a convenient breezeway. The expansive yard offers ample space for gardening, play, or simply enjoying the outdoors. Inside, a striking brick chimney creates a natural separation between the kitchen and the dining/sitting area. A cozy wood stove, nestled at the chimney’s base, adds character and warmth to the home. The spacious living room provides plenty of space for relaxing or entertaining. Offering three comfortable bedrooms & a primary bathroom. A few steps down from the main level reveals an additional oversized room and a full bathroom featuring a jetted tub. The basement includes a laundry area and ample space for a home office, playroom, or storage. Off the kitchen, sliding glass doors open to a beautiful gated deck—ideal for entertaining or enjoying peaceful moments outside, surrounded by nature. This thoughtfully designed split-level home offers the ease of minimal stairs while providing distinct living areas across different levels. Whether you're looking for tranquility, space, or functionality, this home checks all the boxes.

Timeless 1855 classic with historic charm just minutes to downtown Brattleboro. Step back in time with this beautifully preserved home, offering a rare blend of vintage character and modern comfort. Featuring three bedrooms and two bathrooms, this home is perfect for those who appreciate craftsmanship and history. Thoughtful updates complement the historic features without compromising authenticity. Bonus: the home includes generous unfinished space—brimming with potential for additional living area, studio, or guest suite. This property is a true gem with room to make it your own. Delayed showings begin Saturday 8/23. OPEN HOUSE 2pm-4pm.

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. 2BR/2BA; finished 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.

Sweet! It is starting to get chilly, we remember the oversized salt water pool fun and the summer heat on tanned skin, coming again in the spring. The flowers and shrubs will sing again next season, but for now, we get to love the hardscape that comes to life catching flakes and creating breathtaking sculptures that glitter and change as we watch. It is the season for snuggling in, all toasty and warm, a season for baking and giving, inviting your besties to the great room, surrounded by windows, the smile in their eyes reflecting the snow and candle light. Some will sit in the front parlor, faces to the fire, dozing over a favorite book. Soon, the holiday feast will bring them all together with laughter and love to the dining room, the gathering room of stories and memories of years past, in a home that has held generations of children in it's arms. Generations who have loved and cared for this home and brought it to it's remarkable condition in melding old and new. Come home and nestle into the history, but don't forget to make your own, in the kitchen, around the fire, on the slopes and always with room for friends.

First Time on the Market – Premier Brattleboro Location! Nestled on one of the most desirable lots in one of Brattleboro’s finest neighborhoods, this well-maintained home is being offered for sale for the very first time! Custom-built by the current owner in 1970 with attention to detail, this spacious ranch offers comfort, functionality, and an impressive list of amenities. Perfect for both families and empty nesters alike, the home features: 3 bedrooms and 2.5 bathrooms, including a sauna with shower room A bright and open kitchen/dining/family room with an amazing fieldstone fireplace and views of the private backyard A large formal living room ideal for entertaining A finished basement boasting a bar, game room, family room, office, and additional bathroom An attached 2-car garage But the true magic is outside. The expansive grounds include: A separate 4-car garage with its own driveway – ideal for car collectors or a workshop A beautiful in-ground pool with a pool house A basketball/handball court Lovely patios with a built in BBQ and mature landscaping that create a private outdoor oasis Don’t miss this rare opportunity to own a one-of-a-kind property in a truly special location!