Properties Near 301 Maple Street Brattleboro, VT

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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! SHOWINGS BEGIN A PUBLIC OPEN HOUSE SATURDAY 7/5/25 FROM 11AM TO 1PM.
Rare opportunity to own this iconic Queen-Anne Victorian in Brattleboro’s coveted Tyler Street neighborhood. A remarkable and extremely rare blend of country and in-town living. Extraordinary and stunning views of the Connecticut River & Mount Wantastiquet. Lovingly cared for by the same owner for the past 29 yrs. This home sits proudly on the expansive 0.85-acre corner lot, in the core of the Tyler Street neighborhood. Bracketed by majestic Maple trees in front, the home and mature landscaping gently shields the rear yard, where one finds a serene, park-like setting. Many intentionally cultivated trees, shrubs & perennials create a tranquil, oasis-like setting, with many micro-environs in which to relax and enjoy. The 1st FL offers an expansive, central eat-in kitchen and family room area, off of which there are a living room, dining room, den/office, bonus room or bedroom, & bath. The 2nd FL offers 3 BR’s, all with separate entrances to a central BA. Beautiful patina-rich maple, fir & pine wood floors are found throughout. Also, a spacious, 2-level, partially covered deck, overlooking the rear yard, an extended 2-car garage, plus an 8’x12’ shed. An easy stroll to the heart of downtown Brattleboro. Close to golf, hospitals, culture & recreation. Convenient to airports, Boston, NYC & Canada. Extremely rare opportunity to own this unique charmer. Only 2 owners in past 60+ years! Don’t want to miss this choice offering!! Delayed showings beg. 6/20/25.
Turnkey Home in Sought-After Hillwinds! Located in the desirable Hillwinds neighborhood and nestled among the trees, your dream home awaits! This charming and functional home offers open, sun-filled living spaces, softwood floors, and abundant storage. The kitchen is a cook’s dream, featuring granite countertops, a gas stove, farmhouse sink, and a unique pull-out cabinet on wheels for added versatility and easy access to storage. The open-concept kitchen flows seamlessly into the living room, complete with a brick mantel and cozy gas fireplace—perfect for relaxing evenings. With four spacious bedrooms and three bathrooms, there’s room for everyone. The primary suite offers a walk-in closet and a skylit bathroom with radiant heated floors for year-round comfort. A convenient first-floor washer and dryer add to the home’s functionality, and if the interior isn’t enough—just wait until you step outside! Enjoy beautifully landscaped gardens with shrubs and mulched beds throughout the yard. A stone patio offers the perfect spot for small gatherings around the fire pit. Off the three-season room, you’ll find a private hot tub—ideal for unwinding after a long day. A private backyard path leads directly to the scenic Hillwinds trails. Don’t miss the chance to own this special home that blends nature, comfort, and thoughtful design. Delayed Showings begin Saturday 7/5/25 with an OPEN HOUSE 11am-2pm.
This is IT! Summer is here! The gardens are ablaze, the deck is perfect for the evening sip of something cool and there is open sky for sightings like the strawberry moon and shooting stars. Treat yourself to your own spa....the sweet spot is the oversized salt pool, surrounded by lush greenery for privacy and an apron for sunning. Add some of your own fun and you will stay at home, comfortable, affordable and more friends than you can count. Add to all this a pool house for games or a get away on a rainy afternoon of reading and snoozing, indoor but outdoor. The house is amazing, built by a generation who had the pick of the land and ability to create lovely crafted homesteads. Historic, classic architecture to tug your heart, but the modern perks to make life easy. Entertain inside or out ...huge formal dining, butler pantry, coffee station, and a stunning addition...throw open the glass doors and let the party flow....tired of the city, pop up from Boston or New York....when the summer winds down, become a leaf peeper, skier or self indulgent homebody. The choice is yours, but make this home the heart of your family.
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. Showings start July 19, 2025. Open house Saturday 7/19/25 10:00 - 12:00
You can't beat this location, overlooking the Brattleboro Country Club golf course. This home was built circa 1919, and has many cool vintage features such as retro curved metal kitchen cabinets and baths. Generous rooms include a large living room with two field-stone fireplaces, a spacious family room. This is a 3 bedroom house with 3 full bathrooms, but it's really about how you configure the house for yourself. You could live here today, as is, or turn it into something new; it's up to you! Delayed showings begin with an Open House, Saturday, June 21, 11am-1pm. Come see it for yourself!
4 condo units being sold together as a great residential package investment opportunity! Rent them, live in one and/or sell them off individually. This offering includes 4 of 5 units in a charming condo development just minutes from downtown, the hospital, shopping, and I-91. Unit 5 has been sold. The property features a large shared yard, off-street parking, and strong rental potential. The owner currently receives approximately $7,000/month in rental income. Additionally, the town has indicated the lot could support the construction of another house, offering even more upside. All units are fully furnished and currently rented, except one mid-renovation. Unit 1 is a spacious 2BR/1BA with a walk-in pantry, washer/dryer, mudroom, oil heat, and private side porch. Unit 2 is a cozy 1BR+ with a walk-in pantry, electric heat, and small porch. Unit 3, currently under renovation, is a large 2BR with gas heat, generous living room, and private front porch—ready for finishing touches. Unit 4 is an updated 1BR/1BA in excellent condition with charming period details. All units feature classic touches like clawfoot tubs and porches. A unique opportunity to own a versatile, income-producing property with potential for future development.
This very Vermont country home is nestled on a peaceful, beautifully landscaped 1.5 acre lot along Upper Dummerston Road. Built with unparalleled craftsmanship by some of the region’s finest artisans, the home exudes exceptional quality throughout. At the heart of the residence is a large chef's kitchen, complete with a gas fireplace, granite countertops, solid maple cabinetry, and premium Wolf and Jenn-Air side-by-side ovens and range & walk-in pantry. The home features three bedrooms, one located on the first floor, and one upstairs with a soaring cathedral ceiling. Additional spaces include a formal dining room, a spacious living room, two beautifully tiled bathrooms, and a finished basement designed for both relaxation and entertaining. The interior is thoughtfully crafted with warm tones, hardwood cherry and oak floors, and solid wood doors. Energy-efficient windows and a newly installed boiler system, and heat pumps for both floors ensure year-round comfort. A generous 2-car garage offers ample storage space above, while a tiled mudroom provides added convenience. The maintained grounds include perennial and raised vegetable gardens, flowering trees and shrubs, stone walls, and a custom-built outdoor craft/sitting area. A professionally designed Ashfield Stone Patio, complete with a wood-fired oven (Pizza!!) crafted by a local mason, offers the perfect setting for outdoor entertaining.

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