Properties Near 22 Chestnut Street Brattleboro, VT

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.

This beautiful Victorian home is just a short stroll from vibrant Brattleboro and has access to a huge town trail network. Nicely landscaped and has a partially fenced yard for pets or children. The house has lovely Victorian detailing and includes 3 covered porches. The formal entry has hardwood flooring, period staircase, stained glass window and a 3/4 bath. The adjacent front parlor includes oak flooring, ceiling fan and double French doors opening onto a cozy living room w/ornate fireplace w/gas stove, ceiling fan and hardwood floors. There is a formal dining room w/built-in hutch and Southern pine flooring. Then kitchen is delightful boasting elegant wainscoting, spacious center island and a walk-in pantry/mud room. The 2nd level offers a blend of comfort and style w/3 bedrooms, 2 of which share a full tiled bath. The primary bedroom is a serene retreat w/direct access to a 2nd floor covered porch, a private dressing room and an en suite tiled bath. The 3rd level unveils even more versatility with a large finished storage room that opens onto a "Summer Bedroom" w/colored glass windows, perfect for additional living space or creative pursuits (artist studio?). This charming home celebrates period Victorian features and a sense of elegance. There is a 2-Car garage, central air conditioning and the residence is located in a highly sought after neighborhood. A special spot offering comfort, beauty and a unique sense of place. Delayed showings 4/28/25.