Properties Near 164 Chestnut Street Brattleboro, VT

The one you have been waiting for! This traditional New England cape with a twist checks all the boxes! Remodeled in the 90's, it has a cook's delight for a kitchen with tons of cabinets and lots of countertops for baking prep...cookies and breads are a must!. The first floor was expanded to almost double the size of the living room, adding a fireplace and a main bedroom. Again in place is easy here as along with the bedroom, there is laundry and full bath on the first floor. The attached 2 car garage keeps you out of the weather, tidy and dry. An amazingly level lot is great for gardening or games. And, you are on pavement, no mud season here! Easy to get to the mountains or Brattleboro and beyond. This is a must see for those long in the market, looking for just the right home.

This authentic and updated Vermont home is situated on welcoming, dead-end street surrounded by woods on two sides creating a feeling of peacefulness and connection with nature. How fortunate to live in town but also have the calming surroundings of mature plantings, opportunity to garden and de-stress in your private sanctuary. Enjoy outdoor dining on the deck, located just off the dining room/kitchen area. In addition, this is an income-producing property with an accessory living apartment that has a separate entrance. Offset expenses, enjoy multigenerational living, or merge and expand the home back to a single family. The interior, though updated, with a fully modern kitchen and bath, maintains the best of its original features, such as exposed beams, built-ins, large windows, and hardwood floors. The attached antique barn with a workbench is an inviting space for projects or to utilize as a studio. This property offers many choices. The stonework, gardens, and detached, expansive two-car garage all add to the desirability. New oil tank in 2024 and you will be impressed with the condition, the privacy, the large lot, and all the accessible amenities in Brattleboro, as well as the eclectic community at large. Delayed showings until Sat Sept. 13th by appointment.

All work has been done for you on this beautiful, 1932 period home. 4 bedrooms, 2 full baths, set in a high demand, desirable neighborhood. Manicured, corner lot with classical perennial plantings, two covered porches, a slate roof, and detached double garage. There are 20+ upgraded, insulated windows, with antique reproduction filling the home with natural light. Hardwood floors predominate. Renovated kitchen displays striking quartz counter tops. Thoughtfully, the owners preserved the antique hardware, including glass door knobs, as well as doors which feature French and solid-core paneling. The property also includes eye-catching window and baseboard trim, rectangular bay window in dining area, a pantry with cabinetry, and numerous custom-built-ins. The first floor has 2 bedrooms & full bath. Enjoy winter warmth of a working fireplace in the living room. The spacious, renovated upstairs bath has radiant heat flooring, a walk-in shower with glass doors, and a double sink. The full basement houses a newer boiler servicing the hydronic heating system for radiating heat from cast iron radiators, newer oil tank and hot water heater. You’ll also find a spacious laundry area with room for a workout area, workbench and yoga. Be fortunate enough to move in, settle in, and enjoy! Delayed showings until Saturday, Sept. 20th by appointment.

Charming and well-built Cape-style home featuring 4 bedrooms and 2 full baths. The updated kitchen boasts tiled floors, generous counter space, and modern finishes—perfect for the home chef. Just off the kitchen, the dining room includes a sliding door that opens to the backyard and patio, ideal for indoor-outdoor entertaining. Beautiful hardwood floors run throughout the home—no carpet here. The inviting living room offers a classic wood-burning fireplace with an attractive mantel, adding warmth and character. With two bedrooms on the main level and two upstairs, the flexible layout works perfectly for guest rooms, an in-home office, or both. The one-car garage offers direct access to the basement, adding convenience and functionality. Recent upgrades include a paved driveway and a new retaining wall. The high-efficiency Buderus furnace has been recently serviced for peace of mind. Out back, the fully fenced yard offers privacy, lush perennial plantings, and a peaceful setting just minutes from downtown Brattleboro. Enjoy easy access to the hospital, medical offices, shopping, and restaurants. Sale is contingent on the seller securing suitable housing.

Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with sliders to the back for grilling and a living room with a picture window to the front yard, you can tuck in and enjoy. Half of the lower level is finished and is perfect for a den, at home office or playroom. Plenty of storage in the unfinished portion, so stock up on those sale items! Showings will begin on June 14th at the open house 11-1. Please be prequalified before making an appointment to view. POSSESSION EARLY AUGUST, PLEASE

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.

Open House August 1, 5:30-7:00 and August 2, 10-11:30. Welcome to 35 Hillcrest Terrace, a well-loved home owned by the same family for over 20 years, perfectly situated in one of Brattleboro’s most convenient neighborhoods. Just moments from Memorial Park, this charming property offers easy access to recreation, walking trails, and town amenities while providing a peaceful, residential setting. This 3-bedroom home is move-in ready yet offers plenty of potential for updates, making it the perfect opportunity to truly make it your own. The main level features a comfortable layout, filled with natural light, and opens to a delightful 3-season porch—ideal for morning coffee or evening relaxation. Step outside to the spacious deck overlooking the backyard, perfect for gatherings or quiet enjoyment. With a solid foundation, great location, and endless possibilities, 35 Hillcrest Terrace is ready for its next chapter. Whether you’re looking for your first home or a property you can personalize over time, this is one you won’t want to miss!

So much to offer! This 4 bedroom 2 bath has plenty of room for all! It features a large kitchen with lots of counter space and the laundry tucked in for easy access while you cook and bake. The deck overlooks the lower yard where the solar panels live and the perfect spot for the above ground swimming pool (needs a liner). Huge lot, lots of off street parking and on the MOOVER line for non drivers. In a previous life the 4th bedroom was a beauty salon...food for thought...Good bones, owner has updated many features...a home worth considering.

This charming split-level home offers 3 bedrooms and a full bathroom, complete with a single-bay garage in the desirable Carriage Hill neighborhood.  Hardwood floors extend through the living room, hall, and bedrooms, adding warmth and character. The living room features a lovely picture window with opening side windows, perfect for letting in a refreshing breeze and natural light.The lower level offers a fantastic opportunity with a partially finished, extra-large bonus room that can be customized to suit your needs. Additionally, this level includes a convenient laundry/utility room and a small workshop space, offering practical solutions for storage and hobbies.Outdoor living is equally inviting with a private deck off the back of the house, leading to a fenced backyard. This space is ideal for relaxation and entertaining, complete with a firepit perfect for enjoying summer and fall evenings. You'll also appreciate the thoughtful landscape touches, particularly the delightful goldfish pond! What's not to love??

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. All tenants have vacated!!

Charming Sun-Filled Cape on Corner Lot. This sweet and practical 2-bedroom, 2-bathroom Cape offers timeless appeal and everyday comfort on a sunny corner lot. Built in 1942, the home retains its original charm with 3-over-1 windows, built-ins throughout, and even a vintage ironing board cabinet. Inside, enjoy wood floors, a spacious eat-in kitchen with generous counter space, and a bright sunroom perfect for relaxing. Recent upgrades including newer windows, oil tank, furnace, and boiler help balance the cosmetic updates you may wish to make. With a garage and thoughtful layout, this home is ready to shine with your personal touch. Outside, the easy to maintain level lot is great for gardening or gatherings. Come see for yourself!

Beautifully elegant light filled condo in Bluebell Building at Arbor Hill. An abundance of windows throughout creates a magical light filled environment that includes hardwood flooring, a Great Room providing space for Living, Dining and Kitchen, 2 spacious Bedrooms, 2 Full Baths, Entry w/ double closet and Laundry/Pantry. The Primary Bedroom has an en suite Bath, mini split and a large walk-in closet and the Guest Bedroom features 2 large closets and a full Bath with walk-in shower across the hall. Updated Kitchen with granite counters, tile Baths A very special place to call home!!!! (55 and older).