Properties Near 187 Hillwinds Road Brattleboro, VT

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.

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.

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.

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!

Welcome home! Four bedroom, 4-bathroom home with dedicated office space is located in one of the area’s most desirable communities. Just minutes from Brattleboro, it offers the perfect blend of convenience, comfort, and outdoor living, with walking trails right nearby. The bright, open layout is ideal for everyday living and entertaining, featuring a welcoming kitchen, dining, and living area. A private office provides the perfect space for remote work or creative projects. Upstairs, the primary suite includes a fireplace, en-suite bath, with three additional bedrooms and ample bathrooms for family or guests. Set in a friendly, vibrant neighborhood, this home is close to shopping, dining, arts, and year-round recreation. A rare opportunity to enjoy both community and nature in a prime location! Delayed showings begin Saturday 9/20/25.

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!

Nestled in the heart of Vermont, this charming Cape Cod-style home offers the perfect blend of country living and modern convenience. With 3 spacious bedrooms and 2.5 baths, it's designed for both comfort and functionality. The home boasts a large sunroom, perfect for enjoying Vermont's scenic beauty year-round, and a screened-in porch for those warm summer evenings. The outdoor deck provides an ideal space for entertaining or simply relaxing. Inside, you'll find plenty of storage space to keep your home organized and clutter-free. The kitchen offers a bright space with all the essential needs, spacious granite countertops, and gas cook-top make cooking a joy. Upstairs you’ll find 3 nice sized bedrooms. The large primary bedroom is a true retreat, featuring a private bathroom with a jetted tub, a tiled shower, and a skylight that fills the room with natural light. Located just a few minutes from downtown, you can easily access shopping and restaurants. A cul-de-sac road offers privacy, low traffic, and worry-free play. Families will appreciate the proximity to schools, offering Kindergarten through 8th grade education. This Vermont home is more than just a house; it's a place where memories are made.

Get ready for your new favorite property. Located in highly-desirable West Dummerston, just 10 minutes from downtown Brattleboro, this energy-efficient Unity high performance home is waiting for you. It’s a very cozy 3-bedroom, 2 full bathroom single-level home on 0.88 acres. Built of pre-fabricated components in factory-controlled conditions, this house is just some solar panels away from being Net Zero. R-60 insulated roof, R-35 insulated walls. Triple-glazed windows. The two mini-splits are quite sufficient to heat it through the winter months; the propane stove and electric baseboard provides more backup. On demand hot water heater. The house is designed & built to be tight, so there’s an air exchange system in place. Lovely 3-season screened-porch. The siding is very durable fiber cement Hardie board. Attached one-car garage. The front yard pops with the colorful and nicely-landscaped plantings. Delayed showings begin Saturday July 26th with an Open House 11am-1pm .

Sweet! The perfect location...intown...backing up to the retreat trail system...and has a beautiful front porch and private back deck. This has been a much loved home, ready for a new generation to create their own music and harmony of life. The rooms are large, comfortable with lots of windows, real wood paneling reflecting the era, high ceilings, enough room to work from home (even an office entrance), a double sized main bedroom with walk in closet and ensuite bath. The kitchen invites an island or traditional kitchen table to keep the company close. Gardens surround the porch and deck and the sun room extends the sitting out season. Location, location, location!!! and this one has got it....please have buyers prequalified for showings.