$399,900 $299 per sq.ft. Brattleboro VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1339  |  Acres: 0.17
Monday Apr 20, 2026
Description: Tucked away on a quiet dead-end street just moments from downtown Brattleboro, this bright and inviting 3 bedroom, 1.5 bath Colonial offers the perfect blend of comfort, character, and convenience. A spacious mudroom provides a practical and welcoming entry, leading to a thoughtfully laid out interior featuring first-floor laundry, a large living room with flexible space for a home office, and a formal dining room highlighted by a generous window overlooking the private backyard. Hardwood maple floors run throughout, and four recently installed mini-splits provide efficient heating and cooling year-round. Outside, enjoy a beautifully maintained setting with established perennial gardens, raised beds, and a charming tree swing, along with a large rear deck ideal for entertaining or relaxing, an outdoor shed for additional storage, and a paved driveway and fully fenced yard. With its peaceful location and easy access to local shops, dining, and amenities, 16 Willow Street offers an exceptional place to call home. Close to Interstate 91, Mass border, hospitals, skiing, outdoor recreation and so much more! This is a must see! OPEN HOUSE ON SATURDAY, APRIL 25TH FROM 10AM-12PM. See MLS Property & Listing Details & 39 images.

$449,000 $270 per sq.ft. Brattleboro VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1660  |  Acres: 4.81
Monday Mar 9, 2026
Description: Enjoy privacy and nature just minutes from town! This well-cared for 3 bedroom, 2 bath home sits on 4.81 acres, offering space, tranquility, and convenience. Features include a first-floor bedroom, bright and comfortable living areas, a beautiful three-season porch perfect for relaxing and taking in the peaceful setting, and a two-car garage for added storage and functionality. A great opportunity to enjoy country living with easy access to town amenities. OPEN HOUSE SATURDAY 3/21 11AM - 1PM. See MLS Property & Listing Details & 32 images.

$475,000 $192 per sq.ft. Brattleboro VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2480  |  Acres: 0.27
Tuesday Jan 13, 2026
Description: This well-maintained three-bedroom, two-bath single-family home is set on a level, fenced-in lot in a coveted neighborhood close to downtown, with convenient access to major highways. The home features radiant flooring, central air, and a finished basement offering flexible living or recreational space. A spacious kitchen provides ample cabinetry and storage, ideal for everyday living and entertaining. Two bedrooms are located on the main level, while the second-floor primary suite offers vaulted ceilings and added privacy. Outdoor highlights include a 16' x 20' Trex deck, a bluestone walkway, and a large driveway bordered by a stone wall. A detached one-car garage with a carport adds functionality. Enjoy proximity to the Retreat Trails and Harris Hill Ski Jump, combining comfort, convenience, and an exceptional location. See MLS Property & Listing Details & 35 images. Includes a Virtual Tour

$489,000 $212 per sq.ft. Brattleboro VT Home »

Price Change! Reduced by $10,000 down 2% on April 2nd 2026
4 Beds | 4 Baths |   Total Sq. Ft. 2312  |  Acres: 0.27
Saturday Feb 28, 2026
Description: Welcome to 23 Wilsons Woods Road, a meticulously maintained Colonial-style home that offers the perfect Vermont balance: total wooded privacy combined with absolute convenience. Nestled at the end of a quiet road, this property feels like a secluded retreat tucked into the forest, yet you are literally moments away from Brattleboro's vibrant restaurants, local shops, the hospital, and a thriving arts scene. The standout feature of this residence is the thoughtfully designed addition, which serves as a premier mother-in-law suite or guest wing. This expansive space offers flexible multi-generational living without compromise, featuring its own eat-in kitchen and sitting area, and the high-end luxury of radiant floor heating for year-round comfort. With direct access to a private deck and open patio, it is a seamless blend of indoor-outdoor living. The home's exceptional layout includes 4 bedrooms and 4 bathrooms, providing a natural flow that is perfect for both entertaining and quiet daily life. High standards of maintenance are evident throughout, including recent roof renovations and pristine mechanical systems. Whether you are relaxing on the classic covered wraparound porch or hosting a dinner on the beautiful rear deck, the serene surroundings provide a sense of total calm. This move-in-ready property offers the comfort and quality lifestyle Vermont is known for--quality construction, modern upgrades, and a location that puts the very best of Brattleboro right at your fingertips. Open House April 12th 12pm-2pm See MLS Property & Listing Details & 60 images.

$495,000 $180 per sq.ft. Brattleboro VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2756  |  Acres: 0.79
Friday Feb 13, 2026
Description: Step back in time and discover the enchanting potential of this distinguished 1940 Colonial, perfectly positioned to capture the spirit of Brattleboro. Perched on a generous 0.79-acre level lot, this home offers a rare blend of expansive personal space and convenient in-town living. From the moment you arrive, the classic lines, wood siding, and enduring slate roof hint at the craftsmanship of a bygone era. Inside, the home spans a spacious 2,756 square feet, featuring four bedrooms plus bonus room and three bathrooms that provide ample room for family, guests, or creative pursuits. While the interiors are ready for a thoughtful restoration, the home's historic character serves as a beautiful canvas for your vision. This is a unique opportunity to breathe new life into a property with significant provenance, preserving its architectural soul while infusing it with modern comforts and your own personal style.The true magic of this property lies in its setting. Imagine waking up to sweeping, picturesque views of the West River Meadows, a daily reminder of Vermont's natural beauty right from your back yard. Despite this serene visual escape, you are just a short, pleasant walk from the vibrant heartbeat of downtown Brattleboro, where local shops, dining, and community events await. This residence offers the best of both worlds: a private, historic retreat with the convenience of a walkable, connected lifestyle. There are extensive berry bushes, a vegetable garden, and perennials growing on the property. Don't miss this rare opportunity. See MLS Property & Listing Details & 46 images.

$495,000 $397 per sq.ft. Brattleboro VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1246  |  Acres: 0.08
Wednesday Apr 8, 2026
Description: Step into an 1880s Victorian re-imagined for the 21st century. Located moments from downtown Brattleboro, this 3-bedroom, 3-bath home blends historic craftsmanship with a cutting-edge deep-energy retrofit. Enjoy easy access to shops, dining, the Amtrak station, and the Retreat Trails from a peaceful, residential setting. Unlike typical historic renovations, this property underwent a from-the-studs rebuild in 2018, serving as a pilot for high-performance building science. It is now fully electric and fossil-fuel free, featuring : Air-to-water heat pump for heating/cooling and an Energy Recovery Ventilation (ERV) system for superior indoor air quality. The home also has a super-insulated, airtight building envelope ensuring year-round comfort and efficiency, with a durable standing seam roof equipped with solar panels. The interior honors its heritage while embracing sustainable, modern design, using eco- friendly materials: copper countertops, natural linoleum flooring, and Energy Star appliances. Modern mechanical systems and smart features throughout, you get turn-key Peace of Mind.: Every major system-from insulation to infrastructure-is new, offering a rare level of durability in a vintage home. 81 Chapin Street is more than a renovation; it's a blueprint for the future. For those seeking environmental responsibility without sacrificing historic charm, this is a truly unique opportunity. Open House: Saturday, April 11, 11am-1pm. See MLS Property & Listing Details & 27 images.

$499,000 $322 per sq.ft. Brattleboro VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1550  |  Acres: 0.18
Tuesday Mar 31, 2026
Description: 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. PRICED FROM $475,000 - $585,000. HOMES OFFER at least 5 rooms - kitchen, living, dining, primary BR w/ en-suite BA, & bonus room for office/study or guest BR - 2 BA's, & a 1-car garage. UPGRADED HOMES OFFER: 2-car garage, sunroom, expanded living & guest rms, & larger yard. Some special touches that make BME homes beautiful & comfortable: finished 1 or 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. DO NOT MISS THIS OPPORTUNITY. Even if you are not quite ready to commit, reach out right away and ask to have your name put on the waiting list! See MLS Property & Listing Details & 32 images.

$449,000 $302 per sq.ft. Bridgewater VT Home »

Waterfront on River Ottauquechee River
3 Beds | 2 Baths |   Total Sq. Ft. 1489  |  Acres: 0.33
Thursday Jul 24, 2025
Description: This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont country kitchen-dining and family room flow into a south facing sunroom overlooking the Ottauquechee River with a terraced yard providing direct access to the water. The home is midway between the resort communities of Woodstock and Killington 5 and 9 miles away. A public park and the Bridgewater Mill showcasing nationally and internationally recognized handmade furniture and pottery of Charles Shackelton and Miranda Thomas, respectively, in addition to a popular restaurant with live entertainment all within walking distance. Ideally sited offering an array of amenities at an attractive price. See MLS Property & Listing Details & 34 images.

$465,000 $473 per sq.ft. Bridgewater NH Home »

2 Beds | 1 Baths |   Total Sq. Ft. 984  |  Acres: 1.47
Wednesday Apr 15, 2026
Description: BRIDGEWATER, NH Welcome to the perfect weekend retreat or investment property. Conveniently located in the Lakes Region near I-93, Plymouth, Ashland, and Holderness and providing access to ski resorts, hiking and the white mountains. This 2 bedroom, 1 bath home is only 4 years young and comes fully furnished making it move in ready! The first floor features a primary bedroom, full bath with laundry, open concept kitchen and living room with cathedral ceiling. The French doors open to the large deck overlooking the Clay Brook and the natural surroundings. The large loft is the second bedroom and is big enough for 2 queen sized beds. After you have fun exploring this beautiful property, take a cool dip in the river and discover the small island. Great spot for a picnic as well - picnic table already provided! This home was built with ease of living in mind. Vinyl shake siding, trex decking, radiant heating, hot water on demand and vinyl flooring all makes for a low maintenance home. This home has excellent short-term rental history for the investment buyer! Don't miss this opportunity in a low tax town! See MLS Property & Listing Details & 36 images. Includes a Virtual Tour

$485,000 $163 per sq.ft. Bridgewater VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 2977  |  Acres: 0.23
Saturday Feb 28, 2026
Description: This property is conveniently located in Bridgewater Village, situated midway between Woodstock and the Killington Ski Area. While currently configured as three income-producing units, it offers an outstanding opportunity for a creative conversion back into a single-family residence, with the detached rear unit available to supplement the cost of ownership. Recent updates include a new roof, mini-splits, kitchen renovation and a new heating system. Additionally, the high-visibility location is ideal for an entrepreneur or service provider seeking a home occupation. Please come and see the possibilities for yourself. We require 48 hours' notice for all showings, furniture negotiable. See MLS Property & Listing Details & 27 images. Includes a Virtual Tour

$435,000 $175 per sq.ft. Bridport VT Home »

Price Change! Reduced by $14,000 down 3% on April 22nd 2026
3 Beds | 2 Baths |   Total Sq. Ft. 2490  |  Acres: 1.9
Thursday Apr 2, 2026
Description: This charming 1850's Farmhouse set on 1.9 acres, offers a blend of classic character and thoughtful updates in a beautiful country setting. A versatile layout greets you with two rooms off the foyer - serving as a mudroom and a large storage room - perfect for outdoor gear. The first floor also has a home office, a formal dining room, wood floors in the living room, as well as an updated kitchen overlooking the backyard. The primary bedroom is bright and spacious with a full en suite bathroom as well as a walk-in closet. Upstairs, you'll find a large family room, two additional bedrooms, and a bonus room that share a ¾ bath. The second level also has storage space plus an unfinished workout room that is accessible through its own stairwell or through a bedroom closet. Outside, trees create a natural privacy border around the property. Relax on the new stone patio and take in the surrounding country views. Recent updates include a 3-bay garage, a new roof, re-graveled driveway, and some siding. Don't miss this classic Vermont country property! See MLS Property & Listing Details & 57 images.

$260,000 $165 per sq.ft. Bristol NH Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1580  |  Acres: 1.38
Wednesday Apr 22, 2026
Description: Opportunity in Bristol, NH! This ranch-style home is set on a nice lot and offers great potential for investors, flippers, or buyers looking to build equity. The property is in need of repairs and is being sold as-is. A detached cabin on the property also requires renovation, offering additional possibilities for guest space, rental income, or studio use. Bring your vision and restore this property to its full potential. See MLS Property & Listing Details & 57 images.

$299,900 $288 per sq.ft. Bristol NH Home »

2 Beds | 1 Baths |   Total Sq. Ft. 1040  |  Acres:
Wednesday Apr 22, 2026
Description: LIFE IS BETTER at the Lake. Looking for a year round get-away offering easy access to a Lake for summer fun, as well as Skiing close by in the winter? This well maintained, freshly painted, 2 bedroom end unit Townhouse is nestled on 6.8 acres in Lakewood Pines, a small association of only 24 units. Walk through the door and enjoy this turn key property with many upgrades, like new carpet, new stackable washer/dryer, new kitchen stove & more. Property is light, bright and offers an airy feel. Amenities include: basketball & tennis court. Monthly association fee only $275. Just a short walk to sandy beaches on crystal clear Newfound Lake & a short ride to Ragged Mtn Ski Area. A great primary or year round vacation home location. Rentals allowed for 30 days or more. See MLS Property & Listing Details & 24 images.

$300,000 $288 per sq.ft. Bristol NH Home »

Waterfront on Lake Newfound
2 Beds | 1 Baths |   Total Sq. Ft. 1040  |  Acres:
Monday Feb 23, 2026
Description: Just in time for summer! Welcome to Lakewood Pines, a highly desirable association within walking distance to the crystal-clear waters of Newfound Lake. This lovingly maintained 2-bedroom, 1-bath townhouse offers low-maintenance lake life living and the perfect home base for four-season enjoyment in the heart of the Lakes Region. Spend your days swimming, kayaking, paddleboarding, or relaxing at one of Bristol's two town beaches, available to property owners. Enjoy nearby restaurants, shops, and local events, plus easy access to hiking trails, mountain views, and winter skiing. From fall foliage to summer sunshine, this location truly offers a passport to adventure. Inside, the home features a comfortable and functional layout filled with natural light. The private back deck overlooks a peaceful wooded tree line--perfect for morning coffee or unwinding after a day on the lake. The Lakewood Pines association includes 5.55± acres of common land, a tennis court, snow and rubbish removal, affordable monthly dues, and well-maintained buildings. An affordable opportunity to embrace the Newfound Lake lifestyle--ideal as a primary home, vacation getaway, or investment property. See MLS Property & Listing Details & 60 images.

$399,500 $225 per sq.ft. Bristol NH Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1773  |  Acres: 0.44
Saturday Jan 10, 2026
Description: In the tradition of a great Victorian structure, The home has great bones, lots of space and has all those charming features of it's time. Window seats, built in bureaus, curved walls and beautiful scalloped trim. Partial restoration in progress, bring your ideas to finish this beauty. Lots of the materials are there to finish projects. The home is in a commercially zoned location and offers that option. There is a large attic for storage or extra living area. The attached barn has 2.5 stories and is in decent shape and has potential as a business location. Property is close to downtown with many local amenities right out your front door. See MLS Property & Listing Details & 22 images.