$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.

$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

$449,000 $180 per sq.ft. Bridport VT Home »

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.

$399,000 $248 per sq.ft. Brookfield VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1608  |  Acres: 0.9
Thursday Mar 19, 2026
Description: New, new, new! Originally started as a 2018 build but never completed, this home has been expertly finished and thoughtfully elevated by its current owners--resulting in a property that exceeds expectations at every turn. What appears to be a modest exterior opens into a surprisingly spacious and well-designed interior, where every inch of space has been maximized with intention, comfort, and style. The main level features a desirable first-floor primary bedroom and a versatile full bath that can function as either a private ensuite or a guest bath, offering flexibility for a variety of living arrangements. First floor laundry and thoughtful upgrades, including a heated towel rack, add a touch of everyday luxury. The well-appointed kitchen flows seamlessly into the open-concept dining and living areas, creating a bright and welcoming space ideal for both daily living and entertaining. Step through the sliding glass doors onto the expansive rear deck overlooking Sunset Brook just beyond the property line--an inviting setting for morning coffee, evening relaxation, or hosting gatherings with friends and family. Upstairs, you'll find two additional bedrooms, a convenient half bath, and bonus storage spaces. The walkout lower level adds even more versatility, featuring a comfortable media or recreation room, additional storage, and access that lends itself well to covered parking or flexible use. A new Presby septic system and EC Fiber, fiber optic internet already installed! Also inquire about the home being offered fully furnished and professionally staged, which presents an exceptional turnkey opportunity for investors, short-term or long-term rental potential, second-home buyers, or anyone seeking a seamless move-in experience for additional cost. Deceptively spacious, thoughtfully finished, and ready to enjoy--this is a property you won't want to miss! See MLS Property & Listing Details & 48 images.

$429,000 $183 per sq.ft. Brookfield VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2350  |  Acres: 1.7
Wednesday Apr 8, 2026
Description: This lovingly restored home is nestled in the quaint Pond Village community of Brookfield, VT. The property has had the same owners for the last 48 years. A stunning blend of old and new, the stewards of this home meticulously preserved timeless beams, wide pine floors and authentic barn walls, while making modern updates. Enter into the convenient mudroom before stepping into the warm and open kitchen/dining room with large woodstove and brick hearth. Character abounds in the living room with beautiful wide pine floors and exposed beams, den, half bath, and sunny office, which round out the first floor. Upstairs you will find four bedrooms and a full bath. The attached barn provides plenty of storage space and room for one car, or workshop area. Step onto the back deck with direct access off the kitchen, and enjoy the privacy of the back yard. This enchanting space is adorned with lovely stonewalls and perennials. Just down the road from Sunset Lake, the historic Brookfield Floating Bridge, and the newly renovated Green Trails Inn and Pond Village Pub. Properties in this community do not come on the market often, don't miss your chance! Being Sold "As Is" See MLS Property & Listing Details & 60 images.

$297,500 $228 per sq.ft. Burke VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1306  |  Acres: 0.5
Wednesday Apr 15, 2026
Description: Recently and completely renovated, this West Burke home is ready to move into. Situated on a back street in a pleasant neighborhood it provides a practical and attractive home close to all of the Kingdom's recreational opportunities. The VAST snow mobile trail is directly across the street and the property is easily accessible to Route 5, Burke Mtn. and Kingdom Trails. The main floor is an open concept with kitchen, dining, and spacious living room, and there is a mudroom leading into the one car garage. A full bath with laundry is located just off the living room.The upper level has an open landing area that could be an office. two bedrooms and a three quarter bath. The attached garage is over sized with high ceiling. It is partially finished which could be made into more living space or a shop if needed. The basement is unfinished and dry. This is basically a new home that needs nothing but a new owner. See MLS Property & Listing Details & 3 images.

$379,000 $281 per sq.ft. Burke VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1348  |  Acres: 1.1
Tuesday Jul 29, 2025
Description: Welcome to 1289 Bugbee Crossing. This beautifully updated 3-bedroom, 1.5-bath home offers a flexible layout and quality upgrades. With a bright and sunny living room that flows seamlessly into the kitchen, showcasing sleek modern cabinets, a beautiful spacious island, quartz countertops, and premium stainless steel appliances. Down the hall, you'll discover a beautifully renovated bathroom, and 3 bedrooms with generous closet space. The lower level offers a large bonus room including a half bath with washer and dryer hook-ups and Lifeproof luxury vinyl plank flooring throughout. Outside, you'll enjoy a spacious deck overlooking a level yard and a large driveway. Generator hook-up for power outages. New windows and a new architectural roof complete the outside. Conveniently located minutes from East Burke Village, Burke Mountain, and Kingdom Trails. This home blends comfort, style, and functionality. See MLS Property & Listing Details & 14 images.

$449,000 $191 per sq.ft. Burke VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2345  |  Acres: 26.5
Friday Mar 27, 2026
Description: More than a house or a home, this is a retreat! Sited on wooded 26.5 acres with Roundy Brook running through, the 3-bedroom, 3-bath Cape has 2-car garage with overhead storage, paved drive & a gazebo placed in an optimal spot to take full advantage of the brook's sounds and scenery. Serenity is calling! Full woodburning fireplace for those cozy nights with 3 full flues so you can also have supplemental heating, if wanted. Oil-fired boiler with multiple zones also supplies domestic hot water. Full-house automatic generator insures power even during outages, adding safety and security. Ideally located close enough to Kingdom Trails where you cas start from your garage! Minutes from Burke Mountain for exceptional skiing and riding along with other amenities. This is the center of The Northeast Kingdom with adventures in all directions from this driveway. A large deck overlook the brook and with numerous access points, you can fish, take a dip or just admire the water. There is a main floor bedroom as well as an office / work space, creating one-level living if desired. Upstairs is a very large loft with bedroom and family room, all sharing a 3/4 bath. Lower level offers another bedroom, bath and huge laundry. But it's the yard and setting that will make you feel at home. Hidden behind the treelined road you're screened from the bustling world at this retreat that is waiting for you. See MLS Property & Listing Details & 56 images.

$489,900 $284 per sq.ft. Burke VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 1728  |  Acres: 1.5
Monday Apr 6, 2026
Description: This home is ideally located for the mountain bikers, skiers, snowmobilers. Located in East Burke is this well-maintained home, and short drive to Burke MT. Bike from the house. 3 bedrooms full bath on main floor. Finished basement with 2 bedrooms, 3/4 bath and kitchen living room now used as a VBRO rental with good rental history. Could be full time rental or in-law apartment. Large deck to enjoy the view or just to relax. 10 by 20 shed for storage. Whole house generator. All state and town permits in place. Excellent country location. See MLS Property & Listing Details & 27 images.