$720,000 $164 per sq.ft. Grafton VT Home »

Waterfront on River Saxtons River
4 Beds | 3 Baths |   Total Sq. Ft. 4379  |  Acres: 0.25
Listed on Wednesday Apr 1, 2026
Description: The Woolley House, located at 587 Route 121 East and built around 1818, is a rare and remarkably preserved 2.5 story brick residence in the Federal style. This home, originally constructed for early woolen mill owner John Woolley, features a side-hall layout, blind-arch entryway, and fanlight transom. Original details are beautifully preserved throughout including an original central cooking hearth with an iron crane and 2 concealed baking ovens, wide pine floorboards, classic 12-over-12 windows, and a charming hand-crank doorbell that evokes its historic past. A tasteful modern addition expands the living space with a custom marble kitchen, a formal dining room, and three private office suites with outdoor access ideal for remote work or creative pursuits. Upstairs, the home features four comfortable bedrooms, two updated bathrooms, a lounge and a finished loft with a cozy library retreat. Outside, the home is surrounded by mature perennial gardens and one of Windham County's most admired curated Hosta collections, offering a peaceful oasis in every season. With its architectural significance, modern functionality, and ample space to live, work, and explore, the Woolley House is a truly timeless property in the heart of historic Grafton. The property is part of the Mechanicsville Historic District in Grafton, Vermont. A well-preserved 19th-century hamlet recognized for its architectural, community planning, and industrial significance. The district includes 10 contributing historic homes, all built before 1860, and this designation places the Woolley House on the National Register of Historic Places. See Listing Details & 58 images. Includes a Virtual Tour

New Listing! Grafton VT Home for sale $845,000 $323 per sq.ft.

$845,000 $323 per sq.ft. Grafton VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2613  |  Acres: 3.9
Listed on Monday Jun 8, 2026
Description: This handsome turn-key property is available sooner than one might expect! Due to changing life developments, the owners are offering their beloved Vermont home for sale. Not long ago, the 19th century Chapman House underwent a full renovation, including a stunning new kitchen and updated baths. The kitchen features marble countertops, glass-front backlit cabinetry, a deep farmhouse sink, Sub-Zero refrigerator and freezer, and a built-in high-end coffee machine. Blending timeless charm with modern convenience, this space is ideal for both everyday living and entertaining. The kitchen and lovely dining area are bookended by a comfortable den and a formal front parlor, creating a warm and flexible main living space. A first-floor bedroom and full bath complete the main level. Upstairs, you'll find two generously sized bedrooms, each with double closets, along with a beautifully finished bath and two separate office spaces. Combined with fiber optic internet, this home is perfectly suited for working remotely, streaming, or gaming with ease. Additional conveniences include an attached two-car garage with abundant storage space above, as well as a potting area behind. Just off the kitchen is an enclosed porch - the perfect place to enjoy the outdoors in comfort. The setting is equally impressive, a lush lawn, old stone walls, mature trees & this property offers something truly rare - a field in the village! Located near Grafton's infamous Inn & Tavern and only a quarter mile from the Outdoor Recreation Center, the setting is hard to beat. AND-this offering is being sold fully furnished. The current owners have thoughtfully assembled antique furnishings and decor that perfectly complement the character and charm of this antique country village home. Standing seam roof, upgraded electric, 2 fireplace inserts, 2 heat pumps, central air and automatic generator - this house has it all. Just pack your suitcase and come fall in love with this one! See Listing Details & 59 images.

$999,000 $193 per sq.ft. Grafton VT Home »


Price Change! Reduced by $89,000 down 9% on May 1st 2026
6 Beds | 5 Baths |   Total Sq. Ft. 5828  |  Acres: 1.04
Listed on Monday Apr 6, 2026
Description: STRONG RENTAL HISTORY & INVESTMENT OPPORTUNITY IN A TURN-KEY PROPERTY. Located in the heart of Grafton, Vermont, on a spacious one-acre, flat lot a quick stroll from town, this extensively renovated property offers exceptional flexibility and scale. The single family or multi-family property is configured to allow division into two condominium-style living spaces plus a separate artist loft or accessory dwelling, each with its own entrance, creating versatile possibilities for expansive residential living, multi-generational housing, a vacation retreat or investment opportunity with three rentable units. The home features six bedrooms, plus a loft, and has been thoughtfully updated with new kitchens, renovated bathrooms, new windows, roofing, wide plank wood flooring, and all new mechanical systems installed in 2022-2023. An extra-large two-car garage provides abundant storage. Located in close proximity to Grafton's well-known village destinations--including the Grafton Cheese Company, Grafton Inn, Phelps Barn, MKT Market, Grafton Trails & Outdoor Center, and the Nature Museum--the property offers convenient access to local shops, dining, recreation and skiing. With a strong rental history and extensive updates, this turn-key property presents unique opportunities and turn-key living in the heart of historic Grafton. See Listing Details & 60 images.

New Listing! Grafton VT Home for sale $1,650,000 $371 per sq.ft.

$1,650,000 $371 per sq.ft. Grafton VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 4443  |  Acres: 66.8
Listed on Thursday Jun 11, 2026
Description: Set along picturesque Middletown Road, just beyond the historic village of Grafton, this elegant five-bedroom residence enjoys a setting that feels both timeless and deeply peaceful. Perhaps it is the pleasing symmetry and classic proportions of the c.1815 brick Federal home with its Georgian floor plan. Perhaps it is the views of rolling meadows and rounded hills that unfold in both directions. Or perhaps it is simply the feeling of being here--a quiet sense of belonging that is difficult to explain and impossible to forget. Filled with natural light, the property has a welcoming spirit. A pond, apple orchard, perennial gardens, blueberry bushes, ancient maple trees, and historic stone walls create a landscape rich in beauty. The home sits along a quiet gravel road that forms part of one of Grafton's favorite four-mile walking loops, while trails meander through the property's 66 acres of fields and woodland. The Saxtons River traces one edge of the property. In the early nineteenth century, Major Benjamin Dwinell and his wife, Mehitable, built this home and raised eleven children here. The family prospered from the land, tending a large flock of sheep and cultivating one of the most productive apple orchards in town. By the late 1800s, Grouse Hill had begun a new chapter as a country retreat for a New York family. Over the years it has served as a boarding house, an inn, a full-time residence, and a cherished second home. Through each chapter, it has remained what it is today: a gracious and welcoming place that draws people in, encourages them to linger, and leaves a lasting impression. 22 miles from Okemo. 2 hours 44 minutes from Boston and 4 hours 19 minutes from New York. See Listing Details & 33 images.

$2,895,000 $734 per sq.ft. Grafton VT Home »

6 Beds | 4 Baths |   Total Sq. Ft. 3946  |  Acres: 317.09
Listed on Thursday Jun 4, 2026
Description: A rare opportunity to own one of Southern Vermont's most remarkable private estates, Riverledge Farm encompasses more than 300 acres in the historic village of Grafton. Nestled in the Green Mountains, this exceptional property combines natural beauty, recreation, and a large homestead. A winding approach framed by mature maple trees and classic stone walls leads to the elegant white farmhouse, where timeless Vermont character meets modern comfort. The residence features six bedrooms, four bathrooms, and two kitchens, complemented by an impressive collection of outbuildings, including a 4,000+ square foot timber frame barn for events, five-bay garage with workshop and offices, seven-bay pole barn, and a three-stall horse barn with heated tack room. Additional accommodations include a separate guest or caretaker residence and two rustic cottages. The substantial acreage includes timberland and open pastures, a half-acre aerated pond, more than two miles of streams, and 6.7 miles of private roads and trails throughout the property. Bordering Mollie Beattie State Forest and the South Branch of the Saxtons River, the land offers opportunities for outdoor recreation, forestry, conservation, maple sugaring, and agricultural pursuits. Three access points to the VAST trail network add to the property's recreational appeal. Meticulously maintained grounds, diverse natural features, and a location near the village of Grafton complete this rare Vermont offering. See Listing Details & 60 images.

New Listing! Guilford VT Home for sale $475,000 $129 per sq.ft.

$475,000 $129 per sq.ft. Guilford VT Home »

6 Beds | 3 Baths |   Total Sq. Ft. 3682  |  Acres: 10.9
Listed on Monday Jun 8, 2026
Description: Private! Guilford! This unusual combination of a true log home with an incredible center double sided chimney....a fireplace facing the kitchen/dining and wood stove in the living room, bringing the best of both worlds:... ambience and warmth. There is a surprise of one more fireplace on the 2nd floor in the charming primary bedroom...use the ensuite for a huge walk in closet. The other half of the home is a brick and stick built addition with an amazing green house room, built to bring the outdoors in and help warm the floor tiles for passive solar...great for plants or just soaking up the winter sun with a good book. Close the door between the 2 sides and create an in-law with full kitchen, bath and bedroom, all on one floor...for those who want to age in place. The land is a combination of open...for gardening and play and Vermont woods for nature hikes. Enjoy the fruit trees, perennials and plant some veggies for putting by...Private! But, off a paved road for easy access... Loved by the owners for many years, it is time to pass to the next generation who will bring upgrades and new ideas to this very speical home. See Listing Details & 44 images.

$699,000 $297 per sq.ft. Guilford VT Home »


Price Change! Reduced by $100,000 down 14% on June 9th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 2353  |  Acres: 53.5
Listed on Thursday May 14, 2026
Description: A truly magical setting! If you've never experienced the blissfulness of the Green River Village and its historic covered bridge and crib dam/waterfall and one of the most spectacular swimming holes imaginable, it's a must visit southern Vermont destination. Nestled in this picturesque valley village is this charming old home privately situated on 53.5 acres only a short stroll up the driveway from this beautiful waterfall scene. With its open fields, outstanding sun exposure, pond, stonework, established gardens, berry bushes and apple, pear and peach trees this setting will transport you back in time. The towering old growth sugar maples around the house are true giants and are one of the first things that will make your jaw drop as you enter the peaceful homestead. The house needs work but with this stunning location and unique property attributes it's deserving and worthy of the investment. The 4-bedroom, 2.5 bath home features original fir flooring throughout the old portion and oak flooring in the addition, a huge 18' X 34' living/dining room a fireplace and massive hearth, a country kitchen with antique wood cookstove, an office/study (or 1st floor bedroom) and a small bath and laundry on the main level and 3 bedrooms, bath and the primary bedroom suite upstairs. The central heating system was propane hot water baseboard but is not functional at present. The owner currently heats with wood only. Freshly painted in 2025. Roof replaced with standing seam metal in 2005. Property is enrolled in the Use Value Appraisal (current use) with 8 acres excluded encompassing the open land, gardens and pond area around the home site. The true southern exposure, local views of the hills surrounding the river valley, access to the river and the privacy this property provides is special and very difficult to find. See Listing Details & 46 images.

New Listing! Guilford VT Home for sale $849,000 $275 per sq.ft.

$849,000 $275 per sq.ft. Guilford VT Home »

355 Ft. of Waterfront on River Green River
6 Beds | 7 Baths |   Total Sq. Ft. 3877  |  Acres: 0.93
Listed on Tuesday Jun 9, 2026
Description: Only a fortunate few have the privilege of calling Green River Village home--a quintessential Vermont hamlet distinguished by its historic covered bridge, the 1811 timber crib dam, and the iconic wood-spired church perched proudly on the hillside above. Sited adjacent to the bridge, the Green River Bridge House, originally a blacksmith shop, enjoys 300 feet of frontage along the Green River. Built in the 1830s and extensively renovated in 2002, the Inn overlooks a sweeping lawn that stretches to the river's edge, framed by stone-walled perennial gardens & a private porch perfectly positioned for enjoying the beauty and tranquility of the surrounding landscape. The home is thoughtfully designed, with spacious owner's quarters centered around a welcoming country kitchen featuring a six-burner Garland stove, Moffat turbo oven, cozy wood stove, and an impressive marble-topped island ideal for casual dining and gathering. Guests are welcomed through the front door into a gracious living and dining room that is both elegant and inviting. Beyond, you'll find a charming fireplaced pub, a cozy game room, and a sweeping staircase leading to the guest accommodations. Each guest room is uniquely enchanting, featuring remarkable recessed chandeliers, dormer windows, and private en-suite baths, including one with a jetted tub for relaxing after a day of outdoor adventure. An office and a lower-level studio apartment offer private exterior access, providing flexibility for personal or business use. Whether you envision an exceptional private residence for entertaining family & friends or wish to revive the Inn's distinguished international reputation as a bed-and-breakfast, wedding venue, or retreat destination, this property presents a rare opportunity. Cross-country skiing, cycling, hiking, swimming, fishing, kayaking, & endless exploration of Vermont's scenic back roads are all right outside your door. Picture the gentle Green River lulling you asleep each night. Showings 6/13. See Listing Details & 55 images.

$995,000 $355 per sq.ft. Guilford VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 2800  |  Acres: 64.3
Listed on Wednesday Jun 3, 2026
Description: Surrounded by 65 acres of glorious land w/meadows, woodland, stone walls, and the meandering Keets Brook, this exceptional property offers a blend of beauty, privacy, and thoughtful design. The grounds are exquisitely landscaped with Gordon Hayward-designed gardens, specimen trees , stone walkways and mature blueberry bushes. A saltwater pool, private rear deck, oversized two-car garage, Kohler generator and sweet guest house w/bath & kitchenette complete this remarkable setting. The home (half new build and the other half totally renovated, all in 2001) is light-filled with imaginative touches that beautifully blend form and function. A front porch welcomes you into the mudroom featuring slate flooring, built-ins, closet, and adjacent laundry. The stunning kitchen is the centerpiece with maple and porcelain flooring, sloped ceilings, cherry cabinetry, slate countertops, huge windows framing the landscape, a Viking six-burner range, Sub-Zero refrigerator & Bosch dishwasher. To the right of the kitchen is a gracious dining room with oversized windows, cherry cabinetry w/slate counters, and a patio door to the deck and gardens. To the left is an intimate family room w/ a stained-glass window. A spacious living room offers hardwood flooring, fireplace with gas insert, and access to the front porch. The main level also includes a den with built-in cabinetry and a large bay window, along with a powder room and double closets. Upstairs (A/C) are 3 spacious bedrooms and a shared tile bath with double vanity and hand-painted dolphin tiles. The primary suite features cathedral ceilings with fan, a large window overlooking the gardens, walk-in closet, and a luxurious bath with jetted soaking tub surrounded by windows, double marble-top vanity, and a glass-fronted tile shower. A truly magical Vermont retreat where exceptional craftsmanship and breathtaking natural surroundings come together in perfect harmony. (Land is in Current Use for tax savings). Showings start 6/11/26. See Listing Details & 59 images.

$825,000 $674 per sq.ft. Halifax VT Home »

5 Beds | 1 Baths |   Total Sq. Ft. 1224  |  Acres: 216
Listed on Wednesday May 13, 2026
Description: Imagine 216 acres of rolling fields, serene woodlands, and a glowing sugarbush tucked along a quiet country dirt road near the Massachusetts border in Halifax, just a short drive to Brattleboro and Wilmington. Held by the same family for generations, this timeless Southern Vermont property includes a farmhouse, barns, and several outbuildings--many ready for restoration, reimagining, or replacement. Historic stone walls trace through the landscape, while a peaceful wetland area creates a natural haven for wildlife. Blending character with practicality, the property also offers solid infrastructure already in place, including power, a newer well, a newer roof, and the essential groundwork to move your vision forward. The land is truly the centerpiece, featuring sweeping open fields, a productive sugarbush, and marketable timber. See Listing Details & 40 images.

$3,800,000 $300 per sq.ft. Halifax VT Home »


Price Change! Reduced by $2,100,000 down 55% on May 22nd 2026
4 Beds | 8 Baths |   Total Sq. Ft. 16736  |  Acres: 177.4
Listed on Monday Sep 22, 2025
Description: Exceptional 177+ Acre Estate with Luxury Log Home, Event Venue & Craft Beverage Facilities. Experience unmatched luxury and opportunity on this remarkable 177+ acre estate. Featuring an 8,000+ sq ft timber frame log home, a 7,100 sq ft finished event venue, and on-site winery, craft brewery, and champagne-making facilities, this turn-key property is ideal as a private residence, retreat, or destination business. The custom log home showcases vaulted ceilings, radiant in-floor heating, hardwood and stone flooring, and imported Italian tile. A chef's kitchen and expansive 800' wraparound deck offer the perfect space to entertain while enjoying stunning 360-degree mountain, vineyard, and valley views. The boutique vineyard supports in-house wine production, complemented by a dedicated beer brewing system and traditional méthode champenoise champagne facility--perfect for tastings or exclusive label production. The event venue includes a second commercial kitchen, two custom bars, elegant restrooms, and a 7,900 sq ft stone patio with cascading fountains--ideal for weddings, retreats, and celebrations. Freshly painted and impeccably maintained, this estate offers total privacy with year-round recreation nearby, including Wilmington's fine dining, Sunset Lake, and Hermitage Golf Club. A rare opportunity--schedule your private tour today. See Listing Details & 60 images.

Under Contract Hancock VT Home for sale $369,900 $147 per sq.ft.

$369,900 $147 per sq.ft. Hancock VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 2516  |  Acres: 3.76
Listed on Monday Apr 13, 2026
Description: Adjoining the Green Mountain National Forest, this farmhouse has plenty of room and easy access on one of the most scenic Routes in Vermont! Wonderful updates including replacement windows, standing seam roof, 200 amp electric service and modern appliances. Yet retaining the grace and charm of an old farmhouse including wood floors and exposed beams. Other features include a detached garage & attached shed. The mountain views from this location are outstanding. Year-round recreation is very close including skiing/riding at Sugarbush, Middlebury Snow-Bowl and Killington. In the summer, explore the GMNF for swimming holes & wildlife viewing. This is a lot of house for the money! See Listing Details & 55 images.

New Listing! Village of East Hardwick in Town of Hardwick VT Home for sale $349,900 $197 per sq.ft.

$349,900 $197 per sq.ft. Village of East Hardwick in Town of Hardwick VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1773  |  Acres: 0.12
Listed on Monday Jun 8, 2026
Description: This charming village duplex offers warmth, character, and flexibility in a convenient location. The first-floor residence welcomes you with an inviting atmosphere from the moment you step inside. A spacious and flowing floor plan features a large dining area, charming kitchen, and cozy office nook that seamlessly connect to the generous living room, creating an ideal space for both everyday living and entertaining. The main level also includes a comfortable bedroom and full bath, while a second-floor bedroom provides additional privacy and versatility. The upstairs residence is equally appealing, filled with natural light and offering a bright, comfortable living environment. This unit features a large living room, spacious eat-in kitchen, full bath, and two bedrooms, making it an excellent option for rental income, multi-generational living, or guest accommodations. Adding to the property's appeal is the attached direct-entry two-car garage with abundant storage space above, along with two separate driveways providing ample parking for residents and visitors alike. Recent improvements include a new chimney and new garage doors, enhancing both function and peace of mind. Outside, the spacious lawn surrounds the home, offering plenty of room for gardening and outdoor enjoyment. Spend your mornings relaxing on the covered front porch and your evenings unwinding on the private back deck. Whether you're seeking an investment opportunity, owner-occupied income property, or a home with space for extended family, this well-maintained village duplex is ready to welcome its next chapter! See Listing Details & 27 images.

$350,000 $183 per sq.ft. Hardwick VT Home »


Price Change! Reduced by $25,000 down 7% on June 6th 2026
6 Beds | 2 Baths |   Total Sq. Ft. 1913  |  Acres: 0.17
Listed on Monday Apr 13, 2026
Description: Hardwick, VT -- This spacious and beautifully maintained home offers 6 bedrooms and 1.25 baths, all within walking distance to downtown amenities. The kitchen is a standout, featuring finely crafted cherry cabinetry, Corian countertops, and a stunning African granite-finished island, perfect for cooking and gathering. Numerous updates have been completed, including a newer roof, furnace, and exterior paint, along with Efficiency Vermont-supported spray foam insulation in the basement, providing year-round comfort and energy savings. A one car garage (approximately 365 sq. ft.) is currently used as a workshop, offering flexible space for hobbies, storage, or future garage use. This home blends classic charm with modern efficiency in a convenient village location. See Listing Details & 25 images.

$358,500 $220 per sq.ft. Hardwick VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1626  |  Acres: 0.4
Listed on Monday Jun 1, 2026
Description: Conveniently located on a corner lot this well-maintained village home offers the ease of walking to local shops, restaurants, schools & other village amenities while coming home to a property that offers flexibility of living arrangements. Whether you're seeking a residence that has rental income, multi-generational living options, or the potential for single family living, this property delivers. The main level serves as the primary residence and welcomes you through an inviting entry foyer. The large eat-in kitchen offers ample cabinet & counter space along with a convenient laundry closet, creating a practical hub for daily living. The kitchen flows seamlessly into the comfortable living room featuring a bay window that fills the space with natural light and a beautiful wood slat decorative wall. The office provides the perfect space for working from home, hobbies, or simply relaxing with a good book. The primary bedroom is a spacious retreat complete with a propane fireplace, while the second bedroom features sliding glass doors leading to the back deck. A full bath completes the 1st floor living space. The second floor has been thoughtfully configured as an Accessory Dwelling Unit (ADU). The unit includes a full kitchen, stackable laundry, a small living/dining area, a generously sized bedroom currently used as a living room, a second bedroom with direct access to the back exterior staircase, and a full bathroom. Outside, the lot offers a wonderful blend of usable lawn space and gardening opportunities. An attached two-car garage with direct entry into the main residence, provides everyday convenience, while the enormous storage area above offers impressive space for seasonal items, equipment, hobbies, or future expansion possibilities. Properties offering this level of versatility, storage, and village convenience are increasingly hard to find. Come explore the possibilities and discover how this unique property can fit your lifestyle for years to come! See Listing Details & 24 images.

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