Very Cool Houses

MLS Number 5102873

• Residential Single Family
• Full Bath 1
• Village Quechee
• Address 145 Stephen Day Lane
• Construction Existing

Unlike anything else in Quechee, this custom four-bedroom, four and a half bath Greek Revival farmhouse combines the fine craftsmanship of Connor Homes with exceptional custom finishes throughout. Generously proportioned spaces, superb lighting, radiant heat, and meticulous attention to detail create a home of remarkable elegance, warmth, and function. The beautifully designed kitchen features custom Crown Point cabinetry, thoughtful accent lighting, innovative pull-down storage, and a reclaimed chestnut island topped with antique granite and complemented by matching custom-built stools. Crown Point cabinetry extends throughout 12 rooms, reflecting the extraordinary level of craftsmanship found across the home. Carlisle wide plank, old-growth heart pine floors with radiant heat flow throughout the living spaces, while refined millwork and a reclaimed marble fireplace mantel add timeless character. Across the rear of the home, an expansive wall of glass fills the interior with natural light and opens to a full length mahogany deck, creating a seamless connection to the outdoors. From its exquisite cabinetry and millwork to its thoughtfully designed mechanical systems, every element has been carefully considered. This is a truly exceptional home . . . equally suited to comfortable everyday living and gracious entertaining.

Listed by Derek Cosentino of Four Seasons Sotheby's Int'l Realty

MLS Number 5101689

• Residential Single Family
• Full Bath 2
• Construction Existing
• Bedrooms 4
• Bathroom 3

10 MINUTES TO STRATTON RESORT | This beautifully reimagined former schoolhouse blends timeless Vermont character with thoughtful modern updates. Built around the historic Goodaleville Road schoolhouse with a timber-frame addition, and renovated by Vermont Country Builders, the home reflects exceptional craftsmanship, energy efficiency, and enduring design. Just 10 minutes from Stratton Mountain Resort and less than a mile from Honeypie Restaurant and Rawsonville Market, the location offers easy access to the mountain, local favorites, and everything the area has to offer. High ceilings, generous windows, and two sunrooms fill the interior with natural light, while quality construction and thoughtful details are evident throughout. Recent improvements include a standing-seam metal roof, new Marvin windows, mini-split heating and cooling, new appliances, a large new deck, a new drilled well, a whole-house generator, an EV charger, restored floors and fir doors, updated tile, and custom built-ins. The property has a deep connection to the surrounding land. Beautiful landscaping and stonework complement an open field, apple orchard, raised garden beds built with hemlock milled from the property, and a useful storage shed. The large deck with hot tub creates an inviting place to relax and take in the serene setting. Situated along the Winhall River with direct access to the West River Rail Trail, the property makes it easy to walk, bike, swim, and enjoy the outdoors right from home. A five-bedroom septic system provides flexibility for future expansion. This is the Vermont home you have been looking for-full of character, warmth, and history, yet updated with the level of care and quality that makes ownership easy from day one. A trusted local builder has already done the hard work. Make this your Vermont address. Seller is the listing broker. Neighboring property available 494-498 Goodaleville Road - MLS#5101688.

Listed by Cheyanne Pugliese of The Haven Group

MLS Number 5097823

• Residential Single Family
• Full Bath 4
• Construction Existing
• Bedrooms 4
• Bathroom 5

It's hard to say which season you'll enjoy most in this exceptional 4-bedroom, 5-bath fully furnished and equipped custom-built home, privately set on ten acres comprised of two separate 5-acre lots, with the lower lot offering possible development opportunities. Located in an established neighborhood with protective covenants that preserve both value and tranquility, this thoughtfully designed home showcases true pride of ownership with real wood finishes, detailed millwork, and quality materials throughout, offering a level of warmth and character that's increasingly rare. Located on sought-after Cricket Hill Road in Killington, the property is perfectly positioned for year-round recreation, just a mile from Green Mountain National Golf Course and only ten minutes from Killington Resort. Yet despite its convenience, the setting feels worlds away, with sweeping long-range mountain views creating a stunning backdrop in every season. Inside and out, the home is designed for comfort and connection to nature. In the warmer months, relax by the pool while listening to the soothing sounds of a nearby waterfall feature tucked into the greenhouse, surrounded by mature landscaping and vibrant gardens. The property's private pond and outdoor hot tub offer additional spaces to unwind, entertain, and enjoy the peaceful surroundings. As winter arrives, take in panoramic views of snow-covered peaks, including Pico Mountain, before heading out to nearby ski areas or returning home to the serenity of your mountain retreat. The craftsmanship continues throughout the interior, where inviting living spaces and fine details create a cozy yet refined atmosphere. A well-appointed in-law apartment above the attached two-car garage provides both interior and private exterior access, making it ideal for guests or extended family seeking independence without sacrificing comfort. Call today to book your private showing for this unique opportunity.

Listed by Bret Williamson of Killington Valley Real Estate

MLS Number 5095837

• Residential Single Family
• Full Bath 3
• Construction Existing
• Bedrooms 4
• Bathroom 4

At the beginning of a dirt road just outside the historic village of Grafton VT you will find an exceptional country estate that combines timeless New England charm with modern comfort, privacy, and equestrian amenities. Thoughtfully designed to replicate a classic colonial home and extensively updated by its current owners, this meticulously maintained property offers an extraordinary lifestyle in one of Vermont's most picturesque communities. As you arrive you are welcomed by beautifully landscaped grounds, mature perennial gardens, and a private wooded setting that creates a true sense of seclusion. Despite its peaceful surroundings, the property is just minutes from Grafton Village and within 45 minutes of several premier Southern Vermont ski resorts, making it an ideal year-round residence, vacation home, or family retreat. Offering four bedrooms, four bathrooms, and numerous living and gathering spaces, the home is perfectly suited for hosting family and friends. The well-appointed chef's kitchen features an island with seating, abundant workspace, and easy access to the home's entertaining areas. A spacious family room with a stunning stone fireplace, private bath, and loft above serves as a centerpiece of the home, while three additional working fireplaces add warmth and character throughout. A second-floor den and game room provide flexible living space for relaxation, recreation, or remote work. Outdoor amenities are equally impressive. Enjoy summer days by the inground swimming pool, tend to the gardens, or explore the surrounding landscape. For horse enthusiasts, the property includes a four-stall barn and fenced pastures. Additional features include a two-car garage, clean and spacious basement, garden shed, and abundant storage throughout. Whether you're searching for a Vermont equestrian property, luxury country home, or four-season retreat near skiing and outdoor recreation, this remarkable Grafton estate offers you the very best.

Listed by Keith Nowak of Four Seasons Sotheby's Int'l Realty

MLS Number 5096179

• Residential Single Family
• Full Bath 2
• Address 1233 Satterly Road
• Construction Existing
• Bedrooms 4

Welcome to your Vermont equestrian dream! Nestled on 13 beautifully landscaped acres in Ferrisburgh, this exceptional horse property offers an unparalleled blend of country living and functional design. The main residence welcomes guests through a formal foyer or a large mudroom off the oversized, two-bay garage. Inside, the living room features soaring two-story windows, the space designed for passive solar warmth in winter and to remain cool in summer. The main floor also hosts a spacious kitchen with a center island, formal dining room, cozy library, and beautiful three-quarter bathroom complete with fully tiled shower. Upstairs, the second floor houses all three bedrooms, boasting gorgeous views of the surrounding landscape, alongside a spacious full bathroom. The walkout basement adds incredible value with a media room, laundry, ample storage, and fully equipped home office with an exterior entrance and two windows. Step outside to a gorgeous patio featuring stone-walled raised garden beds and easy access to the outbuildings. Car enthusiasts and pet lovers will marvel at the garage, which includes a dedicated dog wash station and protective paneling designed for indoor car washing. Above, a private entrance leads to a stunning studio apartment with vaulted ceilings, full kitchen, full bathroom, and laundry space. The equestrian and workshop facilities are extraordinary. The 36x60 horse barn features five box stalls, one large open stall, four standup stalls, tack room, office, and massive hayloft with room for 4,000 small square bales. Huge barn doors open directly for easy access to the property's riding arena. Additional structures include a massive 60x110 clear-span building (perfect for hay, equipment, or livestock), heated 16x40 shop/RV building with power and lights, 12x24 storage shed with a firewood lean-to, and charming 10x15 former sugarhouse. A truly rare, turnkey country estate.

Listed by Heather Morse of Coldwell Banker Hickok and Boardman

MLS Number 5090626

• Residential Single Family
• Full Bath 3
• Address 1276 Swinton Road
• Construction Existing
• Bedrooms 6

Set on 40 private acres with sweeping views in every direction, this property offers a front-row seat to Vermont's natural beauty from open pastoral fields to the Green Mountains and Adirondacks. The south-facing orientation fills the home with natural light throughout the day, while both sunrises and sunsets become part of everyday life. Designed for comfortable living and easy flow, the home offers the flexibility and space today's buyers are looking for. The first-floor primary suite features a walk-in closet, laundry room, and a spacious bath with both a jetted tub and separate shower. A nearby office provides a quiet work-from-home space or could easily serve as a den or reading room. The heart of the home is the large kitchen and dining area with cherry cabinetry, generous counter space, and a center island ideal for gathering. The living room opens directly into a bright sunroom with access to the wraparound deck, overlooking the in-ground pool, outdoor fireplace and established gardens. The basement is partially finished with several storage rooms, a wine cellar a family room space and all of the utilites. Above the attached three-car garage is a well-appointed in-law or guest suite complete with a living room, bedroom, full bath, and kitchenette. A separate detached building adds even more versatility, offering a workshop, additional garage bay, half bath, separate heating system, and two finished rooms above which are perfect for a home business, studio, gym, or recreation space. The classic red Vermont barn provides additional storage or space for small animals and a whole house generator gives you all the backup you might need! Despite the peaceful setting and exceptional privacy, the property remains conveniently located and is 15 minutes to Middlebury or Vergennes and about an hour to Burlington.

Listed by Amey Ryan of IPJ Real Estate

MLS Number 5083578

• Residential Single Family
• Full Bath 1
• Address 50 Grouse Lane
• Construction Existing
• Bedrooms 4

Custom built Dorset Hollow estate offered for the first time since 1998. Perfectly situated on 10 private acres abutting 3,200 acres of conservation land, this 5,100 sq ft residence combines timeless quality, fine finishes, and Vermont mountain charm. Designed for comfort and entertaining, the home features 4 bedrooms, 5 bathrooms, and an attached 2-car garage. Elegant details include four fireplaces, verdi marble flooring, Marvin windows, a slate roof, and a Viessmann boiler premier materials chosen for durability and style. The dramatic living room boasts a large wood-burning fireplace framed by 8-foot, 12-panel Marvin windows, crescent-shaped upper windows, and soaring 30-foot ceilings that fill the space with natural light. The chef's kitchen will delight serious cooks, offering THOR double ovens, a mini wood-burning brick fireplace, center island with butcher block top, verdi marble floors, soapstone counters, Wood Harbor cabinetry, and a charming built-in breakfast alcove. The formal dining room features 12-foot ceilings, crown molding, and direct access to an elevated synthetic sundeck, ideal for entertaining or relaxing outdoors. The intimate den, with its brick fireplace, wet bar, and copper sink, provides a cozy retreat for quiet evenings. A first-floor half bath and laundry room add convenience. Upstairs, a custom fluted staircase leads to two spacious guest bedrooms, a full tile bath, and a walk-in cedar closet. The primary suite (30x14) is a luxurious escape featuring a gas fireplace, 10-foot ceilings, crown moulding, and peaceful mountain views. Two walk-in closets and a spa-inspired primary bath include a sauna, whirlpool tub, tile shower, and double vanity. A fourth ensuite bedroom completes the upper level. Outdoors, the serene setting offers unmatched privacy while being just minutes from Dorset Village and Manchester amenities. This rare offering combines classic design, privacy, and enduring Vermont elegance.

Listed by David Halligan of Four Seasons Sotheby's Int'l Realty

MLS Number 5103836

• Residential Single Family
• Full Bath 1
• Address 84 Overlook Road
• Construction Existing
• Bedrooms 3

Commanding panoramic mountain views define this exceptional Dorset Overlook residence, where every room is designed to capture the beauty of Southern Vermont's ever-changing landscape. Bathed in natural light, the home's open floor plan creates an effortless flow between living, dining, and entertaining spaces, making everyday living as enjoyable as hosting family and friends. The thoughtfully designed layout offers comfortable living spaces, complemented by expansive windows that frame the spectacular vistas from nearly every angle. Step outside to a stunning marble patio, the perfect setting for al fresco dining, or unwind on the screened porch while taking in the mountain air and unforgettable sunsets. Ideally situated on the sought-after Dorset Overlook Road, this home offers a peaceful setting just minutes from the villages of Dorset and Manchester, renowned for their dining, shopping, recreation, and year-round cultural attractions. For those seeking additional living space, the unfinished second-floor attic offers an excellent opportunity for future expansion, whether envisioned as guest accommodations, a studio, an office, or a recreation space. A rare offering where breathtaking views, timeless design, and one of the area's most desirable locations come together to create an exceptional Vermont lifestyle.

Listed by Carol O'Connor of Four Seasons Sotheby's Int'l Realty

MLS Number 5063214

• Residential Single Family
• Full Bath 3
• Address 187 East Hill Road
• Construction Existing
• Bedrooms 3

Welcome to 187 East Hill Road, an extraordinary 218-acre estate in the serene town of Woodbury, Vermont. This remarkable property is a rare find, offering unparalleled natural beauty and luxurious rustic living. At the heart of this expansive estate lies a charming log cabin, meticulously crafted with exotic hardwoods that infuse warmth and character into every room. Flooring is Brazilian Cherry, the kitchen is custom crafted of Guyana Mahogany, the great room ceiling is finished in Spanish cedar, and the expansive decks and porches are made of luxurious Ipe decking. The cabin seamlessly blends with its surroundings, providing a cozy retreat while offering modern comforts. The property boasts extensive frontage on the pristine Woodbury Lake. Enjoy serene water views from your private dock, or while kayaking, fishing, and peaceful lakeside moments on your private beach, or your additional deeded access to the lake. The estate's vast network of trails invites you to explore the diverse landscape, whether by foot, horseback, or ATV, making it an outdoor enthusiast's dream. Trails follow waterfalls on one border of the property and will allow the perfect location for a zen / meditation garden allowing the opportunity to get lost in the sound of rushing water as your stress melts away. Whether you seek a private retreat, a family compound, or a nature lover's paradise, 187 East Hill Road offers endless possibilities.

Listed by Mathew Ghafoori of RE/Max Heritage