Very Cool Houses

MLS Number 5098424

• Residential Single Family
• PricePerSqFt 659.21
• Full Bath 3
• Construction Existing
• Bedrooms 5

Exceptional Views to Killington! Perched high on a private knoll and surrounded by open lush meadows and surrounded by antique stonewalls. This 5 bedroom, 4 bathroom extended cape styled home was renovated approx 15 years ago with handsome hardwood floors throughout. Large kitchen with Calcutta Marble, Electrolux stainless appliances and ample storage that opens into the dining room- The formal living room also has expansive views beyond the french doors to a covered porch across the back of the house for entertaining family and friends. The living room is anchored by a traditional propane fireplace, custom book shelves, lovely pocket doors... it's easy to want to curl up with a good book in the wintertime. Generous primary suite with custom built-ins, walk in closet and expansive bathroom located on first floor. There is a second guest bedroom with full bath on the first floor as well as a cozy den surrounded by built-in bookcases. Second floor features 3 very large bedrooms and 2.5 bathrooms including a clawfoot tub. A walk out basement for easy access to store patio furniture. Ample storage or potential for a workshop. There is a generator on site, 2 bay attached garage and barn/stables down below the property. The majority of the property is open and mowed to perfection. This estate has been well maintained and in a superior location. Killington/Pico and Okemo a short distance. Easy access to historic Woodstock, championship golf, tennis, cross country skiing and shopping. Come take a look. Not many properties with this exceptional view!

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

MLS Number 5090466

• Residential Single Family
• PricePerSqFt 393.16
• Full Bath 2
• Address 424 Miller Way
• Construction Existing

Nestled on historic Whipple's Point, this extraordinary lakefront estate offers the rare privilege of both breathtaking sunrise and sunset views across the sparkling waters of Lake Memphremagog. Set on 5.1 private acres with 500 feet of pristine shoreline, the property features a sandy beach, private dock, and boat launch area creating an exceptional retreat for boating, entertaining, and year-round enjoyment. At the heart of the estate is a striking contemporary residence offering over 5,000 square feet of thoughtfully designed living space. Nearly every room captures panoramic lake views, while soaring ceilings and expansive windows fill the home with natural light. The open-concept layout seamlessly blends elegance and comfort, featuring a chef's kitchen with abundant cabinetry and a walk-in pantry, a formal dining room, and a stunning glass-enclosed sunroom designed for all-season enjoyment. The luxurious primary suite serves as a private sanctuary, complete with its own den, spa-inspired en-suite bath, and oversized walk-in closet. Upstairs, you'll find two additional bedrooms and a spacious bonus room ideal for guests, a home office, or additional living space. A detached three-bay garage with an upper-level family and entertainment area offers incredible flexibility and sweeping lake views, perfect for hosting or creative use. Most high-end furnishings convey with the sale, allowing for a seamless transition into this meticulously maintained property. More than just a home, this is an opportunity to experience an unparalleled lakefront lifestyle.

Listed by Tina Leblond of Big Bear Real Estate

MLS Number 5044086

• Residential Single Family
• PricePerSqFt 478.13
• Full Bath 3
• Address 248 Gird Lot Road
• Construction Existing

Perched above the Connecticut River Valley with sweeping views to the New Hampshire mountains, this meticulously maintained five bedroom, four and a half bath home offers a rare opportunity just 30 minutes to Hanover, NH, Dartmouth College, and Dartmouth Hitchcock Medical Center. For medical professionals relocating to the Upper Valley, this property provides privacy, acreage, and panoramic views at a value rarely found closer to Hanover or Lebanon. Easy access to I 91 allows a comfortable commute to Dartmouth Hitchcock Medical Center while enjoying a peaceful Vermont setting. The open concept layout offers a desirable main level living option and is well suited for multigenerational living or extended guest stays. Hardwood floors, tall ceilings, and expansive windows fill the home with natural light. The spacious kitchen is ideal for entertaining with granite countertops, high end cabinetry, built in refrigerator, wine fridge, and a generous island with prep sink. Both the living room and den feature fireplaces and custom built ins. Upstairs bedrooms offer comfort and privacy. The walkout lower level with tall ceilings and natural light provides excellent expansion potential for recreation space, gym, or media room. The three-car attached garage includes a separate bay with private entrance and direct access to unfinished space above, ideal for a future guest suite, studio, or in law apartment. Outside, enjoy a spacious deck, fire pit area, cleared yard, fenced pen, and spring fed pond. Convenient to Okemo Mountain Resort, Lake Sunapee, Crown Point Country Club, and Upper Valley amenities. Approximately 2 hours to Boston, MA and under 3 hours to Fairfield County, CT, offering strong appeal for both primary and second home buyers seeking Vermont lifestyle with New England accessibility.

Listed by Karen DeMas and Jay Farrar of Four Seasons Sotheby's Int'l Realty

MLS Number 5097953

• Residential Single Family
• PricePerSqFt 520.45
• Address 634 Lower Dover Road
• Construction Existing
• Bedrooms 5

Discover a once-in-a-generation opportunity to own an extraordinary 745± acre estate in the heart of Southern Vermont. Steeped in centuries of history yet thoughtfully updated for modern living, this remarkable property combines unmatched natural beauty, recreational opportunities, and agricultural potential. The diverse landscape features expansive open fields, mature woodlands, pristine streams, scenic mountains. Miles of historic carriage roads have been transformed into an extensive trail network ideal for mountain biking, hiking, trail running, horseback riding, cross-country skiing, and snowshoeing. Abundant wildlife, a productive sugarbush, and managed timber resources make this an exceptional property for conservation, recreation, or income-producing land management. The 4,400+/1 square foot main residence offers five bedrooms and comfortable, updated living spaces that blend timeless Vermont character with today's conveniences. A charming carriage house includes a private two-bedroom apartment, providing ideal accommodations for guests, family, caretakers, or rental opportunities. An extensive collection of outbuildings offers outstanding flexibility for equestrian pursuits, livestock, woodworking, equipment storage, workshops, or a variety of agricultural and recreational uses. Modern infrastructure includes drilled wells, updated septic systems, a whole-house generator, and high-speed internet, allowing for year-round comfort without sacrificing the property's peaceful rural setting. Conveniently located near renowned ski resorts, shopping, dining, and four-season recreation. Metropolitan areas are easily accessible making this an ideal full-time residence, sporting estate, family compound, working farm, or legacy investment. Properties of this size, quality, and versatility rarely become available. This is a truly exceptional Southern Vermont offering.

Listed by Michael Purcell of Berkley & Veller Greenwood/Dover

MLS Number 5089892

• Residential Single Family
• PricePerSqFt 491.72
• Full Bath 4
• Construction Existing
• Bedrooms 5

A Serene Dorset Hollow Retreat Along the Mettowee River Tucked into the storied Dorset Hollow, this 4.6-acre retreat enjoys 488 feet of Mettowee River frontage, offering a rare blend of tranquility, comfort, and timeless Vermont charm. Expansive mountain views and the soothing sounds of the river surround you-fall asleep each night to its calming presence. Multiple outdoor spaces include a covered front porch, kitchen-side veranda, and a bluestone terrace that seamlessly connects to the open-concept living areas. The home is perfectly positioned for southern light and sweeping views, blending rustic elegance with modern sophistication. Inside, a dramatic two-story foyer and stone fireplace anchor the beautifully maintained residence. Large sliders flood the home with light, creating harmony between indoor and outdoor living. A granite chef's kitchen, dining room, and living room offer stylish functionality. The main-level primary suite features a spa-like bath and walk-in closet. A study and three ensuite bedrooms complete the living spaces. Enjoy the peaceful yard, fish from your private stream frontage, and take in the vibrant foliage or snowy fields. Thoughtful extras include a hot tub, finished bonus room above the garage, and an unfinished basement for future expansion. Just minutes from Dorset Village, this exceptional property offers peace, privacy, and a deep connection to the natural beauty of Southern Vermont.

Listed by Britt Wohler of WOHLER REALTY GROUP, Kim Morgan-Wohler of Wohler Realty Group

MLS Number 5061819

• Residential Single Family
• PricePerSqFt 412.74
• Full Bath 6
• Address 288 Cedar Lane
• Construction Existing

Imagine your own private Vermont resort getaway just a short drive from Bromley Mountain! Nestled on 12 peaceful acres, this property offers the perfect blend of relaxation, recreation, and convenience. Spend summer days swimming or paddling on your private pond, relaxing on the sandy beach, soaking in the hot tub, or unwinding in the sauna after a workout in your home gym. Evenings can be enjoyed fireside under the stars. The main residence boasts a flowing floor plan designed for entertaining, with large windows filling the home with natural light and framing water views from nearly every room. A brand-new septic system, built for seven bedrooms, ensures comfort and space for all. The oversized two-car garage provides ample storage for all your outdoor gear. Set apart among the trees, the guest cottage offers its own sense of retreat with vaulted ceilings, an open living space, two en-suite bedrooms, and an additional two-car garage. A short walking path leads directly to the water's edge. Located less than a mile from Peru's charming Hapgood Store and just 2 miles from Bromley Mountain, this property truly offers four-season enjoyment in the heart of Vermont. The current owner benefits from strong rental income when the properties are not being used for personal enjoyment

Listed by Jessica Citera of Cummings & Co

MLS Number 5067161

• Residential Single Family
• PricePerSqFt 527.67
• Full Bath 3
• Construction Existing
• Bedrooms 4

This architecturally designed contemporary farmhouse sits on 13.4± acres and combines beautiful craftsmanship with attention to detail, including beautiful views from every window. Situated convenient to Burlington, Stowe and The Mad River Valley, and minutes from Waterbury Village (which in 2024 was featured by The Boston Globe as “the best little foodie town in New England”), this home is located on a secluded private road with mountain views, and a serene environment. The first floor has an elegant entry foyer, living room, dining room, primary bedroom suite, office/bedroom, mudroom replete with a dog shower, powder room and gourmet kitchen with Sub Zero, Wolf and Cove appliances, custom made cherry cabinets, Vermont Verde marble countertops and a separate breakfast nook and den. The second floor includes three bedrooms, two full baths, and spectacular views of both the Mansfield and Worcester mountain ranges. The finished basement has a custom-built office, full bathroom, and a workout room. Both the basement and first floors have radiant heated floors. Outdoor features include extensive landscaping with perennial gardens, stone patios, a hot tub, firepit, swimming pond and a post and beam constructed, standalone tree/playhouse. Energy and heating features include solar panels and heat pumps that provide warmth in the winter and air conditioning during the summer months. This home has it all.

Listed by Pall Spera of Pall Spera Company Realtors-Stowe (Phone: 561-762-8188), Susan ORourke of Pall Spera Company Realtors-Stowe Village

MLS Number 5106601

• Residential Single Family
• PricePerSqFt 244.57
• Full Bath 3
• Address 117 Highbridge Road
• Construction Existing

The Inn at Grace Farm is a distinctive Vermont estate with three thoughtfully designed buildings: a 5-bedroom Inn with connected Stone House and a separate octagonal timber-frame barn. Together, they create an exceptional private family compound, multigenerational retreat, luxury second home or continued hospitality/event property. The Inn offers five ensuite bedrooms, half bath, kitchen, great room, dining and living spaces. Connected by a breezeway, the Stone House adds three bedrooms, office, two shared baths, large kitchen, dining and living areas. The buildings can function together or independently, offering exceptional flexibility for family, guests and private living. A 3,300 SF walk-out lower level with multiple access points provides substantial storage, utility and flexible space. Built to rigorous standards, the structures feature traditional wood-pegged mortise-and-tenon joinery, highly efficient stress-skin insulation, standing seam roofing, advanced mechanical systems and integrated fire protection. Constructed in 2014 from locally harvested timber, the separate octagonal barn features a dramatic central timber post, expansive gathering space, radiant-floor heat, gas fireplace, catering kitchen, commercial event infrastructure and two restrooms. Its scale and character make it equally suited to private entertaining, family gatherings, celebrations or events. Set amid conserved pastureland with uninterrupted panoramic Green Mountain views, the grounds offer multiple outdoor gathering areas and room for additional amenities. About 25 minutes from Burlington International Airport, with convenient access to Lake Champlain, ski resorts and year-round recreation, Grace Farm is a rare combination of craftsmanship, privacy, guest accommodations and modern infrastructure. Existing wedding commitments are in place and will be honored under their existing agreements. Also listed in MLS#5106600. Website: innatgracefarm.com

Listed by Carrie Paquette of BHHS Vermont Realty Group/S Burlington

MLS Number 5095474

• Residential Single Family
• PricePerSqFt 585.02
• Full Bath 1
• Address 254 Town Line Road
• Construction Existing

Town Line Estate is a once-in-a-generation offering. This extraordinary 22-acre private estate is a testament to master builder craftsmanship and refined living. From the moment you arrive, every detail speaks to an uncompromising standard, classic beams, rich cherry cabinetry, and two Rumford fireplaces create warmth and character throughout. The heart of the home is a restaurant-quality kitchen designed for serious entertaining, flowing seamlessly to a spacious back deck and elegant stone patio. Soak in natural light year-round in the stunning solarium, or retreat to the dramatic tower atrium, an architectural showpiece unlike anything in the market. The estate's grounds are simply breathtaking: manicured gardens of rare beauty, a serene glacial pool, and outdoor spaces that invite both grand gatherings and quiet reflection. Two distinguished carriage houses complete this remarkable compound, one housing an impressive classic car collection and memorabilia, offering the discerning collector a showcase space worthy of the collection itself. Thoughtfully designed for the way you live, the home also features a dedicated exercise room, an expansive private office, a charming potting room for the avid gardener, 4 baths, and heated garages. Whether you seek a private sanctuary, a generational family estate, or an entertainer's dream, this property delivers on every level. Visit the Okemo real estate community today. Taxes are based on the current town assessment.

Listed by Kevin Barnes of William Raveis Real Estate Vermont Properties

MLS Number 5111781

• Residential Single Family
• PricePerSqFt 1066.35
• Full Bath 4
• Address 165 High Meadow Road
• Construction Existing

Wandering Moose: a rare heated-pool ski house on High Meadow, on the Stratton winter shuttle route. Rebuilt top to bottom in 2024 with a designer interior, then finished with a heated in-ground pool (2025), hot tub, barrel sauna, Level 2 EV charger and rooftop solar. Open great room with stone wood-burning fireplace and indoor swing, open kitchen and dining, walkout lower level with wet bar and arcade, 4 bedrooms and 4.5 baths. One of the only private heated-pool rentals near Stratton, and it earns like it: $155,716 gross in 2025 and $216,999 trailing 12 months; about $102,000 in confirmed future bookings on the books (9 stays). GOLF-COURSE ESTATE OPPORTUNITY: the seller also owns the adjoining Indian Paint Brush building lots (Lots E-13R & E-14R, 2.48± ac), which abut the Stratton golf course and are listed separately at $500,000. Buy both: live in or rent the Moose while you build your estate next door. Featured on the Destination Channel's Staycation TV program. PORTFOLIO FOR SALE: This property is one of five 42 North properties in Winhall offered individually or together (four turnkey short-term rentals + the Indian Paint Brush building lot; ~$560K combined trailing-12-month gross rental revenue). Ask about package pricing. Listing broker is a principal and beneficial owner of the selling entity. Potential tax advantages for STR buyers (non-passive treatment, cost segregation, bonus depreciation) - consult your tax advisor. Revenue figures are gross rental revenue excluding taxes, before expenses; unaudited; past results do not guarantee future results.

Listed by David Powers of 42 North LP