Very Cool Houses

MLS Number 5056222

• Land
• Address 215 Vt Route 30
• Acreage 60
• Area VT-Bennington
• Utilities None

Opportunities are Knocking! Welcome to an extraordinary 50+ acre estate parcel in Dorset, perfectly positioned along Route 30. This remarkable property offers the ultimate trifecta-location, natural beauty, and limitless potential. Bordering a gentle brook and featuring a mix of rolling meadows and scenic mountain logging trails, this raw, untouched farmland is a rare find in one of Vermont's most sought-after areas. Held in the same family for generations, the land is ready for new owners to bring their vision to life. Its open fields invite cattle to graze, gardens to flourish, and dreams to take shape. With two convenient access points off Route 30 and an unrestricted deed, the possibilities are endless-whether you envision a private country estate, a residential subdivision, or even a condominium development. The property straddles the Manchester/Dorset town line, offering easy access to both communities. You're just five minutes from downtown Manchester, the Dorset Quarry, and The Green, and within a short drive to Bromley, Magic, and Stratton Mountain ski resorts. Rarely does such a unique combination of location, size, and opportunity come to market. Don't let this exceptional Dorset property slip away-your Vermont dream begins here. All lines and maps are approximate. Call today to explore the possibilities.

Listed by Margretta Fischer of Wohler Realty Group

MLS Number 5100794

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

Uncommonly Superb View -- A Vermont Meadow Retreat Tucked quietly into a broad meadow and surrounded by lush Vermont landscape, this property enjoys one of those rare, completely unspoiled western vistas: a full, harmonious sweep of the Taconic Mountain ridgeline, framed perfectly within human scale. The almost 40 acre setting--meadow bordered by deep woodland--creates a sense of arrival, privacy, and permanence that is difficult to replicate. The architect designed home blends natural materials inside and out, offering a calming, organic environment that feels inseparable from the land around it. One of the sellers' guiding goals the architect skillfully interpreted, was harmony with the landscape, expressed most beautifully in the roofline: a broad expanse of split shake cedar shingles that subtly echoes the rolling contours of the surrounding mountains, allowing the home to settle into the meadow as though it has always belonged there. After watching the setting sun from the screened porch, gatherings naturally flow around the kitchen or into the dramatic living room, featuring a X' high beamed cathedral ceiling, 29.0 x 30.7 dimension, and a massive stone fireplace that anchors the space during the colder seasons. Western views remain a constant presence throughout the year. Two of the main bedrooms open with large walls of glass to the air and landscape, while the third bedroom or office welcomes the morning sun from the east. The primary suite includes a soaking tub positioned to overlook manicured flower gardens and the mountains beyond. A second bedroom suite shares a bath with the office/bedroom, connected by three broad steps that subtly define the private wing. The oversized two car garage offers shelter from winter storms and summer heat, with ample space for vehicles, gardening equipment, and other pursuits. The home's placement within the meadow ensures exceptional privacy in every direction. See documents for more.

Listed by Paul Harsch of Harsch Associates

MLS Number 5081792

• Condo
• Square Feet 1,796
• Bedrooms 3
• New Contruction Existing
• Complex Okemo Trailside

Direct slopeside 3-bedroom plus family room townhome with numerous updates. Wonderful mountain location abuts Okemo State Forest and offers outstanding views. Expanded mudroom with built-ins leads out to private exterior ski closet and ski slopes. Kitchen updates include stainless steel appliances, tile floor and backsplash, and wood cabinetry. Open living room/dining room design with cathedral ceiling is centered by a woodburning fireplace and accesses a covered deck with substantial easterly views overlooking the village of Ludlow, the Black River Valley, and the mountains of New Hampshire. Primary suite includes updated skylit three-quarter bath with wood cabinetry, quartz countertop, and tile floor and backsplash. Two additional bedrooms and a family room occupy the ground level and include a full bath and a three-quarter bath. The three-quarter bath was added to the original floor plan and includes updated laundry with full size washer and dryer. Additional features include wood accent paneling, updated windows and sliders, and specialty lighting.

Listed by Andre Menard of Mary W. Davis Realtor & Assoc.,Inc.

MLS Number 5091163

• Residential Single Family
• Full Bath 2
• Construction Existing
• Bedrooms 6
• Bathroom 6

Set on approximately 49 acres of picturesque Vermont countryside, this extraordinary property offers exceptional privacy, natural beauty, and the rare advantage of two separate homes-perfectly suited for a primary residence with an entertaining guest house, multi-generational living, or short-term rental opportunity. This one-of-a-kind offering provides space, comfort, and endless four-season recreational potential. The main home is filled with natural light, highlighted by expansive windows that frame the surrounding landscape. Thoughtfully designed for both everyday living and hosting, it features two bedrooms, two and a half baths, and a dedicated office space ideal for remote work. Two inviting living rooms create flexible gathering spaces, while the fully equipped kitchen serves as the heart of the home. Rooftop access offers a unique vantage point to take in sweeping countryside views, and central air ensures year-round comfort. The second home functions beautifully as an entertaining guest house, offering four bedrooms, two and a half baths, an additional kitchen and living room designed for hosting family and friends. A bonus room provides even more versatility for recreation, a game room, gym, or studio. Below the homes, a substantial four-bay garage offers abundant storage for vehicles, outdoor equipment, and seasonal gear. The land itself is a private playground, complete with a pond and expansive acreage to create trails for hiking, snowshoeing, or ATV riding. Enjoy sledding in winter, wildlife watching, and peaceful seclusion in every season. Ideally located near Pico Mountain, Killington Resort, and Okemo Mountain Resort, as well as the charming town of Manchester, the property is approximately three hours to Boston and four and a half hours to New York City. A rare opportunity to own a truly special Vermont retreat offering both lifestyle and investment appeal.

Listed by Hughes Group Team of Casella Real Estate

MLS Number 5096180

• Residential Single Family
• Full Bath 2
• Address 328 Gravelin Road
• Construction Existing
• Bedrooms 4

High Shelter Farm offers the ultimate Vermont lifestyle on 64.64 extraordinary acres of fields, forests, and breathtaking views.. Direct access to Vermont's VAST trail network makes this a true outdoor enthusiast's paradise. The meticulously maintained 4,500+ sq. ft. home is perfectly positioned to capture spectacular views of Mount Ascutney and the White Mountains of New Hampshire. Floor-to-ceiling windows fill the living room with natural light and showcase the surrounding landscape. Recent updates include, newly painted interior, beautifully renovated bathrooms and refinished hardwood floors. The home offers four bedrooms, a spacious eat-in kitchen, formal dining room, and inviting gathering spaces throughout. An owned, fully paid-for net-metered solar system transfers with the property, helping power the home while enhancing energy efficiency and long-term value. A permitted one-bedroom accessory apartment with private entrance and patio provides flexibility for guests, extended family, or rental income. Outside, an inground gunite pool and gazebo create the perfect setting for summer entertaining. The recently built barn, now an exceptional event space, has hosted family weddings and gatherings while honoring the property's agricultural heritage. Ideally located near Hanover, Dartmouth, Woodstock, Crown Point Country Club, area ski resorts, Hartness State Airport, and the Upper Valley, High Shelter Farm is a rare opportunity to own a property that truly embodies the best of Vermont living-where recreation, sustainability, privacy, and natural beauty come together in one extraordinary setting. Available with more acreage see MLS 5096178. OPEN HOUSE. SATURDAY JUNE 27TH, 1-4PM AND SUNDAY JIUNE 28TH 11-2PM. ALL ARE WELCOME!

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

MLS Number 5060964

• Residential Single Family
• Full Bath 3
• Address 81 Top Deck Lane
• Construction Existing
• Bedrooms 4

A unique opportunity to own a piece of the history of the Northeast Kingdom. Locally known as the "Top Deck" , which was a restaurant and a campground, but now has been a single family home for about 50 years. Over 7 acres and 217 feet of sandy beach waiting for a sunny day. Mostly open land with room for a stable? Golf hole? And, bring the family. Room for all. The 2nd floor has 10 foot wooded ceilings and a great room concept. with kitchen, dining room, and living room. All facing the lake and overlooking the inground pool. Fully furnished. 3 bedrooms, a pantry, and 2 bathrooms complete this level. A massive brick fireplace doubles as a wall between the DR and LR. On the ground level are 1 more bedroom and family room. A 3rd full bath, and large mudroom. Also, over 1,000 square feet for the 2 car garage and even the left over locker rooms from the campground days.

Listed by Michael Conley of Conley Country Real Estate & Insurance

MLS Number 5100399

• Residential Single Family
• Full Bath 1
• Address 81 Fern Hill
• Construction Existing
• Bedrooms 2

Nestled in one of Dorset's most desirable private settings, this enchanting storybook Cape is a rare offering that blends timeless New England charm with exceptional beauty. Surrounded by lush perennial gardens and magnificent specimen maple trees and an extraordinary acre of mature pachysandra, the property offers a sense of peace and privacy that is increasingly hard to find. The welcoming living room is centered around a classic colonial fireplace and opens to a slate terrace overlooking established perennial gardens - an ideal place for relaxing or entertaining. Filled with natural light, the dining room features elegant built in cabinetry and flows seamlessly into a custom-designed kitchen with a Dutch door to a covered porch for morning coffee. The tranquil sunroom and charming powder room complete the first floor. Upstairs, you'll find a primary bedroom with fireplace and attached bath and a guestroom with bath and a generous storage attic. The exceptional grounds offer endless possibilities, including a detached barn with exciting guest cottage, studio, or workshop (subject to permits) potential, a colonial style potting shed and seven acres of picturesque land that provides privacy, beauty and room to explore. A home of exceptional warmth, character and timeless appeal in one of Southern Vermont's most coveted communities. Owner is a Vermont licensed Real Estate Agent.

Listed by Elena Atwill of Four Seasons Sotheby's Int'l Realty

MLS Number 5086028

• Residential Single Family
• Full Bath 1
• Address 366 Knapp Pond Road
• Construction Existing
• Bedrooms 4

Did I read that right? 172 acres?! Impeccably renovated farmhouse on +-172 acres - what more could you ask for? ~131 acres of this property are located in Cavendish while the other ~41 are in Reading. Enjoy apples straight from the backyard. Listen and watch the brook babble down by the road and enjoy the peace that comes from this lovely home. All new Marvin Elevate windows, all new appliances, new plumbing, new boiler, new electrical panel, new lighting, new paint, new spray foam insulation, new concrete poured in the basement. No detail was too small. All the work has been done so you can simply move in and enjoy. With 4 bedrooms plus an office there is plenty of space for everyone to feel comfortable. With one bedroom downstairs, it is possible to age in place and have single level living should one want to! Along with the house is an oversized two car two story garage and separate barn. ~15 minutes to the South Woodstock general store, this is the perfect spot to stay nearby but still experience vast amounts of privacy through the land. More exterior photos coming soon. Schedule a private showing.

Listed by Franchesca Collins and Holly Hall of Hall Collins Real Estate Group

MLS Number 5103259

• Residential Single Family
• Full Bath 2
• Construction Existing
• Bedrooms 6
• Bathroom 4

Located .25 of a mile from the Stratton Mtn Gondola, Village and Resort. Corner lot with mature, professionally planned landscaping to enjoy all year. New roof and skylights were installed in 2024. One large expansion to the whole side of the house, all 3 levels, was 30 years ago. Lovingly maintained but needs a new kitchen floor and floor refinishing of the hard woods. Recently the bamboo floored in law suite bathroom has a modified tub to allow easier step in. This private suite includes its own entrance/exit to a deck and with gardens. This main floor primary suite has a kitchenette and a walk in closet. Enter the house by the driveway or garage and step into a foyer with 3 deep closets, 4 bedrooms and a 3/4 bathroom in the hallway to share. On the 3rd level is another primary suite with a walk in closet, jacuzzi tub, open shower and semi private toilet, and 2 sinks. This luxurious, tiled and wood floored primary bedroom leads to cozy a screened in porch that feels like a treehouse. The main floor, 2nd level is where all the living and entertaining happens. There are 3 fireplaces on the main level: in the kitchen, in the enclosed heated porch and the main star of the show in the living room with a huge slate hearth big enough to seat 4 people! Chef's kitchen with 2 dishwashers, an ice maker, gas oven/range and an outdoor grill hooked up to the house gas line just off the kitchen on a covered deck. This house is amazing! It's location is the best Stratton has to offer.

Listed by Derek Greene of Derek Greene

MLS Number 5088175

• Residential Single Family
• Full Bath 1
• Address 76 Goldthwaite Road
• Construction Existing
• Bedrooms 4

Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation. Inside, you'll find four spacious bedrooms, wide plank wood floors, and inviting gathering spaces designed for relaxed country living. The heart of the home is the warm and welcoming country kitchen featuring soapstone counters, a center island, and ample room for entertaining. A large living room with a pellet stove creates a cozy retreat after a day on the slopes or trails, while the den offers an ideal space for a home office or quiet study. The screened front porch captures the essence of Vermont living perfect for morning coffee, evening conversations, and taking in the peaceful surroundings. Outdoors, enjoy evenings around the fire pit beneath star filled skies, surrounded by the natural beauty and privacy of the property. A standout feature is the remarkable multi-level 55' x 40' barn, full of rustic character and endless potential. Having hosted countless gatherings and celebrations, it offers incredible space for entertaining, hobbies, storage, or future creative use. Tucked away just two miles from town, this serene retreat offers both privacy and convenience, with easy access to skiing, snowmobiling, hiking, and all the outdoor adventure and small town charm that make Vermont so special.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty