Very Cool Houses

MLS Number 5100512

• Residential Single Family
• Full Bath 2
• Address 16 Church Street
• Construction Existing
• Bedrooms 4

This wonderful Vermont Cape-style home has overlooked the Ottauquechee River and the former Woodstock woolen mill (now the 'new' mill and community pools and recreation center) since 1890. On long summer days, the sounds of children enjoying the swimming holes and tubing in the rapid runs below float up. The floor plan has been adapted to modern lifestyles across three levels. The main level, entered from the garden walkway or garage, connects to an open country kitchen via a mudroom, which flows into the dining area and living room, offering extraordinary upriver views west toward Killington. A spacious main-floor primary bedroom with an en suite bath opens to a riverside deck, and an expanse of lawn and gardens surrounds the residence. Upstairs are two large bedrooms with a shared bath and a reading loft overlooking the living room below. The walkout lower level includes another bedroom, a bath, a recreation room, and a laundry. The soothing music of the water rose to a crescendo in August 2011 as Hurricane Irene swept into Vermont as a tropical storm, resulting in a FEMA-designated 500-year flood event that inundated basements, as it did many homes in Woodstock and other river towns. Subsequently, the owners have replaced the lower-level sheetrock and boiler and have invested in an engineered barrier wall. The home is within walking distance of Village shops, restaurants, and resort amenities. A peaceful hideaway close to everything.

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

MLS Number 5090534

• Residential Single Family
• Full Bath 1
• Address 39 Eagle Ridge
• Construction Existing
• Bedrooms 5

5.7 beautiful acres just off of Morse Hill Road where the southern exposures are to behold, a warm and inviting modern designed residence, post and beam barn and sweeping mountain views await your attention! The 5 Bedroom mostly ensuite house features the grand open concept where living areas are spacious and distinctive areas yet transition beautifully from space to space with newly finished hickory flooring and all areas are walking out to a great deck that overlooks the bucolic 5.7 acres. There's stone walls, easy perennial gardens, the classic red barn, some fruit trees, a small pond, and meadow. Plenty of room to maximize it's potential for vegetable beds... a pool... or any lifestyle whimsy. The great-room marble cooks kitchen has vast cabinetry and upgrade stainless appliances, the dining room would entertain large or small gatherings with ease and the step down living room with cathedral wood ceiling and massive stone hearth wood burning fireplace is lovely with warm natural light. There's an office, powder room and laundry room convenient to the central family command center. The primary suite is quite luxurious with the soaking tub, separate stone shower, double vanity and walk in closet. There are two ensuite bedrooms upstairs boasting new baths. The lower level sun soaked family room can work for recreation, lounging, media, or exercise... there's two other lower level bedrooms or one is considered more in line with flex-space such as a second office. There is a new bath there as well! All baths are just finished. Add central air, the three car attached garage, with and work-shop/studio extension, the fantastic barn that also has a work-shop addition where parties can be had with a separate drive. The possibilities are endless in how this property and house can be utilized. Easy single floor living for the empty nester with plenty of room for the generations to reappear, or a terrific family home. Mountain Views! Welcome to 39 Eagle Ridge!

Listed by Laura Beckwith and Elizabeth Romano of Josiah Allen Real Estate,Inc.

MLS Number 5091076

• Residential Single Family
• Full Bath 4
• Address 163 Chapin Road
• Construction Existing
• Bedrooms 4

Set on over 10 private acres with access to an additional 26 acres of common land, this exceptional 4-bedroom, 5-bathroom Essex property offers a rare combination of privacy, flexibility, and everyday convenience. Located just minutes from local amenities with an easy commute to Burlington, the University of Vermont Medical Center, and Burlington International Airport. With over 6,000 square feet of living space, the home was thoughtfully designed for both entertaining and comfortable daily living. Soaring cathedral ceilings and expansive windows fill the main living areas with natural light, anchored by a dramatic floor-to-ceiling stone fireplace. The kitchen features rich wood cabinetry, stainless appliances, generous counter space, breakfast bar seating, and a sunny breakfast nook, all flowing easily into the formal dining room and spacious living area. A screened porch and expansive wraparound deck extend the living space outdoors. A standout feature of the home is the flexible first-floor layout, including a guest suite with vaulted ceilings, en suite bath, and direct deck access ideal for guests or a comfortable first-floor primary option. A dedicated den or office adds even more versatility. Upstairs, the primary suite includes a gas fireplace, walk-in closet, and spacious bath with soaking tub, along with two additional bedrooms and second-floor laundry. The finished walkout lower level offers exceptional bonus space with a fireplace, bar, game room, gym, and additional flexible areas for entertaining, hobbies, or guests. Outdoor features include an attached heated garage, stone patio, reinforced deck with hot tub hookup, gas grill hookup, pole barn ideal for equipment or RV storage, and a detached barn/2-car garage with finished space above and a 3/4 bath. Perfect for hobbies, studio space, guests, or flexible use. A truly special Essex property offering exceptional space, privacy, and opportunity both inside and out.

Listed by Nancy Warren of Coldwell Banker Hickok and Boardman

MLS Number 5085625

• Residential Single Family
• Full Bath 2
• Address 14 School Street
• Construction Existing
• Bathroom 5

Positioned in the vibrant heart of Bristol Vermont, this iconic former high school presents an exceptionally rare opportunity to acquire a fully leased, income-producing asset with both commercial use and residential zoning, offering multiple avenues for future value and flexibility. Assets of this scale, history, and versatility especially at an approachable price point are rarely brought to market. Steeped in heritage, the property has served the community since the early 1800s, evolving from its origins as a schoolhouse to Bristol High School and now the well-known Bristol Suites. Today, it is meticulously maintained and fully occupied, delivering immediate and stable income from day one. More than just a building, this is a true community hub. A diverse tenant mix including a chiropractor, skin care boutique, forest conservation office, yoga studio, fitness facility, and more drives consistent daily activity and creates a resilient, multi-industry income stream that supports long-term stability. The upper levels are currently configured as professional office suites and open studio spaces, while the lower level is anchored by a popular local gym, reinforcing visibility and steady use. Beyond its current income-producing profile, the property offers meaningful long-term optionality. With residential zoning in place, a future owner may explore conversion to apartments, a mixed-use redevelopment, or even repositioning the property as a distinctive single-family residence, subject to applicable permits and approvals. Its historic character, generous scale, central village location, and flexible interior layout create a compelling foundation for a one-of-a-kind private home or legacy estate. This is not just an investment, it is a scarce legacy asset with built-in income, community integration, residential potential, and meaningful upside in the Bristol, Vermont real estate market.

Listed by Kate Earley and Flex Realty Group of Flex Realty

MLS Number 5072995

• Residential Single Family
• Full Bath 2
• Address 47 Salvas Lane
• Construction Pre-Construction
• Bedrooms 3

Moscow Meadows the latest build package option from Gristmill Builders, known for their attention to detail, eco-friendly building, and luxury finish work. Sitting on the gateway to Stowe, Moscow Meadows offers beautiful mountain and river views, a prime location surrounded by conserved open meadows, and the ease of a new high-end home. This exciting new development will offer hand-crafted homes in a tranquil neighborhood setting. The modern design features an open concept main floor, highlighting the mountain views towards Stowe Mt. Resort. The living room comes complete with a gas-burning stove, while the center island in the kitchen makes for a perfect gathering space. The primary suite is conveniently located on the main floor, perfect for single-level living. White oak flooring throughout this level brightens the space as much as the large and plentiful windows. The walk-out lower level is an ideal space for guests to spread out. Taking advantage of the views, this level features a guest bedroom, an entertainment space, and a shared bath. The lower level features troweled concrete floors, adding to the home's modern feel. Touches of Vermont synergized with modern flare create a unique Stowe home. Photos are of lot 4 and differ from plans for lot 1. Kitchen for lot 1 will be located in the dining area seen in photos. Upgrade options include en suite bath on lower level bedroom, screened porch, heated garage, fireplace, wood stove.

Listed by Smith Macdonald Group of Coldwell Banker Carlson Real Estate

MLS Number 5102515

• Residential Single Family
• Full Bath 2
• Address 420 O'brien Drive
• Construction Existing
• Bedrooms 4

There are few places where mornings begin with the sun rising over rolling hills, evenings end beneath colorful western sunsets, and the drive home feels like an escape from the everyday. Tucked along one of Shelburne's most scenic winding roads, surrounded by picturesque countryside and seasonal wildflower fields, this exceptional home offers peaceful Vermont living just minutes from local favorites. Enjoy coffee on the covered front porch, tee off at Kwiniaska Golf Club, or reach Spear Street in just 4 minutes, explore Shelburne Road's shopping and restaurants in 8 minutes, or spend the day along the trails and waterfront at Shelburne Farms only 11 minutes away. Inside, the entryway features soaring ceilings, and an airy, light-filled design create an immediate sense of openness. The spacious living room flows into the dining area and out to the west-facing deck, making entertaining effortless. The kitchen features a large center island with abundant storage and opens to a comfortable family room perfect for movie nights or relaxing weekends. A mudroom and half bath complete the main level. Upstairs, the sunny primary suite offers a spa-like en suite bath and generous walk-in closet. Three additional bedrooms, a full bath, provide plenty of space for everyone. The finished lower level expands the living space with a large recreation room, generous wet bar, dedicated office behind a stylish barn door, and a flex room with a three-quarter bath featuring radiant heated floors. An unfinished utility and storage area adds everyday functionality. An attached two-car garage with direct basement access completes this thoughtfully designed home, where peaceful surroundings, beautiful views, and an exceptional Shelburne location come together effortlessly!

Listed by Sarah Harrington of Coldwell Banker Hickok and Boardman

MLS Number 5093049

• Residential Single Family
• Full Bath 4
• Address 20 Hillside Terrace
• Construction Existing
• Bedrooms 5

Perched gracefully atop 10+ private acres in the rolling hills of St. Albans, this home is a rare Vermont estate where timeless craftsmanship, extraordinary privacy & sweeping natural beauty converge. From the moment you arrive along the tree-lined drive, framed by manicured gardens, raised beds & a tranquil pond, the property unfolds like a secluded countryside retreat; designed to capture the majesty of Lake Champlain & the Adirondacks from every vantage point w/views stretching northward to Montreal. Step through the impressive entryway & into a residence that immediately evokes warmth & elegance. A grand staircase sets the tone for interiors rich in architectural detail & refined finishes that create a sophisticated yet inviting atmosphere. Sunlight pours through Marvin windows, illuminating thoughtfully designed living spaces enhanced by custom details at every turn. Designed for both everyday living & effortless entertaining, the home offers multiple gathering spaces anchored by 3 fireplaces, expansive lake-facing windows & seamless access to an oversized deck where sunsets over Lake Champlain become your daily ritual. A spectacular bonus space offers the perfect setting for a guest bedroom or studio. The primary suite is a sanctuary complete w/breathtaking views that greet you each morning. The in-law apartment adds remarkable versatility for guests or multi-generational living, opening directly onto an extensive patio amongst flourishing perennial gardens & panoramic vistas. Impeccably maintained & thoughtfully designed, this home embodies the very best of Vermont luxury living~peaceful & deeply connected to the outdoors. Minutes to Historic Downtown St. Albans, Lake Champlain & an easy drive to Montreal, the location offers year-round recreation & endless opportunities for outdoor adventure. A true legacy property offering the privacy of an estate, the beauty of Vermont's landscape & a lifestyle defined by tranquility & unforgettable views!

Listed by Karen Bresnahan of Four Seasons Sotheby's Int'l Realty

MLS Number 5054780

• Residential Single Family
• Full Bath 4
• Village Quechee
• Construction Existing
• Bedrooms 6

The Dewey House joins timeless elegance with contemporary convenience. Situated on a quiet road adjacent to the Quechee Gorge waterfall in the charming town of Quechee, this property offers easy access to I-89, I-91, and Route 4. Nearby walking trails and direct water access lend themselves to outdoor pursuits, while the views from the house and its decks over the mill pond and hills create the perfect place to visit with friends, relax to the soothing sounds of the waterfall, or watch for eagles and hot air balloons. Whether you intend to run this as a private home, a short-term rental, or a B&B, you'll love being on this gracious property. Enter through the front door to an expansive foyer. To the left is the double-sized living room, which opens to the dining room. Beyond that, there is a study and a bathroom. To the right of the front door, you'll find a small sitting area, and then the expansive kitchen/breakfast room and deck access. Upstairs are the bedrooms, sitting rooms, and bathrooms. The second floor features an elegant office/sitting room/bedroom and bath on one end, two bedrooms and a bath on the other. The bifurcated third floor features two bedrooms and a bathroom accessible via one staircase, and an en-suite bedroom accessible via the other. All of the rooms enjoy views of the Vermont hills and blue sky, most overlooking the water. Many recent updates bring this antique treasure up to modern standards while preserving the historic integrity of this home.

Listed by Jennifer Falvey of KW Vermont Woodstock

MLS Number 5096246

• Residential Single Family
• Full Bath 1
• Address 42 Cedar Drive
• Construction Existing
• Bedrooms 4

Welcome to Okemo Pines! Tucked away just moments from the slopes, 42 Cedar Drive stands as a premier example of elegant timber frame architecture. This luxurious 4-bedroom, 3.5-bath residence combines rustic Vermont character with modern, high-end finishes. Step inside to an open-concept main level adorned with premium white oak floors. The breathtaking great room serves as the heart of the home, where a towering cathedral ceiling and a dramatic fieldstone fireplace create a warm, inviting ambiance beneath walls of glass that frame the surrounding scenery. The epicurean kitchen is a chef's dream, outfitted with custom cherry cabinetry, a farmhouse sink, and a walk-in pantry. For ultimate convenience, the main floor features a private, luxurious primary suite with an expansive walk-in closet. The upper levels host two additional guest rooms and a quiet office space. Below, the bright, walk-out lower level is an entertainment haven, featuring a massive game and billiards room, a comfortable den, a fourth bedroom, and a full bath. With an attached two-car garage and an unbeatable location just sixty seconds from downtown Ludlow and the Okemo base lodge, this home represents the pinnacle of mountain living. Visit the Okemo real estate community today. Taxes are based on the town assessment.

Listed by Katherine Burns of William Raveis Real Estate Vermont Properties

MLS Number 5095533

• Residential Single Family
• Full Bath 3
• Address 323 Turnpike Road
• Construction Existing
• Bedrooms 4

Where to begin, this property has so many special facets: Antique Cape that has been sensitively updated consistent with the style of the house; a guest house (Cape) built in 2004; an amazing renovated barn ready to host gatherings of all sorts and plenty of storage under the main level; stonewalls, stone patio, raised stone patio, fenced garden space, large open lawn area at the back of the property with access to the brook. Upon stepping onto the front porch you enter the light and bright kitchen with ample cupboards and shelves, an eating area with direct access to the raised stone patio. In addition, the main level has a generous sized living/dining room graced by a fireplace and built-ins; family room, primary bedroom with ensuite bathroom and set off nicely is a study/den. The upstairs has three bedrooms, full bathroom and nice open hallway area. Oh my gosh, the Cottage will bring a smile and an immediate sense of calm with its well thought out open concept plan which allows each space to embrace the other no matter the season; access to a patio for warm weather dining and relax by the fireplace in cooler weather. To complete the picture there is bedroom and bathroom on the first level and a very sweet loft on the second floor!! I'm excited for you to view this must see property!!

Listed by Berna Rexford of Four Seasons Sotheby's Int'l Realty