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Very Cool Houses

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65 Bentley Lane Jericho VT 05465

Jericho, VT65 Bentley Lane

Price$2,500,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5081998

  • Residential Single Family
  • Full Bath 1
  • Address 65 Bentley Lane
  • Construction Existing
  • Bedrooms 3

In a picturesque valley nestled between the majestic slopes of Camel's Hump and Mount Mansfield, where sweeping, panoramic views stretch across the horizon, lies a truly special place; Simpson's High Meadow. Spanning 201+ acres of pristine Vermont landscape, this remarkable property is a tapestry of wildflower meadows, lush forests, and winding recreational trails perfect for walking, skiing and exploring in every season. A lovely home and a rustic post and beam cabin rich with Vermont charm, are thoughtfully built on the land, creating welcoming spaces for gathering, reflection, and simple living. A spring-fed pond with a dock invites summer swims and relaxing afternoons by the water, while a nearby fire-pit becomes the heart of evenings shared with family, friends, and guests beneath star-filled skies. Follow a woodland trail that climbs gently to a hilltop, where the quiet remains of a historic barn still stand-once part of the property connected to the famed photographer and naturalist “Snowflake” Bentley, whose legacy lives on along Bentley Road. For more than fifty years, the Simpson family lovingly stewarded this land across generations. They built the homes and cabin, created the trails, and cared for the meadows and forests that make this place so extraordinary. Simpson's High Meadow is the essence of Vermont: a timeless landscape where dreams take root and memories are made.

Listed by Tony Shaw and Stephanie Douglas of KW Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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269 Billings Hill Road Stowe VT 05672

Stowe, VT269 Billings Hill Road

Price$2,500,000

Est. Mortgage: $/month

MLS Number 5097864

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

Tucked into the exclusive Robinson Springs neighborhood of Stowe, 269 Billings Hill Road is a beautifully maintained and custom updated home set on nearly four acres with sweeping views of Mount Mansfield and the ski trails. Private trails on the property offer peaceful spots to rest and connect to the Robinson Springs Waterfall Trail, while association trails for hiking, snowshoeing, and cross-country skiing place some of Vermont's finest natural terrain right at your door. The layout is made for both comfortable living and gracious entertaining. The living room anchors the main level with a wood-burning fireplace, flowing into a spacious kitchen with an island and a dining area warmed by a second fireplace. A comfortable den connects the main living areas to the original primary suite, a true retreat that offers guests exceptional privacy. The upper-level primary is a destination unto itself, featuring its own sitting room, two walk-in closets, and a large modern bathroom with a soaking tub that enjoys direct mountain views. A third en suite bedroom and a fourth bedroom with shared bath complete the upper level. The large deck, accessible from the dining area, den, and downstairs suite, faces directly toward the mountains and is perfectly positioned for morning coffee or evening gatherings. A finished walkout lower level adds a recreation room and bath for additional flexibility. A two-car garage, hot tub, vaulted ceilings, natural woodwork, and fiber optic internet round out an exceptional Stowe property.

Listed by Smith Macdonald Group of Coldwell Banker Carlson Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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61 Academy Circle Woodstock VT 05071

Woodstock, VT61 Academy Circle

Price$2,500,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5002873

  • Residential Single Family
  • Full Bath 2
  • Address 61 Academy Circle
  • Construction Existing
  • Bedrooms 6

Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The back ell seamlessly ties into the original brick Federal and offers additional spaces for entertaining guests including the Pine Room with its' large fireplace for snowy winter nights. The brick Federal consists of formal living room, dining room, library and gourmet kitchen with walk in pantry. On the second floor there are 2 ensuite bedrooms,4 more bedrooms, 2 baths and large laundry room. The third floor offers the surprise of a family room that was originally a ballroom with curved ceiling. There is also a bright studio and half bath on that level. The new attached oversize 2 car garage is accessed from the Pine Room and the fully renovated basement. The 2+/- acres comprises of lovely landscaping around the home and plenty of land for gardens . The 18th century barn and corn crib lend much charm to the setting. There are 8 additional acres for sale if one would like to expand the property. Walk to the charming village store and enjoy dinner on the porch of the Ransom Tavern. Only 5 miles to Woodstock and a short drive to multiple ski areas. South Woodstock is truly a bucolic place to call home! Call today for a private viewing.

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty

$
$
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$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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57 Farrants Point Newport City VT 05855

Newport City, VT57 Farrants Point

Price$2,500,000

Est. Mortgage: $/month

MLS Number 5096870

  • Residential Single Family
  • Full Bath 2
  • Address 57 Farrants Point
  • Construction Existing
  • Bedrooms 4

Private Lakefront Estate awaits... resting majestically on 7.2 deeded acres overlooking Farrants Point, Owl's Head, Bear Mountain, and views into Canada. Live comfortably in this well-appointed home with 3 finished floors, lots of natural light, 2 full kitchens, w/ open floor plan. 2 floors with wrap around decks/patios to enjoy the mesmerizing views of Lake Memphremagog Sunrises. Choose from several beaches on the properties, even catch the Sunset views off Farrants Point! Do you have a sea plane? You can land it here... You can boat across the bay for fine dining at "The Eastside" Restaurant, which includes a Pub, Bakery, and Boutique Shopping! Plenty of room for all your hobbies with a 5 bay garage including 1 w/ radiant heat, 1 w/ lift, separate chicken coop, and a 72'LX32' WX35'H Boat House w/27' door, includes prep kitchen, office & balcony! Stroll along the point to enjoy the natural habitat w/ nesting birds, or fish off the point. Great swimming, boating, fishing, and opportunities to recreate. Minutes to Interstate, Airport, hospital, hiking and biking trails, 25 minutes to Jay Peak Resort, and easy travel to Boston, Montreal, and Burlington. Bonus of municipal water & sewer...imagine an art gallery, a gated community, a wedding venue, it's an open canvas ready for the new owners to cherish. (Boat dock, pontoon boat and side by side will convey). Once in a lifetime opportunity...

Listed by Rachel Smith and Patricia Wilder of S. R. Smith Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2043 Stowe Hollow Road Stowe VT 05672

Stowe, VT2043 Stowe Hollow Road

Price$2,500,000

Est. Mortgage: $/month

MLS Number 5097463

  • Residential Single Family
  • Full Bath 5
  • Construction Existing
  • Bedrooms 6
  • Bathroom 5

Original 1887 Farmhouse on 7 Picturesque Acres. A rare piece of Stowe's history. This original 1887 farmhouse sits on 7 beautiful acres in coveted Stowe Hollow, offering unobstructed views of the Worcester Range, Stowe Pinnacle, Mount Mansfield, and the Trapps. The home's 19th-century character is anchored by massive hand-hewn beams running the full length of the house, built over a classic, full fieldstone basement. Space: 6 bedrooms and 5 bathrooms offer ultimate flexibility for a grand estate, multi-generational retreat or premium ski lodge. Water Features: The pristine grounds feature a private pond, a rushing creek and deeded natural springs. The Setting: Complete privacy and 360-degree mountain backdrops, just minutes from world-class skiing and downtown Stowe.

Listed by Derek Eisenberg of Continental Real Estate Group,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3039 Route 30 Dorset VT 05251

Dorset, VT3039 Route 30

Price$2,495,000

Est. Mortgage: $/month

MLS Number 5089828

  • Residential Single Family
  • Full Bath 3
  • Address 3039 Route 30
  • Construction Existing
  • Bedrooms 4

Tucked away at the end of a long, winding driveway, this remarkable Dorset Village estate sits on one of the area's largest parcels-over six private acres. A rare blend of privacy, history, and elegance, the home features four stunning stone fireplaces, exposed antique beams, reclaimed wood details, and abundant natural light throughout its flowing layout. Designed for gathering and making memories, it offers unique touches like theater-inspired stair railings and a vaulted-ceiling game room. Outdoor living is unmatched with a spacious wraparound deck, screened porch, wood-fired brick pizza oven, and a tucked-away sauna. The charming barn includes two horse stalls, a tack room, and room for more animals, plus a fenced paddock and serene pond. An oversized three-car garage adds functionality to this character-filled property. Just a short walk to town and trails, yet feeling worlds away-this is a one-of-a-kind Vermont estate.

Listed by Carrie Mathews of Winhall Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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56 Handle Road Dover VT 05356

Dover, VT56 Handle Road

Price$2,495,000

Est. Mortgage: $/month

MLS Number 5063234

  • Residential Single Family
  • Full Bath 5
  • Address 56 Handle Road
  • Construction Existing
  • Bedrooms 6

Incredible Legacy Property. This extraordinary estate blends timeless elegance with modern comfort. The first floor features a welcoming den, gourmet eat in kitchen with DCS range, stainless appliances, sub- zero refrigerator and wet bar. A dining room, gracious living room, office, and butler's panty with fridge and ice maker make entertaining effortless. Five fireplaces, custom-built-ins, wood floors and beautifully tiled baths create a warm refined atmosphere. Upstairs the primary suite offers a fireplace and luxurious bath. An additional en-suite bedroom and three more bedrooms, laundry room, and two full baths provide plenty of space for family and guests. Dual staircases, tiled entry, and both front and back foyers highlight the home's thoughtful design. The grounds are equally impressive with a covered front porch that overlooks the sprawling south facing lawn with winter views of haystack. A serene screened veranda, back deck and stone patio with fire pit invite outdoor gatherings. An oversized-attached two car garage, whimsical children's playhouse and an incredible post and beam barn with full lower level perfect for all your recreational vehicles complete the offering. Exquisite gardens, stone walls and meticulous land scaping surround this rare property, ideally located across from the esteemed Hermitage Inn and exclusive Hermitage Club with easy access to all area activities.

Listed by Richard Caplan of Deerfield Valley Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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481 Hills Point Road Charlotte VT 05445

Charlotte, VT481 Hills Point Road

Price$2,495,000

Est. Mortgage: $/month

MLS Number 5088043

  • Residential Single Family
  • Full Bath 1
  • Address 481 Hills Point Road
  • Construction Existing
  • Bedrooms 4

Stunning panoramic lake and Adirondack views highlight this four-bedroom, two-bath LAKEFRONT home, offering a rare opportunity to renovate or rebuild in one of Charlotte's most sought-after neighborhoods. Set on 0.89 acres with 150+ feet of lake frontage, the property features a gently sloping lawn leading to a shale beach ideal for kayaking, paddleboarding, boating, swimming, or simply enjoying spectacular sunsets. The existing home offers two finished levels ready for renovation, while the exceptional setting provides endless potential for a custom lakeside retreat. Located in the desirable Hills Point neighborhood with easy access to Charlotte Village, Town Beach, the nearby covered bridge, and convenient commuting to Burlington or Middlebury.

Listed by Geri Reilly of Geri Reilly Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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654 Moulton Lane Stowe VT 05672

Stowe, VT654 Moulton Lane

Price$2,450,000

Est. Mortgage: $/month

MLS Number 5091926

  • Residential Single Family
  • Full Bath 2
  • Address 654 Moulton Lane
  • Construction Existing
  • Bedrooms 4

Set on a beautifully private 3-acre parcel with spring fed pond and sweeping Worcester mountain views, this four bedroom ensuite property offers the perfect balance of comfort, functionality, and refined Vermont living. Thoughtfully designed with an open-concept floor plan, European floor-to-ceiling windows bring Vermont's natural beauty into every room of the home. Anchored by a warm wood-burning fireplace in the living room, the home offers inviting spaces ideal for both entertaining and comfortable everyday living. The chef-inspired kitchen features an elegant oversized granite island accented by butcher block, subzero fridge, large 48" 8-burner stove, bar sink, and mini beverage fridge offering a seamless flow into the dining and living areas. Double French doors off the kitchen open to a spacious deck, perfect for outdoor dining or relaxing in Adirondack chairs while taking in the surrounding views. A spacious mudroom provides practicality for all seasons with a 3/4 bath, while the main-level ensuite bedroom offers a peaceful retreat with convenience and privacy. Upstairs you will find two primary suites with gas fireplaces, custom showers and Japanese soaking tubs offering peaceful retreats with stunning mountain and pond views. The lower level offers a nature-inspired private bedroom suite with pond views, and an ensuite bathroom. The lower level also hosts a second living room and game room providing another great spot to relax or take in the game or a movie. A double slider door provides easy walkout access from the game room to the yard with lounge chairs and pathway to the pond. Outdoor living is equally impressive. An expansive deck overlooks idyllic mountain vistas and a stunning crystal-clear swimming pond complete with a dock and stocked with fish, creating a truly serene setting for summer days and evening gatherings. This is a rare opportunity to enjoy privacy, natural beauty, and timeless Vermont charm in a property that truly checks every box.

Listed by Pall Spera and Joni Gaines of Pall Spera Company Realtors-Stowe

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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109 Mountainside Drive Killington VT 05751

Killington, VT109 Mountainside Drive

Price$2,450,000

Est. Mortgage: $/month

MLS Number 5088805

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • Bedrooms 3
  • Bathroom 5

This fully furnished, high end home delivers opulence from the moment you pull in. From the recently resurfaced driveway your eyes are immediately drawn to the newly installed daltile porcelain roof, offering you peace of mind for decades to come. Park your car in the 2 car garage and enter into a dedicated mudroom with copper fire slate flooring. The dedicated laundry room offers LQ Signature washer/dryer, soap stone counter top and a deep work sink. Entering into the grand foyer you will be met with floor to ceiling windows in the living room that deliver breathtaking mountain views, giving you a sense of seclusion. Unwind by the beautiful floor to ceiling stone hearth fireplace. For your comfort there is a 30,000 BTU AC in the great room. Immerse yourself into the stunning chefs kitchen with Brazilian Venata countertops, cherry cabinets and stainless steel appliances. The Bruce Kennedale Prestige maple hardwood flooring throughout the living room, dining room and kitchen adds beauty, durability and is designed to last a lifetime. The spacious primary suite located on the main floor offers a large bedroom with miles of mountain views, a walk in closet, sitting area, 9000 BTU AC, large whirlpool tub, walk in shower, double sink, toilet room and sauna. Relax in the 4 season sunroom offering 180 degree mountain views and the tranquility of the natural brook. Host a gathering on the large two wing wood deck. Whether it is a bbq or sitting by the on deck fire pit, entertaining is made easy here. Upstairs you will find 2 large ensuite bedrooms both offering incredible mountain views. Downstairs in the family room there is a Westwood Tuscany 8 foot pool table that converts to a ping pong table. Enjoy the ambiance of an additional fireplace. You will find additional sleeping space, a 3/4 bath and storage rooms as well. The property comes with 3 additional parcels which can be divided off, retained for privacy or create your family compound. This is a must see property!

Listed by Michelle Lord of Ski Country Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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431 Mcgregor Point Alburgh VT 05440

Alburgh, VT431 Mcgregor Point

Price$2,435,000

Est. Mortgage: $/month

MLS Number 5087147

  • Residential Single Family
  • Full Bath 2
  • Address 431 Mcgregor Point
  • Construction Existing
  • Bedrooms 3

Lakefront Luxury Awaits! Nestled on over 20 sprawling acres with 500+ feet of direct, gradual Lake Champlain frontage, this stunning contemporary estate offers breathtaking views of the Inland Sea and Vermont's Green Mountains. Featuring 3 spacious bedrooms, 5 elegant baths, and over 4,000 sq ft of beautifully maintained living space, this home is ready for you to move in and start living the dream. Enjoy outdoor living at its finest with a sauna, swimming pool, and a screened pergola, the perfect spots to unwind by the lake. The level lot invites endless outdoor activities, and with an attached two-car garage plus a large detached shed, there's plenty of room for all your boats and recreational gear. Just an hour from Montreal and Burlington, this is lakefront living at its best! Your new lakefront lifestyle begins here!

Listed by Michael Savage of RE/MAX North Professionals

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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424 Miller Way Newport Town VT 05857

Newport Town, VT424 Miller Way

Price$2,400,000

Est. Mortgage: $/month

MLS Number 5090466

  • Residential Single Family
  • Full Bath 2
  • Address 424 Miller Way
  • Construction Existing
  • Bedrooms 4

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Broker Reciprocity 

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated August 8, 2026 1:52 AM UTC