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Very Cool Houses

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133 Kent Hill Road Dorset VT 05251

Dorset, VT133 Kent Hill Road

Price$1,185,000

Est. Mortgage: $/month

Pending

MLS Number 5105753

  • Residential Single Family
  • PricePerSqFt 570.26
  • Full Bath 1
  • Address 133 Kent Hill Road
  • Construction Existing

The moment you step through the front door of Kent Hill Cottage, your shoulders drop, and you immediately exhale. Nestled along a quiet, tree-lined road at 133 Kent Hill Road in Dorset, Vermont, this home is a true sanctuary designed for peaceful living. It strikes an effortless balance between cozy comfort and stylish design, welcoming you with authentic warmth from the very first step inside. Inside, open and sun-drenched spaces invite you to slow down and stay a while. Warm exposed beams, soft natural light, and an inviting fireplace set a relaxed scene in the main living space, while the thoughtful layout seamlessly connects to a kitchen built for simple, joyful living. Every room feels like a gentle embrace, combining sleek modern finishes with timeless New England character. Beyond the front door, the quiet magic of Vermont awaits on your private porch, surrounded by lush greenery and crisp mountain air. While the cottage offers an idyllic, tucked-away feel, you are just minutes from the iconic Dorset Field Club, local farm stands, restaurants, bakeries, pristine hiking trails, and year-round outdoor adventure. Kent Hill Cottage is more than just a house; it is a place to settle in, recharge, and truly breathe easy.

Listed by Tim Post and Laura Kottler of LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 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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88 Windward South Dorset VT 05251

Dorset, VT88 Windward South

Price$1,175,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5108534

  • Residential Single Family
  • PricePerSqFt 379.77
  • Full Bath 2
  • Address 88 Windward South
  • Construction Existing

Beautifully maintained contemporary home on 3.62 private acres with elevated westerly views of Mt. Equinox and spectacular sunsets. Designed by renown architect Deborah Berke, Dean of the Yale School of Architecture, this light-filled home offers the ease of main-level living with a first-floor primary suite, laundry, bright office, den with custom built-ins, and spacious living room with vaulted ceiling, wood-burning fireplace, and oak floors. The kitchen features a center island and Aga stove, opening to dining and living areas ideal for everyday comfort and entertaining. Upstairs are two generous guest bedrooms, abundant closets - including a cedar-lined walk-in - and a full bath. Enjoy the seasons from the screened porch or custom fieldstone patio with sitting wall and awnings. Quality features include central air, whole-house generator, security system, water filtration, standing-seam metal roof, Andersen windows, attached two-car garage, and excellent dry basement storage. Minutes to Manchester and Dorset, this private, move-in-ready property offers convenience, comfort, and enduring Vermont charm.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 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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576 Hampshire Hill Road Worcester VT 05682

Worcester, VT576 Hampshire Hill Road

Price$1,175,000

Est. Mortgage: $/month

MLS Number 5103408

  • Residential Single Family
  • PricePerSqFt 455.43
  • Full Bath 2
  • Construction Existing
  • Bedrooms 2

$75K PRICE IMPROVEMENT - Tucked at the end of a winding driveway on 85.7 acres adjoining Putnam State Forest, this remarkable Worcester property has been shaped over decades into a private world of its own where one immediately feels the serenity and tranquility. At its heart is a 15 ft deep spring-fed swimming pond, thoughtfully designed with hand-laid stone walls, broad stone steps, diving rocks, sandy beach and the constant serenade of the waterfall making it an extraordinary place to swim, gather, or simply sit at the water's edge and take in the quiet and natural beauty. From mist rising over the pond in the morning to changing light across the mountains at day's end, the landscape reveals a different mood with every hour and every season. The contemporary home is warm and inviting, with natural wood, generous windows and mountain views that keep the surrounding landscape present from room to room. Beyond the house, trails wind through the property, connecting woods, gardens and open spaces with a tea house, artist studio and guest cabin tucked into the landscape. There is a sense of intention here that is difficult to recreate: a property designed not around excess, but around experience...swimming at dawn, walking the trails, making art, tending gardens, watching the seasons move across the mountains. With direct access to thousands of acres of protected forest and Montpelier just down the road, it offers exceptional privacy without isolation. More than a home with acreage, this is a place that has been carefully loved, thoughtfully shaped and is ready for its next steward to make it their own.

Listed by Krista Harness of Heney Realtors - Element Real Estate (Montpelier)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 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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882 Mitchell Road Shrewsbury VT 05738

Shrewsbury, VT882 Mitchell Road

Price$1,170,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5076056

  • Residential Single Family
  • PricePerSqFt 566.59
  • Full Bath 1
  • Address 882 Mitchell Road
  • Construction Existing

Snowlight Farm spans 137 acres along the western slopes of the Green Mountains, with sweeping views across the Green Mountains to the Taconic Range. The offering includes a 2,692 square foot Federal-style farmhouse, built in 1812, with four bedrooms and 1.5 baths, complemented by a circa-1850 repurposed barn with 2,065 square feet of living space including four bedrooms and 3.25 baths. The early 19th-century main house has the kind of proportion and presence that only time can give, elegant, grounded, and deeply Vermont, while benefiting from extensive renovations completed in 2025. Original doors, period hardware, and wide-plank pine floors remain throughout. The kitchen features slate countertops, a six-burner BlueStar gas range with dual ovens, a Sub-Zero four-drawer refrigerator, and a Galley farm sink. The mid-19th-century barn was thoughtfully reimagined into two residences: a three-bedroom residence on the upper levels and a one-bedroom residence below, each with a full kitchen and private entrance--ideal for extended family or guests. A cold, clear spring provides water for both homes. Two branches of a brook wind through the land. Approximately 27 acres of open meadow, currently in active agriculture, along with managed woodland, are enrolled in Current Use and protected by a conservation easement held by the Vermont Land Trust. This is a property that invites stewardship, whether for farming, conservation, recreation, or simply living well. Within Shrewsbury, enjoy access to the Long Trail and the 1,850-acre Plymsbury Wildlife Management Area, with miles of trails for walking and cross-country skiing. Killington and Okemo are close by, and Rutland Regional Airport is less than five miles away.

Listed by Dia Jenks and T Story Jenks of LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 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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1472 Carpenter Hill Road Guilford VT 05301

Guilford, VT1472 Carpenter Hill Road

Price$1,165,000

Est. Mortgage: $/month

MLS Number 5104005

  • Residential Single Family
  • PricePerSqFt 349.01
  • Full Bath 1
  • Construction Existing
  • Bedrooms 4

The Governor Carpenter Homestead, a pivotal piece of American history in Guilford, VT, is now accepting applications for its next Steward. This remarkable property was constructed in 1772 by Benjamin Carpenter, Vermont's first Lieutenant Governor. Lovingly maintained for decades, the residence combines historic integrity with modern functionality. Key features include: Architectural Significance: A gracious, charming house featuring a central chimney and a unique, squared-off Palladian window over the front door - one of only four known examples in Vermont. Historic Details: Five working fireplaces (including a large living room hearth with a beehive oven), and the original one-hole privy in the carriage house. Scenic Surroundings: Located across a dirt road from a lovely pond with remnants of an old barn foundation. Revolutionary Lore: An enclosed garden near the house is traditionally believed to have been a former campsite of Ethan Allen and the Green Mountain Boys. Modern Comfort: Features 21st-century plumbing while preserving its authentic character. New septic system installed in 2020. This is an unparalleled opportunity to own a property rich in history, charm, and character. A short drive to Brattleboro and everything it has to offer. Boston: 2.5 hrs. NYC 4 hrs. {Additional 30+/- acres available for an additional $250,000}

Listed by Thom Dahlin of Berkley & Veller Greenwood Country

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 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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82 North Brookwood Road Stratton VT 05155

Stratton, VT82 North Brookwood Road

Price$1,160,000

Est. Mortgage: $/month

MLS Number 5086826

  • Residential Single Family
  • PricePerSqFt 316.59
  • Full Bath 4
  • Construction Existing
  • Bedrooms 5

Location , Location , Location! Situated on North Brookwood just below the covered brige you'll enjoy easy access to the Wanderer ski trail as well as the resort shuttle that picks you up at your driveway! This iconic resort property features a great room with custom wood barrel cathedral ceilings, a wall of glass, wood burning fireplace and wrap around deck. Designed for the mountain enthusiast, this propery has the features you look for in a Resort Residence, 5 bedrooms (which includes a spacious and private primary suite wing), 4 updated bathrooms, a spacious media room that opens to a patio with hot tub and fire pit. The galley kitchen opens to a dining room and all with ease to entertaining and apres ski. This location is prime for winter ski and snowboarding as well as an incredible mountain biking trail system during the summer and fall. Hike, bike, golf and enjoy incredible year round activities. Very few homes become available in the North Brookwood neighborhood. Don't miss an opportunity to create your own mountain lifestyle in this great resort location.

Listed by Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 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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Lot 12 Mountainside Drive Killington VT 05751

MLS Number 5024574

  • Land
  • PricePerSqFt 424354.24
  • Acreage 2.71
  • Area VT-Rutland
  • Utilities Cable Available

Build Your Dream Home in One of Killington's Most Exclusive Communities Set within the prestigious Mountainside development, this exceptional 2.71-acre, single-family building lot at 2,450 ft elevation offers the opportunity to create your own private Killington retreat in an increasingly exclusive community of high end homes. Tucked just off East Mountain Road, Mountainside combines privacy and tranquility with convenient access to everything Killington has to offer. Enjoy spectacular views of Killington Mountain and the valley, with the High Ridge trail providing an added level of convenience for winter & summer enthusiasts. The thoughtfully planned community features underground utilities and sewer to each lot, making the path to building your dream home that much easier. Mountainside's protective covenants and high-quality homes help preserve the character, desirability, and long-term value of the community, making this more than just a building lot it is an opportunity to become part of one of Killington's premier residential neighborhoods. Create a home designed around the mountain lifestyle, with skiing, biking, hiking, restaurants, nightlife, and year-round recreation just out your door. Private showings and detailed development information available by appointment. Call today to explore this rare opportunity to build in Mountainside.

Listed by Bret Williamson of Killington Valley Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 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 Wright Avenue Burlington VT 05401

Burlington, VT56 Wright Avenue

Price$1,150,000

Est. Mortgage: $/month

MLS Number 5083392

  • Multifamily
  • PricePerSqFt 1078.8
  • Address 56 Wright Avenue
  • Units 3
  • Bathroom 3

Incredible opportunity to own a beautifully updated 3-unit property in Burlington's highly desirable South End, offering stunning views of Lake Champlain from each apartment. This well-maintained building features three one-bedroom units, each thoughtfully upgraded with quality finishes and modern systems. Recent improvements include all new windows, Therma Tru exterior doors, and new flooring throughout. The bathrooms have been tastefully updated with tiled showers, and the property benefits from a new electrical service, upgraded plumbing, and an on-demand hot water system (2026). Additional highlights include energy-efficient mini-split systems, professional insulation for year-round comfort, and newly constructed covered porches with durable Trex decking perfect for taking in the lake views. Ideally located, this property offers easy access to the Burlington Bike Path, University of Vermont Medical Center, and the vibrant Church Street Marketplace. Enjoy close proximity to the Burlington waterfront, along with an array of local shops, restaurants, and all that downtown Burlington has to offer.A rare opportunity to own a turnkey multi-family property in one of Burlington's most sought-after neighborhoods.

Listed by Brian French of Brian French Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 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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14 Sunset Drive Waterbury VT 05677

Waterbury, VT14 Sunset Drive

Price$1,150,000

Est. Mortgage: $/month

MLS Number 5106848

  • Multifamily
  • PricePerSqFt 220.56
  • Address 14 Sunset Drive
  • Units 2
  • Acreage 0.59

Exceptional investment opportunity in a prime Waterbury location along the highly traveled Waterbury-Stowe/Route 100 corridor. Offering approximately 5,214 finished square feet, this versatile property combines existing residential and income-producing spaces with exciting potential for future multifamily use. The property currently includes spacious residential accommodations featuring three bedrooms with private en suite baths, a chef's kitchen and inviting living areas. An additional portion is currently utilized as a short-term rental, providing an established rental component. Existing retail/commercial space adds another layer of flexibility and may offer potential for conversion into additional residential units, subject to municipal and state approvals. With its generous square footage and adaptable layout, investors may wish to explore opportunities to create additional apartments or further develop the property as a multifamily investment. More than 2,300 square feet of basement space provides substantial storage and utility space, while a two-car garage, ample on-site parking and an elevator/dumbwaiter system add functionality. Location is a standout feature. Situated directly across from Cold Hollow Cider Mill on the Waterbury-Stowe Rd (rte 100) and minutes from Ben & Jerry's, Waterbury Reservoir, downtown Waterbury and Stowe, the property offers convenient access to skiing, hiking, mountain biking, restaurants, shopping and year-round recreation. Whether continuing the property's current combination of uses or exploring additional residential possibilities, 14 Sunset Drive offers a rare combination of location, square footage, parking, flexibility and income potential in one of Central Vermont's most desirable destinations. Buyer to complete due diligence regarding permitted uses, unit count, zoning and conversion possibilities.

Listed by Shannon Kane of CENTURY 21 North East

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 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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476 Dix Hill Plymouth VT 05056

Plymouth, VT476 Dix Hill

Price$1,150,000

Est. Mortgage: $/month

MLS Number 5098107

  • Residential Single Family
  • PricePerSqFt 439.1
  • Full Bath 1
  • Address 476 Dix Hill
  • Construction Existing

This perfect country get-away offers privacy, views to the west of Okemo Mountain and easy access to skiing and the lakes region, all just a short drive away. With over 4,000 sq. ft. and generous size rooms throughout, the (3) floors of quality living space have been beautifully updated and maintained by the current owners. A few of the homes many notable features include a large air lock entry, wood flooring in the living/ dining/kitchen areas, central AC and radiant heating, master suite on the 1st floor, vaulted ceilings in the living area and kitchen with custom cabinets and countertops and is being offered fully furnished. Enjoy the views and spectacular sunsets over Okemo Mountain from the expansive deck off the main floor as well as from most of the rooms in the home. The walkout lower level has multiple windows and offers a huge bonus/game room area. With an oversize garage with (4) doors and an unfinished 2nd floor, you have plenty of room for your toys and storage for your gear. For those who enjoy a peaceful walk in the woods or snow-shoe in the winter, there have been trails cut and maintained on the property. Come and experience the natural beauty of the homes surroundings and all this home has to offer.

Listed by Roger Danyew of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 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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528 Pinnacle Road Stowe VT 05672

Stowe, VT528 Pinnacle Road

Price$1,150,000

Est. Mortgage: $/month

MLS Number 5097095

  • Residential Single Family
  • PricePerSqFt 1277.78
  • Full Bath 1
  • Address 528 Pinnacle Road
  • Construction Existing

Stowe Retreat with Modern Updates and Room to Grow Tucked into a peaceful wooded setting on a quiet residential road, this thoughtfully renovated home offers the perfect balance of privacy, outdoor access, and modern comfort. Located just a short walk from the Stowe Pinnacle trailhead, it's an ideal basecamp for year-round adventure while remaining close to everything Stowe has to offer. The home's flexible layout works equally well as a primary residence, vacation getaway, or investment property. The lower level features a spacious mudroom, a bunk room that sleeps four, a king bedroom, and a three-quarter bath. Upstairs, you'll find an open living, dining, and kitchen area, a full bath with a deep soaking tub, and a queen bedroom. Extensively renovated from top to bottom, the home blends clean, contemporary finishes with the warmth and character that make Vermont homes so inviting. Every major system has been updated, allowing the next owner to move in and immediately enjoy the property. Highlights o Fully renovated throughout with modern finishes and updated systems o Proven rental history with strong guest appeal o Flexible floor plan for full-time living, weekend escapes, or rental use o Quiet, wooded setting on a low-traffic residential street o Walkable access to the Stowe Pinnacle trailhead o Potential mountain views with selective tree clearing o Detached garage offering future expansion possibilities Major Improvements o All new electrical and plumbing throughout o Upgraded 200-amp electrical service o Heat pump system providing efficient heating and cooling o Fully renovated kitchen with updated fixtures and finishes o Two updated bathrooms, including a soaking tub o New flooring throughout o Updated lighting and interior finishes Additional Potential The detached garage presents exciting possibilities for future use, whether as a workshop, recreation space, expanded living area, or accessory apartment (subject to local approvals). Offered separa

Listed by Jonathan Minerick of homecoin.com

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 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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240 Ghia Farm Road Ludlow VT 05149

Ludlow, VT240 Ghia Farm Road

Price$1,150,000

Est. Mortgage: $/month

MLS Number 5100934

  • Residential Single Family
  • PricePerSqFt 517.09
  • Full Bath 2
  • Address 240 Ghia Farm Road
  • Construction Existing

Located just a few minutes walk from Okemo's Sachem trail, this two family spacious 5-bedroom, 3-bathroom multi-level home offers exceptional flexibility for year-round living, vacationing, or hosting family and friends. Lovingly owned for almost 30 years, this home is designed with a versatile multi-family layout. Each level provides its own inviting living space while maintaining the warmth and charm of a classic Vermont mountain home. The main level features a bedroom and bath while the open-concept floor plan features a full kitchen flowing into the dining area and living room. All this is anchored by a cozy wood-burning brick floor to ceiling fireplace. Step outside onto the expansive deck, where you'll enjoy peaceful wooded views and the privacy of a natural Vermont setting. Above, the loft overlooks the main living area and is complemented by two additional bedrooms, bath and a convenient laundry area. The walkout lower level functions as its own comfortable living space with two bedrooms, a second full kitchen, dining area, and living room centered around another wood-burning fireplace. Glass doors lead to a private backyard surrounded by mature trees, featuring beautifully established perennial gardens that create a tranquil outdoor retreat. Whether you're looking for a vacation home or a property with space for extended family and guests, this home offers outstanding versatility in one of Okemo's most desirable locations. Enjoy easy access to skiing at Okemo Mountain Resort, Fox Run Golf Club, nearby lakes, hiking and snowmobile trails, and the shops and restaurants of Ludlow Village, making this the perfect home base for four seasons of Vermont adventure. Visit the Okemo real estate community today. Taxes are based on town assessment.

Listed by Joseph Karl of William Raveis Real Estate Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 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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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 October 7, 2026 12:37 AM UTC