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Very Cool Houses

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27 Mountain View Road Winhall VT 05340

Winhall, VT27 Mountain View Road

Price$1,990,000

Est. Mortgage: $/month

MLS Number 5092802

  • Residential Single Family
  • Full Bath 5
  • Construction Existing
  • Bedrooms 6
  • Bathroom 7

Direct views of Stratton Mountain set the stage for this exceptional post-and-beam residence, offering a rare combination of luxury living, entertaining space, and rental flexibility. Handcrafted timber framing creates warmth and character throughout, while four fireplaces including a gas fireplace in the primary suite enhance the home's mountain atmosphere. Designed for gathering, the lower level features a full bar, game room, family room, and wood-burning fireplace, creating an ideal setting for aprs-ski entertaining. The primary suite serves as a private retreat with a spa-like bath, indoor sauna, hot tub, and oversized shower. Outdoor living is equally impressive. The expansive deck functions as a four-season outdoor kitchen and lounge complete with a covered porch, wood-fired pizza oven, gas grill, and gas fire pit. A landscaped level yard provides additional usable outdoor space, while a second outdoor hot tub extends the home's resort-style amenities. Recent improvements include updated Thermador appliances and a new roof. Additional features include a heated two-car garage and direct access to the Stratton shuttle route. A standout feature is the home's ability to operate as two fully independent residences, each with its own kitchen and laundry. This flexible configuration creates opportunities for personal use, hosting guests, or maximizing rental income throughout the year.

Listed by Jamie Wylie of Stratton Real Estate

$
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$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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25 Cavendish Cove South Hero VT 05486

South Hero, VT25 Cavendish Cove

Price$1,979,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5083045

  • Residential Single Family
  • Full Bath 1
  • Address 25 Cavendish Cove
  • Construction Existing
  • Bedrooms 3

Located on sought-after Kibbe Point, this stunning two-story contemporary island home sits on 2.75 private acres with 249 feet of pristine Lake Champlain shoreline. Designed to embrace its natural surroundings, the home features a bright open-concept great room with hardwood floors, stainless steel appliances, granite countertops, white cabinetry, and a large center island-perfect for entertaining. Expansive windows and sliding doors lead to a full-length lakeside deck offering breathtaking panoramic views of the lake, surrounding islands, and distant mountains. Enjoy year-round comfort in the 4 season sunroom with warm buttery pine walls, radiant heat and an LP gas fireplace for cozy evenings. The spacious primary suite boasts vaulted ceilings, large custom walk-in closet with built in drawers and shelving and an elegant ensuite bath with large double vanity, walk-in shower w/ custom tile work and double shower heads. There are two nicely appointed spacious bedrooms on the second floor and a walk in pantry. The lower level features a 15 x 29 ft family/media room with radiant heat, built-in surround sound system and sliders to access the lake. This level also includes another guest room with ensuite 3/4 bath and a dedicated office with lake views with sliders to a private patio. After a day out on the water fire up the grill and hang out with the crew at your Tiki Bar overlooking the lake, islands and mountains. Recent improvements include a new roof, freshly painted interior and exterior, new mini-split heat pumps with A/C. Looking for a space for projects and storage for all your lake gear? The 24 x 36 detached garage is heated and insulated and includes a 2nd floor shop space and 1st floor workout room. Deep-water access makes this the ideal property for boating, swimming, and lakeside living. Peaceful, private, and well-appointed-this exceptional home offers the perfect blend of modern comfort and natural beauty, a convenient 20 minute drive from Burlington.

Listed by Franz Rosenberger of Coldwell Banker Islands Realty

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$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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74 N Brookwood Road Stratton VT 05155

Stratton, VT74 N Brookwood Road

Price$1,975,000

Est. Mortgage: $/month

MLS Number 5088735

  • Residential Single Family
  • Full Bath 3
  • Address 74 N Brookwood Road
  • Construction Existing
  • Bedrooms 4

PRIME LOCATION near the coveted STRATTON MOUNTAIN RESORT. This EXCEPTIONAL four bedroom three bathroom turn-key home is PRIVATELY SITUATED on 1.5 acres and READY TO BE ENJOYED YEAR ROUND. Snowmobile right from the house to access thousands of acres of pristine VAST snowmobile trails for ENDLESS WINTER ADVENTURE. Ski home to the Covered Bridge neighborhood or hop on the resort shuttle, which runs every weekend and picks up right at the end of the driveway for an EFFORTLESS TRIP TO AND FROM THE MOUNTAIN. This property also coveys with the coveted Stratton Mountain and Fitness bond, granting FULL ACCESS to the golf course, fitness center, and an EXCLUSIVE PRIVATE HOMEOWNERS LODGE AT THE MOUNTAIN. The spacious great room features CATHEDRAL CEILINGS, walls of glass and a DRAMATIC WOOD BURNING FIREPLACE. The GOURMET KITCHEN with stone countertops and UPSCALE APPLIANCES opens seamlessly to the dining and great room. The primary suite offers privacy with a BEAUTIFUL BATH, walk in closets and WOODLAND VIEWS. A family room with SUNNY EXPOSURE opens to the back deck where you can ENJOY THE SPA. Multiple decks provide both covered and open spaces to enjoy the seasons, including a beautiful front upper deck that offers AMAZING SUNRISE AND SUNSET VIEWS. Wood floors, tile baths, and a lovely entry and mudroom complete the interior. IDEAL FOR WINTER AND SUMMER ENTHUSIASTS seeking a premier resort.

Listed by Paul Marino of WWW.FLATFEEMLS4FREE.COM

$
$
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$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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59 Meadow Street Rutland City VT 05701
Active With Contract

MLS Number 4997552

  • Commercial
  • Address 59 Meadow Street
  • Year Built 1903
  • Square Feet 20,341
  • Acreage 1.33

Welcome to the Loretto Home, a captivating 20,000 SF historic brick building located in the vibrant heart of Rutland, Vermont. This distinguished property, formerly a senior living facility owned by the Roman Catholic Diocese, offers a unique blend of historic charm and modern potential. Nestled on 1.33 acres of beautifully landscaped grounds, the Loretto Home stands as a testament to architectural elegance and timeless design. Located in the bustling downtown area, the Loretto Home is perfectly positioned to benefit from Rutland's rich community life and economic opportunities. Its proximity to local shops, restaurants, and cultural attractions makes it an ideal location for both commercial and residential endeavors.

Listed by Kendra Kenney of Pomerleau Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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4647 Lake Road Newport Town VT 05857

Newport Town, VT4647 Lake Road

Price$1,945,000

Est. Mortgage: $/month

MLS Number 5086492

  • Residential Single Family
  • Full Bath 2
  • Address 4647 Lake Road
  • Construction Existing
  • Bedrooms 3

WELCOME TO HIDDEN HAVEN-an extraordinary country estate set on 137 private acres with breathtaking views of Lake Memphremagog and Vermont's Green Mountains. Tucked away just ½ mile off Lake Rd and accessed by a private gated drive, this one-of-a-kind property offers the perfect blend of luxury living and outdoor recreation. The custom 13-room residence features nearly 6,000 sq.ft. of finely crafted living space highlighted by 10' ceilings, custom-milled woodwork, a stunning stained-glass skylight and a beautifully appointed library. The gourmet kitchen is designed for the serious chef with a gas cooktop, pot filler, imported tile backsplash, granite counters, double ovens and a spacious walk-in pantry. The main level primary suite offers a true retreat with a spa-like bath, walk-in shower, generous walk-in closet and convenient laundry area. The second level provides two additional bedrooms, a full bath and a second laundry space. The walk-out lower level is ideal for entertaining with a home theater, expansive bar and game room. A massive 40'x100' outbuilding makes a perfect place to park your RV/Motorhome with a full upper-level workshop offering endless possibilities for storage, hobbies or business use. Energy-efficient features include an 8KW grid-tied solar array, high-speed internet and a 15KW automatic standby generator. The land itself is equally impressive with an established trail network, over 100 acres of forest, a productive garden, apple orchard and a separately deeded 10-acre parcel suitable for additional development. A rare opportunity to own a private Vermont retreat where peace, privacy and natural beauty define the lifestyle.

Listed by James Campbell of Jim Campbell Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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351 Ledgewood Drive Williston VT 05495

Williston, VT351 Ledgewood Drive

Price$1,925,000

Est. Mortgage: $/month

MLS Number 5087443

  • Land
  • Address 351 Ledgewood Drive
  • Acreage 33.6
  • Area VT-Chittenden
  • PricePerSqFt 57291.67

This is the type of property that quietly grabs your attention and keeps it! The views here are genuinely impressive-wide open and stretching southwest across the Champlain Valley to Lake Champlain, with the Adirondack Mountains rising beyond. You'll enjoy year-round sunsets from this vantage point. Turn to the east, and the perspective shifts to expansive views of the Green Mountains, with sunrises greeting you every morning. On a clear day, you can see for miles, with Burlington in the distance, set against the rolling hills. It's a straightforward, expansive setting that's hard to overlook. The land is ready for your build, with a level meadow site positioned to capture the full 270-degree view. While part of a desirable neighborhood, the setting feels notably private, with no homes in sight. At the same time, you're just minutes from everyday conveniences-restaurants, grocery stores, gyms, and more. This balance of privacy, acreage, and proximity within Chittenden County makes it a smart place to invest, with strong long-term appeal. This is the place to build your forever home and experience a more peaceful Vermont lifestyle. The land could easily support beautiful gardens, walking paths through the meadows, and gathering spaces to enjoy every season. Picture bonfires under the stars, watching the Northern Lights from one of the best vantage points in the county, or creating a rooftop deck to take in the incredible scenery. Vermont's beauty here is something you'll appreciate both day and night. The property gently rolls into additional meadows dotted with cedar, birch, and maple trees, adding natural character and depth. A State of Vermont wastewater permit is in place for a 5-bedroom home, and a drilled well is already on site. Krebs & Lansing has completed a full survey. The property is approved for one single-family home. The owners have architectural drawings prepared by Truex Cullins, an award-winning architecture firm, which are available upon request.

Listed by Kathleen OBrien and Patrick O'Connell of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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709 Us Route 4 Killington VT 05751

MLS Number 5073937

  • Commercial
  • Address 709 Us Route 4
  • Year Built 1970
  • Square Feet 13,438
  • Acreage 12.3

Own a high-demand hospitality asset in Killington Vermont's most iconic resort town and a proven tourism powerhouse. With a track record of Gross Sales over $1MM, this hotel and bar attract consistent year-round traffic from skiers, hikers, and vacationers, while maintaining strong local patronage. With proven demand and a prime location in one of New England's most resilient leisure markets, it represents a rare opportunity for investors seeking stable revenue and long-term growth potential.

Listed by Shem Nelson of Badger Peabody & Smith Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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00 Vt Route 11 Peru VT 05152

Peru, VT00 Vt Route 11

Price$1,900,000

Est. Mortgage: $/month

MLS Number 5077219

  • Land
  • Address 00 Vt Route 11
  • Acreage 199
  • Area VT-Bennington
  • Utilities None

Bordering Green Mountain National Forest with southern exposure and views of Stratton Mountain and the surrounding Green Mountains, this 199 +/- acre offering in Peru, Vermont captures the scale, landscape, and natural beauty that define Southern Vermont mountain living. Rolling terrain, wooded ridgelines, and changing elevation create exceptional natural light, long-range mountain vistas, and a strong connection to the surrounding forested landscape. The property offers direct access to Green Mountain National Forest while presenting multiple potential building locations positioned to preserve view corridors, separation, and the character of the land itself. Imagine mornings with mountain light moving across the ridgeline, afternoons exploring nearby trails and wilderness, and winter weekends centered around some of Southern Vermont's most recognized ski destinations just minutes away. The acreage offers exceptional flexibility for a private estate, multi-generational retreat, or conservation-minded Vermont holding shaped around the surrounding landscape and four-season outdoor lifestyle. Located near Bromley Mountain and within easy reach of Magic Mountain, Stratton Mountain Resort, and the shops and dining of Manchester, the setting balances expansive acreage and direct forest access with convenient proximity to year-round recreation and amenities. A remarkable Southern Vermont land offering combining significant acreage, Green Mountain National Forest frontage, southern exposure, and mountain views in one of the region's most desirable four-season settings. Additionally listed under MLS #5072898

Listed by Kevin Moran of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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709 Us Route 4 Killington VT 05751

Killington, VT709 Us Route 4

Price$1,900,000

Est. Mortgage: $/month

MLS Number 5085656

  • Residential Single Family
  • Full Bath 23
  • Address 709 Us Route 4
  • Construction Existing
  • Bedrooms 26

Fully staffed Inn, Restaurant & Pub with Owner's Wing. Own a high-demand hospitality asset in Killington; Vermont's most iconic resort town, and a proven tourism powerhouse. With a track record of gross sales over $1MM, this hotel and bar attract consistent year-round traffic from skiers, hikers, and vacationers, while maintaining strong local patronage. With proven demand and a prime location in one of New England's most resilient leisure markets, it represents a rare opportunity for investors seeking stable revenue and long-term growth potential. Also perfect for anyone looking to shorten their commute; work where you live and play! The owner's apartment is a massive 4 bedroom, 2 1/2 bath, two story apartment with spectacular views and a fenced yard making it the perfect owner occupied business opportunity.

Listed by Shem Nelson and Andy Smith of Badger Peabody & Smith Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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751 Main Road Stamford VT 05352

Stamford, VT751 Main Road

Price$1,900,000

Est. Mortgage: $/month

MLS Number 5085047

  • Residential Single Family
  • Full Bath 3
  • Address 751 Main Road
  • Construction Existing
  • Bedrooms 6

Step into the most amazing Victorian house you will ever see! Built in 1880, you will feel like you've walked back in time. Beautiful architecture and woodwork. The house was built by John Tudor, a Welsh immigrant who had made a fortune as a mill owner in northern Vermont and settled in Stamford. There is a stunning 3 floor Post & Beam Barn built in 2000 with a 2 car garage built-in. Barn also features 4 stalls with room for a 5th, tack room, hayloft, along with some finished sq ft with electric, heat and water. Also included is a 2nd home on the property. It's a 2 bedroom 870 sq ft 1 story Modular. Other amenities include a very large in ground salt water pool with new liner along with a beautiful pool house with outdoor kitchen and bathroom, sauna, green houses, shed and a tiny vineyard with 50 vines! Two duck houses and a small 10 x 8 cow barn. Oh, I almost forgot the chicken coop! 400 amp Whole House Generator. 2 septics and 2 drilled wells. Located on the southern border of Vermont with mountain views of Mt Greylock in the Berkshire Mountains. Just under 10 acres of level land with fruit trees. 2 Stone Lions in the front yard have been a marque in the village for years. This property has so much to offer in a small southern Vermont town!

Listed by Michael Jarvis of United Country Real Estate Mike Jarvis Group Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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200B Burgess Road Shoreham VT 05770

Shoreham, VT200B Burgess Road

Price$1,899,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5087745

  • Residential Single Family
  • Full Bath 2
  • Address 200B Burgess Road
  • Construction Existing
  • Bedrooms 3

Set against the backdrop of Vermont's Champlain Valley, Peaceable Hill Farm spans 227± acres of open fields, woodlands, and Lemon Fair River frontage. With sweeping Green Mountain views and a carefully restored late 1800s post-and-beam farmhouse, the property balances historic character with modern comfort in a setting defined by conservation and natural beauty. Peaceable Hill Farm is more than acreage-it is a place to slow down, connect with the land, and enjoy Vermont's enduring landscapes. Wander along the riverbanks, explore wooded trails, or take in the quiet views across miles of protected farmland. With its combination of privacy, scale, and thoughtful stewardship, the farm is well-positioned for its next chapter. The restored late 19th-century post-and-beam residence has been renovated to showcase its period craftsmanship while incorporating modern updates for year-round living. The 227± acre landscape includes rolling countryside, open meadows, forested acreage, and river frontage suitable for farming, recreation, or conservation. Permanently protected by a Vermont Land Trust easement with right of first refusal, the property carries a lasting conservation legacy, while neighboring conserved parcels contribute to over 3,000 acres of protected land in the area. Peaceful yet convenient, Peaceable Hill Farm offers the rare chance to own a significant piece of Vermont's agricultural and scenic heritage, where the land itself becomes part of the home.

Listed by Wade Weathers and Averill Cook of LandVest,Inc-Burlington

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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2394 Fletcher Hill Road Woodstock VT 05091

Woodstock, VT2394 Fletcher Hill Road

Price$1,895,000

Est. Mortgage: $/month

MLS Number 5084536

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 2,944

Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is comprised of a large, open-format living space with gourmet kitchen, dining and living spaces, plus a first level bedroom with modern ensuite bath. Upstairs is another large open floor plan living space with a half-bath, and a full bedroom with ensuite bath. Each side of the upstairs living space has loft sleeping bunk-areas for kids (of all ages!). SEE DEDICATED PROPERTY WEBSITE FOR VIDEOS, VIRTUAL WALKTHROUGH, FLOORPLANS AND MORE.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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 June 9, 2026 1:07 AM EDT