32

Winhall, VT Homes for Sale with Acreage

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  • /42

    $1,100,000

    • 5 Beds
    • 4.5 Baths
    • 4,453 Sq Ft

    6 Old Ridge Rd, Winhall, VT 05340

    Welcome to High Meadow, one of Stratton’s most desirable neighborhoods. This expansive residence at 6 Old Ridge Road offers over 4,600 sq. ft. across three finished levels, combining mountain convenience with comfort, privacy, and style. The main level features an open kitchen, dining and vaulted living room with fireplace, plus a sunroom, screened porch, stone patio, and a private primary suite.

    Agent Photo

    Trent Stephens

    Wohler Realty Group

    (802) 213-9409

    6 Old Ridge Rd, Winhall, VT 05340
  • /15

    $115,000

    • Land
    • 2.9 Acres
    • $39,655 per Acre

    Lot 3 Route 11 30, Winhall, VT 05340

    Spectacular West and Southerly Views over Manchester Valley and boasts a bird's eye view across to the Equinox Mountain!Located on the Manchester side of Winhall, this property is at the end of a private lane offering privacy... engineered and offering VT Waste Water and Potable Water Supply Permit: WW-2-3614, design for 3 BR single family residence. Bordered by the Green Mountain Nat'l

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 808-6197

    Lot 3 Route 11 30, Winhall, VT 05340
  • /43

    $1,100,000

    • 5 Beds
    • 4 Baths
    • 4,788 Sq Ft

    6 Chad Cir, Winhall, VT 05340

    Tucked away at the end of a private cul-de-sac and just minutes from Stratton's slopes, this beautifully designed mountain home offers the perfect blend of comfort and luxury. The open-concept floor plan features a chef’s kitchen with granite countertops, a 6-burner professional gas stove, double ovens, a farm sink, and a wet bar with ice maker—ideal for entertaining. Wide pine floors and a

    Carrie Mathews Winhall Real Estate

    6 Chad Cir, Winhall, VT 05340
  • /37

    $2,400,000

    • 5 Beds
    • 4.5 Baths
    • 3,252 Sq Ft

    115 Benson Fuller Dr, Jamaica, VT 05343

    Perched on 3.5 private acres with commanding views from Stratton’s iconic slopes to Bromley’s trails, this architecturally striking residence blends the serenity of the mountains with sophisticated modern design. A dramatic central staircase anchors the home, leading to a sleek custom kitchen and a vaulted great room where walls of glass frame panoramic vistas. A floor-to-ceiling stone fireplace

    Carrie Mathews Winhall Real Estate

    115 Benson Fuller Dr, Jamaica, VT 05343
  • /60

    $1,825,000

    • 3 Beds
    • 4 Baths
    • 2,872 Sq Ft

    36 Beaver St, Bondville, VT 05340

    Your Ultimate Vermont Mountain Retreat Awaits! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape—crafted for adventure, relaxation, and making lasting memories in every season. Whether you’re hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage, this property delivers! Plus, it's only a 10-minute

    MaryKate Grey Stratton Real Estate

    36 Beaver St, Bondville, VT 05340
  • /55

    $2,225,000

    • 4 Beds
    • 4.5 Baths
    • 5,000 Sq Ft

    16 Hunter Ridge Rd, Bondville, VT 05340

    Custom built Wadsworth Design Build timber-frame mountain retreat blends luxury, craftsmanship, and convenience just minutes from Stratton Mountain Resort. Set on 2.66 acres and spanning 5,000± square feet, this 4-bedroom, 5-bath home includes two additional sleeping space ideal for hosting friends and family. A grand entry framed by oversized Douglas fir posts welcomes you into a lodge style

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    16 Hunter Ridge Rd, Bondville, VT 05340
  • /46

    $1,350,000

    • 4 Beds
    • 4 Baths
    • 4,640 Sq Ft

    33 Forest Haunts Rd, Winhall, VT 05340

    Discover Your Vermont Retreat Nestled amidst 20.8 private acres of tranquil woods, this French country manor offers an exceptional opportunity to own a piece of Vermont paradise. Situated near the serene North Branch Ball Mountain Brook, enjoy the soothing sounds of cascading water and the breathtaking beauty of nature. Property Highlights: Prime Location: Just minutes from Stratton Resort for

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    33 Forest Haunts Rd, Winhall, VT 05340
  • /40

    $1,975,000

    • 4 Beds
    • 4 Baths
    • 4,270 Sq Ft

    14 Old Ridge Rd, Winhall, VT 05155

    This mountain home is beautifully furnished with a refined design that perfectly balances comfort and style, offering a seamless move-in ready experience. Located in the sought-after High Meadow neighborhood, this four bedroom, four bathroom property sits high on a perch, with clear views of Stratton’s trails, and a view of Bromley from the front of the house. Rebuilt in 2023/2024, the home is

    Christiane Carroccio TPW Real Estate

    14 Old Ridge Rd, Winhall, VT 05155
  • /37

    $1,695,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,688 Sq Ft

    143 Stratton Mountain Access Rd, Winhall, VT 05340

    Just Completed by DG Builders in Stratton, Vermont143 Stratton Mountain Access Road, a newly completed 5-bedroom, 5-bath residence, located just minutes from Stratton Mountain Resort and all the year-round activities it has to offer. Blending modern mountain style with timeless Vermont charm, this home is move-in ready and waiting for its first owners.The light-filled open floor plan

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    143 Stratton Mountain Access Rd, Winhall, VT 05340
  • /21

    $425,000

    • 2 Beds
    • 1 Bath
    • 974 Sq Ft

    21 Deep Woods Cir Unit Lot 27, Winhall, VT 05255

    A cozy chalet style home tucked in the woods in Winhall. Enjoy peaceful and private living with three seasons of beautiful mountain views and twinkling valley below. Hot tubbing and star gazing year round. Second owner since 1976. Updates include new metal roof, siding, deck, hot tub, kitchen, floors, bath, detached shed and more. A short drive to Bromley and Stratton Resorts. Lots of easily

    Patti Trudel RE/MAX Four Seasons

    21 Deep Woods Cir Unit Lot 27, Winhall, VT 05255
  • /39

    $650,000

    • 5 Beds
    • 3.5 Baths
    • 2,468 Sq Ft

    17 Signal Hill Rd, Winhall, VT 05340

    17 Signal Hill Road offers Vermont charm in a secluded mountain setting. With over 2,400 square feet of living space, this five-bedroom, three-and-a-half-bath home has been thoughtfully maintained and move-in ready. The main level features a spacious living room with a dramatic fieldstone fireplace, vaulted ceilings, and skylights that fill the home with natural light. A loft overlooking

    Christiane Carroccio TPW Real Estate

    17 Signal Hill Rd, Winhall, VT 05340
  • /58

    $975,000

    • 5 Beds
    • 3.5 Baths
    • 3,500 Sq Ft

    20 Jamie Ln, Winhall, VT 05340

    Get ready for ski season! Plenty of space for the whole family. Set up for fun with two living rooms, a hot tub and barrel sauna. Great rental history. Owner is Listing Broker.

    David Powers 42 North LP

    20 Jamie Ln, Winhall, VT 05340
  • /22

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    3 Kimball Hill Rd Unit 1, Winhall, VT 05340

    Escape to the mountains in this charming A-frame, ideally located between the bustling town of Manchester and the area's best ski mountains. This home is your perfect base for year-round adventure, putting you just minutes from world-class skiing, hiking, mountain biking, and shopping.Inside, you'll find a comfortable layout featuring 3 bedrooms, 2 bathrooms, and a home office that can

    Robin Apps Four Seasons Sotheby's Int'l Realty

    3 Kimball Hill Rd Unit 1, Winhall, VT 05340
  • /60

    $685,000

    • 3 Beds
    • 2.5 Baths
    • 2,034 Sq Ft

    3 Short Rd, Bondville, VT 05340

    Charming Vermont Homestead: Ideal for Ski Lovers or Those Seeking a Homesteading Lifestyle Escape to the serene beauty of Vermont with this renovated Cape located in Winhall, offering a perfect blend of rustic charm and modern updates. This home is ideal for anyone looking for a home near the slopes or a peaceful getaway with room to relax.Modern Updates Meet Classic Vermont

    Mike England Michael England Real Estate

    3 Short Rd, Bondville, VT 05340
  • /37

    $999,000

    • 4 Beds
    • 3.5 Baths
    • 2,280 Sq Ft

    17 Roundtree Rd, Winhall, VT 05340

    Contemporary ski chalet on shuttle route located on a short cul-de-sac in the coveted North Brookwood neighborhood, a stone's throw from the Stratton base lodge. This 4 bedroom, 3 1⁄2 bath home boasts an open plan, walls of windows, and floor-to-ceiling stone fireplace in the Great Room. The pass-through kitchen was fully renovated in 2021 in addition to many other upgrades. Test your skills at

    Sarah Nichols Winhall Real Estate

    17 Roundtree Rd, Winhall, VT 05340
  • /59

    $2,800,000

    • 3 Beds
    • 3.5 Baths
    • 3,938 Sq Ft

    23 Valley View Rd, Winhall, VT 05340

    Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings

    Kim Morgan-Wohler Wohler Realty Group

    23 Valley View Rd, Winhall, VT 05340
  • /28

    $729,000

    • 4 Beds
    • 2 Baths
    • 2,055 Sq Ft

    21 Burnt Hill Rd, Winhall, VT 05341

    Welcome to Gone Ski Inn, your cozy, all-season mountain retreat in the heart of Vermont!This charming home features four inviting bedrooms and two well-appointed bathrooms, offering plenty of space to unwind after a day of adventure. In the winter, cozy up by the crackling wood-burning fireplace , toasty wood stove or relax in the soothing hot tub under the stars. With ski trails just

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    21 Burnt Hill Rd, Winhall, VT 05341
  • /38

    $860,000

    • 4 Beds
    • 3.5 Baths
    • 4,104 Sq Ft

    25 Benson Fuller Dr, Jamaica, VT 05343

    Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape.Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for

    Robin Apps Four Seasons Sotheby's Int'l Realty

    25 Benson Fuller Dr, Jamaica, VT 05343
  • /6

    $110,000

    • Land
    • 1 Acre
    • $110,000 per Acre

    88A Sylvan Ridge Rd, Winhall, VT 05340

    Wooded lot with hardwoods, evergreens and birch trees. Potential views of Bromley Mountain and beyond. Town maintained road. Close to VAST snowmobile trails. Build your dream home in the Golden Triangle of ski areas, Stratton, Bromley, and Magic Mountains. Only 10 minuets to Manchester. Available on request:Wastewater System and Potable Water Supply PermitSeptic

    Andrew King Stratton Real Estate

    88A Sylvan Ridge Rd, Winhall, VT 05340
  • /21

    $370,000

    • 3 Beds
    • 1.5 Baths
    • 1,116 Sq Ft

    6 Deep Woods Rd, Winhall, VT 05255

    Escape to your cozy log ski chalet nestled on a private acre in the charming town of Winhall, Vermont! This delightful 3-bedroom, 1.5-bath home offers 1116 square feet of rustic charm and modern comfort. Imagine returning from a thrilling day on the slopes of nearby Stratton or Bromley, just a short drive away, and unwinding by the crackling outdoor fireplace on your spacious patio, with festive

    Robin Apps Four Seasons Sotheby's Int'l Realty

    6 Deep Woods Rd, Winhall, VT 05255
  • /13

    $135,000

    • Land
    • 1.36 Acres
    • $99,265 per Acre

    0 Stratton View Rd, Winhall, VT 05340

    Stratton View Road lives up to its name. Big Views of Stratton, just 3 minutes to Stratton access road. Minutes to the snow making pond, great for walking and a dip in. the summer. There are 3 ski resorts with in 15 minutes as well as Manchester for shopping and dining. Own your piece of Vermont.

    Mike England Michael England Real Estate

    0 Stratton View Rd, Winhall, VT 05340
  • /8

    $65,000

    • Land
    • 1.02 Acres
    • $63,725 per Acre

    0 Stratton View Rd, Winhall, VT 05340

    Stratton View Rd Lot # 59 , 1.02 +- acres wooded parcel. Just 3 minutes to Stratton access road. Minutes to the snow making pond, great for walking and a dip in. the summer. There are 3 ski resorts with in 15 minutes as well as Manchester for shopping and dining. Addition lot MLS #5036988 available. Own your piece of Vermont.

    Mike England Michael England Real Estate

    0 Stratton View Rd, Winhall, VT 05340
  • /6

    $495,000

    • Land
    • 6.93 Acres
    • $71,429 per Acre

    lot#2 Margeaux Ln, Stratton, VT 05155

    This stunning 6.93-acre parcel offers the perfect setting to build the home of your dreams, just moments from the Sun Bowl at Stratton. Nestled in a serene wooded landscape, the property provides both privacy and tranquility while being ideally located for easy access to all that Stratton has to offer. With a septic permit already approved for a 4-bedroom home, this lot is ready for you to begin

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    lot#2 Margeaux Ln, Stratton, VT 05155
  • /5

    $465,000

    • Land
    • 5.54 Acres
    • $83,935 per Acre

    Lot #4 Margeaux Ln, Stratton, VT 05155

    Nestled along a peaceful babbling brook, this 5.54-acre parcel offers an idyllic setting for building the home of your dreams. Surrounded by a serene wooded landscape, the property provides both privacy and tranquility, while still being just moments from the Sun Bowl at Stratton. With a septic permit already approved for a 4-bedroom home, this lot is ready for construction, allowing you

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    Lot #4 Margeaux Ln, Stratton, VT 05155
  • /31

    $949,000

    • 4 Beds
    • 4.5 Baths
    • 2,658 Sq Ft

    73 Cranberry Hill Rd, Winhall, VT 05340

    Nestled at the end of a quiet road in the highly sought-after Strattonwald community, 73 Cranberry Hill Road is the quintessential European-style ski house, offering the perfect Vermont retreat. This impeccably upgraded home has never been rented and is turn-key, ready for immediate enjoyment. It combines timeless charm with modern conveniences, featuring air conditioning for year-round comfort.

    Carrie Mathews Winhall Real Estate

    73 Cranberry Hill Rd, Winhall, VT 05340
  • /35

    $649,000

    • 8 Beds
    • 3.5 Baths
    • 2,520 Sq Ft

    405 Vermont 30, Winhall, VT 05340

    Ski Resort Investment Gem! 2-Family Home Near Stratton & BromleyRare investment opportunity in the heart of Vermont's premier ski region. Located on scenic Vermont Route 30, this property offers unparalleled access to both Stratton Mountain Resort and Bromley Mountain Ski Resort. Whether you're looking to live in one unit and rent the other, or convert it to a single-family home, this

    Robin Apps Four Seasons Sotheby's Int'l Realty

    405 Vermont 30, Winhall, VT 05340
  • /56

    $2,999,000

    • 6 Beds
    • 6.5 Baths
    • 6,650 Sq Ft

    25 Mountain Haunts Rd, Winhall, VT 05340

    Attend the PUBLIC OPEN HOUSE Monday February 17 from 10:00-2:00. Exceptional 40.8 acre newly expanded and renovated Stratton Mountain estate with unrivaled views of Stratton just minutes from the Base Lodge or Sun Bowl. This is your own personal winter playground where you can hit the slopes or snowmobile and hike on your own land with additional acreage available.This Grand Lodge NOW BOASTS 4

    Kim Morgan-Wohler Wohler Realty Group

    25 Mountain Haunts Rd, Winhall, VT 05340
  • /50

    $4,999,000

    • 6 Beds
    • 7.5 Baths
    • 8,720 Sq Ft

    454 Mountain Rd, Stratton, VT 05155

    Welcome to a one-of-a-kind 141-acre mountaintop retreat at Stratton Mountain Resort - an extraordinary sanctuary with panoramic views of Stratton, Mount Snow, and Bromley. Designed for elegance and ease, this home is a rare blend of architectural beauty, comfort, and sophistication.A gracious entryway opens to a sunlit living room and library anchored by an 18-foot stone fireplace.

    Lisa Sullivan Four Seasons Sotheby's Int'l Realty

    454 Mountain Rd, Stratton, VT 05155
  • /21

    $235,000

    • Land
    • 1.3 Acres
    • $180,769 per Acre

    80 the Hollow Rd, Winhall, VT 05340

    We can build it for you. Nestled in the heart of the picturesque **High Meadow at Stratton**, this captivating lot awaits your vision. Embrace the opportunity to own one of the last available parcels in this highly sought-after neighborhood, where extraordinary living blends seamlessly with the tranquility of the Vermont mountains. Enjoy breathtaking views of the iconic **Stratton ski

    Jacek / Realtor Mikolajczyk BHHS Verani Upper Valley

    80 the Hollow Rd, Winhall, VT 05340
  • /15

    $298,500

    • Land
    • 3.7 Acres
    • $80,676 per Acre

    69 Benson Fuller Dr, Winhall, VT 05340

    High dry and spectacular views of the Equinox Mountain range and Bromley Mountain! Oversized building lot with lots of privacy. Approved septic system for a 5 bedroom house!

    Andrea Linkin-Butler Stratton Buyer Brokerage

    69 Benson Fuller Dr, Winhall, VT 05340
  • /23

    $135,000

    • Land
    • 5.1 Acres
    • $26,471 per Acre

    1192 Haven Hill Rd, South Londonderry, VT 05155

    This 5+ acre building lot is ready for planning and designing your 5 bedroom dream-home, WW-2-3657 on a quiet country road, and Land Use Permit 2W0032-3. Just minutes to Gale Meadows and Stratton Mountain Resort, there are plenty of summer and winter outdoor adventures to embark on from hiking, kayaking, and fishing in the summer to skiing and snowshoeing in the winter. Only 25-minutes from

    Mike England Michael England Real Estate

    1192 Haven Hill Rd, South Londonderry, VT 05155
  • /8

    $65,000

    • Land
    • 2 Acres
    • $32,500 per Acre

    585 Sawmill Rd, Stratton, VT 05360

    Ready to build! Nestled in the picturesque Snow Mountain Farms development, this prime 2 acre property offers the perfect canvas for your dream home. Situated in a great neighborhood with a convenient location, it provides easy access to both Mount Snow and Stratton. The property is equipped with a wastewater permit, septic design, an already cleared building envelope, and a driveway.

    Carrie Mathews Winhall Real Estate

    585 Sawmill Rd, Stratton, VT 05360

Home Trends in Winhall, VT

Housing Trends

Median Sale Price
$717,500
Median Single Family Sale Price
$812,500
Median Townhouse Sale Price
$617,000
Median 2 Bedroom Sale Price
$205,000
Average Price Per Sq Ft
$374
Number of Homes for Sale
23
Last 12 months Home Sales
42
Months of Supply
6.60
Median List Price
$795,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-3%
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