Under 500k

MLS Number 5074721

• Land
• PricePerSqFt 21226.42
• Acreage 21.2
• Area VT-Bennington
• Utilities None

Set along Lower Taylor Hill Road in Winhall, this 21.2 +/- acre offering captures the privacy, natural beauty, and four-season lifestyle that define Southern Vermont living. Rolling terrain, mature woodland, and natural clearings create an exceptional setting for a private Vermont retreat, with the potential for Bromley Mountain views depending on house placement and design. Supported by a State-approved wastewater permit for a six (6) bedroom single-family residence, the property offers the flexibility to design and position a substantial home that responds thoughtfully to the land and surrounding landscape. Whether envisioning a refined mountain retreat or a legacy property for gathering family and friends, the setting offers both privacy and a strong sense of place. Imagine arriving on a quiet Friday evening, unwinding after a day on the slopes, or spending summer evenings outdoors surrounded by the calm of the Green Mountains. The property feels private and removed, yet remains minutes from Stratton Mountain Resort and within easy reach of Bromley and Magic Mountain. Manchester Village, with its restaurants, shopping, and everyday conveniences, is just a short drive away. An exceptional land offering in one of Southern Vermont's most desirable locations.

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

MLS Number 5073637

• Land
• PricePerSqFt 43859.65
• Address 4.1 Pearl Buck Drive
• Acreage 10.26
• Area VT-Bennington

One of the last significant VIEW lots available on the mountain , with unrivaled 360 degree views, including dead on views of Stratton Mountain trails. The pinnacle of this 10.26 acre lot is deserving of an exceptionally designed and expansive home in this premium location with commanding views. Prime for a legacy property in a most desirable location, just 5 minutes to the Stratton Base Area, with an additional acrea available. You'll have the perfect vantage point for watching and enjoying the changing seasons with everything the area has to offer at your door step. Year round outdoor recreation, Weston Theatre, Manchester Music Festival, The Southern Vermont Arts Center and plenty of options for dining and shopping. Rare opportunity to create a lasting legacy for you, your family and friends.Explore this parcel and you will experience its magic and why it is so SPECIAL.

Listed by Kim Morgan-Wohler of Wohler Realty Group

MLS Number 5079084

• Land
• PricePerSqFt 6521.74
• Address 00 Vt Route 12
• Acreage 69
• Area VT-Windsor

A 69 acre mountaintop building lot with dramatic views of distant mountains in an area of Barnard populated with estate properties. The road is in to a potential building site at the height of the land. Soil testing for septic will be completed as soon as snow clears. Subdivision pending. This parcel is currently comprised of two parcels, one being 40+/- acres and the second being 29+/- which can be deeded as two parcels or a single 69+/- acre parcel. The location is a short drive to Woodstock and an even shorter drive to all the amenities of Teago including Saskadena Ski Area. Easy access to I89.

Listed by Stan Butler of Four Seasons Sotheby's Int'l Realty

MLS Number 5105434

• Land
• PricePerSqFt 12857.14
• Address Lot 3 Campbell Road
• Acreage 35
• Area VT-Windsor

Spectacular 35-acre parcel with magnificent mountain and valley views. Abutting the Green Mountain National Forest, and a rare 5-bedroom septic permit, this property presents an exceptional opportunity to create a Vermont estate to be enjoyed for generations. With a cleared homesite and roughed-in driveway already in place, much of the groundwork is done; now your vision can take center stage. Like a page from Vermont Life Magazine, the journey to this remarkable property is part of the experience. Just a few miles south of the quaint, historic village of Rochester, you'll travel along a designated scenic byway, passing the iconic Liberty Hill Farm before ascending a gently winding hill where the landscape gradually unfolds around you. Arriving at the property, magnificent southern views stretch across the mountains and valleys, while the Green Mountain National Forest forms a natural backdrop and ensures an enduring sense of privacy and connection to the surrounding wilderness. Whether you envision a grand country estate, a family retreat, or a private mountain sanctuary, this extraordinary parcel offers the space, setting and infrastructure to make it possible. Showings by appointment only.

Listed by Kyle Kershner of Killington Pico Realty

MLS Number 5025379

• Residential Single Family
• PricePerSqFt 231.6
• Full Bath 2
• Address 24 Antler Loop
• Construction Existing

This charming 3-bedroom, 2-bath dutch colonial home sits atop a knoll, overlooking a picturesque half-acre pond in the front yard. Nestled on 2.06 acres in a tranquil neighborhood, the property offers an excellent floor plan for family living. The home features spacious bedrooms, a cozy brick fireplace in the living room with a cathedral ceiling, and a dining area with pine floors and pond views. A sitting area upstairs connects two bedrooms, while the first-floor bedroom and living room both have sliders leading to the backyard. The beautifully landscaped yard boasts a stone walkway lined with perennials, a deck off the side door, and an oversized attached garage. The basement is 3/4 full and unfinished with a bulkhead, plus a 1/4 crawl space. Located in the desirable Dover Manor, this home is just 6 miles from Mount Snow and 7.5 miles from the Hermitage Club, with convenient access to Brattleboro and Bennington. Built and lovingly maintained by the original owner, this home combines comfort, charm, and an unbeatable setting.

Listed by Jennifer Densmore of Deerfield Valley Real Estate

MLS Number 5094522

• Residential Single Family
• PricePerSqFt 344.04
• Full Bath 2
• Construction Existing
• Bedrooms 3

Tucked within the Hawk community, this charming mountain retreat offers the perfect blend of privacy, recreation, and convenience. Set within a private 1.09-acre wooded lot, owners are also able to enjoy access to Hawk's common land with room to explore, including trails ideal for snowshoeing, hiking, and cross-country skiing. Perfectly positioned between Killington and Okemo Mountain, and just minutes to area lakes and scenic Route 100, this location is ideal for year-round Vermont living and exploring. Inside, the open kitchen, dining, and living area is filled with natural light from large windows that frame the peaceful wooded setting. A beautiful stone fireplace with a wood stove insert creates a warm and inviting focal point, perfect after a day on the slopes or trails. The dining area opens to a spacious deck, offering an easy transition to outdoor living and quiet moments surrounded by nature. The lower level features three bedrooms, including charming built-in storage and built-in bunks that make this a fun and functional escape for younger guests. Whether used as a vacation getaway, ski retreat, or four-season home base, this Hawk property captures the relaxed mountain lifestyle in a setting that feels wonderfully private while remaining close to everything the Okemo Valley and Killington region have to offer. Visit the Okemo real estate community today. Taxes are based on current town assessment.

Listed by Sarah Sheehan of William Raveis Real Estate Vermont Properties

MLS Number 5094943

• Residential Single Family
• PricePerSqFt 288.83
• Full Bath 1
• Construction Existing
• Bedrooms 2

Discover year-round lakeside living with this inviting 3-bedroom, 2-bath home on the shore of Spectacle Pond in the town of Brighton. Built in 2002, this home offers over 1,500 square feet of comfortable living space, with plenty of room for relaxing and entertaining. On the main level, you'll find a spacious living room and a large, fully equipped eat-in kitchen-both offering stunning views of the pond. Tucked off the main living area is a cozy den that exudes a lodge feel, with knotty pine walls and ceiling and a wood-burning fireplace set in a floor-to-ceiling stone surround. A convenient ¾ bath completes this floor. The entire top level is dedicated to the primary suite, featuring a full bath and a balcony that provides the perfect spot to enjoy your morning coffee while taking in tranquil water views. Two additional bedrooms are located in the walk-out basement, offering easy access to 138 feet of sandy beach and the like-new 33-foot-long FLOE dock thta's ideal for swimming, boating, fishing, or simply soaking up the peaceful setting. An attached 2-bay garage, an outbuilding perfect for storing watercraft and outdoor gear, and a woodshed complete the property. Set on a 0.31-acre lot along a private road with direct VAST trail access, this home combines convenience with the natural beauty of Vermont's Northeast Kingdom. Whether you're seeking a year-round residence or a four-season retreat, this waterfront home is ready to help you make lasting memories.

Listed by Howard Birchard of Century 21 Farm & Forest

MLS Number 5095895

• Residential Single Family
• PricePerSqFt 467.29
• Full Bath 1
• Construction Existing
• Bedrooms 2

LOG HOME, 10 ACRES, HORSE BARN. Is your love for riding horses, hunting, hiking or soaking in the great outdoors; if so, let the adventure begin right here with this story book setting. Hidden on 10 acres of complete privacy with a 24'x30' two story horse barn with heated artist studio ( this space would also make a great office space with lots of natural light), paddock, stonewalls, the sweetest duck pond/house and chicken coop. Enjoy the orchard with many fruit trees, the raised vegetable beds and the abundance of wild life. Whether you are looking for a primary residence or vacation getaway this absolutely adorable and charming log home with rocking chair porch will create memories of a life time. Love to hunt or hike, take your own path with picnic lunch right to the top of Pond Mountain. Lake St. Catherine, both the state and town beaches along with the trailhead of the slate Valley Biking Trails are only minutes away - come and enjoy this Vermont getaway.

Listed by Lori Winn of New England Lakeside Realty

MLS Number 5096882

• Residential Single Family
• PricePerSqFt 174.55
• Full Bath 1
• Address 4 Larkin Road
• Construction Existing

Currently rented to a long-standing business, this property could be used either commercially or converted back into a residential home with a separate 2 car garage and huge finished barn (currently operating as a warehouse - it even has a dumbwaiter!!). A corner parcel with road frontage along Route 110 (paved) and Larkin Road (gravel), this is a very easy location to access. The kitchen opens to a great little dining room, a bright and sunny living room - currently setup as a board room with table and chairs. The property has central air, a finished basement with plenty of storage and a half bath, beautiful river frontage, lovely large lawn/meadow spaces for a garden, and the quintessential covered porch. With fiber optic internet this is the ideal property who wants to run a business from home and have a separate work space, or continuing renting it for a little income on the side. Schedule a private showing, 48 hours notice needed.

Listed by Holly Hall and Franchesca Collins of Hall Collins Real Estate Group

MLS Number 5093324

• Residential Single Family
• PricePerSqFt 122.22
• Full Bath 1
• Address 4303 Hinesburg Road
• Construction Existing

Private! Guilford! This unusual combination of a true log home with an incredible center double sided chimney....a fireplace facing the kitchen/dining and wood stove in the living room, bringing the best of both worlds:... ambiance and warmth. There is a surprise of one more fireplace on the 2nd floor in the charming primary bedroom...use the ensuite for a huge walk in closet. The other half of the home is a brick and stick built addition with an amazing green house room, built to bring the outdoors in and help warm the floor tiles for passive solar...great for plants or just soaking up the winter sun with a good book. Close the door between the 2 sides and create an in-law with full kitchen, bath and bedroom, all on one floor...for those who want to age in place. The land is a combination of open...for gardening and play and Vermont woods for nature hikes. Enjoy the fruit trees, perennials and plant some veggies for putting by...Private! But, off a paved road for easy access... Loved by the owners for many years, it is time to pass to the next generation who will bring upgrades and new ideas to this very special home.

Listed by Christine Lewis of Brattleboro Area Realty

MLS Number 5102572

• Residential Single Family
• PricePerSqFt 611.41
• Full Bath 2
• Construction Existing
• Bedrooms 3

Tucked away on a quiet road in Hawk Resort, this charming 3-bedroom, 2-bath mountain retreat offers privacy, warmth, and easy access to Vermont's best four-season recreation. Just under 1,300 square feet, the home is thoughtfully designed to make the most of its inviting spaces, with random-width pine floors, a classic fieldstone fireplace, and abundant windows that bring in natural light and views of the surrounding woods. The open living area flows to a spacious deck, creating the perfect setting for morning coffee, evening gatherings, or simply enjoying the peaceful natural surroundings. Ideally located halfway between Killington Resort and Okemo Mountain Resort, you'll enjoy convenient access to skiing, golf, hiking, mountain biking, and endless outdoor adventure. Nearby lakes offer swimming, kayaking, and fishing, while the charming village of Woodstock is just 30 minutes away for shopping, dining, and exploring. Showings start 8/4.

Listed by Debra Staniscia of Four Seasons Sotheby's Int'l Realty