Bears Crossing Homes for Sale

Welcome to Bears Crossing, an enchanting community nestled in the picturesque town of Dover, Vermont, within the beautiful Windham County. This charming development is a haven for nature lovers and outdoor enthusiasts alike, offering a perfect blend of serene mountain living and modern comforts.

Bears Crossing features a selection of stunning homes for sale that cater to various tastes and lifestyles. Each residence is thoughtfully designed to harmonize with the breathtaking natural surroundings, showcasing high-quality finishes, spacious layouts, and an abundance of natural light. Whether you’re seeking a cozy retreat for weekends or a year-round residence, these homes provide the ideal backdrop for creating cherished memories with family and friends.

The community is surrounded by the majestic Green Mountains, offering endless opportunities for adventure. In the winter months, you can hit the slopes at nearby ski resorts, while the warmer seasons invite you to explore hiking trails, mountain biking paths, and the tranquil waters of local lakes. Additionally, Bears Crossing is conveniently located near charming shops, delightful eateries, and vibrant cultural attractions that enhance the quality of life in this quaint Vermont town.

Investing in a home at Bears Crossing means embracing a lifestyle filled with outdoor activities, community spirit, and the beauty of Vermont’s changing seasons. Don’t miss out on the chance to be part of this idyllic setting—explore the homes for sale at Bears Crossing today and discover the perfect place to call home in Dover!

Newest Bears Crossing Homes for Sale

$649,000

5 Beds ⋅ 3 Baths ⋅ 5095145 MLS

Lovely ski home home in an ideal location, offering the privacy of a single-family residence with the convenience of a groomed ski-home trail and direct shuttle service just steps from your front door. Nestled on a well-positioned lot in the desirable Bears Crossing community, the home backs directly to the ski-home trail with a bridge to cross right to your deck on your way home and offers ample parking with easy year-round access. Unlike many properties, this home provides the peace-of-mind amenities of condo living — at a fraction of the cost — including an outdoor pool for summer enjoyment, clubhouse with fitness area, ping pong and pool table, tennis court, and fire pit. Inside, a gorgeous open floor plan welcomes you with abundant natural light from large new windows. The vaulted great room features a wood burning fireplace with brick hearth and flows seamlessly into the updated kitchen with stainless appliances, quartz countertops, large island, and generous dining area. The main level includes a large primary suite with full bath, and an additional half bath for guests. Upstairs are two more bedrooms, a full bath, and a spacious loft ideal for play or overflow sleeping. The functional mudroom entry is perfectly designed for mountain gear with cubbies, coat closet, and bench. The finished lower level offers two additional bedrooms, a full bath, and a large family room — providing excellent separation for guests or rental flexibility. Additional upgrades include an energy efficient direct vent propane heating system, a sizeable rear deck, summer 2026 ongoing painting, and lovely landscaping. This rare combination of ski-home convenience, easy access, generous living space, and sought-after amenities does not come along often. Tremendous rental potential as well.

36 Bears Den Rd, Dover

$775,000

3 Beds ⋅ 3 Baths ⋅ 5077225 MLS

A rare opportunity to enjoy the best of both worlds — the privacy of a single-family home with the convenience and access of condo-style living. This unique vacation home offers direct ski-home access in the sought-after Bears Crossing community on the slopes of Mount Snow. Ski back from the Carinthia trails and step out of your gear just across the street from your front door. Designed with both comfort and accessibility in mind, this contemporary chalet features direct shuttle service from your driveway, ample parking for guests, and a private backyard bordering forest. Enjoy easy access to nearby hiking and biking trails, along with strong curb appeal in a peaceful setting. Inside, the main level offers a spacious open floor plan with natural woodwork and abundant light throughout. The upscale kitchen includes custom hickory cabinetry, stainless appliances, natural wood island, walk-in pantry, and laundry. A wood-burning fireplace with stone hearth anchors the living space, while the dining area opens to a rear deck with hot tub. A large screened-in porch provides ideal year-round entertaining space, complemented by an updated half bath and a newly designed mudroom entry with cubbies and hidden storage for gear. Upstairs, the primary suite features a second fireplace and full bath, along with two additional guest bedrooms and a third bath. Additional improvements include energy-efficient direct-vent heating. Enjoy all the benefits of Bears Crossing amenities — including outdoor pool, clubhouse with fitness area, ping pong, pool table, tennis courts, and shuttle service — at a fraction of typical ownership costs. A rare blend of privacy, convenience, and true ski-home access.

15 Bears Den Rd, Dover

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