Fall Forward | 5 Homes with Dramatic Fall Foliage

Fall’s the time for sweaters, apple cider, and scenic drives to enjoy fall foliage. In locales from West Coast to East, these estates offer private showings, allowing for appreciation of autumn’s colors without leaving home.

The Crane Estate

Woods Hole, Massachusetts | John WeyandSotheby’s International Realty – Falmouth Brokerage

Perched on Nantucket Sound’s Juniper Point, this historic eight-bedroom residence has been updated and augmented with every desirable modern amenity. It offers 7,500 square feet of timeless living space on three levels and enjoys 380 feet of frontage on the water and a sandy beach. The striking lighthouse-like tower provides guest living quarters, a full kitchen, a window-wrapped aerie, and a wraparound deck for surveying all the sights on land and sea, including the swaths of trees, sporting New England’s legendary fall hues.

Oldfield Farm

Greenwich, Connecticut | Joseph BarbieriSotheby’s International Realty – Greenwich Brokerage

One of the most significant estates in Greenwich, 18.39-acre Oldfield Farm is a peerless property featuring a majestic 14,956-square-foot manor, a pool, tennis courts, and equestrian facilities. The dazzling landscaping provides year-round color: woodland perennials, herb gardens, flowering plants, and an array of mature trees, from maple and ash to dogwood, willow, cherry, and pear. The grounds have been configured to create a variety of enchanting outdoor living spaces with views of paddocks, the captivating foliage, and sunsets.

The Highlands Estate

Yorkville, California | Todd SheppardSotheby’s International Realty – Wine Country – East Napa Street Brokerage

Awash in the autumnal tones of mature trees, vineyards, fruit and olive orchards, and rolling golden hills, this classically charming 7,000-square-foot residence estate accommodates every need with six bedrooms, a chef’s kitchen, a formal dining room, a study, a great room, a gym, a billiards room, a wine cellar, a theater with stadium seating, wraparound porches, spacious decks, and a swimming pool. The 21.59-acre property also includes a pond and a delightful party barn.

Central Park West Penthouse

New York, New York | Kathryn SteinbergSotheby’s International Realty – East Side Manhattan Brokerage

The pièce de résistance of this one-of-a-kind penthouse is its wraparound terrace, designed for appreciation of outdoor living and views that encompass the southern skyline, the Hudson River, and ever-changing foliage of Central Park. Other highlights include a living room with a vaulted ceiling, a wood-burning fireplace, and a set of arched windows facing the Park. Also on this floor are a dining room, a study, a library, a southwest inspired eat-in kitchen, and a restful owner’s suite. There are two bedrooms, a gym, ample closet space, and a bath on the lower level.

Classic Style on the Waterfront

Water Mill, New York | Pat Petrillo & Dawn PetrilloSotheby’s International Realty – Southampton Brokerage

This delightful Shingle-style home and its charming one-bedroom guesthouse are nestled amid tall colorful trees on the banks of Mill Pond, an 85-acre lake perfect for sailing, kayaking, canoeing, and fishing. The home features a light-flooded living room with a fireplace, a formal dining room, a large eat-in kitchen, an adjoining family room with a fireplace, a sunroom, and five lovely bedrooms. The three-acre property also offers an oversized two-car garage, gardens, a swimming pool, and two private docks.

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