Feasting Alfresco: Seven Elegant Outdoor Dining Areas

Author Claudia Roden’s notion that “everything tastes better outdoors” is never more true than in these seven open-air dining spaces, where meals come with a side of wine country hills, lush East Coast greenery, and sparkling city lights.

Unprecedented East Hampton Compound

Minutes from East Hampton Village, a rare assemblage of 11 parcels has created this majestic 23-acre estate, which includes an 18,000-square-foot 12-bedroom home, a six-bedroom carriage house, a tennis court, charming horse stables with paddocks and riding fields, two guest cottages, idyllic gardens, and impeccable landscaping. At the Cotswold-inspired main residence, a covered dining terrace gazes out over brilliant green lawn toward the refreshing swimming pool—one of two on the grounds—and an enviable outdoor kitchen and grilling area with bar seating.

Offered at: $35,000,000
Location: 172 Cedar Street, East Hampton, NY 11932


Sophisticated Healdsburg Estate

A quiet lane winds through rolling hills, vineyards, and mature oaks toward this secluded wine-country estate, a timeless, sophisticated retreat offering alluring living and entertaining spaces, relaxed private quarters, an entertaining barn, an enchanting tree house, and a professional-caliber golf practice green. Beyond the heated infinity-edge pool and spa, emerald lawn, a terrace with a fire pit, and a serene covered outdoor living area, the acreage cascades toward an outdoor grilling and dining area with a stacked-stone fireplace, tucked beneath twinkling lights.

Offered at: $15,900,000
Location: 6255 Dry Creek Rd, Healdsburg, CA 95448


Chic California Contemporary

Designed by an award-winning Santa Barbara architectural firm, this three-bedroom home in the prestigious Pepper Hill area of Montecito is suffused with expressive modern style. It feels at once grand yet livable, with approximately 6,200 square feet of space for fabulous living and entertaining, top-of-the-line amenities, modern flourishes, clean lines, and floor-to-ceiling walls of glass. The kitchen and dining room open effortlessly to a tranquil dining terrace with tasteful landscaping and a 15-foot stone-backed waterfall.

Offered at: $8,750,000
Location: 396 Woodley Road, Montecito, CA 93108


Artful SoHo Penthouse

This three-bedroom penthouse loft was carefully crafted to include multiple outdoor oases. A perfect pied-à-terre, it offers a spacious living and dining room, an expertly appointed chef’s kitchen, a great room, and three bedrooms—all deftly blending prewar architecture with modern urban elements. Taking the stylish living outdoors are multiple lushly landscaped open-air spaces, including a secluded terrace with an alfresco hot tub, an expansive west-facing entertaining terrace, and a delightful grilling and dining terrace with an herb garden.

Offered at: $7,995,000
Location: 82 Greene Street, Apt PH5, New York, NY


Tranquil San Francisco Contemporary

This serene contemporary home was designed for versatility and enjoyment of San Francisco’s lovely natural light. On the main level, an open living, dining, and kitchen area opens to a terrace, while the lower-level family or media room gives way to a turf yard enveloped by a glorious living garden wall. Above the home’s four bedrooms is a stunning roof deck with an alfresco kitchen and dining area enjoying a panorama of the city skyline, the Golden Gate Bridge, and the bay.

Offered at: $7,200,000
Location: 1372 Francisco St, San Francisco, CA 94123


Stylish Sonoma Living

Clean sophisticated style pervades the airy, light-filled living spaces and serene private quarters of this modern Sonoma estate, which includes gardens, an olive grove, and a pinot noir vineyard. The main residence offers three warm, well-appointed bedroom suites and public spaces perfect for effortless wine country living and entertaining. Outdoor areas include patios, an infinity-edge pool, and delightful one-bedroom pool house with an outdoor kitchen and bar as well as a cool covered dining area.

Offered at: $6,495,000
Location: 19307 7th St E, Sonoma, CA 95476


Exceptional Oyster Harbors Estate

This timeless property—with its five-bedroom residence, two-bedroom guesthouse, and gloriously landscaped grounds—offers more than 10,000 square feet of extraordinary space for exceptional living and entertaining indoors and out. In addition to a theater, a wine storage room, a chef’s kitchen, a billiards room, and charming light-filled bar, it offers an expertly appointed outdoor kitchen and dining area overlooking the home’s enticing gunite swimming pool and lush green lawn.

Offered at: $4,750,000
Location: 440 Grand Island Drive, Osterville, MA 02655



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