As the crisp autumn air settles over New York City, there's no better time to embrace the beauty of the season from the comfort of a luxurious penthouse. Imagine sipping your morning coffee on a sprawling terrace adorned with the hues of fall foliage or hosting an intimate dinner party under the starlit sky. Indoor-outdoor living isn't just a West Coast fantasy—it's a reality in the heart of NYC. We've rounded up some incredible penthouses, each offering unique private outdoor spaces that make the most of the enchanting fall weather.

1. Penthouse B at Nine Chapel, Downtown Brooklyn

Price: $3.7 million

Tucked away in the vibrant neighborhood of Downtown Brooklyn, Penthouse B at Nine Chapel is a sanctuary that reimagines urban living. Spanning an entire floor of a 14-story boutique building, this 3-bedroom, 2.5-bathroom home offers nearly 800 square feet of private outdoor spaces. Think of it as your personal oasis above the bustling streets.

What sets this penthouse apart are the four separate loggias—enclosed terraces that function as year-round outdoor rooms. Protected by the building's innovative folded metal façade, these spaces blur the lines between indoors and out. The kitchen and primary bath open directly onto their own loggias, allowing you to indulge in fresh air and natural light throughout the day.

The interior is just as impressive, boasting 1,969 square feet of living space with floor-to-ceiling windows offering panoramic views in all directions. With a corner great room and a custom kitchen featuring glass window walls and a butcher block-topped island, this penthouse feels more like a private house than a high-rise apartment.

2. Penthouse 2 at The Astor, Upper West Side

Price: $13.95 million

For those who crave classic New York elegance, The Astor on the Upper West Side is a dream come true. Originally built by the legendary Astor family in 1901, this glamorous condo building now houses three exclusive penthouses. Penthouse 2 is a duplex masterpiece spanning 4,805 square feet with five bedrooms and seven baths.

The true showstopper here is the 1,700-square-foot private outdoor space—one of the largest on the Upper West Side. A magnificent wraparound terrace extends from the triple-exposure great room, complete with a gas fireplace, offering stunning views of the cityscape. The primary suite boasts its own private terrace, perfect for morning reflections or evening unwinding.

Interiors designed by Pembrooke & Ives pay homage to the building's pre-war history with custom moldings and herringbone-patterned floors, all while incorporating modern luxuries like gas fireplaces and high-end appliances. It's the perfect blend of old-world charm and contemporary comfort.

Curious about celebrity homes in NYC? Dive into our article on where the stars live to see how your potential new pad stacks up.

3. Penthouse 21D at Front & York, DUMBO

Price: $3.45 million

Modern design meets natural serenity at Front & York in DUMBO, Brooklyn. Designed by renowned architect Morris Adjmi, this full-service, resort-style development offers a unique opportunity to live amidst greenery while staying connected to the city's pulse.

Penthouse 21D is a 1,424-square-foot, two-bedroom residence that features 10-foot ceilings and floor-to-ceiling windows. The private terrace is not just an outdoor space—it's an extension of your living area, complete with a gas grill and views overlooking the building's half-acre private park. Imagine hosting barbecues or simply enjoying a good book surrounded by lush landscaping.

The interiors are sleek and contemporary, with high-end finishes that exude understated luxury. Plus, with amenities like a state-of-the-art fitness center, swimming pool, and concierge services, you'll experience resort living without ever leaving home.

Final Thoughts

These penthouses aren't just properties; they're lifestyles. Each offers a unique way to experience indoor-outdoor living in New York City, making the most of the delightful fall weather. Whether you're drawn to the innovative design of Nine Chapel, the historic elegance of The Astor, or the modern serenity of Front & York, there's a dream home waiting for you.

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