Annie Leibovitz's Central Park W. home hits the market for a loss; Explore price-reduced Classic 5, 6, and 7 homes across NYC

By CityRealty Staff | From Get To Know Wednesday, October 18, 2023

Renowned photographer Annie Leibowitz and classic seven living room at The Brentmore, 88 Central Park West, #5N

Celebrity photographer Annie Leibovitz has put her apartment in The Brentmore on the market for $8.6 million, just over nine years after purchasing it for $11.25 million in 2014. Her initial intention was to be closer to her daughters' school, leading to a significant renovation that retained elegant features like high ceilings, oak floors, and decorative moldings. However, as an empty nester who now lives and works downtown, she finds the apartment too large, and the listing broker, Deborah Kern, mentioned to The New York Times that the apartment is attractively "priced to sell," though it may result in a financial loss for Ms. Leibovitz.

Located within a prewar cooperative designed by Schwartz & Gross, Ms. Leibovitz's apartment shares a building with notable residents such as movie star Robert DeNiro, musician Paul Simon, producer Lorne Michaels, and stage actress Joan Copeland. With only 37 units spanning 12 floors, residents enjoy exceptional privacy, while its prime location on Central Park West offers a front-row seat to the Macy's Thanksgiving Day Parade and close proximity to Lincoln Center, Central Park, and fine dining options on the Upper West Side.

The Brentmore, #5N
$8,600,000

Central Park West | Cooperative | 4 Bedrooms, 3 Baths

The Brentmore, #5N (Corcoran Group)

From the Listing: 88 Central Park West, 5N 4 BD 3 BA 1 Powder Room Co-op Upper West Side Spanning two levels, Apartment 5N at 88 Central Park West pairs sought-after prewar elegance with a thoughtful floor plan optimized for today's living. High ceilings, inlaid hardwood floors, and exquisite moldings hallmark this pinnacle of parkside luxury on Manhattan's storied Upper West Side. See full details here.

Classic Five

Some things can sound self-explanatory in the New York real estate lexicon, but a bit of clarification may be in order. In classic fives, “classic” refers to the prewar era in which they were popularized, and “five” refers to the rooms this floor plan must include: a living room, a formal dining room, a kitchen, and two equitably sized bedrooms. These are often confused with the “Edwardian five,” which have the same number of rooms but were designed with a single adult and live-in servant in mind; as a result, one bedroom is significantly larger than the other in such units.

Classic five floor plan via Brown Harris Stevens

Classic Six

Classic six apartments offer the same rooms as classic fives, but with the addition of a maid’s room, typically located near the kitchen and with an en suite bath. While those without live-in staff can certainly use this as a third bedroom, it must be noted that this one often has significantly less space and privacy than the full-size bedrooms. This space would also work well as a home office, gym, media room, artist’s studio, or whatever else the buyer can dream up.

Classic six floor plan via Douglas Elliman

Classic Seven

Classic seven apartments have been described as classic sixes with an extra bedroom: They feature a living room, formal dining room, three equitably sized bedrooms (which makes this model a good fit for families with children), and a maid’s room with en suite bath.

Classic seven floor plan via Compass

As a result of the era in which they were built, classic five through seven apartments are often rich in architectural details from the time, including high ceilings, gracious foyers, hardwood floors, eye-catching moldings, well-proportioned rooms, and, for some lucky owners, wood-burning fireplaces and private outdoor space.

Classic layouts such as these are most frequently found in prewar cooperatives in established neighborhoods like the Upper East Side and Upper West Side. Newer construction has mostly abandoned these traditional models in favor of an open plan that makes for an airier atmosphere and more natural light; however, after months of families trying to live, work, and study in one apartment, apartments with clearly divided rooms might experience a new appreciation. Some modern condos have tried to present a contemporary take on these layouts, but there's no substitute for these timeless units.

A full, sortable list of classic five, six, and seven apartments may be found below. We also take a look at some price-improved options on the market today.

Price-Improved Classic Four & Five Listings

315 Riverside Drive, #10D
$1,995,000 (-4.8%)

Riverside Dr./West End Ave. | Cooperative | 3 Bedrooms, 2 Baths | 1,700 ft²

315 Riverside Drive, #10D (Corcoran Group)

From the Listing: Wondrous river views unfold from a grand scale 5 room, 3 BR classic high up in one of Riverside Drive's finest prewar buildings. Non-pareil sunsets paint the sky as the flowing Hudson does a worthy imitation of the Grand Canal below. The apartment faces the river directly from the 10th floor carrying a heaven-sent luminosity throughout its generous expanse. See floor plan and full details here.

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Westwind, #11A
$1,650,000 (-2.7%)

Broadway Corridor | Cooperative | 2 Bedrooms, 2 Baths | 1,400 ft²

Westwind, #11A (Corcoran Group)

From the Listing: Welcome to Apartment 11A at The Westwind, a sunny spacious Classic 5 room coop with 2 bedrooms, 2 bathrooms and a dining room. This beautifully proportioned Rosario Candela designed home showcases a perfect layout, plenty of closets and the timeless elegance of prewar details. The apartment is in excellent condition and boasts excellent light, east and west exposures, a large welcoming entry foyer, beautiful hardwood floors and high beamed ceilings. See floor plan and full details here.

345 East 57th Street, #16B
$895,000 (-5%)

Midtown East | Cooperative | 2 Bedrooms, 1 Bath

345 East 57th Street, #16B (Compass)

From the Listing: This classic 5 into 4 room apartment gem features a bright 2-bedroom apartment in a boutique pre-war co-op in the Sutton Place neighborhood. The apartment is on the 16th floor facing south with open and bright city views. See floor plan and full details here.

Price-Improved Classic Six Listings

15 West 81st Street, #8D
$3,995,000 (-11.2%)

Central Park West | Cooperative | 3 Bedrooms, 2.5 Baths

15 West 81st Street, #8D (Douglas Elliman Real Estate)

From the Listing: Grand Classic South Facing 6 with Incredible Views at 15 West 81st Street.Outstanding residence on one of the Upper West Side's finest Emery Roth Landmark cooperative buildings.This oversized Classic 6 room home is truly magnificent. The perfect layout has rooms with grand proportions, original pre-war details intact, and magical views of The Rose Planetarium, Museum of Natural History, Skyline Views of Central Park South and Midtown which are dramatically lit in the evening, and sweeping views of Central Park, which change with the seasons. The coveted vantage point from this apartment is a front row seat to the festivities the eve of The Macy's Thanksgiving Day Parade, when 81st Street between Central Park West and Columbus Avenue, is a staging area for The Giant Balloons. See floor plan and full details here.

285 Riverside Drive, #11G
$2,300,000 (-16.4%)

Riverside Dr./West End Ave. | Cooperative | 3 Bedrooms, 3 Baths | 1,968 ft²

285 Riverside Drive, #11G (Douglas Elliman Real Estate)

From the Listing: Beautifully redesigned classic-6 with cityscape views on Riverside Dr! Over 1900 square feet of 3 bedrooms and 3 full bathrooms, overlooking rooftops and water towers, with views of open sky to the east through oversized windows. A living and dining layout expansive enough to handle anything you can envision...from a twelve-person dining table to a massive sectional. See floor plan and full details here.

419 East 57th Street, #EM
$2,250,000 (-17%)

Beekman/Sutton Place | Cooperative | 3 Bedrooms, 2.5 Baths | 2,237 ft²

419 East 57th Street, #EM (Sothebys International Realty)

From the Listing: A rare opportunity to own a truly one-of-a-kind home! This stunning, duplex maisonette feels like living in a private house, with the added luxury of 24-hour staff at your call. This Classic 6 home offers a gracious layout across two levels, an abundance of natural light, and details that exude elegance and glamour. Uncommonly private, high-end city living that is truly a class apart! See floor plan and full details here.

1070 Park Avenue, #11D
$2,050,000 (-10.9%)

Carnegie Hill | Cooperative | 3 Bedrooms, 3 Baths

1070 Park Avenue, #11D (Berkshire Hathaway HomeServices New York Properties)

From the Listing: Prewar Carnegie Hill Classic 6 Residence 11D is a grand scale Classic 6 home in one of Carnegie Hill's premier, white glove cooperatives. Enter through the formal entrance gallery which sets the tone for the home's elegance. Radiating from the gallery is the elegant living room featuring double, north-facing windows, 9'4" beamed ceilings, hardwood herringbone floors, and a wood-burning fireplace. See floor plan and full details here.

The Adamston, #11B
$1,950,000 (-10%)

Riverside Dr./West End Ave. | Condominium | 3 Bedrooms, 2 Baths | 1,568 ft²

The Adamston, #11B (Compass)

From the Listing: Introducing Residence 11B at the Admaston, a pre-war condo building in the heart of the Upper West Side, now available at an even more attractive price and presenting an excellent opportunity for buyers and investors alike!

This spacious Classic 6 condo apartment boasts timeless pre-war features, including high beamed ceilings, hardwood floors, and an ornate fireplace.The layout provides both versatility and privacy, while its corner orientation ensures abundant natural light throughout. This home offers the ideal blend of classic pre-war details and modern potential. See floor plan and full details here.

179 East 70th Street, #2B
$1,795,000 (-10%)

Lenox Hill | Cooperative | 3 Bedrooms, 3.5 Baths

179 East 70th Street, #2B (Corcoran Group)

From the Listing: Gracious classic six in a white glove, full service cooperative on a lovely tree-lined Upper East Side street. Every room of this three bedroom, three and one-half bath residence has oversized windows allowing natural light from the south and east. See floor plan and full details here.

50 Plaza Street East, #6C
$1,750,000 (-7.7%)

Prospect Heights | Cooperative | 2 Bedrooms, 2 Baths

50 Plaza Street East, #6C (Corcoran Group)

From the Listing: Pre-war elegance, a classic six reimagined and designed for today's distinctive contemporary living. Welcome to 50 Plaza Street East, Apartment 6C in Prospect Heights. A sprawling five-room coop on desirable Plaza Street East across from Prospect Park. Enter into the 17-foot foyer, lined with three closets which opens into an expansive dining room and living room. The living and dining room are separated by handsome columns which accentuate the 9.5-foot ceiling height. These sun-filled rooms are perfect for entertaining either an intimate crowd or a large sit-down dinner in your formal dining room. See floor plan and full details here.

Beekman Terrace, #4F
$1,195,000 (-34%)

Beekman/Sutton Place | Cooperative | 3 Bedrooms, 2 Baths

Beekman Terrace, #4F (Corcoran Group)

From the Listing: Welcome to 455 East 51st Street, apt. 4F New York, NY 10022. Beautiful, Pre-War Classic 6-room Co-op home with sunny, southeast views overlooking the East River located in the heart of Beekman Place. Luxury and attention to detail are showcased in this home with large living room, formal dining room, three bedrooms, and 2 bathrooms. See floor plan and full details here.

Price-Improved Classic Seven Listings

52 Riverside Drive, #7A
$2,750,000 (-28.6%)

Riverside Dr./West End Ave. | Cooperative | 3 Bedrooms, 2.5 Baths

52 Riverside Drive, #7A (Sothebys International Realty)

From the Listing: Newly painted and floors refinished to show their natural beauty. Riverside Drive Gold Coast gem! Rarely available grand classic 7 room apartment, with living room, dining room, primary bedroom and second bedroom, 8 windows, all facing West over the Hudson River. Spectacular sunsets await you in this elegant prewar apartment with all details intact: hardwood floors, high beamed ceilings, solid doors and bathrooms lined with marble imported from Italy. See floor plan and full details here.

1035 Park Avenue, #4A
$5,125,000

Carnegie Hill | Cooperative | 3 Bedrooms, 3 Baths | 2,225 ft²

1035 Park Avenue, #4A (Sothebys International Realty)

From the Listing: Designed in 1926 by architect Henry C. Pelton, 1035 Park Avenue is a statuesque and highly sought-after white-glove cooperative. Within, this wonderful and meticulously renovated residence wraps the northwest corner of the building and seamlessly offers a rare combination of traditional prewar elegance and modern convenience.Central air conditioning, exquisite millwork, new hardwood floors, and gleaming white kitchen and baths are underpinned by the apartment's prewar sensibility, which includes tall ceilings and pleasingly proportioned rooms. See floor plan and full details here.

170 East 79th Street, #13B
$1,900,000 (-29%)

Lenox Hill | Cooperative | 3 Bedrooms, 3 Baths

170 East 79th Street, #13B (Douglas Elliman Real Estate)

From the Listing: This is the first time this Classic Seven is being offered in over 50 years. This high-floor, sun-flooded apartment boasts exposures to the south, east, and north, and views to the midtown skyline. Prewar details are everywhere you look, including the original wood-burning fireplace, millwork, and 9'6" beamed ceilings. After passing through the semi-private elevator vestibule, the gracious 20' entrance foyer opens up into the south-facing living room with big city views. To the left is your formal dining room with seating for eight. The kitchen and home office are tucked behind the dining room and offer a great opportunity for a larger eat-in kitchen. See floor plan and full details here.

955 Park Avenue, #7E
$1,995,000 (-15%)

Carnegie Hill | Cooperative | 3 Bedrooms, 3 Baths

955 Park Avenue, #7E (Corcoran Group)

From the Listing: Apartment 7E at 955 Park is a 4-bedroom, classic 7 room home located on Park Avenue and 81st Street. Designed by the renowned firm of Bing and Bing working with designer Robert Lyons in 1915, this pre-war home retains all of its original details and classic features. With 10-foot ceilings, original hardwood floors and moldings, all of the turn of the century mainstays remain for you to reimagine or restore. See floor plan and full details here.

Amele Hall, #27
$1,647,000 (-9.8%)

Morningside Heights | Cooperative | 3 Bedrooms, 2 Baths

Amele Hall, #27 (Brown Harris Stevens Residential Sales LLC)

From the Listing: Experience the Upper West Side lifestyle at its finest with this exquisite 3-4 bedroom gem on a picturesque, tree-lined street. Welcome to 536 West 111th Street, a prewar boutique coop that places you right in the heart of everything. Conveniently close to subways, renowned restaurants, Columbia University, and just a block away from the serene Morning Side Park and charming shops! See floor plan and full details here.

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The Brentmore, #5N
$8,600,000

In this article:

Classic Five

Classic Six

Classic Seven

Price-Improved Classic Four & Five Listings

315 Riverside Drive, #10D
$1,995,000 (-4.8%)

Select which properties are of interest to you:

Westwind, #11A
$1,650,000 (-2.7%)

345 East 57th Street, #16B
$895,000 (-5%)

Price-Improved Classic Six Listings

15 West 81st Street, #8D
$3,995,000 (-11.2%)

285 Riverside Drive, #11G
$2,300,000 (-16.4%)

419 East 57th Street, #EM
$2,250,000 (-17%)

1070 Park Avenue, #11D
$2,050,000 (-10.9%)

The Adamston, #11B
$1,950,000 (-10%)

179 East 70th Street, #2B
$1,795,000 (-10%)

50 Plaza Street East, #6C
$1,750,000 (-7.7%)

Beekman Terrace, #4F
$1,195,000 (-34%)

Price-Improved Classic Seven Listings

52 Riverside Drive, #7A
$2,750,000 (-28.6%)

1035 Park Avenue, #4A
$5,125,000

170 East 79th Street, #13B
$1,900,000 (-29%)

955 Park Avenue, #7E
$1,995,000 (-15%)

Amele Hall, #27
$1,647,000 (-9.8%)

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In this article:

Classic Five

Classic Six

Classic Seven

Price-Improved Classic Four & Five Listings

Select which properties are of interest to you:

Price-Improved Classic Six Listings

Price-Improved Classic Seven Listings

Select which properties are of interest to you:

Listings in this article

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