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Madison Square Park Tower, 45 East 22nd Street, #46A (Elegran) Madison Square Park Tower, 45 East 22nd Street, #46A (Elegran)
Although many Boomer-age empty nesters are hanging on to their generously sized homes (in fact, they own twice as many homes with three or more bedrooms than younger generations with children), at least some are opting to downsize. This article explores the advantages of downsizing as an empty nester and what to look for if you're an empty nester hoping to downsize and purchase a New York City apartment.

In this article:

Madison Square Park Tower, 45 East 22nd Street
Madison Square Park Tower, 45 East 22nd Street Flatiron/Union Square
130 East 75th Street
130 East 75th Street Park/Fifth Ave. to 79th St.
West End and Eighty Seven, 269 West 87th Street
West End and Eighty Seven, 269 West 87th Street Riverside Dr./West End Ave.
The Cloister, 321 East 43rd Street
The Cloister, 321 East 43rd Street Turtle Bay/United Nations
Jardim, 525 West 27th Street
Jardim, 525 West 27th Street Chelsea

Advantages to downsizing as an empty nester

There are many advantages to downsizing as an empty nester, but the number one reason is its potential to simplify home maintenance. From ongoing repairs to cleaning, more square footage means dedicating more time and energy to your home. If you're making the move from a single-family house to an apartment, the superintendent and other staff is responsible for snow removal, maintaining the boiler and HVAC, and other building maintenance chores. Finally, a strategic move might also help you drastically reduce your monthly overhead.

For example, if you're downsizing from a three-bedroom to a one-bedroom coop or condo in New York City, your monthly fees will likely decrease if you move to a comparable building. If you still have one, your mortgage payments will also likely decrease, or the move may enable you to finally eliminate the need for financing. If you’re moving from a home you own outright in the suburbs to a coop or condo in New York City, however, even if you can buy in a cash-only deal, your coop fees or combined condo fees and taxes may be considerably higher than your current monthly overhead. However, if this is the case, the advantages of downsizing to a coop or condo in New York City could still be well worth it, especially if your new property is in a full-service, amenity-rich building.

Considerations when buying as an empty nester

If you’ve spent the past three or four decades living in a home in the suburbs or a smaller city or town, it is important to understand that New York City’s housing market is home to many different types of properties. While there are single-family, duplex, and multiplex properties available, most of the city’s housing stock is coops and condos. Buying coops and condos is similar, though there are some notable financial advantages to buying a coop (e.g., they tend to be priced lower and will enable you to avoid some taxes, including the mortgage recording tax, though that is only a concern if you’ll require financing).

Whether you’re purchasing a coop or condo, property prices will be determined by three key factors: the prestige of the building, location, and access to building amenities (e.g., a gym, workspace, or rooftop garden) and services (e.g., 24-hour doormen). With so many choices to consider, this raises an obvious question: What is the best type of property to buy, and where are the best neighborhoods to look if you’re an empty nester? While only you can determine which property or neighborhood is best, as an empty nester, a few considerations are likely to be particularly important.
Location: If you plan on ditching your car, especially in light of congestion pricing, a location close to public transportation will be important. For this reason, it may be wisest to focus on neighborhoods south of 125th Street in Manhattan. For example, the Upper East Side offers easy access to the 4/5/6 and Q trains and also happens to be home to one of the oldest populations in New York City (though it is also a popular neighborhood for families with young children).

Elevator building or walk-up: Even if you’re extremely spry, there is no shame in wanting to live in an elevator building. Many people in their 20s and 30s and nearly anyone with small children also prefer elevator buildings over walk-ups. If you purchase in an elevator building, you’ll also be more likely to be able to age in place, which is something many New Yorkers are able to do, even those who find themselves living alone.

Services: If you have never lived in a full-service building (i.e., a building with 24-hour door staff, a live-in superintendent, and porters), the advantages might not be immediately obvious, but in New York City, full-service buildings are highly sought for a good reason. If you have a country home or frequently travel, owning in a full-service building can offer additional peace of mind (e.g., if you’re gone for an extended period, you can even arrange for your superintendent or a porter to check on your apartment from time to time, though if you do, be sure to tip generously).

In addition, it is important to note that doormen not only collect packages and ensure that only authorized people are permitted to enter your building but also perform a host of other duties. For example, since doormen know who is in the building at any time, they are often the first people to recognize the need for a wellness check, which can be especially reassuring for empty nesters who live alone.
Connaught Tower, 300 East 54th Street, #11H (Sothebys International Realty)
Amenities: In New York City, amenities can range from luxury gyms with pools, squash courts, and steam rooms to rooftop gardens to co-working spaces. Like a hotel or resort, you get what you pay for, but if you're looking for a residence that feels like living in a hotel (or is a hotel), the option exists.

Space: Whether you’re working from home or want to ensure you have plenty of space for visiting relatives, in a city where every square foot counts, you'll need to have a clear sense of your room needs before going on the market.

Monthly fees: Even if you’re still working, chances are you’ll eventually want to retire or at least scale down your hours. For this reason, it is also important to consider a building's current fees, history of fee hikes, and likelihood of drastic fee spikes in the future. For example, if you're concerned about future fee hikes, you'll likely want to avoid buying in a land lease building, at least if the lease is due to come up for renewal in the near future.

Lifestyle: Above all else, you'll want to consider your lifestyle. If you enjoy walking everywhere, consider what the local neighborhood has to offer. Is there a grocery store, pharmacy, and dry cleaners nearby? If you have a pet, is the building universally pet-friendly, or are there size or breed restrictions on dogs? If you have grandchildren who are likely to visit often and even stay overnight, is the building child-friendly? While it can be difficult to assess the culture of a building and the surrounding neighborhood from a listing alone, don't worry—that is precisely the type of information your real estate agent will be able to answer.

Manhattan resale apartments selling at a loss

As the first quarter of 2024 draws to a close, CityRealty data shows that prices have softened all over Manhattan. It is hard to pinpoint any one factor, but higher interest rates, limited new development inventory, and election year anxiety could be at work here. Regardless, New York has always bounced back and New York City real estate almost always proves to be a good investment. For those reasons, now may be the time to get a great deal.

While most sellers either break even or sell at a profit in New York City, unique circumstances that prompt an owner to sell in a sluggish market can offer opportunities for homebuyers seeking properties priced below market value. Find below a selection of listings priced below their last closing price.


155 East 49th Street, #3G (Compass)

105 East 38th Street, #1B
$439,000 (-2.2%)

Murray Hill | Cooperative | 1 Bedroom, 1 Bath
Last Sold: 6/13/2018 | Last Sale Price: $515,000 (17% more than current ask)
105 East 38th Street, #1B (THE LION REAL ESTATE)

257 West 86th Street, #8C
$458,000 (-7.5%)

Riverside Dr./West End Ave. | Cooperative | 1 Bedroom, 1 Bath | 625 ft2
Last Sold: 9/14/2020 | Last Sale Price: $540,000 (18% more than current ask)
257 West 86th Street, #8C (Tungsten Property)
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The Cloister, #812
$795,000 (-4.8%)

Turtle Bay/United Nations | Cooperative | 2 Bedrooms, 1 Bath
Last Sold: 10/26/2018 | Last Sale Price: $1,003,076 (26% more than current ask)
The Cloister, #812 (Compass)

Cannon Point South, #15J
$799,000 (-8.7%)

Beekman/Sutton Place | Cooperative | 1 Bedroom, 1.5 Baths
Last Sold: 1/22/2019 | Last Sale Price: $950,000 (19% more than current ask)
Cannon Point South, #15J (Douglas Elliman Real Estate)

345 East 57th Street, #7D
$865,000

Midtown East | Cooperative | 2 Bedrooms, 1 Bath
Last Sold: 8/30/2018 | Last Sale Price: $1,035,000 (20% more than current ask)
345 East 57th Street, #7D (Brown Harris Stevens Residential Sales LLC)

The Beaumont, #11E
$895,000 (-3.2%)

Lincoln Center | Condominium | 1 Bedroom, 1 Bath | 670 ft2
Last Sold: 3/8/2022 | Last Sale Price: $1,069,000 (19% more than current ask)
The Beaumont, #11E (Corcoran Group)

One Carnegie Hill, #25H
$970,000 (-2.5%)

Yorkville | Condop | 2 Bedrooms, 2 Baths | 1,169 ft2
Last Sold: 8/28/2019 | Last Sale Price: $1,210,000 (25% more than current ask)
One Carnegie Hill, #25H (Corcoran Group)

North Park Tower, #9C
$985,000

East Harlem | Condominium | 2 Bedrooms, 2 Baths | 962 ft2
Last Sold: 6/30/2022 | Last Sale Price: $1,211,718 (23% more than current ask)
North Park Tower, #9C (Corcoran Group)

Connaught Tower, #11H
$995,000

Midtown East | Cooperative | 2 Bedrooms, 2 Baths
Last Sold: 7/12/2018 | Last Sale Price: $1,225,000 (23% more than current ask)
Connaught Tower, #11H (Sothebys International Realty)

West End and Eighty Seven, #6C
$1,300,000

Riverside Dr./West End Ave. | Condop | 2 Bedrooms, 3 Baths
Last Sold: 3/28/2019 | Last Sale Price: $2,400,000 (85% more than current ask)
West End and Eighty Seven, #6C (Christies International Real Estate Group LLC)

The Boulevard, #432
$1,500,000

Riverside Dr./West End Ave. | Condop | 2 Bedrooms, 2 Baths
Last Sold: 11/10/2022 | Last Sale Price: $1,795,000 (20% more than current ask)
The Boulevard, #432 (Compass)

Brevoort East, #4H
$1,595,000 (-3.3%)

Greenwich Village | Cooperative | 1 Bedroom, 2 Baths
Last Sold: 3/29/2018 | Last Sale Price: $1,900,000 (19% more than current ask)
Brevoort East, #4H (Compass)

Liberty Tower, #PH31A
$1,695,000

Financial District | Cooperative | 4 Bedrooms, 4 Baths
Last Sold: 12/12/2018 | Last Sale Price: $2,295,000 (35% more than current ask)
Liberty Tower, #PH31A (Serhant LLC)

West Village Houses, #GA
$1,695,000

West Village | Cooperative | 3 Bedrooms, 1.5 Baths | 1,350 ft2
Last Sold: 1/25/2022 | Last Sale Price: $1,850,000 (9% more than current ask)
West Village Houses, #GA (THE LION REAL ESTATE)

Carlton Regency South, #21F
$1,700,000

Murray Hill | Cooperative | 2 Bedrooms, 2.5 Baths | 1,565 ft2
Last Sold: 7/17/2018 | Last Sale Price: $2,050,000 (21% more than current ask)
Carlton Regency South, #21F (Douglas Elliman Real Estate)

The Bryant, #24D
$1,950,000 (-29.1%)

Midtown West | Condominium | 1 Bedroom, 1 Bath | 1,067 ft2
Last Sold: 1/11/2019 | Last Sale Price: $2,520,169 (29% more than current ask)
The Bryant, #24D (Corcoran Group)

The Sherry Netherland, #1205 (Douglas Elliman Real Estate)

130 East 75th Street, #10C
$2,995,000 (-4.9%)

Park/Fifth Ave. to 79th St. | Cooperative | 3 Bedrooms, 3 Baths
Last Sold: 2/1/2018 | Last Sale Price: $3,646,772 (22% more than current ask)
130 East 75th Street, #10C (Brown Harris Stevens Residential Sales LLC)

Place 57, #29A
$3,050,000 (-1.6%)

Midtown East | Condominium | 3 Bedrooms, 3 Baths | 1,795 ft2
Last Sold: 1/26/2021 | Last Sale Price: $3,850,000 (26% more than current ask)
Place 57, #29A (Compass)

Jardim, #5S
$3,895,000

Chelsea | Condominium | 2 Bedrooms, 2.5 Baths | 1,997 ft2
Last Sold: 8/6/2019 | Last Sale Price: $5,165,028 (33% more than current ask)
Jardim, #5S (Corcoran Group)

Fifteen Hudson Yards, #66B
$6,299,000 (-11.9%)

Midtown West | Condominium | 2 Bedrooms, 2.5 Baths | 2,320 ft2
Last Sold: 1/7/2020 | Last Sale Price: $7,939,250 (24% more than current ask)
Fifteen Hudson Yards, #66B (Douglas Elliman Real Estate)

Madison Square Park Tower, #46A
$6,999,950

Flatiron/Union Square | Condominium | 3 Bedrooms, 3 Baths | 2,490 ft2
Last Sold: 5/24/2018 | Last Sale Price: $8,824,118 (26% more than current ask)
Madison Square Park Tower, #46A (Elegran LLC)

The Mayfair, #PH16E
$19,500,000

Park/Fifth Ave. to 79th St. | Condominium | 6+ Bedrooms, 5.5 Baths | 7,643 ft2
Last Sold: 2/14/2020 | Last Sale Price: $32,000,000 (64% more than current ask)
The Mayfair, #PH16E (Douglas Elliman Real Estate)
Would you like to tour any of these properties?
Just complete the info below.
  1. Select which properties are of interest to you:

Or call us at (212) 755-5544
Would you like to tour any of these properties?
Contributing Writer Cait Etherington Cait Etherington has over twenty years of experience working as a journalist and communications consultant. Her articles and reviews have been published in newspapers and magazines across the United States and internationally. An experienced financial writer, Cait is committed to exposing the human side of stories about contemporary business, banking and workplace relations. She also enjoys writing about trends, lifestyles and real estate in New York City where she lives with her family in a cozy apartment on the twentieth floor of a Manhattan high rise.