Selling at a Loss: NYC’s rare underwater listings

By CityRealty Staff | From Great Listings Wednesday, July 9, 2025

252 East 57th Street, #59A (Douglas Elliman Real Estate) | https://cityrealty.com/n/I2731561

Manhattan real estate is widely regarded as a safe long-term investment, but occasionally, rare and compelling scenarios arise, such as sellers willing to take a loss on their home purchase. Even during the depths of the COVID years in 2021, more than 75% of Manhattan apartments last purchased between 2014 and 2020 resold at a gain. Fast-forward to today: of nearly 9,000 active sale listings across core NYC neighborhoods, we found fewer than 500 are priced below their previous sale price.

So, why would anyone willingly take a loss in one of the world’s most expensive and resilient housing markets? The reasons vary. The reasons vary. Some sellers are under financial pressure, whether from business setbacks or rising carrying costs (especially in land-lease buildings). Others may be making personal or strategic exits or have discovered that renting out their apartment wasn’t as profitable as hoped.

A closer look at the roughly 500 listings now asking less than their last sale show some trends: many were purchased at the height of the market between 2014 and 2017. Certain properties, such as within Trump-branded buildings, for instance, have average prices down by over 25% since 2016. And some neighborhoods, including East Harlem, Hell’s Kitchen, and the Financial District, have yet to fully recover from the pandemic for reasons ranging from less of a need to be close to the office to quality-of-life issues that increased during the pandemic.

Meanwhile, recently constructed units with generic white box designs, units in need of renovation/updating, overly efficient layouts, and fixtures and flourishes that may become dated once newer product hits the market, also seem to hold their value less than their timeless or more traditionally designed counterparts.

Brooklyn, on the other hand, has almost no “underwater” listings. as prices have been dramatically increasing over the last two decades. But still, Manhattan, the island that it is, remains a market unto itself: where housing is scarce, cranes are bewilderingly few, demand is constant, and the housing crisis trudges on, all of which help keep the soil fertile for long-term appreciation.

252 East 57th Street, #59A (Douglas Elliman Real Estate) | https://cityrealty.com/n/I2731561

For buyers, these rare loss listings offer a potential window of opportunity, especially in today’s high-interest-rate, low-inventory environment, where contract activity is cooling and many sellers are more negotiable than usual.

Of course, some owners might have simply overpaid for the unit at the time of purchase, since not every sale is about timing the market and thinking of the unit as an investment vehicle. Nevertheless, homes in well-run buildings with solid financials, distinctive layouts, and proximity to transit, dining, and cultural centers are best positioned to hold their value over time.

Below, you'll find a table and select listings currently asking less than their last recorded purchase price.

Select listings selling at a loss

-19% off from 2018 closing price of $524,399

305 West 150th Street, #501
$424,000 (-4.5%)
Harlem | Condominium | 1 Bedroom, 1 Bath | 526 ft²

305 West 150th Street, #501 (Corcoran Group)

From the Listing: Welcome to this stunning corner unit in the beautifully renovated 305 West 150th Street, a seven-story prewar elevator building that perfectly blends charm with modern convenience. With open park views and an airy layout, this home is bathed in natural light through its tree -lined windows. See floor plan and full details here.

-1% off from 2022 closing price of $455,000

811 Cortelyou Road, #2L
$450,000

Kensington | Cooperative | 1 Bedroom, 1 Bath | 720 ft²

811 Cortelyou Road, #2L (Compass)

From the Listing: Welcome to 811 Cortelyou Road, Apartment 2L – a beautifully gut-renovated, oversized one-bedroom home perfectly situated on the border of Kensington and Ditmas Park. Fully updated in 2022, this move-in ready apartment seamlessly blends pre-war charm with modern upgrades. See floor plan and full details here.

-17% off from 2022 closing price of $715,000

Castle Village, #72
$595,000 (-8.5%)

Washington Heights | Cooperative | 1 Bedroom, 1 Bath | 920 ft²

Castle Village, #72 (Compass)

From the Listing: Breathtaking views of the Hudson River, Palisades and GWB south to lower Manhattan await you in this absolutely stunning 2-line one bedroom in Castle Village. Here a modern classic is born. Dentil crown moldings adorn the sunken living room grounded by pretty herringbone floors, while the kitchen and bathroom offer a sleek modern aesthetic and all the luxury that delivers. See floor plan and full details here.

-29% off from 2018 closing price of $842,115

The Style, #5C
$599,000 (-19%)

East Harlem | Condominium | 2 Bedrooms, 2 Baths | 858 ft²

The Style, #5C (Next Stop NY)

From the Listing: Welcome to residence 5C at The Style Condominium, a lovely split two bedroom, two full bathroom home located at 48 East 132nd Street. With sunny southern and western exposires, this quiet and serene residence offers everything you've been searching for, even a private outdoor balcony with room for a table and chairs to relax away from the noise of the city! See floor plan and full details here.

-2% off from 2018 closing price of $665,000

Gramercy Arms, #8H
$649,995

Gramercy Park | Cooperative | Studio, 1 Bath

Gramercy Arms, #8H (Compass)

From the Listing: Welcome to this expansive and serene alcove studio in the heart of Gramercy. Thoughtfully updated and exceptionally quiet, this oversized home offers ample space for living, dining, sleeping, and working from home, all in one beautifully designed layout. See floor plan and full details here.

-10% off from 2016 closing price of $779,000

The Peter James, #7F
$699,000 (-10.3%)

Gramercy Park | Cooperative | 1 Bedroom, 1 Bath | 750 ft²

The Peter James, #7F (Compass)

From the Listing: Unit 7F at The Peter James Cooperative is a beautiful, sun-drenched one-bedroom apartment offering unobstructed views of the Empire State Building. With approximately 750 square feet of well-designed living space, this home seamlessly combines modern upgrades with timeless elegance, making it an ideal choice for primary residence buyers or investors seeking a prime location. See floor plan and full details here.

-4% off from 2021 closing price of $885,000

2 Fifth Avenue, #2E
$850,000 (-14.6%)

Greenwich Village | Cooperative | Studio, 1 Bath

2 Fifth Avenue, #2E (Douglas Elliman Real Estate)

From the Listing: Apartment 2E at 2 Fifth Avenue offers an unparalleled opportunity to own a designer-crafted studio in one of Greenwich Village's most coveted addresses. This exceptional home celebrates mid century design with a contemporary twist, presenting a turn-key residence that's both striking and sophisticated - a true rarity. See floor plan and full details here.

-22% off from 2016 closing price of $1,150,000

432 West 52nd Street, #7H
$895,000 (-8.2%)

Midtown West | Condominium | 1 Bedroom, 1 Bath | 682 ft²

432 West 52nd Street, #7H (Brown Harris Stevens Residential Sales LLC)

From the Listing: Step into penthouse luxury in this stunning space with unobstructed views of Billionaires" Row Price Reduction! Immaculate finishes, pin-drop silence, and over-sized windows in every sunlit room, make this new Penthouse home a rare find.

Facing north, the H Line is flooded with light in the bedroom, living room, dining area, and kitchen, grading it the favorite and most desirable line. 9-foot ceilings, white oak hardwood floors below, and an expansive great room provide extensive space for living, dining, and entertaining, with an open kitchen model that effortlessly blends style with stainless steel appliances and elegant Caesarstone countertops. See floor plan and full details here.

-5% off from 2015 closing price of $999,999

The Adlon, #10D
$945,000

Midtown West | Cooperative | 1 Bedroom, 1 Bath

The Adlon, #10D (Corcoran Group)

From the Listing: Welcome to Residence 10D, a beautifully renovated 1-bedroom, 1-bathroom home at the iconic Adlon Cooperative, located at 200 West 54th Street. This gracious prewar residence blends timeless architectural charm with thoughtful modern renovation. Upon entering, you're greeted by a stately foyer adorned with original moldings, classic wainscoting, and soaring 9.5-foot ceilings-setting the tone for the elegance that continues throughout. See floor plan and full details here.

-13% off from 2017 closing price of $1,150,000

100 Avenue A, #2B
$995,000 (-11.6%)

East Village | Condominium | 1 Bedroom, 1 Bath | 678 ft²

100 Avenue A, #2B (Compass)

From the Listing: Welcome home to residence 2-B, located at 100 Ave A in a full-service doorman building in the vibrant East Village, next to Tompkins Square Park. This bright & sunny 1-bedroom, 1-bathroom home features a spacious layout, oversized casement windows with western exposure, gorgeous finishes, white oak herringbone floors, washer/dryer in unit and central A/C. See floor plan and full details here.

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-15% off from 2016 closing price of $1,175,000

London Terrace Towers, #6J
$999,000 (-4.9%)

Chelsea | Cooperative | 1 Bedroom, 1 Bath

London Terrace Towers, #6J (Compass)

From the Listing: Renovated One Bedroom at London Terrace. Bring your toothbrush and settle right into this fabulous home. Designed with clean, modern lines while retaining its pre-war character. If you have been searching for that perfect one-bedroom, but are feeling let down by everything out there, this is the one that will change your mind. See floor plan and full details here.

-21% off from 2017 closing price of $1,270,000

Coda Condominium, #11A
$999,000 (-8.8%)

Gramercy Park | Condominium | 1 Bedroom, 1 Bath | 770 ft²

Coda Condominium, #11A (Compass)

From the Listing: Discover one of the best bedroom layouts in the building with this spacious one-bedroom, one-bathroom home, 11A, where floor-to-ceiling windows flood the space with southern light and breathtaking city views. See floor plan and full details here.

-16% off from 2021 closing price of $1,425,000

The Alameda, #2D
$1,199,000 (-7.7%)

Riverside Dr./West End Ave. | Cooperative | 2 Bedrooms, 2 Baths

The Alameda, #2D (Douglas Elliman Real Estate)

From the Listing: This turn-of-the-century beauty offers a sunny living and dining area with soaring ceilings. There are two bedrooms, each with double exposures, as well as an additional third bedroom or home office and two updated windowed bathrooms. The windowed kitchen has an entrance to the living room and another into the foyer and offers room (with proper approvals) for a washer/dryer. See floor plan and full details here.

-15% off from 2016 closing price of $1,471,371

325 Lex, #27D
$1,250,000 (-20.9%)

Murray Hill | Condominium | 1 Bedroom, 1 Bath | 643 ft²

325 Lex, #27D (Nest Seekers LLC)

From the Listing: Welcome to 325 Lexington, this stunning one bedroom apartment features soaring ceilings, floor to ceiling windows with sunny Southern and Eastern exposure and inspiring views of the East River and Manhattan city skyline. The open kitchen is outfitted with custom walnut cabinetry, quartz countertops as well as fully integrated appliances from top-of-the-line Liebherr, Bosch and Bertazzoni stainless steel appliances. See floor plan and full details here.

-14% off from 2016 closing price of $1,624,109

The Beekman Residences, #21B
$1,395,000 (-12.5%)

Financial District | Condominium | 1 Bedroom, 1 Bath | 855 ft²

The Beekman Residences, #21B (Compass)

From the Listing: Welcome to Residence 21B at The Beekman Residences — a spacious, corner one-bedroom home boasting iconic views of Manhattan including the beloved Chrysler Building. This meticulously redesigned apartment stands apart from any other in the building, offering sophisticated style and luxurious comfort. See floor plan and full details here.

-11% off from 2023 closing price of $1,750,000

993 Park Avenue, #8E
$1,550,000 (-11.4%)

Carnegie Hill | Cooperative | 2 Bedrooms, 2 Baths

993 Park Avenue, #8E (Brown Harris Stevens Residential Sales LLC)

From the Listing: Very Spacious Prewar 2 Bedroom on Park Avenue Arriving from your semi private elevator landing, once you enter apartment 8E you immediately notice the amazing scale of the apartment. The square foyer measuring roughly 10' x10' flows seamlessly into the large 27'5" x 18'4" living room (which can easily be divided into 2 sizeable rooms) with open views. See floor plan and full details here.

-15% off from 2021 closing price of $1,934,675

North Park Tower, #17A
$1,650,000

East Harlem | Condominium | 3 Bedrooms, 3 Baths | 2,018 ft²

North Park Tower, #17A (Bond New York Properties LLC)

From the Listing: Stunning corner three bedroom, three bathroom residence features an open chef's kitchen with great counter space and pantry for extra storage. The sprawling living / dining space is complete with sound attenuated floor-to-ceiling windows with three exposures, offering incredible light and air and views of Central Park and beyond. Kitchen finishes include Athens Silver Cream Marble countertops and backsplash, custom oak cabinetry, range by Thermador, Hood by Elica, with Refrigerator and Dishwasher by Bosch. See floor plan and full details here.

-22% off from 2019 closing price of $2,150,000

Trump Parc East, #11D
$1,670,000 (-11.9%)

Midtown West | Condominium | 1 Bedroom, 1 Bath | 838 ft²

Trump Parc East, #11D (Trump International Realty New York)

From the Listing: Wonderful opportunity to own in one of New York City's most desirable locations right on Central Park South. This spacious one bedroom apartment was recently gut renovated and offers hardwood floors, fireplace, high ceilings and views of Central Park! With an open floorplan, the gourmet kitchen counter seating is the perfect spot to relax and enjoy your morning coffee while looking out over Central Park. See floor plan and full details here.

-20% off from 2017 closing price of $2,199,420

50 West, #17C
$1,749,000 (-2.3%)

Financial District | Condominium | 1 Bedroom, 1 Bath | 1,080 ft²

50 West, #17C (Time Equities Brokerage LLC)

From the Listing: Welcome to a world of elegance and serenity high above the city, in this sun-drenched, south-facing one-bedroom, one-bathroom residence at the prestigious 50 West Street—one of Downtown Manhattan’s most luxurious condominiums. Spanning nearly 1,100 square feet, this thoughtfully designed home is framed by floor-to-ceiling, 10-foot windows, offering beautiful, views of New York Harbor. See floor plan and full details here.

-10% off from 2017 closing price of $2,167,000

51 Jay Street, #5D
$1,950,000 (-10.3%)

DUMBO | Condominium | 2 Bedrooms, 2.5 Baths | 1,382 ft²

51 Jay Street, #5D (Compass)

From the Listing: 51 Jay Street, Residence 5D is a 2 Bedroom/2.5 Bathroom loft in a beautifully converted warehouse, designed by the acclaimed architecture firm, ODA. The high ceilings (9'6"), herringbone oak flooring and the Western light pouring through the oversized casement windows will wow you upon entry. See floor plan and full details here.

-13% off from 2017 closing price of $2,853,850

551W21, #3E
$2,475,000 (-10%)

Chelsea | Condominium | 1 Bedroom, 1.5 Baths | 1,521 ft²

551W21, #3E (Douglas Elliman Real Estate)

From the Listing: BEST ONE BEDROOM LOFT AT FOSTER & PARTNERS This spectacular 1,520+ Sq Ft residence features an uttely grand and gracious 36-foot long by 15-foot wide living room with solid oak floors and over ten-foot ceilings with floor to ceiling windows. This expansive south-facing and corner 1-bedroom 1.5 bathroom home is defined by perfectly scaled, column-free space and top of the line finishes. See floor plan and full details here.

-17% off from 2017 closing price of $3,000,000

12 East 88th Street, #2D
$2,500,000 (-9.1%)

Carnegie Hill | Condominium | 2 Bedrooms, 2 Baths | 1,449 ft²

12 East 88th Street, #2D (Compass)

From the Listing: NEW PRICE! 300 feet from Central Park and The Guggenheim Museum, this Mint Carnegie Hill 2-Bedroom Pre-War Candela Condominium is a find! See floor plan and full details here.

-1% off from 2021 closing price of $3,035,000

11 Hoyt, #39F
$2,995,000

Downtown Brooklyn | Condominium | 3 Bedrooms, 3 Baths | 1,743 ft²

11 Hoyt, #39F (Elegran LLC)

From the Listing: Residence 39F is perched in a prized corner location and takes full advantage of the breathtaking South and East open views over Brooklyn. Natural light floods the 1,743sqft layout which is complete with three bedrooms, three bathrooms and generous living spaces that will delight even the most discerning buyer. See floor plan and full details here.

-15% off from 2015 closing price of $3,750,000

130 East 75th Street, #5A
$3,195,000 (-3%)

Park/Fifth Ave. to 79th St. | Cooperative | 3 Bedrooms, 2.5 Baths

130 East 75th Street, #5A (Douglas Elliman Real Estate)

From the Listing: Expansive and elegant Upper East Side home on quiet tree-lined 75th Street, in a handsome full-service prewar co-op. This beautiful, airy residence offers comfortable, luxurious living, with generously-sized rooms, high beamed ceilings, 3 spacious bedrooms, a bonus guest/staff room/office, and 2 and a half tastefully designed baths. Oversized windows in every room and triple exposures to the south, north and west bathe the interiors in lovely natural light. See floor plan and full details here.

-26% off from 2017 closing price of $6,112,500

252 East 57th Street, #59A
$4,500,000

Midtown East | Condominium | 3 Bedrooms, 3 Baths | 2,246 ft²

252 East 57th Street, #59A (Douglas Elliman Real Estate)

From the Listing: Spectacular Corner Residence with Iconic Views at 252 East 57th Street Welcome to this stunning corner home perched on the 59th floor, offering sweeping panoramic views of Central Park, the East River, and the iconic NYC skyline. Originally configured as a three-bedroom, three-and-a-half-bath residence, this custom layout has been thoughtfully transformed into a spacious two-bedroom plus home office. See floor plan and full details here.

-34% off from 2019 closing price of $7,004,719

Fifteen Hudson Yards, #63A
$4,600,000 (-16.4%)

Midtown West | Condominium | 2 Bedrooms, 2.5 Baths | 2,080 ft²

Fifteen Hudson Yards, #63A (Brown Harris Stevens Residential Sales LLC)

From the Listing: MOTIVATIED SELLER, BIRNG YOUR OFFER Experience luxury living at its finest in this exquisite two-bedroom, two and a half-bathroom condominium located in the heart of Hudson Yards. Unit 63A boasts a modern open kitchen, perfect for entertaining, and offers stunning south and east exposures, filling the space with natural light and showcasing breathtaking views. See floor plan and full details here.

-22% off from 2016 closing price of $6,417,500

One Vandam, #9B
$4,999,000 (-9%)

SoHo | Condominium | 3 Bedrooms, 3.5 Baths | 2,221 ft²

One Vandam, #9B (Serhant)

From the Listing: Introducing a bright and spacious 3-bedroom, 3.5-bathroom apartment with 2 private outdoor spaces in a full-service building in the heart of Soho. 2,221 sq ft + 106 sq ft outdoor space. Key Features: Light-Filled Apartment: Enjoy floor-to-ceiling windows, a 30 ft long great room, two terraces, and beautiful views of Hudson Yards and Soho. See floor plan and full details here.

-18% off from 2018 closing price of $10,500,000

101 West 78th Street, #3A
$8,650,000 (-3.8%)

Broadway Corridor | Condominium | 4 Bedrooms, 3.5 Baths | 4,050 ft²

101 West 78th Street, #3A (Compass)

From the Listing: Residence 3A at 101 West 78th Street is one of the largest 4 bedroom/3.5 bath (approx 4050 sq ft) condominiums on the Upper West Side. This sprawling, sunny and renovated southeast corner home with 10’6 ceilings and elegant herringbone floors is located in a boutique, full-service prewar condominium on one of the most desirable streets. See floor plan and full details here.

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