The Chesterfield
186 West 80th Street, at Amsterdam Avenue, Upper West Side, Manhattan, NY 10024
Upper West Side
BBL 1012107502 · BIN 1082723
- Type
- Condominium
- Units
- 91
- Floors
- 13
- Landmark
- Designated
Every recorded sale at this building, 2003–2026
Price-per-square-foot over time, the line- and floor-premium curves, and every recorded sale.
- Median $/sf
- $1,284
- Listing discount
- 2.9%
- Recorded sales
- 135
- On record
- 2003–2026
Own an apartment here? See what it would sell for.
A Private Pricing Opinion — what your apartment at The Chesterfield; originally The Chesapeake would likely sell for today, what it costs to sell, and what you’d walk away with — reviewed personally against condition, exposures, renovation quality, and the competition actually on the market.
The Chesterfield combines a nineteenth-century apartment-house base with a substantial enlargement from the late 1980s. The original five-story flats were designed by Thom & Wilson in 1886–1887; Ted Reeds & Associates’ later work brought the property to thirteen stories. That construction history explains why the condominium has both an older street presence and a taller residential section above it.
The apartments range from studios and one-bedroom homes to larger layouts and combinations. Full-time door service gives even the smaller homes access to an attended entrance, and the condominium structure allows individually deeded ownership within the historic district.
The entrance is on West 80th Street at Amsterdam Avenue. The corner places the building close to the Broadway subway and the Museum of Natural History area, with Central Park to the east. The avenue frontage and the side-street position create different exposures within the building.
Architecture and unit composition
LPC describes the older portion as neo-Grec with Queen Anne elements, built in brick with masonry bearing walls. The later enlargement uses a mixed construction system and a modern architectural treatment. The original property included storefronts at its base.
The residential inventory includes compact studios with separate kitchen areas, one-bedroom apartments and larger two-bedroom homes. Some corner plans have more than one exposure, while other apartments have a single principal outlook toward the avenue or the surrounding block.
Upper-floor homes include examples with private terraces. Larger combinations also appear in the resale history, creating layouts that differ from the original studio and one-bedroom inventory. The existence of a large apartment in the building does not imply that the same footprint repeats throughout its vertical line.
Renovations have changed the interiors considerably over time. Some smaller homes retain a compact kitchen arrangement, while others have reconfigured cabinetry and appliances to open the living space. Ceiling heights, window positions and the relationship between rooms should be read in the context of the particular part of the building where the home sits.
Building operations
The condominium has a full-time doorman and live-in superintendent. Laundry is available in the building, and a garage provides a parking option separate from the apartment itself. The combination of staffed entry and a large share of smaller homes is a defining operational feature of the property.
The tax lot includes both residential and commercial condominium units. Common expenses are allocated through the condominium, while each residential unit has a separate real estate tax bill. Personal exemptions can change an eligible owner’s taxes without constituting a building-wide development abatement.
The property is inside the Upper West Side/Central Park West Historic District. Its two construction periods both contribute to the existing exterior, so façade work needs to account for the older masonry and the later addition. Proposed visible changes to windows or exterior equipment can also involve the district’s preservation requirements.
Policy framework
Pied-à-terre use: Permitted — confirm with the managing agent.
Leasing: Investor ownership and apartment rentals are permitted, with a condominium application process — confirm with the managing agent.
Pets: Pets are permitted for owners, with restrictions described for some rentals — confirm with the managing agent.
Recent sales
Recent closings at this building, curated by The Roebling Team research desk. Prices are the transfer amounts recorded with the NYC Department of Finance; apartment-level detail is checked against the building’s own file in The Roebling Research Library before publishing.
| Date | Unit | Apartment | Price | PPSF | vs. Ask |
|---|---|---|---|---|---|
| Dec 5, 2025 | 7K | 1 BR · 1 BA · 510 sf | $815,000 | $1,598/sf | -1.2% |
| Aug 22, 2025 | 7D | 1 BA · 401 sf | $520,000 | $1,297/sf | off-mkt |
| Aug 19, 2025 | 6J | 1 BR · 1 BA · 650 sf | $770,000 | $1,185/sf | -12.0% |
| May 12, 2025 | 4M | 1 BA · 400 sf | $504,000 | $1,260/sf | -8.4% |
| Sep 16, 2024 | 3A | 1 BR · 1 BA · 541 sf | $767,000 | $1,418/sf | +6.5% |
| May 6, 2024 | 11C | 1 BR · 530 sf | $1,925,000 | $3,632/sf | off-mkt |
| Apr 23, 2024 | 4G | 1 BA · 450 sf | $575,000 | $1,278/sf | -7.1% |
| Sep 15, 2023 | 5G | 1 BA · 400 sf | $505,000 | $1,263/sf | -3.8% |
Market read. $/sf is measured on the latest sales with reliable square footage (2025): a median $1,284/sf across 4 sales. The building has traded as recently as 2026. Median listing discount 2.9% from the last ask — a recurring negotiation gap worth pricing into any offer or listing strategy.
The retrade record
Lines that have traded more than once in the public record — the building’s appreciation arc, apartment by apartment.
Full closing history with price-per-square-foot over time, the complete retrade record, and every line that has traded.
Sales sourced from NYC Department of Finance recorded transfers (BBL 1-01210-7502) and verified listing data. Apartment-level facts (line, condition, asking-price context) curated and cross-verified by The Roebling Team research desk. Not all transactions cross-verify with ACRIS records — sponsor and LLC purchases sometimes record at stipulated values rather than market price; square footage from recorded condo declarations and offering plans.
At the recent median sale of $770K (4 sales since 2024), a buyer putting 25% down would pay about $29,791 to close, or 3.9% of the price.
- Mansion tax: $0
- Mortgage recording tax: $11,117
- Title insurance: $3,465
- Attorneys, lender, building fees, reserves and filings: $15,210
Assumes a resale (the seller pays transfer taxes), a $4,500 attorney fee and a mortgage on the rest.
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What to know if you’re buying
An owner’s pet permission may not carry into a rental. This condominium has both owner-occupied apartments and a continuing rental market, and rental terms can impose restrictions beyond those described for ownership. A purchaser intending to lease an apartment should confirm the tenant rules separately from the rules governing personal occupancy.
Comparable buildings
- The Avonova — A nearby prewar condominium conversion with a larger residential inventory.
- The Rousseau — A prewar condominium of broadly similar apartment count with a Broadway setting.
- The Barrington — A smaller nearby prewar condominium for comparing association scale.
- The Hopkins — A taller prewar condominium a block south, with a similar overall residential count.
- The Marlow — A smaller prewar conversion with a different apartment mix and building scale.
More Upper West Side buildings
- 176 West 87th Street — 1916 co-op by Schwartz & Gross
- The Packard, 176 West 86th Street — 1986 condominium
- 182 West 82nd Street (The Pontiac) — 1892 condominium
- 200 Amsterdam Avenue — 2021 condominium
- 200 Riverside Boulevard — 1997 condominium by Philip Johnson and Costas Kondylis
- 200 West 72nd Street (The Corner) — 2010 condominium by Handel Architects
The neighborhood
For the full corridor — architecture, transit, and pricing across Upper West Side — read The Roebling Team Guide to Upper West Side.
How to read the facts on this page. Items attributed to an offering plan describe the building as it was offered at that filing — unit mix, square footage, the amenity program as planned. They are not a statement about how the building operates today. Tax and compliance figures are sourced separately to current City records and carry their own dates. House rules, staffing and fee policy can change by board resolution without any public filing: treat every policy line here as a starting point for diligence and confirm it with the managing agent. Where this page compares one building or neighborhood to another, that is our analysis of the recorded record — it names the measure, the period and the sample it rests on, and it is an observation about medians rather than a prediction about any particular apartment.
Considering a move at The Chesterfield; originally The Chesapeake?
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