“Daddy, tell me a story.”

“Ok, it was December 1990 and First Infantry was…”

“No daddy, not that kind. I mean one of your real estate stories. With a little economic theory, some obscure historical reference, maybe a personal anecdote. Like the ones you write for the New Canaan Sentinel. And hurry, you have 2 hours before deadline.”

“All right then. Let’s begin in 1794 with a failed land speculator who picked up a paintbrush…

Born in Maryland in 1794, 26-year-old George Esten Cooke taught himself to paint after failing as a merchant and land speculator. After 5 years copying masterpieces in Europe discouraged by the competition and broke, he returned to the East Coast and established himself as a portrait artist, mostly in the South, where, in the 1830’s he was the only one around – and the best. Portraits paid the bills, but they didn’t feed the soul. Cooke painted 30 landscapes in his lifetime, just two in New York. This story is about one of them.

That painting, New York from Brooklyn Heights once hung in the antique home of a New Canaan neighbor on Seminary Street. When he sold the house, he passed it to me. Today, it’s on loan to the College of William & Mary in Colonial Williamsburg, Virginia. Cooke’s work also hangs in the Oval Office and at the University of Georgia, which holds the largest collection. 

In 1834, Cooke first exhibited New York from Brooklyn Heights, depicting the bustling heart of the city – Manhattan’s southern tip, including Battery Park, the Financial District, and the South Street Seaport. The economy was booming after victory in the War of 1812 and the opening of the Erie Canal in 1825. Much of the land in the painting was city-owned, leased to shipping companies. Speculators snapped up the rest from prominent families like the Livingstons and the Schuylers as the population surged past 200,000 and an affordable housing crisis was already taking root (a thing even in 1834).

At the time, a prime Manhattan waterfront lot (25’ x 100’) cost between $1,000 and $5,000 Inland lots sold for half that. Adjusting for inflation, $1,000 in 1834 equates to $35,000 today. Commercial land now sells for $3,000 – $5,000 per square foot, about $130-$217 million per acre. A single 2,500 square-foot-lot today is worth between $8 and $13 million, reflecting a compound annual growth rate (CAGR) on the land of 4.87%

In today’s Financial District (Battery-Wall-Pine) condos sell for a median sale price of $955,000 or $1,312 per-square-foot. The buildable square foot price is $390, its lowest since 2010. To put it another way, the $1,900 Wall Street lot George Cooke painted now supports a high-rise where the land alone  might be valued at $35-$40 million (25,000 buildable-square-feet at $1400 per-square-foot once entitled).

Brooklyn, at the time, was appealing to wealthy New Yorkers looking for quiet. In 1834, Hezekiah Pierrepont began subdividing Brooklyn Heights into 25’ x 100’ lots, priced from $200 to $500 each depending on proximity to the waterfront. An acre fetched $10,000, or $50,000. with docking rights. Today, Brooklyn Heights is one of the most expensive neighborhoods in the city with prices ranging from $1500 to $2000 per-square-foot. A rare acre might go for $65 – $87 million, while a brownstone lot sells for $3 – $4 million or $8 – $15 million fully built. That’s a CAGR of 5.03%. 

The slightly higher return in Brooklyn Heights reflects its evolution from rural retreat to one of the city’s most desirable residential neighborhoods, whereas Manhattan’s southern tip was already the country’s most expensive real estate. (these figures exclude taxes and development costs.) 

Like real life, real estate is never a smooth ride though. 

Cooke’s painting captures the final quiet pre-industrial sunrise before the 1835 Great Fire and the speculative bust of 1837 – a moment when both shores were still recognizable for their pastures, mills and church steeples, not yet dominated by iron-framed skyscrapers. 

On December 16, 1835, 600 buildings in the painting – spanning 17 blocks between South, Pearl, Wall and Exchange Streets – burned. Merchants needed to rebuild quickly. Prices surged, especially near Broadway and north of Pine, and brick began replacing wood. Insurers went bankrupt under the weight of claims. Credit tightened, but speculative credit arrived. A lot on Broadway and Wall worth $6,000 in 1834 sold for $12,000 in 1836, even as the broader market trembled.

Then came the Panic of 1837. Sparked by speculative lending and a collapse in credit, it sent land prices tumbling – 30% to as much as 70% in parts of New York City. Harlem, Upper Manhattan and Brooklyn were hit hardest. Projects were abandoned. Houses stood unfinished and empty. That $2,000 Brooklyn lot from which Cooke painted New York fell below $1,000 in 1839 and stayed there for a decade.

Cooke painted New York from Brooklyn Heights in 1834, on the brink of a real estate mania, just before fire and financial collapse. Many of the steeples, storehouses, and rooftops he painted vanished in smoke a year later. The painting’s calm, golden serenity belies the rapid loss of wealth and stability that followed. From a collector’s standpoint, this painting captures not just topography, but a vanished moment of confidence and growth in early Manhattan—arguably the last moment before the modern city was born through disaster and recovery.

Real estate’s historical returns deserve context. The 4.87% CAGR for Manhattan land and 5.03% for Brooklyn Heights reflect nearly two centuries of compounding—land that kept its footing through war, fire, depression, and reinvention. By comparison, a savings account earning 3.5% over the same period would yield just over $600,000 on a $1,000 deposit. The S&P 500, with a real CAGR near 6.7%, compounds to over $86 million. Gold, which preserves purchasing power over centuries, does not generate compound returns, and has returned less than 1% real CAGR since 1834—precious, but inert. 

Even in Connecticut, where suburban land saw slower, steadier growth, returns on well-located property have compounded wealth over generations. But unlike equities or bullion, land has form, function, and memory. Cooke’s painted lot carried 1830s promise, burned in 1835, collapsed in 1837, and now holds a skyscraper worth forty million. That is how cities—and fortunes—are built.

I value New York from Brooklyn Heights not just for its beauty, but for what it reveals: behind every chart, every lot price, there’s a story. Sometimes a fire. Sometimes a crash. Often, a recovery. And occasionally, a painting that preserves the moment before everything changed.

John Engel is a broker on The Engel Team at Douglas Elliman in New Canaan. In the museum he sometimes spends as much time reading and thinking about the description of the painting as the art itself. His favorite part of the New Canaan Men’s Club meetings on Friday mornings is when Tom Davies tells stories of history and art.

John Engel is a broker with The Engel Team at Douglas Elliman, and he understands why furniture matters. Each piece tells a story. And some houses only make sense when they are furnished in a similar style. Frank Lloyd Wright believed “form and function are one” and created custom pieces for his houses, as did Marcel Breuer and Allan Gelbin. In contrast, New Canaan’s legendary furniture designer, Jens Risom believed “Good design means anything good will go well with other equally good things.”  Mix and match away, but keep in mind Le Corbusier famously said, “Chairs are architecture, sofas are bourgeois.”

Check out John Engel’s Podcast, Boroughs & Burbs, the National Real Estate Conversation here.

Read this article on the New Canaan Sentinel website here.