Delray Beach, Florida · Community Guide · Updated November 2026

Downtown Delray Beach and Pineapple Grove Homes for Sale (ZIP 33444): 2026 Guide

Pineapple Grove, Old School Square and the neighborhoods north of Atlantic Avenue: what is for sale today, what homes cost and what to know before you buy.

By Enrique Urdaneta, Real Estate Advisor, Engel & Völkers · Last updated November 4, 2026 · Data: Miami MLS and Beaches MLS

145For sale today
$819KMedian asking price
$1.2MMedian single-family home price
176Structures in Old School Square district

What is Downtown Delray Beach and Pineapple Grove? Downtown Delray Beach runs along Atlantic Avenue from I-95 to the ocean. North of the avenue, the Pineapple Grove Arts District runs along NE 2nd Avenue, a name that recalls the pineapple farming that became the area's main crop after canneries opened in 1911. The Old School Square Historic Arts District, the City's largest historic district, has 176 structures built from 1902 to 1945. This page covers ZIP code 33444, which includes Pineapple Grove, Lake Ida, Del-Ida Park and other neighborhoods north of Atlantic Avenue.

On November 7, 2026, there were 145 active homes and condos for sale in ZIP code 33444, from $180K to $15M, per the MLS feed on my site. The listings and numbers on this page cover ZIP code 33444.

Downtown Delray Beach and Pineapple Grove: Quick Facts (2026)

Fact Detail
Location North of Atlantic Avenue, downtown Delray Beach
Pineapple Grove Arts district along NE 2nd Avenue
Old School Square Historic Arts District 176 structures built 1902 to 1945
ZIP code 33444
For sale, November 7, 2026 145 active listings, from $180K to $15M
Median asking price About $819K

How Much Are Homes in Downtown Delray and Pineapple Grove?

On November 7, 2026, these were the active listings by type, per the MLS feed on my site:

Type For sale Asking prices Median Median size Median price per sq ft
Single-family homes 95 $375K to $15M $1.2M About 1,670 sq ft About $750
Condos 40 $180K to $1.3M $330K About 1,030 sq ft About $330
Townhouses 10 $318K to $1.75M $500K About 1,600 sq ft About $310

What to Know Before You Buy in Downtown Delray and Pineapple Grove

  • ZIP-wide numbers: ZIP 33444 covers more than downtown, so compare each listing with its own block and street.
  • Historic districts: homes in the City's historic districts go through preservation review for exterior changes.
  • Condo buildings: review the association budget, reserves and recent inspections before you sign.
  • Flood zones and insurance: check the flood zone of each home and get insurance quotes early.

Downtown Delray and Pineapple Grove Compared With Nearby Communities

For the historic neighborhoods north of downtown, see Lake Ida and Del-Ida Park. For the area south of Atlantic and the beach, see my ZIP 33483 page. For restaurants, see my Delray Beach restaurant guide. See all Delray Beach communities.

Downtown Delray Beach and Pineapple Grove FAQ

Where is Pineapple Grove?

Pineapple Grove is north of Atlantic Avenue in downtown Delray Beach, along NE 2nd Avenue, in ZIP code 33444.

How much are homes in Pineapple Grove?

On November 7, 2026, active listings had a median asking price of about $819K, from $180K to $15M, per the MLS feed on my site.

How many homes are for sale in Pineapple Grove?

On November 7, 2026, there were 145 active listings.

What ZIP code is Pineapple Grove?

Pineapple Grove is in ZIP code 33444.

Thinking About Downtown Delray Beach and Pineapple Grove?

Want a tour of a home in Downtown Delray Beach and Pineapple Grove, or current pricing and availability? Message me on WhatsApp.

East of I-95, the street, the lot and what the city lets you build often matter as much as the house. I help buyers compare neighborhoods and weigh renovating against rebuilding, and I help owners understand what their property is worth today.

Message me on WhatsAppTalk to me about Downtown Delray Beach and Pineapple Grove

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Enrique Urdaneta, Real Estate Advisor, Engel & Völkers
I don't sell houses. I help you make strategic decisions about your wealth.

See all Delray Beach communities

About the author

Enrique Urdaneta is a real estate advisor with Engel & Völkers in South Florida. He has lived in Boca Raton since 2009 and has 14 years in U.S. real estate, more than 25 years as a real estate investor, and 16 years in private banking focused on construction and pre-construction lending.

Sources

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