530 S ORANGE AVENUE, SARASOTA, FL, 34236
Active147 days on marketListed Mar 16, 2026MLS #A4686338
About this home
530 S ORANGE AVENUE
The Historic Pineapple Apartments, the centerpiece of Burns Square. This building has deep ties to Sarasota history, built by Owen Burns (our city's first developer) in 1925. Last purchased in 1986, you will never walk a more curated and cared-for building. It's a step back into the Roaring '20s and a modern-day reminder that community is local. At one time an apartment building, it now serves as a thriving vacation rental. It has 8 suites (could be 13), 7 retail shops below, and a 3,000 sq ft owner's suite. Wrought-iron balconies align the exterior walls, Venetian plaster the interiors, multiple exposed beams, and a historical monument next to the fountain at Little Five Points. It's Sarasota's "Flatiron Building," triangulated architecture, impossible to go unnoticed. It is the entrance to downtown from the south, a beacon, a landmark for our great city.
Facts & features
The home at a glance
10
Bedrooms
13,762
Sqft
0.14 ac
Lot size
1925
Year built
$618
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$51,214 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$51,214/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
$/sqft vs Sarasota actives
$618 vs $343
Days on market
147 vs 63 typical
Where $618/sqft sits among the 400 Sarasota actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Burns Square
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Sarasota. See the full Sarasota guide →
Burns Square — neighborhood snapshot
Population
221
Median age
72
Median income
$126,388
Median home value
$977,862
Avg household
2
Households w/ children
2%
For the school run
Sarasota County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Sarasota market
$475K → $493K
Sarasota median sold, yr/yr
95.2%
Sale-to-list ratio (12 mo)
160 of 400
Sarasota actives have cut their price
Median sold price, Sarasota, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 953% above the SARASOTA 34236 median. See the full Sarasota market guide →
Paper trail
This home's history
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Jillian Kobylesky
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 530 S ORANGE AVENUE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 530 S ORANGE AVENUE — before you fall in love.
See it in person
Schedule a tour
Live availability from Jillian's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
530 S ORANGE AVENUE FAQs
What would the monthly payment be for 530 S ORANGE AVENUE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $51,214/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 530 S ORANGE AVENUE?+
The most recent tax bill on record (2025) was $24,013. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Sarasota?+
At $8,500,000, this home is listed about 1421% above the Sarasota median of $559,000. The market section on this page shows how the area is trending.
Which schools are assigned to 530 S ORANGE AVENUE?+
Sarasota High School (high), Southside Elementary School (elementary), Booker Middle School (middle) — Sarasota County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Positioned at the premium end
$8,500,000 runs 953% above the SARASOTA 34236 median — but at 13,762 sqft it's also nearly 8 times the size of the typical Sarasota listing.
02City views
The city view is part of what you're buying — views hold value independently of the structure.
03Time on market is leverage
147 days on market against a Sarasota median of 63 — sellers in this position are usually ready to negotiate.
04Strong assigned schools
Sarasota High School, Southside Elementary School, Booker Middle School — Southside Elementary School rates 5 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of COMPASS FLORIDA LLC · Jason Skowronski. MLS #A4686338.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
Never miss a listing
New Sarasota homes, in your inbox
Like 530 S ORANGE AVENUE but not quite? A daily digest of every new listing in Sarasota — straight from the MLS, hours after it goes live. Unsubscribe anytime.
Just watching this one home? Ask Jillian to ping you on any price or status change →