
PINEAPPLE STREET, ENGLEWOOD, FL, 34223
Active143 days on marketListed Mar 18, 2026MLS #D6146625
About this home
PINEAPPLE STREET
Exceptional and Almost an Acre in the Heart of Old Englewood! Opportunities like this are becoming increasingly rare. This homesite offers an impressive amount of space in one of Englewood’s most desirable and convenient locations. The size of this vacant lot provides flexibility for a spacious primary residence while still leaving room for additional features such as a detached garage, workshop, outdoor living areas, or extra storage for recreational vehicles and boats. The property is surrounded by mature Old Florida vegetation that creates a naturally private setting and a beautiful backdrop for future construction. With RSF3 zoning, there is potential to divide and create multiple homesites, making it an appealing option for builders, investors, or those simply looking to secure a large piece of land close to the water and downtown. Just a few blocks away, Historic Dearborn Street offers a true Old Englewood feel with locally owned restaurants, unique shops, art galleries, and seasonal community events. Nearby marinas, boat ramps, and waterfront parks make it easy to spend time on Lemon Bay, while both Englewood Beach and Manasota Key Beach are only a short drive away. Golf courses, pickleball, medical facilities, and everyday shopping are also conveniently close. A previous home was located on the property, so public water, sewer, and electric service are available, and three existing culvert driveways are already in place to provide convenient access to the property. If you have been searching for a larger homesite with an outstanding location and plenty of flexibility for future plans, this property is well worth a look at Pineapple Ave in Englewood.
Facts & features
The home at a glance
0.9 ac
Lot size
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.
$1,584 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
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
Estimated payment
$1,584/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. 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.
Where it sits
Inside Old Englewood Village
Get to know Englewood. See the full Englewood guide →
Old Englewood Village — neighborhood snapshot
Population
3,260
Median age
64
Median income
$60,523
Median home value
$320,216
Avg household
2
Households w/ children
124
For the school run
Sarasota County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Englewood market
$330K → $330K
Englewood median sold, yr/yr
94.6%
Sale-to-list ratio (12 mo)
Median sold price, Englewood, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 46% below the ENGLEWOOD 34223 median. See the full Englewood market guide →
Paper trail
This home's history
Reality check
What actually sold near PINEAPPLE STREET
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Feb ’26$285,000
638 YALE STREET · same community
2 bd · 1 ba · 672 sqft · $424/sqft · 12 DOM
Sold · Jan ’26$200,000
635 LEWIS STREET · same community
2 bd · 1 ba · 743 sqft · $269/sqft · 104 DOM
Sold · Apr ’26$165,000
645 LEWIS STREET · same community
2 bd · 1 ba · 744 sqft · $222/sqft · 129 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
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
Julian Rivera
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about PINEAPPLE STREET — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for PINEAPPLE STREET — before you fall in love.
See it in person
Schedule a tour
Live availability from Julian's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
PINEAPPLE STREET FAQs
What would the monthly payment be for PINEAPPLE STREET?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $1,584/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 PINEAPPLE STREET?+
The most recent tax bill on record (2025) was $1,216. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at PINEAPPLE STREET?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Englewood?+
At $209,000, this home is listed about 42% below the Englewood median of $362,500. The market section on this page shows how the area is trending.
Which schools are assigned to PINEAPPLE STREET?+
Englewood Elementary School (elementary), Lemon Bay High School (high), L. A. Ainger 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
01Under the ENGLEWOOD 34223 market on paper
$209,000 is 46% below the ENGLEWOOD 34223 median of $388,250.
02Time on market is leverage
143 days on market against a Englewood median of 68 — sellers in this position are usually ready to negotiate.
03Strong assigned schools
Englewood Elementary School, Lemon Bay High School, L. A. Ainger Middle School — Englewood Elementary School rates 4 of 5. Always verify assignments with the district.
04The price has already moved
Listed at $295,000, now $209,000 — a $86K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of RE/MAX ALLIANCE GROUP · Carla Stiver, PA. MLS #D6146625.
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.
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