8399 CYPRESS ROAD, ENGLEWOOD, FL, 34224
Active383 days on marketListed Jul 21, 2025MLS #A4659561
About this home
8399 CYPRESS ROAD
Located in the beautiful Englewood, Florida area lies this 15 +/- Are development site with frontage on the new Winchester Boulevard Extension. This new extension is the north-south connector bisecting historic Englewood from Englewood East and Rotonda as a new Central Boulevard. It provides access to South River Road (connecting to Interstate-75) and Placida Road to the south giving access to the world-famous Boca Grande. This offering consists of one to three parcels for development into retail, multi-family, or both. Opportunities consist of either purchasing the entire site for retail development as it is already zoned CG - Commercial General, or multifamily development under the Florida Legislature's Live Local Act allowing multi-family development without a rezoning provided certain affordable housing criteria are met. Seller will also subdivide as two 1.2 +/- Acre future corner retail development sites with frontage on Winchester Boulevard and one 12.6 +/- Acre site that could be used for Multi-Family Development with partial frontage on Winchester Boulevard and partial frontage on the future Cypress Road. The multi-family residential site is located in an area that can utilize the Residential live local zoning allowing for apartments or a build-to-rent community on the site. Recent revisions to Live Local in 2025 assures that Charlotte County's "Transfer Density Unit" program does not impair implementation of the Live Local Act. The 1.2+/- acre retail sites at the corner of Winchester Boulevard and Cypress Road could have the potential to be at a future traffic light. The lots are zoned Commercial General (CG) allowing for a variety of uses including Bank, Pharmacy, Gas Station, Retail, Car Wash, Restaurant, among others. 15 +/- total acres for $5,500,000. Seller will also consider subdividing; Parcel A: 1.2 +/- Acres - $775,000 Corner Lot Retail Parcel Parcel B: 1.2 +/- Acres - $675,000 Retail Parcel Parcel C: 12.5 +/- Acres - $4,500,000 Multifamily Parcel
Facts & features
The home at a glance
5 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.
$32,380 /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
$32,380/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.
Where it sits
Inside Englewood
Get to know Englewood. See the full Englewood guide →
ENGLEWOOD 34224 — neighborhood snapshot
Population
15,971
Median age
63.6
Median income
$56,862
Median home value
$262,200
Avg household
2.02
Households w/ children
795
For the school run
Charlotte 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 6080% above the ENGLEWOOD 34224 median. See the full Englewood market guide →
Paper trail
This home's history
Reality check
What actually sold near 8399 CYPRESS ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Sep ’25$79,900
96 BOUNDARY BOULEVARD UNIT 112
1 bd · 1 ba · 780 sqft · $102/sqft · 89 DOM
Sold · May ’26$106,000
96 BOUNDARY BOULEVARD UNIT 129
1 bd · 1 ba · 780 sqft · $136/sqft · 131 DOM
Sold · Apr ’26$165,000
9027 KESTRAL CIRCLE
2 bd · 2 ba · 972 sqft · $170/sqft · 16 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
Gianfranco Di Flumeri Petrelli
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 8399 CYPRESS ROAD — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 8399 CYPRESS ROAD — before you fall in love.
See it in person
Schedule a tour
Live availability from Gianfranco's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
8399 CYPRESS ROAD FAQs
What would the monthly payment be for 8399 CYPRESS ROAD?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $32,380/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 8399 CYPRESS ROAD?+
The most recent tax bill on record (2024) was $5,756. 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 Englewood?+
At $5,500,000, this home is listed about 1417% above the Englewood median of $362,500. The market section on this page shows how the area is trending.
Which schools are assigned to 8399 CYPRESS ROAD?+
Lemon Bay High School (high), L. A. Ainger Middle School (middle), Vineland Elementary School (elementary) — Charlotte 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
$5,500,000 runs 6080% above the ENGLEWOOD 34224 median.
02Time on market is leverage
383 days on market against a Englewood median of 68 — sellers in this position are usually ready to negotiate.
03Strong assigned schools
Lemon Bay High School, L. A. Ainger Middle School, Vineland Elementary School — Vineland Elementary School rates 4 of 5. Always verify assignments with the district.
04The price has already moved
Listed at $6,600,000, now $5,500,000 — a $1.1M cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of SVN COMMERCIAL ADVISORY GROUP · Tony Veldkamp, CCIM. MLS #A4659561.
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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