539 FOREST WAY UNIT 539, LONGBOAT KEY, FL, 34228
Active32 days on marketListed Sep 23, 2026MLS #A4706129
Come see it
Upcoming open house
Sun, Oct 25
1:00 PM – 3:00 PM
About this home
539 FOREST WAY UNIT 539
Second-home buyers and investment-minded buyers, take note. This beautifully furnished, turnkey residence at Cedars East on Longboat Key offers the rare combination of a polished coastal retreat, an established rental history, and meaningful upside potential. The home has generated approximately $50,000 in average annual rental payout revenue, after Airbnb and VRBO fees, providing a proven income history while maintaining the flexibility of up to 26 rental opportunities a year—an unusually flexible arrangement for Longboat Key. The owners have invested more than $130,000 in upgrades and improvements since 2021, creating a home that is not simply rental-ready, but thoughtfully maintained and continually enhanced. The current owners have created a home designed to deliver an exceptional guest experience. The sale includes the home's high-quality furnishings, top-of-the-line kitchenware—including All-Clad cookware—solid dishware, premium beach equipment and carefully selected décor. The result is reflected in the property's rental reputation, with more than 40, 5-Star Airbnb reviews from previous guests. Positioned near the front of Cedars East, the residence offers more convenient access to the Gulf beaches than many locations within the community and is next to the Longboat Key bike path. Inside, the 1,440-square-foot, two-bedroom, 2½-bath residence features an open living and dining area, a large garage, and a private, wooded outlook from the living room and lanai. The lush greenery creates a wonderfully private, almost treehouse-like setting—a peaceful contrast to the Gulf just moments away. Residents of Cedars East enjoy a resort-style setting with HOA amenities including the community pool, kayak and paddle board launch, fishing pier, cable, water, sewer, trash and pest control.Optional membership at the Cedars Tennis Resort & Club provides access to additional tennis, pickleball and fitness amenities. Whether you're looking for a beautifully finished Longboat Key retreat, a second home that can generate income, or a turnkey vacation property with an established rental history, this residence offers a compelling combination of lifestyle and flexibility. Come experience The Longboat Key Life.
Facts & features
The home at a glance
2
Bedrooms
2.5
Bathrooms
1,440
Sqft
0 ac
Lot size
1
Garage
1990
Year built
Three Or More
Levels
$444
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.
$4,750 /mo · 10% down Conventional, 30-yr fixed at 7.5%
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
$4,750/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.
Can I afford this home? → See what you can comfortably afford from your income, debts and savings.
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.
vs edgeAI estimate
+10.2%
$/sqft vs Longboat Key actives
$444 vs $676
Days on market
32 vs 107 typical
Where $444/sqft sits among the 235 Longboat Key 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 Longboat Key
Get to know Longboat Key. See the full Longboat Key guide →
LONGBOAT KEY 34228 — neighborhood snapshot
Population
7,512
Median age
71.5
Median income
$143,365
Median home value
$959,200
Avg household
1.8
Households w/ children
51%
For the school run
Sarasota County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Longboat Key market
$820K → $948K
Longboat Key median sold, yr/yr
93.1%
Sale-to-list ratio (12 mo)
94 of 235
Longboat Key actives have cut their price
Median sold price, Longboat Key, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 8% above the LONGBOAT KEY 34228 median. See the full Longboat Key market guide →
Paper trail
This home's history
Reality check
What actually sold near 539 FOREST WAY UNIT 539
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jul ’26$575,000
528 FOREST WAY · same community
2 bd · 2.5 ba · 1,440 sqft · $399/sqft · 13 DOM
Sold · Jul ’26$1,575,000
2525 GULF OF MEXICO DRIVE UNIT 3D
2 bd · 2 ba · 1,468 sqft · $1,073/sqft · 7 DOM
Sold · Oct ’26$850,000
5055 GULF OF MEXICO DRIVE UNIT 532
3 bd · 2 ba · 1,484 sqft · $573/sqft · 1 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
Shawn Headley
Realtor · CENTURY 21 Edge
Tours, negotiation, and every question about 539 FOREST WAY UNIT 539 — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 539 FOREST WAY UNIT 539 — before you fall in love.
See it in person
Schedule a tour
Live availability from Shawn's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
539 FOREST WAY UNIT 539 FAQs
What would the monthly payment be for 539 FOREST WAY UNIT 539?+
With 10% down on a 30-year Conventional loan at 7.5%, the all-in payment lands around $4,750/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 539 FOREST WAY UNIT 539?+
The most recent tax bill on record (2025) was $3,954. 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 539 FOREST WAY UNIT 539?+
The listing reports pets: Cats OK, Dogs OK, Number Limit, Size Limit, 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 Longboat Key?+
At $639,000, this home is listed about 27% below the Longboat Key median of $877,500. The market section on this page shows how the area is trending.
Which schools are assigned to 539 FOREST WAY UNIT 539?+
Booker High School (high), Booker Middle School (middle), Southside Elementary School (elementary) — Sarasota County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY · Sharon Austin. MLS #A4706129.
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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