2339 HARBOUR OAKS DRIVE, LONGBOAT KEY, FL, 34228
Active121 days on marketListed Apr 4, 2026MLS #A4688776
About this home
2339 HARBOUR OAKS DRIVE
Enjoy resort-style living on prestigious Longboat Key in this completely updated and renovated 3-bedroom, 2.5-bathroom villa. Located in Harbour Circle, an enclave of 42 villas in the guard-gated, maintenance-free, community of Bay Isles, this 2,396 SF open floorplan has soaring ceilings and an abundance of natural light through the new high-impact doors and windows that uplifts and illuminates. The spacious kitchen cannot help but impress with stainless steel appliances and an ample amount of quartz countertops perfect for aspiring chefs or for entertaining. An island with a sink, doubles as a breakfast bar and striking, wood cabinets offer plenty of storage space. Beautiful light-colored ceramic tile and wood floors flow throughout. As you enter the oversized screened terrace you are greeted with sweeping views of the golf course. The built-in barbeque is perfect for hosting dinner parties or relaxing with friends while enjoying breathtaking sunsets. Harbour Circle residents enjoy a community pool and spa, lush landscaping and membership to the Bay Isles Beach Club. Publix, CVS, post office, banks and beaches are all in close proximity, and Longboat Key’s Town Center and the Longboat Key Club Marina are less than a mile away. Act fast to enjoy the best of Florida living in this spacious and sleek turn-key furnished villa. VACATION RENTALS SARASOTA, LONGBOAT KEY VACATION RENTALS, GULF OF MEXICO
Facts & features
The home at a glance
3
Bedrooms
2.5
Bathrooms
2,396
Sqft
0.15 ac
Lot size
1
Garage
1986
Year built
One
Levels
$5
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Principal and interest plus estimated taxes and insurance. Run your own numbers below.
$247 /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
$247/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Estimates only — taxes at 1.1%/yr and typical insurance; 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 Longboat Key actives
$5 vs $693
Days on market
121 vs 95 typical
Where $5/sqft sits among the 263 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 → $893K
Longboat Key median sold, yr/yr
92.8%
Sale-to-list ratio (12 mo)
113 of 263
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 98% below the LONGBOAT KEY 34228 median. See the full Longboat Key market guide →
Paper trail
This home's history
Reality check
What actually sold near 2339 HARBOUR OAKS DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Dec ’25$1,285,000
2333 HARBOUR OAKS DRIVE · same community
3 bd · 2.5 ba · 2,396 sqft · $536/sqft · 10 DOM
Sold · Mar ’26$950,000
2323 HARBOUR OAKS DRIVE · same community
3 bd · 2.5 ba · 2,395 sqft · $397/sqft · 108 DOM
Sold · Nov ’25$980,000
2358 HARBOUR OAKS DRIVE · same community
3 bd · 3 ba · 2,381 sqft · $412/sqft · 12 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
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 2339 HARBOUR OAKS DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 2339 HARBOUR OAKS DRIVE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
2339 HARBOUR OAKS DRIVE FAQs
What would the monthly payment be for 2339 HARBOUR OAKS DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $247/mo — principal and interest, estimated property taxes 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.
Are pets allowed at 2339 HARBOUR OAKS DRIVE?+
The listing reports pets: No. 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 $12,000, this home is listed about 99% below the Longboat Key median of $960,000. The market section on this page shows how the area is trending.
Which schools are assigned to 2339 HARBOUR OAKS DRIVE?+
Booker 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.
Keep looking
Similar homes nearby
Listing courtesy of JENNETTE PROPERTIES INC · Teresa Ribaudo. MLS #A4688776.
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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