2301 GULF OF MEXICO DRIVE UNIT 44N, LONGBOAT KEY, FL, 34228
Active40 days on marketListed Jul 9, 2026MLS #A4699335
About this home
2301 GULF OF MEXICO DRIVE UNIT 44N
Simply magnificent! This beautifully renovated residence offers the perfect blend of sophisticated design, comfort, and effortless coastal living. Thoughtfully updated with designer finishes throughout, this move-in-ready home features an open, light-filled floor plan highlighted by floor-to-ceiling windows and a spectacular 38-foot covered terrace overlooking lush tropical gardens. Accessible from the living room and both bedrooms, the expansive terrace is the perfect place to enjoy your morning coffee, entertain guests, or relax with refreshing Gulf breezes. The updated kitchen flows seamlessly into the dining and living areas, creating an inviting space for everyday living and entertaining. Beautiful wood flooring, custom architectural details, stainless steel appliances, and abundant natural light add warmth and elegance throughout the home. The spacious primary suite serves as a private retreat with terrace access and a beautifully renovated ensuite bath featuring light wood cabinetry and granite countertops. The generous guest bedroom also opens to the terrace and includes a built-in Murphy bed, offering exceptional flexibility for visiting family and friends or a home office. Life at The Islander Club is truly resort-inspired. Residents enjoy over 400 feet of private Gulf-front beach, a heated beachfront swimming pool, a newly renovated state-of-the-art fitness center, two new sauna rooms, a Har-Tru® tennis court, two pickleball courts, a beautifully updated social room, library, secure key-fob entry, on-site management, and exceptional lock-and-leave convenience. Adding even greater value, The Islander Club has recently completed an extensive program of capital improvements, including exterior restoration and stucco repairs, balcony waterproofing, new roofs on both residential towers, clubhouse, and carports, modernized pool facilities with new tile, resurfacing, and equipment, refreshed landscaping and lighting, hurricane-rated windows and doors, and a completely renovated fitness center. These significant investments provide both peace of mind and long-term value for future owners. Whether you are searching for a full-time waterfront residence, a seasonal escape, or an exceptional investment opportunity, this beautifully updated condominium offers the very best of Longboat Key's coveted beachfront lifestyle.
Facts & features
The home at a glance
2
Bedrooms
2
Bathrooms
1,235
Sqft
5.38 ac
Lot size
1970
Year built
One
Levels
$506
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 and the real association fee — not generic estimates.
$5,523 /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
$5,523/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.
vs edgeAI estimate
−19.3%
$/sqft vs ISLANDER CLUB OF LONGBOAT
$506 vs $971
Days on market
40 vs 95 typical
Where $506/sqft sits among the 7 homes for sale in ISLANDER CLUB OF LONGBOAT
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.
The investor lens
Two ways this home pays
This home sits inside Island Club, a community zoned to allow true short-term rentals — so it can earn as a nightly rental or a traditional lease. Here’s how the two paths compare.
Short-term rental
Zoned & eligible
Projected nightly rate, occupancy and annual revenue for this exact home.
Long-term rental
$7,000/mo median
Live Longboat Key rental listing data — this home’s rate depends on size, condition and furnishing.
Where it sits
Inside Island Club
Island Club is a short-term-rental community. See the full 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 → $1.4M
Longboat Key median sold, yr/yr
93.1%
Sale-to-list ratio (12 mo)
1 of 7
ISLANDER CLUB OF LONGBOAT have cut their price
Median sold price, Longboat Key, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 2% 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 2301 GULF OF MEXICO DRIVE UNIT 44N
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Aug ’25$1,400,000
2301 GULF OF MEXICO DRIVE UNIT 52N · same community
2 bd · 2 ba · 1,235 sqft · $1,134/sqft · 149 DOM
Sold · Apr ’26$550,000
2301 GULF OF MEXICO DRIVE UNIT 54N · same community
2 bd · 2 ba · 1,235 sqft · $445/sqft · 140 DOM
Sold · Jan ’26$590,000
2301 GULF OF MEXICO DRIVE UNIT 34N · same community
2 bd · 2 ba · 1,235 sqft · $478/sqft · 13 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 2301 GULF OF MEXICO DRIVE UNIT 44N — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 2301 GULF OF MEXICO DRIVE UNIT 44N — 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
2301 GULF OF MEXICO DRIVE UNIT 44N FAQs
What would the monthly payment be for 2301 GULF OF MEXICO DRIVE UNIT 44N?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $5,523/mo — principal and interest, the actual property-tax bill, the $1,530/mo association fee 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.
How much are the HOA fees at 2301 GULF OF MEXICO DRIVE UNIT 44N?+
The association fee works out to $1,530 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 2301 GULF OF MEXICO DRIVE UNIT 44N?+
The most recent tax bill on record (2025) was $2,713. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Can 2301 GULF OF MEXICO DRIVE UNIT 44N be rented short-term?+
Yes — this home sits inside Island Club, a community zoned to allow short-term rentals. Nightly-rental income could change the math on this purchase entirely; request a free rental income analysis and our team will prepare projections for this exact home.
Are pets allowed at 2301 GULF OF MEXICO DRIVE UNIT 44N?+
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 $625,000, this home is listed about 34% below the Longboat Key median of $950,000. The market section on this page shows how the area is trending.
Which schools are assigned to 2301 GULF OF MEXICO DRIVE UNIT 44N?+
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.
The brief
Four things that matter here
01Zoned for nightly rentals
Island Club is one of the communities zoned to allow true short-term rentals — nightly income could change the math on this purchase entirely. Ask for the free rental analysis below.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Know the monthly fee
The association fee is $1,530/mo. That usually buys real services — verify what's covered before comparing this home against fee-free alternatives.
04Strong assigned schools
Booker 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 COLDWELL BANKER REALTY · Judy Kepecz-Hays. MLS #A4699335.
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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