2020 HARBOURSIDE DRIVE UNIT 446, LONGBOAT KEY, FL, 34228
Pending69 days on marketListed May 28, 2026MLS #A4695127
About this home
2020 HARBOURSIDE DRIVE UNIT 446
Experience luxury island living in this beautifully remodeled 2-bedroom, 2-bath residence located in the highly sought-after Fairway Bay community within Bay Isles on Longboat Key. Available for immediate occupancy, this turnkey furnished coastal retreat offers flexible lease terms from 6 to 12 months. Step inside to discover a bright and open floor plan featuring upscale contemporary finishes, , updated flooring, a stunning modern kitchen with premium appliances, and elegantly renovated bathrooms. The spacious primary suite provides a peaceful retreat, while the second bedroom offers comfortable accommodations for guests or an ideal home office. Expansive living spaces and a private balcony create the perfect setting to relax and enjoy the Florida lifestyle. Residents of Fairway Bay enjoy an exceptional array of resort-style amenities, including a heated community pool, a beautifully maintained clubhouse, and a fully equipped fitness center. Tennis and pickleball enthusiasts will appreciate access to two regulation tennis courts that can also be configured into four pickleball courts, offering year-round recreation just steps from home. As part of the exclusive Bay Isles community, residents also enjoy access to the private Bay Isles Beach Club, featuring deeded Gulf-front beach access with some of Longboat Key's most beautiful sand beaches. The Beach Club offers gated parking, picnic areas, grills, restrooms, and the perfect setting to enjoy spectacular Gulf sunsets. Outdoor enthusiasts will also appreciate access to the Bay Isles marina area and kayak launch with direct access to Sarasota Bay. Ideally situated on Longboat Key, this residence is just minutes from St. Armands Circle, Longboat Key Club, championship golf courses, waterfront dining, marinas, boutique shopping, and the cultural attractions of downtown Sarasota. Whether you're seeking a seasonal retreat or an extended island stay, this residence offers the perfect combination of luxury, convenience, and coastal living. Available immediately with lease terms ranging from 6 to 12 months.
Facts & features
The home at a glance
2
Bedrooms
2
Bathrooms
1,270
Sqft
3.9 ac
Lot size
1
Garage
1984
Year built
One
Levels
$4
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.
$196 /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
$196/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
$4 vs $693
Days on market
69 vs 94 typical
Where $4/sqft sits among the 274 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 → $1.2M
Longboat Key median sold, yr/yr
93.1%
Sale-to-list ratio (12 mo)
115 of 274
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 99% 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 2020 HARBOURSIDE DRIVE UNIT 446
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Nov ’25$650,000
2020 HARBOURSIDE DRIVE UNIT 432 · same community
2 bd · 2 ba · 1,312 sqft · $495/sqft · 12 DOM
Sold · Apr ’26$890,000
2016 HARBOURSIDE DRIVE UNIT 317 · same community
2 bd · 2 ba · 1,442 sqft · $617/sqft · 13 DOM
Sold · Jul ’26$724,000
2020 HARBOURSIDE DRIVE UNIT 457 · same community
2 bd · 2 ba · 1,442 sqft · $502/sqft · 2 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
Erwin Vazquez
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 2020 HARBOURSIDE DRIVE UNIT 446 — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 2020 HARBOURSIDE DRIVE UNIT 446 — before you fall in love.
See it in person
Schedule a tour
Live availability from Erwin's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
2020 HARBOURSIDE DRIVE UNIT 446 FAQs
What would the monthly payment be for 2020 HARBOURSIDE DRIVE UNIT 446?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $196/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 2020 HARBOURSIDE DRIVE UNIT 446?+
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 $4,995, this home is listed about 99% below the Longboat Key median of $949,950. The market section on this page shows how the area is trending.
Which schools are assigned to 2020 HARBOURSIDE DRIVE UNIT 446?+
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
01Under the LONGBOAT KEY 34228 market on paper
$4,995 is 99% below the LONGBOAT KEY 34228 median of $649,000, and at $4/sqft it sits under the Longboat Key average of $846.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Strong assigned schools
Booker High School, Southside Elementary School, Booker Middle School — Southside Elementary School rates 5 of 5. Always verify assignments with the district.
04The price has already moved
Listed at $5,950, now $4,995 — a $955 cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of VIVE REALTY · Jeffrey Swanson. MLS #A4695127.
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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