2020 HARBOURSIDE DRIVE UNIT 442, LONGBOAT KEY, FL, 34228
Active4 days on marketListed Sep 17, 2026MLS #A4705717
About this home
2020 HARBOURSIDE DRIVE UNIT 442
Enjoy direct Sarasota Bay views and deeded private beach access from this updated fourth-floor residence in Fairway Bay, an established gated Bay Isles community within the Longboat Key Club setting. Residence #442 at 2020 Harbourside Drive offers 1,312 square feet of bright, airy living space with two bedrooms and two bathrooms—an inviting coastal retreat where the bay becomes part of everyday life. Floor-to-ceiling views from the kitchen, dining area, and living room create a memorable backdrop for daily living and entertaining, while the private balcony is an ideal place to begin the day with a Sarasota Bay sunrise or settle in for the evening as the sky changes over the water. Keep watch for passing boats, coastal birds, and the occasional manatee in the bay below. The residence has been thoughtfully updated with a kitchen featuring granite countertops, a granite breakfast bar, stainless-steel appliances, and a newer microwave. A front-loading LG washer and dryer are included for everyday convenience. Ceramic tile flooring extends throughout the main living areas and guest spaces, while the primary bedroom features warm wood flooring. Fairway Bay offers a resort-inspired waterfront lifestyle with scenic walking paths, a heated swimming pool and spa, fitness facilities, social spaces, tennis courts, and paddle sports. Beyond the bayfront setting, owners enjoy deeded access to the Bay Isles Beach Club, providing a private connection to Longboat Key’s renowned Gulf beaches. It is the best of both waterfront worlds: tranquil Sarasota Bay just outside your door and the Gulf of Mexico’s white-sand shoreline close by. The community’s central island location makes it easy to walk or bike to nearby conveniences, including grocery shopping, pharmacy services, and tennis. For those who wish to expand their recreational options, membership opportunities may be available through the nearby Longboat Key Club, with its golf, tennis, dining, fitness, spa, and full-service deep-water marina amenities. St. Armands Circle is moments away for boutique shopping and acclaimed dining, while downtown Sarasota offers a vibrant extension of the island lifestyle with arts, culture, restaurants, and waterfront attractions. This is a rare opportunity to enjoy a beautifully updated fourth-floor bayfront residence where views, private beach access, resort-style amenities, and the effortless rhythm of Longboat Key living come together.
Facts & features
The home at a glance
2
Bedrooms
2
Bathrooms
1,192
Sqft
0 ac
Lot size
1984
Year built
One
Levels
$586
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.
$4,947 /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
$4,947/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
−23.4%
$/sqft vs Longboat Key actives
$586 vs $663
Days on market
4 vs 93 typical
Where $586/sqft sits among the 219 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 → $1.4M
Longboat Key median sold, yr/yr
93.1%
Sale-to-list ratio (12 mo)
92 of 219
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 19% 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 2020 HARBOURSIDE DRIVE UNIT 442
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
Jillian Kobylesky
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 2020 HARBOURSIDE DRIVE UNIT 442 — 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 442 — before you fall in love.
See it in person
Schedule a tour
Live availability from Jillian's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
2020 HARBOURSIDE DRIVE UNIT 442 FAQs
What would the monthly payment be for 2020 HARBOURSIDE DRIVE UNIT 442?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $4,947/mo — principal and interest, the actual property-tax bill, the $115/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 2020 HARBOURSIDE DRIVE UNIT 442?+
The association fee works out to $115 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 2020 HARBOURSIDE DRIVE UNIT 442?+
The most recent tax bill on record (2025) was $7,658. 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 2020 HARBOURSIDE DRIVE UNIT 442?+
The listing reports pets: 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 $699,000, this home is listed about 26% 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 2020 HARBOURSIDE DRIVE UNIT 442?+
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.
The brief
Four things that matter here
01Positioned at the premium end
$699,000 runs 19% above the LONGBOAT KEY 34228 median.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Fresh on the market
Only 4 days on market in a Longboat Key market that averages 93 — if it fits, move quickly.
04Strong assigned schools
Booker High School, Booker Middle School, Southside Elementary School — Southside Elementary School rates 5 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of MICHAEL SAUNDERS & COMPANY · Steve Walter. MLS #A4705717.
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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