Neighborhood · Boca Grande, Florida
Harbor Drive Waterways
Deep-water living at the tip of Gasparilla Island
2
Homes for sale
$5,122,500
Median list price
$1,730
Avg price / sqft
121
Median days on market
Harbor Drive Waterways is a small waterfront enclave on Gasparilla Island, where canal-front homes open to the kind of boating access that defines life in Boca Grande. Days here run on tides and tarpon season more than traffic, and the streets stay quiet even when the harbor is busy. If you want a place where the water is the front yard, this is the address.
The market is intentionally thin: right now there are just two homes for sale, both waterfront and both with pools, listed between $4,995,000 and $5,250,000. That scarcity shows up in the numbers — the one home sold in the past year closed at $5,750,000, and homes here trade at a median of $1,730 per square foot. Buyers who want in should be ready to move when the right listing appears, and to consider nearby options like East Shore Acres or North Village as inventory shifts.
Harbor Drive Waterways is a community in Boca Grande, Florida.
Quick facts
$4,995,000 – $5.3M price range
3,024 sqft median home
1 sold in 12 months
On the market now
Homes for sale in Harbor Drive Waterways
$5,250,000$5,495,000
252 WATERWAYS AVENUE, BOCA GRANDE
4 bd · 4 ba · 3,500 sqft
$4,995,000$5,375,000
161 1ST STREET E, BOCA GRANDE
4 bd · 3 ba · 2,548 sqft
Every active listing inside the Harbor Drive Waterways boundary
Open full map search →Find your fit
Browse Harbor Drive Waterways
By feature — on the live map
The numbers that matter
The Harbor Drive Waterways market
1
Sold, last 12 months
$5,750,000
Median sold price
89%
Sale-to-list ratio
What sellers actually get vs asking
267 days
Median time to sell
Harbor Drive Waterways vs Boca Grande
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Harbor Drive Waterways boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Harbor Drive Waterways is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Harbor Drive Waterways home
≈ $29,676/mo
$5,122,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
20
Median age
67
Median income
$250,001
Median home value
$2,000,000
Beyond the listings
Living in Harbor Drive Waterways
Relationships
Top 14% in the U.S.Happily Ever After
Whether it's the stress of wedding planning or looking back on that special day, this population has their eyes and hearts focused on lifelong commitment.
Lifestyles
Wealth Signaling
Interested in the finer things life has to offer, this population wants to display their lifestyle by discussing luxury products. Often references jewelry, cars, and home features.
Hobbies & Interests
Wanderlust
Always thinking about their next destination, this population loves exploring new places abroad or right in their own backyard. They hold onto past trips by sharing their favorite memories and pictures year round.
Appearance oriented
Smart Chic
Passionate about style, smart chic searches high and low for the perfect look - but not one that will break the bank.
Relationships
Girl Squad
From girls night out to a movie night in with their closest gal pals, this population is all about getting the girls together for an evening of fun.
Appearance oriented
Men's Style
This population is all about finding the latest in men's style - from fashion to grooming. Captures guys looking to stay on trend and significant others assisting with shopping.
Straight answers
Harbor Drive Waterways FAQs
Is Harbor Drive Waterways a good place to live?+
It suits buyers who prioritize boating and privacy — every active home is waterfront with a pool, set within the quiet residential fabric of Gasparilla Island. You get direct canal access and proximity to Boca Grande's beaches and village while staying off the busier stretches of the island.
Is Harbor Drive Waterways expensive?+
Yes — this is a luxury waterfront market. The median list price is $5,122,500, and the single home sold in the past 12 months closed at $5,750,000, so budgets here start in the high seven figures.
What do homes cost in Harbor Drive Waterways?+
The two current listings range from $4,995,000 to $5,250,000, with a median size around 3,024 square feet and a median price of $1,730 per square foot. For a broader look at price points, compare with Boca Grande homes for sale across the island.
How is the market here?+
It's a low-inventory, slow-turnover market: just two active listings and one sale over the last year. Homes take a median of about 120 days to sell, and sellers averaged 89% of asking, so there's room to negotiate on the right property. Watch the live map to catch new listings as they hit.
What about HOA fees and property taxes?+
HOA data isn't available for this small enclave, so verify any dues on a per-home basis. Property taxes run a median of roughly $29,720 per year, in line with the area's high-value waterfront homes.
Keep exploring
More Boca Grande neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. 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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