7303 JESSIE HARBOR DRIVE UNIT 7303, OSPREY, FL, 34229
Active40 days on marketListed Sep 28, 2026MLS #A4706429
About this home
7303 JESSIE HARBOR DRIVE UNIT 7303
Welcome to luxury coastal living in this exceptional 3rd-floor penthouse condo nestled in the secluded, resort-style waterfront community of Heron House in Osprey. Offering 1,883 sq. ft. of beautifully light-filled, fully furnished living space, this impressive 3-bedroom, 2-bathroom residence features high-end finishes, warm hardwood floors, plantation shutters, a decorative wood-burning fireplace, and a built-in wet bar perfect for entertaining. The gourmet kitchen is equipped with rich wood cabinetry, granite countertops, stainless steel appliances, and a cozy eat-in breakfast area. Unwind in the expansive primary suite boasting two walk-in closets, a spa-like bath with double vanities, a deep soaking tub, and a separate shower. Step outside onto multiple private balconies to take in tranquil views of lush tropical greenery and calm canal waters—an idyllic setting for outdoor dining or evening cocktails. Located directly on Jessie Harbor with bridge-free, direct access to the Intracoastal Waterway and the Gulf, this gated community offers extraordinary waterfront amenities, including a kayak launch, boat slips (available on a first-come, first-served basis), and frequent visits from local wildlife like otters and dolphins. Residents enjoy a highly active, beautifully maintained HOA complete with a newly installed entrance security gate, heated pool, water aerobics, tennis and pickleball courts, shuffleboard, clubhouse, fitness center, walking trails, locked storage, bike storage, and two assigned covered parking spaces under the building with elevator access. Situated just 10 minutes from Venice Beach, Nokomis Beach, and Casey Key, 20 minutes from world-famous Siesta Key, and minutes from I-75, Oscar Scherer State Park, the Legacy Trail, and Sarasota’s vibrant cultural hub, this hidden gem combines peaceful privacy with unbeatable access to Florida’s finest coastal living.
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,883
Sqft
1985
Year built
One
Levels
$238
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 — not generic estimates.
$3,850 /mo · 3.5% down FHA, 30-yr fixed at 7.5%
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
$3,850/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. 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.
Can I afford this home? → See what you can comfortably afford from your income, debts and savings.
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
−13.2%
$/sqft vs Osprey actives
$238 vs $378
Days on market
40 vs 59 typical
Where $238/sqft sits among the 94 Osprey 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 Sorrento
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Osprey. See the full Osprey guide →
Sorrento — neighborhood snapshot
Population
2,609
Median age
61
Median income
$96,884
Median home value
$496,323
Avg household
2
Households w/ children
156
For the school run
Sarasota County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Osprey market
$625K → $665K
Osprey median sold, yr/yr
94.3%
Sale-to-list ratio (12 mo)
41 of 94
Osprey actives have cut their price
Median sold price, Osprey, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 35% below the OSPREY 34229 median. See the full Osprey market guide →
Paper trail
This home's history
Reality check
What actually sold near 7303 JESSIE HARBOR DRIVE UNIT 7303
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$570,000
213 BAYSIDE COURT
3 bd · 2 ba · 1,882 sqft · $303/sqft · 234 DOM
Sold · Oct ’26$3,425,000
1604 CASEY KEY ROAD
3 bd · 2 ba · 1,940 sqft · $1,765/sqft · 22 DOM
Sold · Nov ’25$699,900
5529 CANTUCCI STREET
3 bd · 2 ba · 1,945 sqft · $360/sqft · 4 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
Anealya Hammad
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 7303 JESSIE HARBOR DRIVE UNIT 7303 — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 7303 JESSIE HARBOR DRIVE UNIT 7303 — before you fall in love.
See it in person
Schedule a tour
Live availability from Anealya's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
7303 JESSIE HARBOR DRIVE UNIT 7303 FAQs
What would the monthly payment be for 7303 JESSIE HARBOR DRIVE UNIT 7303?+
With 3.5% down on a 30-year FHA loan at 7.5%, the all-in payment lands around $3,850/mo — principal and interest, the actual property-tax bill 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.
What are the property taxes on 7303 JESSIE HARBOR DRIVE UNIT 7303?+
The most recent tax bill on record (2025) was $4,911. 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 7303 JESSIE HARBOR DRIVE UNIT 7303?+
The listing reports pets: Size Limit, 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 Osprey?+
At $449,000, this home is listed about 42% below the Osprey median of $772,000. The market section on this page shows how the area is trending.
Which schools are assigned to 7303 JESSIE HARBOR DRIVE UNIT 7303?+
Laurel Nokomis School (elementary), Venice Senior High School (high) — Sarasota County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Under the OSPREY 34229 market on paper
$449,000 is 35% below the OSPREY 34229 median of $695,000, and at $238/sqft it sits under the Osprey average of $404.
02Trees/Woods views
The trees/woods view is part of what you're buying — views hold value independently of the structure.
03Strong assigned schools
Laurel Nokomis School, Venice Senior High School — Laurel Nokomis School rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of COLDWELL BANKER REALTY · Mairead Smialek. MLS #A4706429.
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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