
1819 HIGHLAND ROAD, OSPREY, FL, 34229
Active2 days on marketListed Aug 27, 2026MLS #A4703963
Come see it
Upcoming open house
Sun, Aug 30
1:00 PM – 4:00 PM
About this home
1819 HIGHLAND ROAD
This beautifully appointed 2-bedroom, 2-bath townhome offers a wonderful blend of comfort, privacy, and Florida living in "The Osprey", a community of just 12 residences. The open-concept floor plan features high ceilings, generous living spaces, and large windows that fill the home with an abundance of natural light. The spacious owner’s retreat provides a peaceful setting for relaxation, while the second bedroom offers flexibility for guests, an office, or additional living space. Located in flood zone X, the oversized garage offers the perfect opportunity to add to your living space or provides an abundance of storage. The private outdoor spaces are a true highlight of the home. The beautifully landscaped yard and garden create a peaceful retreat, while the private terrace provides an ideal setting for al fresco dining and entertaining. A mature specimen lemon tree serves as the star of the garden, providing fresh lemons for lemonade, cooking, or homemade limoncello. Residents also enjoy access to the community pool, adding to the relaxed, resort-like feel of the property. The location is equally appealing. Situated in Osprey, the property is conveniently located near the beaches of Casey Key, local shops, restaurants, and a variety of recreational amenities directly across the street from Oscar Scherer State Park, home to over 17 miles of trails and nearly 1400 acres of natural habitats, launch a kayak, or simply take in the peaceful surroundings along the water. The nearby Casey Key Resort offers the opportunity to enjoy its pool, facilities, and restaurant for the day, providing an additional resort-style experience close to home. Downtown Sarasota and downtown Venice are also easily accessible, offering an outstanding selection of dining, shopping, cultural attractions, and entertainment. With its private outdoor spaces, community pool, beautiful natural light, and convenient location, this exceptional townhome offers a refined yet relaxed approach to coastal Florida living. Whether enjoyed as a full-time residence or a seasonal retreat, this home offers an exceptional opportunity to embrace the Florida lifestyle.
Facts & features
The home at a glance
2
Bedrooms
2.5
Bathrooms
1,240
Sqft
0.1 ac
Lot size
2
Garage
1998
Year built
Two
Levels
$257
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.
$2,630 /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
$2,630/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.
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 Osprey actives
$257 vs $328
Days on market
2 vs 107 typical
Where $257/sqft sits among the 80 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 Southbay Yacht & Racquet Club
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Osprey. See the full Osprey guide →
Southbay Yacht & Racquet Club — neighborhood snapshot
Population
1,031
Median age
64
Median income
$98,565
Median home value
$807,000
Avg household
2
Households w/ children
44%
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
$723K → $765K
Osprey median sold, yr/yr
93.8%
Sale-to-list ratio (12 mo)
42 of 80
Osprey actives have cut their price
Median sold price, Osprey, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 41% below the OSPREY 34229 median. See the full Osprey market guide →
Paper trail
This home's history
Reality check
What actually sold near 1819 HIGHLAND ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jun ’26$375,000
1795 HIGHLAND ROAD · same community
3 bd · 3 ba · 1,879 sqft · $200/sqft · 24 DOM
Sold · Jan ’26$231,000
209 LAKE SHORE DRIVE
3 bd · 2 ba · 1,246 sqft · $185/sqft · 74 DOM
Sold · May ’26$230,000
449 BOTTICELLI DRIVE UNIT 449
2 bd · 2 ba · 1,232 sqft · $187/sqft · 57 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
Zack Zonker
President Tampa Division · CENTURY 21 Edge
Tours, negotiation, and every question about 1819 HIGHLAND ROAD — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1819 HIGHLAND ROAD — before you fall in love.
See it in person
Schedule a tour
Live availability from Zack's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
1819 HIGHLAND ROAD FAQs
What would the monthly payment be for 1819 HIGHLAND ROAD?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $2,630/mo — principal and interest, the actual property-tax bill, the $150/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 1819 HIGHLAND ROAD?+
The association fee works out to $150 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 1819 HIGHLAND ROAD?+
The most recent tax bill on record (2025) was $3,615. 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 1819 HIGHLAND ROAD?+
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 Osprey?+
At $319,000, this home is listed about 52% below the Osprey median of $669,500. The market section on this page shows how the area is trending.
Which schools are assigned to 1819 HIGHLAND ROAD?+
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
Four things that matter here
01Under the OSPREY 34229 market on paper
$319,000 is 41% below the OSPREY 34229 median of $540,000, and at $257/sqft it sits under the Osprey average of $394.
02Garden & Trees/Woods views
The garden and trees/woods view is part of what you're buying — views hold value independently of the structure.
03Fresh on the market
Only 2 days on market in a Osprey market that averages 107 — if it fits, move quickly.
04Strong 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 MICHAEL SAUNDERS & COMPANY · Jennifer Linehan. MLS #A4703963.
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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