
154 LOOKOUT POINT DRIVE, OSPREY, FL, 34229
Active23 days on marketListed Aug 28, 2026MLS #TB8543439
About this home
154 LOOKOUT POINT DRIVE
Welcome to exceptional Florida living in the highly sought-after Southbay Yacht & Racquet Club. Offering approximately 4,578 square feet under roof, this spacious 4-bedroom, 3.5-bath residence combines beautifully updated interiors, exceptionally generous rooms and an extraordinary indoor-outdoor lifestyle. The heart of the home is a completely renovated kitchen featuring quartz countertops, soft-close cabinetry and drawers, built-in organizers, pull-out spice storage, a specialty appliance lift for a mixer or blender, a new refrigerator and dishwasher, and abundant functional storage. The main living area is anchored by a fully functioning wood-burning fireplace with an elegant travertine stone surround, adding warmth and character to the home. All four bedrooms are exceptionally spacious and feature large walk-in closets with custom organization systems. The primary suite and a guest bedroom are conveniently located on the first floor, providing an ideal layout for family and guests. Additional conveniences include a whole-home central vacuum system and a spacious two-car garage with an already-installed Tesla EV charging station. Major recent improvements provide additional peace of mind, including two brand-new air-conditioning systems and brand-new hurricane-rated windows installed in August 2026. The outdoor living space is truly a standout. More than 1,500 square feet of screened lanai and outdoor living area surrounds an exceptionally large residential pool ranging from approximately 3 to 8 feet deep. Two covered outdoor areas provide comfortable spaces for entertaining and relaxing, including an outdoor kitchen with a brand-new THOR grill and a separate covered TV lounge area. A pool bath is conveniently accessible directly from the lanai. Across the back of the pool enclosure, an impressive approximately 50-foot panoramic screen creates a virtually unobstructed view with no intermediate posts interrupting the sightline. Beyond the pool is an expansive green space, creating a wonderful sense of openness and privacy. The newly landscaped yard and more than 25 palm trees lining the backyard complete the lush, tropical setting. Living in Southbay Yacht & Racquet Club is about much more than the home itself. Residents enjoy an impressive collection of community amenities, including a clubhouse, heated community pool, fitness center, tennis courts, pickleball courts, basketball courts, bocce ball, library, card and game room, ballroom and banquet facilities, and the community’s highly desirable marina, where residents have opportunities to rent or lease boat slips, subject to availability. The location is equally exceptional. Pine View School is approximately one mile away, while the bay, Gulf beaches, Publix, restaurants, coffee shops, fitness and yoga studios, CVS and everyday conveniences are all close at hand. The golf-cart-friendly community makes enjoying the neighborhood and surrounding area even easier. From its oversized bedrooms and beautifully renovated kitchen to its remarkable pool, panoramic screened view and expansive outdoor entertaining areas, this home offers an uncommon combination of space, thoughtful upgrades and Florida lifestyle. Add the boating and recreational amenities of Southbay Yacht & Racquet Club, and this is a home designed to enjoy everything the Sarasota area has to provide.
Facts & features
The home at a glance
4
Bedrooms
3.5
Bathrooms
4,578
Sqft
0.32 ac
Lot size
2
Garage
1979
Year built
Two
Levels
$481
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.
$14,075 /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
$14,075/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.
$/sqft vs Osprey actives
$481 vs $343
Days on market
23 vs 107 typical
Where $481/sqft sits among the 79 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)
35 of 79
Osprey actives have cut their price
Median sold price, Osprey, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 291% above the OSPREY 34229 median. See the full Osprey market guide →
Paper trail
This home's history
Reality check
What actually sold near 154 LOOKOUT POINT DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Oct ’25$1,200,000
1484 SEAFARER DRIVE · same community
4 bd · 3.5 ba · 3,479 sqft · $345/sqft · 82 DOM
Sold · May ’26$2,000,000
304 YACHT HARBOR DRIVE · same community
3 bd · 4 ba · 3,324 sqft · $602/sqft · 0 DOM
Sold · Apr ’26$1,025,000
1218 YACHT HARBOR DRIVE · same community
3 bd · 3 ba · 3,297 sqft · $311/sqft · 203 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
Moe Thouk Oo
Licensed Realtor® · CENTURY 21 Edge
Tours, negotiation, and every question about 154 LOOKOUT POINT DRIVE — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 154 LOOKOUT POINT DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Moe's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
154 LOOKOUT POINT DRIVE FAQs
What would the monthly payment be for 154 LOOKOUT POINT DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $14,075/mo — principal and interest, the actual property-tax bill, the $219/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 154 LOOKOUT POINT DRIVE?+
The association fee works out to $219 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 154 LOOKOUT POINT DRIVE?+
The most recent tax bill on record (2025) was $11,995. 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 154 LOOKOUT POINT DRIVE?+
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 $2,199,999, this home is listed about 229% above the Osprey median of $669,500. The market section on this page shows how the area is trending.
Which schools are assigned to 154 LOOKOUT POINT DRIVE?+
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
01Positioned at the premium end
$2,199,999 runs 291% above the OSPREY 34229 median — but at 4,578 sqft it's also nearly twice the size of the typical Osprey listing.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
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 FLAT FEE MLS REALTY · Stephen Hachey. MLS #TB8543439.
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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