
5103 WINDWARD AVENUE, SARASOTA, FL, 34242
Active211 days on marketListed Jan 3, 2026MLS #A4676707
About this home
5103 WINDWARD AVENUE
Completed new construction! Built safely and securely ten feet above the island’s flood plain, 5103 Windward is unparalleled new construction with saltwater boating access to the Intracoastal Waterway and Gulf beyond. Along the water’s edge, this homesite spans nearly 1/3 acre on the Grand Canal with 90 ft. of new seawall. The central Siesta Key location makes getting to the spectacular white sand beaches and charming Siesta Village easy and convenient. The free-flowing plan, offering 3,034 sq. ft. of open living, will seduce you with its inviting atmosphere wrapped in casual elegance and modern sophistication. With plenty of natural light, the great room boasts double-height ceilings adorned with rich architectural detail, an elaborate floor-to-ceiling fireplace wall, and see-through views to the expansive outdoor space and coveted canal setting. Beyond the great room’s glass doors, an entertaining lounge with wood ceiling accents, a professional grill station, and a heated pool/spa await your plans for spending cherished time with family and friends. As evening approaches, night lighting transforms the beautiful backyard and creates a timeless ambiance that encourages relaxation and reflection. A gorgeous kitchen is enhanced with an abundance of amenities including a premium Sub-Zero and Wolf appliance package, stone counters, stylized fixtures and finishes, a walk-in pantry, and adjoining laundry. The formal dining room features a built-in buffet and French doors leading to a brick paver patio, making it a wonderful spot for dining alfresco under the stars. The bonus room, with wet bar and pool bath, features two walls of glass sliders showcasing the extensive outdoors and picturesque water views. The primary suite is an oasis of serenity with an office outfitted with built-ins, a generous wardrobe for two, and an exquisite bath intended to pamper and spoil with a free-standing tub, a frameless glass shower with rain head, separate vanities with stone tops, and a water closet. Two additional en-suites offer plenty of room to unwind and rejuvenate in comfortable privacy. A brick paver drive, a 3-car garage, professional landscaping with timed irrigation, eye-catching curb appeal, and other notable customizations inside and out, complete this magnificent waterfront home. This fresh new residence, designed by the award-winning team at Allegra Homes, has been artfully designed and crafted to offer the highest quality to those who live here. An exciting opportunity to make this island paradise yours!
Facts & features
The home at a glance
3
Bedrooms
4.5
Bathrooms
3,034
Sqft
0.33 ac
Lot size
3
Garage
2026
Year built
One
Levels
$1,120
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.
$20,108 /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
$20,108/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 Sarasota actives
$1,120 vs $343
Days on market
211 vs 58 typical
Where $1,120/sqft sits among the 400 Sarasota 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 Sara Sands
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Sarasota. See the full Sarasota guide →
Sara Sands — neighborhood snapshot
Population
390
Median age
60
Median income
$128,111
Median home value
$1,088,700
Avg household
2
Households w/ children
19%
For the school run
Sarasota County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Sarasota market
$470K → $470K
Sarasota median sold, yr/yr
95.1%
Sale-to-list ratio (12 mo)
155 of 400
Sarasota actives have cut their price
Median sold price, Sarasota, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 593% above the SARASOTA 34242 median. See the full Sarasota market guide →
Paper trail
This home's history
Reality check
What actually sold near 5103 WINDWARD AVENUE
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$1,075,000
5073 HIGEL AVENUE · same community
3 bd · 3.5 ba · 2,920 sqft · $368/sqft · 96 DOM
Sold · Jan ’26$4,095,000
5078 SANDY BEACH AVENUE · same community
4 bd · 4 ba · 3,164 sqft · $1,294/sqft · 2 DOM
Sold · Oct ’25$2,875,000
5169 SANDY SHORE AVENUE · same community
3 bd · 3.5 ba · 2,885 sqft · $997/sqft · 219 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
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 5103 WINDWARD AVENUE — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 5103 WINDWARD AVENUE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
5103 WINDWARD AVENUE FAQs
What would the monthly payment be for 5103 WINDWARD AVENUE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $20,108/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 5103 WINDWARD AVENUE?+
The most recent tax bill on record (2024) was $4,091. 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 5103 WINDWARD AVENUE?+
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 Sarasota?+
At $3,397,500, this home is listed about 496% above the Sarasota median of $570,000. The market section on this page shows how the area is trending.
Which schools are assigned to 5103 WINDWARD AVENUE?+
Phillippi Shores Elementary School (elementary), Brookside Middle School (middle), Sarasota High School (high) — Sarasota County School District. Always verify school assignments with the district before relying on them.
The brief
Five things that matter here
01Positioned at the premium end
$3,397,500 runs 593% above the SARASOTA 34242 median — but at 3,034 sqft it's also nearly twice the size of the typical Sarasota listing.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Time on market is leverage
211 days on market against a Sarasota median of 58 — sellers in this position are usually ready to negotiate.
04Strong assigned schools
Phillippi Shores Elementary School, Brookside Middle School, Sarasota High School — Phillippi Shores Elementary School rates 5 of 5. Always verify assignments with the district.
05The price has already moved
Listed at $3,657,625, now $3,397,500 — a $260K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of GRECO REAL ESTATE · Karen Greco. MLS #A4676707.
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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