
1404 KENILWORTH STREET, SARASOTA, FL, 34231
Active210 days on marketListed Jan 15, 2026MLS #A4672697
About this home
1404 KENILWORTH STREET
Privately positioned in gated Oyster Bay Landings with water views stretching down a short canal to Sarasota Bay, this stunning iconic masterpiece from world-renowned architect Guy Peterson is a breathtaking example of the Sarasota School of Architecture’s style and vision. A comfortable modernistic ambiance flows freely throughout the 5,428 sq. ft. of open living where walls of glass capture spectacular displays of the cerulean blue water and evening skies of fiery beauty. No detail has been overlooked. No expense has been spared. Architecturally striking, this 4-bedroom, 4.5-bath waterfront residence is the ultimate indulgence offering rarity, cachet and grandeur. Dock with 2 lifts is conveniently situated on a waterway unencumbered by any bridge. Floor to ceiling windows frame expansive vistas and abundant natural light complements the thoughtfully-appointed and expertly-planned space. Over 4,000 square feet of outdoor area is inviting and festive, and presents unique vantage points to deliver an exhilarating experience. Expansive terraces promote seamless indoor-outdoor living. Covered entertaining is abundant among the verdant tropical gardens and immaculately manicured grounds. Resort-style amenities including an elevator, courtyard with fire pit and heated pool/spa, and breathtaking reflecting pool with fountain. The stunning kitchen is a culinary delight and complemented by an extravagant amenities package of top-tier appliances, island with seating for 6, 20-ft. long counter for 2 desk workstations, side-by-side but separate refrigerator and freezer, 2 dishwashers, and deep walk-in pantry. The family room is equipped with built-in entertainment wall and opens to a waterfront patio with outdoor cooking center. The great room has travertine floors and cypress ceiling detail, and the office provides a desk with stone countertops and plenty of solid wood cabinetry. A 400-bottle wine room is the highlight of the gaming area with wet bar, electric shades and unique glass chandelier. On the second level are spa-inspired en-suite bedrooms with custom closet systems and elevated ceilings. A 30-ft. bridge leads to the master wing highlighted by incredible water views, sitting room with morning bar, and home gym/office. The primary bath creates an immersive experience with a 16-ft. long dressing hall with a wall of built-ins and mirrors, large walk-in specialty closet, multi-faceted shower, deep soaker Jacuzzi tub, separate bidet and laundry chute. In addition, there are two laundry areas, an elevator from ground level to the 2nd and 3rd floors, Creston music and lighting system, Generac generator, and 4-car garage. In one of Sarasota’s most coveted locations along the waterfront, this home redefines coastal living is just minutes from beaches, golf, fine dining and downtown Sarasota’s beloved arts and cultural offerings. When scheduling your exclusive tour of this amazing MODERN waterfront estate, make sure to allow plenty of time for exploring its incredible features, both inside and out. It must be seen in person to be fully appreciated. Even the most discerning buyer will fall in love!
Facts & features
The home at a glance
4
Bedrooms
4.5
Bathrooms
5,428
Sqft
0.23 ac
Lot size
4
Garage
2007
Year built
Three Or More
Levels
$889
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.
$32,733 /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
$32,733/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
$889 vs $345
Days on market
210 vs 64 typical
Where $889/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 Sarasota
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Sarasota. See the full Sarasota guide →
SARASOTA 34231 — neighborhood snapshot
Population
32,203
Median age
55.1
Median income
$69,721
Median home value
$363,400
Avg household
2.03
Households w/ children
2,803
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
$475K → $493K
Sarasota median sold, yr/yr
95.2%
Sale-to-list ratio (12 mo)
167 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 2313% above the SARASOTA 34231 median. See the full Sarasota market guide →
Paper trail
This home's history
Reality check
What actually sold near 1404 KENILWORTH STREET
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jan ’26$1,715,000
5197 FLICKER FIELD CIRCLE
5 bd · 3.5 ba · 4,554 sqft · $377/sqft · 32 DOM
Sold · Mar ’26$3,900,000
5326 SIESTA COVE DRIVE
5 bd · 6 ba · 4,435 sqft · $879/sqft · 39 DOM
Sold · Apr ’26$2,625,000
5236 SIESTA COVE DRIVE
4 bd · 4.5 ba · 4,254 sqft · $617/sqft · 258 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
Anthony Richardson
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 1404 KENILWORTH STREET — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1404 KENILWORTH STREET — before you fall in love.
See it in person
Schedule a tour
Live availability from Anthony's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
1404 KENILWORTH STREET FAQs
What would the monthly payment be for 1404 KENILWORTH STREET?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $32,733/mo — principal and interest, the actual property-tax bill, the $333/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 1404 KENILWORTH STREET?+
The association fee works out to $333 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 1404 KENILWORTH STREET?+
The most recent tax bill on record (2024) was $52,740. 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 1404 KENILWORTH STREET?+
The listing reports pets: Cats OK, Dogs OK, 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 $4,825,000, this home is listed about 763% above the Sarasota median of $559,000. The market section on this page shows how the area is trending.
Which schools are assigned to 1404 KENILWORTH STREET?+
Phillippi Shores Elementary School (elementary), Riverview High School (high), Brookside Middle School (middle) — 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
$4,825,000 runs 2313% above the SARASOTA 34231 median — but at 5,428 sqft it's also nearly 3 times 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
210 days on market against a Sarasota median of 64 — sellers in this position are usually ready to negotiate.
04Strong assigned schools
Phillippi Shores Elementary School, Riverview High School, Brookside Middle School — Phillippi Shores Elementary School rates 5 of 5. Always verify assignments with the district.
05The price has already moved
Listed at $6,350,000, now $4,825,000 — a $1.5M cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of GRECO REAL ESTATE · Karen Greco. MLS #A4672697.
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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