
800 W 2ND AVENUE, WINDERMERE, FL, 34786
Active6 days on marketListed Jul 23, 2026MLS #O6422976
Come see it
Upcoming open house
Sat, Aug 1
12:00 PM – 3:00 PM
About this home
800 W 2ND AVENUE
Set beneath a canopy of majestic live oaks along the shores of the Butler Chain of Lakes, this timeless estate has been comprehensively reimagined to blend enduring architecture with modern luxury. Rebuilt with uncompromising attention to detail, every major component of the home has been replaced, including the roof, windows & doors, HVAC systems, water heaters, pool equipment, dock, and landscaping. The home is also complete with a professionally curated furnishing package by Wassers. A refined palette of natural materials and exceptional craftsmanship defines every space, including custom Italian cabinetry, a premium SKS appliance suite, Taj Mahal quartzite countertops and full-height backsplashes, imported Portuguese limestone extending seamlessly from the interior to the pool terrace, and wide-plank light oak flooring throughout the upper level. Arched impact-rated windows and doors frame picturesque lake views while filling the home with natural light. Privately positioned to maximize the home's spectacular waterfront setting, the primary suite serves as a luxurious retreat featuring its own fireplace, a spacious sitting area, and a private balcony overlooking the lake. The spa-inspired bath rivals those found in the world's finest resorts, showcasing a dramatic wet room with a hand-carved marble soaking tub, handcrafted marble vanity, exquisite limestone, and an extraordinary custom Italian wardrobe system. Designed for effortless indoor-outdoor living, the private courtyard is inspired by timeless Mediterranean estates and framed by graceful arcades, tapered stone columns, restored architectural lanterns, and custom lighting. A freeform pool and elevated spa create a tranquil focal point, while the fully equipped summer kitchen, multiple covered terraces, and expansive entertaining spaces provide an exceptional setting for lakeside gatherings. Beyond the courtyard, beautifully landscaped grounds lead to a restored private dock and covered boathouse with direct access to the renowned Butler Chain of Lakes. No detail was overlooked, with additional highlights including a private elevator, custom wine room, designer lighting, thoughtfully restored architectural details, and curated finishes that create a timeless residence balancing warmth, elegance, and seamless indoor-outdoor living. Situated on renowned 2nd Avenue just moments from downtown Windermere, this remarkable residence establishes an entirely new benchmark for luxury renovation. Meticulously executed, flawlessly designed, and unlike anything else available today, this is more than a home it is a legacy property destined to become one of Central Florida's most iconic waterfront estates.
Facts & features
The home at a glance
5
Bedrooms
4.5
Bathrooms
5,511
Sqft
0.45 ac
Lot size
3
Garage
1993
Year built
Two
Levels
$1,089
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.
$38,965 /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
$38,965/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.
vs edgeAI estimate
+158.5%
$/sqft vs Windermere actives
$1,089 vs $345
Days on market
6 vs 32 typical
Where $1,089/sqft sits among the 240 Windermere 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 Windermere
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Windermere. See the full Windermere guide →
WINDERMERE 34786 — neighborhood snapshot
Population
43,700
Median age
37.9
Median income
$131,409
Median home value
$621,300
Avg household
2.9
Households w/ children
6,277
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Windermere market
$839K → $1.0M
Windermere median sold, yr/yr
96.4%
Sale-to-list ratio (12 mo)
112 of 240
Windermere actives have cut their price
Median sold price, Windermere, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 650% above the WINDERMERE 34786 median. See the full Windermere market guide →
Paper trail
This home's history
Reality check
What actually sold near 800 W 2ND AVENUE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Sep ’25$2,400,000
800 W 2ND AVENUE · same community
5 bd · 4.5 ba · 5,111 sqft · $470/sqft · 709 DOM
Sold · Sep ’25$4,125,000
805 W 2ND AVENUE · same community
5 bd · 5 ba · 4,783 sqft · $862/sqft · 103 DOM
Sold · Jun ’26$2,335,000
105 PINE STREET
5 bd · 5.5 ba · 5,696 sqft · $410/sqft · 9 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
Rui Ma
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 800 W 2ND AVENUE — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 800 W 2ND AVENUE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Rui's phone and CRM.
Straight answers
800 W 2ND AVENUE FAQs
What would the monthly payment be for 800 W 2ND AVENUE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $38,965/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 800 W 2ND AVENUE?+
The most recent tax bill on record (2025) was $50,219. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Windermere?+
At $5,999,000, this home is listed about 446% above the Windermere median of $1,099,500. The market section on this page shows how the area is trending.
Which schools are assigned to 800 W 2ND AVENUE?+
Windermere Elementary (elementary), Olympia High (high), Gotha Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Positioned at the premium end
$5,999,000 runs 650% above the WINDERMERE 34786 median — but at 5,511 sqft it's also 72% larger than the typical Windermere listing.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Fresh on the market
Only 6 days on market in a Windermere market that averages 32 — if it fits, move quickly.
04Strong assigned schools
Windermere Elementary, Olympia High, Gotha Middle — Windermere Elementary rates 5 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of ONE LUXURY INTERNATIONAL LLC · Julie Christensen. MLS #O6422976.
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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