1221 OAKDALE STREET, WINDERMERE, FL, 34786
Active12 days on marketListed Oct 1, 2026MLS #O6446547
About this home
1221 OAKDALE STREET
Build Your Dream Lakefront Home in the Town of Windermere! Opportunity is knocking in one of Central Florida’s most desirable areas! This exceptional one-acre lakefront homesite on Oakdale Street in the town offers a rare opportunity to bring your vision to life and build the custom home you have always dreamed of. With an impressive 105 feet of direct frontage on beautiful Lake Bessie, this property provides the space, privacy, and waterfront setting to create something truly special. One of the biggest advantages of this property is NO HOA. Enjoy the freedom and flexibility that comes with owning your own piece of land without the restrictions and monthly fees often associated with planned communities. Whether you envision a stunning custom estate, a spacious family home, or a private lakeside retreat, this property gives you the opportunity to create a home that is uniquely yours. The expansive one-acre lot provides plenty of room to design the lifestyle you want. Imagine a beautiful custom residence with expansive living spaces, a resort-style pool, outdoor entertaining areas, lush landscaping, a private garden, oversized garage, and breathtaking views of Lake Bessie. With 105 feet of lake frontage, you can take full advantage of the waterfront setting and enjoy the beauty and tranquility of lakefront living right in the heart of Windermere. Instead of settling for someone else’s floor plan, start with a blank canvas and create a home designed around the way you live. Bring your architect, builder, and ideas and transform this exceptional homesite into your own private sanctuary. Location is everything, and this property offers the best of the Old Windermere lifestyle. Ideally located within a short distance of the Windermere Farmers Market, local shops, restaurants, and more, while beautiful Lake Butler is just blocks away. Town residents also have access to a boat ramp on Lake Butler and Lake Bessie, along with tennis courts, providing even more opportunities to enjoy the outdoors and the unique lifestyle that makes Windermere so desirable. Windermere is known for its beautiful lakes, charming community atmosphere, desirable residential neighborhoods, and convenient proximity to everything that makes Central Florida such a sought-after place to live. Opportunities to own a large lakefront homesite with no HOA and 105 feet of Lake Bessie frontage are truly special. This is your opportunity to stop dreaming about the perfect home and start building it. Make your vision come to life. Make this exceptional Windermere lakefront property the place you call home. Don't miss this rare opportunity!
Facts & features
The home at a glance
1 ac
Lot size
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.
$8,602 /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
$8,602/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.
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
$875K → $850K
Windermere median sold, yr/yr
96.5%
Sale-to-list ratio (12 mo)
Median sold price, Windermere, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 81% above the WINDERMERE 34786 median. See the full Windermere market guide →
Paper trail
This home's history
Reality check
What actually sold near 1221 OAKDALE STREET
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Sep ’26$690,000
811 MAIN STREET · same community
2 bd · 1.5 ba · 1,398 sqft · $494/sqft · 53 DOM
Sold · May ’26$710,000
305 OAKDALE STREET · same community
2 bd · 1 ba · 1,424 sqft · $499/sqft · 0 DOM
Sold · Jan ’26$752,500
825 OAKDALE STREET · same community
3 bd · 2 ba · 1,664 sqft · $452/sqft · 2 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
Kemarie Johnson
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 1221 OAKDALE STREET — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1221 OAKDALE STREET — before you fall in love.
See it in person
Schedule a tour
Live availability from Kemarie's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
1221 OAKDALE STREET FAQs
What would the monthly payment be for 1221 OAKDALE STREET?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $8,602/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 1221 OAKDALE STREET?+
The most recent tax bill on record (2026) was $14,736. 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 1221 OAKDALE STREET?+
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 Windermere?+
At $1,250,000, this home is listed about 15% above the Windermere median of $1,090,000. The market section on this page shows how the area is trending.
Which schools are assigned to 1221 OAKDALE STREET?+
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
Three things that matter here
01Positioned at the premium end
$1,250,000 runs 81% above the WINDERMERE 34786 median.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Strong 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 THE SIMON SIMAAN GROUP · Simon Simaan. MLS #O6446547.
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.
Never miss a listing
New Windermere homes, in your inbox
Like 1221 OAKDALE STREET but not quite? A daily digest of every new listing in Windermere — straight from the MLS, hours after it goes live. Unsubscribe anytime.
Just watching this one home? Ask Kemarie to ping you on any price or status change →