3739 WINDING LAKE CIRCLE, ORLANDO, FL, 32835
Active2 days on marketListed Aug 6, 2026MLS #O6426943
Come see it
Upcoming open house
Sun, Aug 9
12:00 PM – 3:00 PM
About this home
3739 WINDING LAKE CIRCLE
Move in, unpack, and start enjoying the Florida lifestyle from day one! This beautifully updated pool home takes the stress out of renovations giving you more time to do what you love. Nestled in the highly sought-after Cypress Landing community, this exceptional residence sits on an oversized lot with peaceful green space behind it, offering the privacy of no rear neighbors. With four bedrooms, a dedicated office that can easily serve as a fifth bedroom, three full bathrooms, and a versatile upstairs bonus room, there's plenty of space to fit your lifestyle. Step inside to a bright, open floor plan featuring soaring ceilings, elegant formal living and dining rooms, and a spacious family room centered around a cozy wood burning fireplace. The thoughtfully designed three way split floor plan provides comfort and privacy for everyone. The kitchen is complete with granite countertops, a decorative tile backsplash, abundant cabinetry, stainless steel appliances and generous prep space. At the end of the day, retreat to the primary suite, where the spa inspired bathroom, with its pristine soaking tub, creates the perfect place to relax and recharge. Upstairs bonus room offers endless possibilities as a home office, media room, fitness area, playroom, or hobby space, adapting easily to your changing needs. Just wait until you see all you have out back! The expansive lanai sets the stage for unforgettable gatherings, featuring a custom heated pool and spa that's perfect for everything from weekend barbecues to relaxing evenings. Living in Cypress Landing means enjoying both comfort and convenience. Windy Ridge K–8 School is just a short walk away. You're only about eight minutes from Universal Studios, ten minutes from Orlando's renowned Restaurant Row and just a short 20 minute drive to Walt Disney World and SeaWorld. ROOF - 2012, HVAC 2018. Schedule your private showing today!
Facts & features
The home at a glance
4
Bedrooms
3
Bathrooms
3,404
Sqft
0.34 ac
Lot size
3
Garage
1997
Year built
Two
Levels
$275
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.
$6,194 /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
$6,194/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
−17.1%
$/sqft vs Orlando actives
$275 vs $251
Days on market
2 vs 42 typical
Where $275/sqft sits among the 400 Orlando 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 Cypress Landing
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Orlando. See the full Orlando guide →
Cypress Landing — neighborhood snapshot
Population
2,625
Median age
43
Median income
$193,800
Median home value
$652,800
Avg household
3
Households w/ children
419
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Orlando market
$400K → $395K
Orlando median sold, yr/yr
97.0%
Sale-to-list ratio (12 mo)
180 of 400
Orlando actives have cut their price
Median sold price, Orlando, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 428% above the ORLANDO 32835 median. See the full Orlando market guide →
Paper trail
This home's history
Reality check
What actually sold near 3739 WINDING LAKE CIRCLE
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$885,000
3609 BELLINGTON DRIVE · same community
5 bd · 4.5 ba · 3,419 sqft · $259/sqft · 67 DOM
Sold · Jul ’26$255,000
3962 CYPRESS LANDING W · same community
2 bd · 2.5 ba · 1,775 sqft · $144/sqft · 18 DOM
Sold · Dec ’25$259,900
4020 CYPRESS LANDING S · same community
3 bd · 2 ba · 1,675 sqft · $155/sqft · 49 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
Iain Robinson
Broker Associate · CENTURY 21 Edge
Tours, negotiation, and every question about 3739 WINDING LAKE CIRCLE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 3739 WINDING LAKE CIRCLE — before you fall in love.
See it in person
Schedule a tour
Live availability from Iain's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
3739 WINDING LAKE CIRCLE FAQs
What would the monthly payment be for 3739 WINDING LAKE CIRCLE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $6,194/mo — principal and interest, the actual property-tax bill, the $60/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 3739 WINDING LAKE CIRCLE?+
The association fee works out to $60 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 3739 WINDING LAKE CIRCLE?+
The most recent tax bill on record (2025) was $6,943. 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 3739 WINDING LAKE CIRCLE?+
The listing reports pets: Cats OK, Dogs OK. 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 Orlando?+
At $935,000, this home is listed about 137% above the Orlando median of $394,500. The market section on this page shows how the area is trending.
Which schools are assigned to 3739 WINDING LAKE CIRCLE?+
Windy Ridge K-8 (elementary), Olympia High (high), Chain Of Lakes 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
$935,000 runs 428% above the ORLANDO 32835 median — but at 3,404 sqft it's also nearly twice the size of the typical Orlando listing.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Fresh on the market
Only 2 days on market in a Orlando market that averages 42 — if it fits, move quickly.
04Strong assigned schools
Windy Ridge K-8, Olympia High, Chain Of Lakes Middle — Windy Ridge K-8 rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of EXP REALTY LLC · Jacquie Sosa. MLS #O6426943.
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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