499 CLUB DRIVE, WINTER SPRINGS, FL, 32708
Active145 days on marketListed Mar 20, 2026MLS #O6391855
About this home
499 CLUB DRIVE
Beautiful 2 bedroom 2 bathroom townhome (Not a condo which means more financing choices for you as a buyer) located in the desirable Cypress Club within the Highlands Community. Brand New Roof on this townhome. The 20ft high ceiling in the Great Room gives this home a very open design with lots of natural light. Sliding doors lead out to a screened porch with separate locked storage space. Guest/2nd bedroom on the first floor with direct access to the 2nd bathroom. All appliances purchased New in 2022 and are included with sale. New A/C 2023. Upstairs flexible loft space makes for a nice home office. Large primary bedroom has beautiful laminate floors and plenty of closet space and updated bathroom. Two assigned parking spaces directly in front of your townhome makes coming home convenient. Cypress Club residents enjoy their Own Private Community Pool in addition to All Highlands amenities. They include Audibon Park with BBQ/Picnic Area, Playgrounds, Olympic Size Pool, Kiddie Pool, Nature Walking Trails & Tennis & Pickleball Courts and a Clubhouse. Zoned for highly rated Seminole County Schools with The Highlands elementary school located within the community. Nearby Cross Seminole Trail and Central Winds Park. Located close to 17-92, SR417, grocery stores, fitness clubs.
Facts & features
The home at a glance
2
Bedrooms
2
Bathrooms
1,224
Sqft
0.04 ac
Lot size
1987
Year built
Two
Levels
$172
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.
$2,175 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
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
Estimated payment
$2,175/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. 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
−9.4%
$/sqft vs Winter Springs actives
$172 vs $240
Days on market
145 vs 37 typical
Where $172/sqft sits among the 128 Winter Springs 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 Club
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Springs. See the full Winter Springs guide →
Cypress Club — neighborhood snapshot
Population
1,087
Median age
36
Median income
$63,194
Median home value
$255,700
Avg household
2
Households w/ children
129
For the school run
Seminole County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Springs market
$433K → $440K
Winter Springs median sold, yr/yr
97.8%
Sale-to-list ratio (12 mo)
78 of 128
Winter Springs actives have cut their price
Median sold price, Winter Springs, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 42% below the WINTER SPRINGS 32708 median. See the full Winter Springs market guide →
Paper trail
This home's history
Reality check
What actually sold near 499 CLUB DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jul ’26$209,000
502 CLUB DR · same community
2 bd · 2 ba · 1,224 sqft · $171/sqft · 87 DOM
Sold · Oct ’25$282,000
466 CLUB DR · same community
3 bd · 2 ba · 1,182 sqft · $239/sqft · 18 DOM
Sold · Oct ’25$245,000
120 Cypress Club Dr # 203, Pompano Beach FL 33060 · same community
2 bd · 2 ba · 982 sqft · $249/sqft · 13 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 499 CLUB DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 499 CLUB DRIVE — 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
499 CLUB DRIVE FAQs
What would the monthly payment be for 499 CLUB DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $2,175/mo — principal and interest, the actual property-tax bill, the $520/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 499 CLUB DRIVE?+
The association fee works out to $520 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 499 CLUB DRIVE?+
The most recent tax bill on record (2025) was $1,987. 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 499 CLUB DRIVE?+
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 Winter Springs?+
At $210,000, this home is listed about 47% below the Winter Springs median of $399,000. The market section on this page shows how the area is trending.
Which schools are assigned to 499 CLUB DRIVE?+
Highlands Elementary School (elementary), Winter Springs High School (high), South Seminole Middle School (middle) — Seminole County School District. Always verify school assignments with the district before relying on them.
The brief
Five things that matter here
01Under the WINTER SPRINGS 32708 market on paper
$210,000 is 42% below the WINTER SPRINGS 32708 median of $365,000, and at $172/sqft it sits under the Winter Springs average of $246.
02Know the monthly fee
The association fee is $520/mo. That usually buys real services — verify what's covered before comparing this home against fee-free alternatives.
03Time on market is leverage
145 days on market against a Winter Springs median of 37 — sellers in this position are usually ready to negotiate.
04Strong assigned schools
Highlands Elementary School, Winter Springs High School, South Seminole Middle School — Highlands Elementary School rates 4 of 5. Always verify assignments with the district.
05The price has already moved
Listed at $255,000, now $210,000 — a $45K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of FLORIDA HOME TEAM REALTY LLC · Paul Buscemi. MLS #O6391855.
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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