499 CLUB DRIVE, WINTER SPRINGS, FL, 32708
Active3 days on marketListed Oct 13, 2026MLS #O6447987
About this home
499 CLUB DRIVE
Virtually Staged. As you arrive at this beautiful 2 bedroom + loft, 2 bath residence in a serene townhome community within The Highlands in Winter Springs, you’ll note a feeling of privacy, relaxation, and tranquility among the lush landscaping, fantastic amenities, and peaceful walking trails. TOUR THE HOUSE WITH THE VIRTUAL TOUR AND WALK THRU VIDEO LINKS. Step inside to a spacious open floorplan where light bathes the soaring vaulted ceilings and tile flooring runs throughout the main living areas. The family cook will enjoy preparing meals among the new appliances (2022) in the functional kitchen layout, while overlooking the great room and exterior nature views. Step out to the screened patio to enjoy your morning coffee, where you’ll also find an outside storage closet offering a convenient place for your bikes, tools, or gardening supplies. The layout of this home offers double suites, thoughtfully split between the two levels, each with a full bath with shower/tub combo. Upstairs, a bonus loft provides an ideal flex space for a home office, reading nook, or more! Life here is stress-free with a new roof (2026) and A/C (2023), and 2 reserved parking spaces, side-by-side, right outside your front door. Beyond the home itself, this community provides you a carefree lifestyle with the HOA taking care of exterior maintenance and landscaping, leaving you plenty of time to meet up with friendly neighbors to enjoy the private community pool within the neighborhood, as well as the Highlands’ exceptional amenities -- including a junior Olympic-size lap pool, tennis/pickleball courts, clubhouse, playground, and picnic areas, perfect for relaxing moments or social gatherings. Conveniently located with easy access to main thoroughfares, everyday conveniences are close by -- groceries, restaurants, shopping, banks, fitness centers, etc. – as well as top-rated Seminole County schools. Come see why your new neighbors already love to call the area home and are enjoying the care-free lifestyle you deserve!!
Facts & features
The home at a glance
2
Bedrooms
2
Bathrooms
1,224
Sqft
0.03 ac
Lot size
1987
Year built
Two
Levels
$167
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.
$2,150 /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
$2,150/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
−21%
$/sqft vs Winter Springs actives
$167 vs $242
Days on market
3 vs 40 typical
Where $167/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)
76 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 41% 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 · Apr ’26$165,000
40 SHEOAH BOULEVARD UNIT 27
2 bd · 2 ba · 1,187 sqft · $139/sqft · 56 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
Seth Cabrera - Rothschild
Realtor · 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
Live availability from Seth's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
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 $2,150/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 $2,065. 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 $205,000, this home is listed about 49% 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
Four things that matter here
01Under the WINTER SPRINGS 32708 market on paper
$205,000 is 41% below the WINTER SPRINGS 32708 median of $349,950, and at $167/sqft it sits under the Winter Springs average of $244.
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.
03Fresh on the market
Only 3 days on market in a Winter Springs market that averages 40 — if it fits, move quickly.
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.
Keep looking
Similar homes nearby
Listing courtesy of BLOOM HOME GROUP REALTY LLC · Chris Winn. MLS #O6447987.
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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