335 KIRKCALDY DRIVE, WINTER SPRINGS, FL, 32708
Active90 days on marketListed May 5, 2026MLS #O6400818
About this home
335 KIRKCALDY DRIVE
Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like Highlands community, offering 1,178 sq. ft. of living space. This home features vaulted ceilings, ceramic tile throughout, fresh interior paint, and a newly renovated kitchen with granite countertops, solid wood shaker-style cabinets, and black appliances. Major updates include a 2025 water heater and a new electrical panel inside and outside. The generously sized primary bedroom includes a built-in California Closets system, providing stylish and highly functional custom storage. The secondary and third bedrooms are also well-sized—perfect for guests, family, or easily converted into a home office. Washer and dryer are included in the sale. Enjoy the covered and screened lanai overlooking a charming New Orleans-style courtyard with pavers, a firepit, and a lamp post. The oversized, fully fenced, and cleared backyard offers plenty of space to relax, entertain, or garden, providing a strong sense of privacy. The Highlands is a highly sought-after, established community with low HOA fees and beautiful mature trees throughout. Amenities include an Olympic-size community pool, walking trails, playground, tennis court, volleyball court, and a clubhouse. Ideally situated just off State Road 434 Florida and Tuskawilla Road, this home offers quick access to Winter Springs Town Center for shopping and dining, and is just a short stroll from Torcaso Park—a lively neighborhood park featuring basketball courts, soccer and football fields, playgrounds for all ages, a splash pad, sand play areas, and picnic pavilions, perfect for both active days and relaxed family outings.
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,178
Sqft
0.11 ac
Lot size
1984
Year built
One
Levels
$280
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.
$2,592 /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
$2,592/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
+6.3%
$/sqft vs Winter Springs actives
$280 vs $240
Days on market
90 vs 38 typical
Where $280/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 Highland Village
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Springs. See the full Winter Springs guide →
Highland Village — neighborhood snapshot
Population
1,449
Median age
35
Median income
$62,902
Median home value
$247,221
Avg household
3
Households w/ children
196
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
$420K → $462K
Winter Springs median sold, yr/yr
97.8%
Sale-to-list ratio (12 mo)
83 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 12% 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 335 KIRKCALDY DRIVE
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$307,000
309 KIRKCALDY DRIVE · same community
3 bd · 2 ba · 1,326 sqft · $232/sqft · 38 DOM
Sold · Dec ’25$339,900
409 MURPHY ROAD
3 bd · 2 ba · 1,168 sqft · $291/sqft · 110 DOM
Sold · Nov ’25$290,000
865 TURTLE MOUND DRIVE
3 bd · 2 ba · 1,157 sqft · $251/sqft · 14 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 335 KIRKCALDY DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 335 KIRKCALDY 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
335 KIRKCALDY DRIVE FAQs
What would the monthly payment be for 335 KIRKCALDY DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $2,592/mo — principal and interest, the actual property-tax bill, the $36/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 335 KIRKCALDY DRIVE?+
The association fee works out to $36 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 335 KIRKCALDY DRIVE?+
The most recent tax bill on record (2025) was $3,693. 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 335 KIRKCALDY DRIVE?+
The listing reports pets: Cats OK, Dogs OK, 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 $329,900, this home is listed about 21% below the Winter Springs median of $420,000. The market section on this page shows how the area is trending.
Which schools are assigned to 335 KIRKCALDY 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
$329,900 is 12% below the WINTER SPRINGS 32708 median of $374,950.
02Trees/Woods views
The trees/woods view is part of what you're buying — views hold value independently of the structure.
03Time on market is leverage
90 days on market against a Winter Springs median of 38 — 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 $339,900, now $329,900 — a $10K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of MILLENIUM REALTY GROUP · Irina Carp. MLS #O6400818.
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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