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.
Property Details
Price:
$339,900
MLS #:
O6400818
Status:
Active
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
HIGHLAND VILLAGE 1
Neighborhood:
32708casselberrrywinterspringstuscawilla
Listed Date:
May 5, 2026
Finished Sq Ft:
1,178
Total Sq Ft:
1,440
Lot Size:
4,672 sqft / 0.11 acres (approx)
Year Built:
1984
See this Listing
Schools
Elementary School:
Highlands Elementary
Middle School:
South Seminole Middle
High School:
Winter Springs High
Interior
Appliances
Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Ceramic Tile, Tile
Heating
Central, Electric
Interior Features
Built-in Features, Ceiling Fan(s), High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Walk-In Closet(s)
Laundry Features
Inside, Laundry Room
Levels
One
Exterior
Architectural Style
Contemporary
Community Features
Clubhouse, Deed Restrictions, Playground, Pool, Sidewalks, Tennis Court(s)
Construction Materials
Vinyl Siding, Wood Frame
Direction Faces
Northwest
Exterior Features
Sliding Doors
Fencing
Wood
Lot Features
City Lot
Patio And Porch Features
Covered, Enclosed, Rear Porch
Roof
Shingle
View
Trees/Woods
Financial
HOA Fee
$36
HOA Fee 2
$72
HOA Fee 2 Frequency
Annually
HOA Fee Frequency
Monthly
HOA Name
Highlands Homeowners’ Association Inc
HOA Name 2
The Highlands HOA
HOA Phone
352-366-0234
Tax Year
2025
Taxes
$3,693
Map
Community
- Address335 KIRKCALDY DRIVE WINTER SPRINGS FL
- SubdivisionHIGHLAND VILLAGE 1
- CityWINTER SPRINGS
- CountySeminole
- Zip Code32708
Subdivisions in WINTER SPRINGS
- AMHERST
- ARROWHEAD AT TUSCAWILLA UNIT 2
- AVERY PARK
- BARCLAY RESERVE TWNHMS
- BARRINGTON ESTATES
- BAY TREE SEC 08
- BAY TREE SEC 09
- BAY TREE SEC 10
- BAYTREE VILLAGE
- BENTLEY CLUB AT BENTLEY GREEN
- CASA PARK VILLAS PH 1
- CHESTNUT RIDGE
- COUNTRY CLUB VILLAGE
- COUNTRY CLUB VILLAGE UNIT 1
- COUNTRY CLUB VILLAGE UNIT 3
- CYPRESS CLUB
- CYPRESS VILLAGE 3RD REP TR C PH 1
- DEER RUN UNIT 19A
- DEER RUN UNIT 23C
- DEERSONG
- DEERSONG 2
- DOUGS UNIT 1
- DUNMAR ESTATES 5 ACRE DEV 28 PARCELS
- EAGLES POINT PH 2
- EAGLES POINT PH 5
- EAGLES POINT PH 6
- EAGLES WATCH PH 1
- ENCLAVE AT DUNMAR
- ENTZMINGER FARMS ADD 2
- FAIRWAY OAKS UNIT 1
- FLAMINGO SPGS
- FOX GLEN AT CHELSEA PARC TUSCAWILLA PH 2
- FOXMOOR
- FOXMOOR UNIT 1
- FOXMOOR UNIT 3
- GARDEN CLUB APTS
- GEORGETOWNE UNIT 1
- GEORGETOWNE UNIT 2
- GLEN EAGLE UNIT 1
- GREENBRIAR SUB PH 1
- GREENBRIAR SUB PH 2
- GREENS AT TUSCAWILLA
- GREENS AT TUSCAWILLA BUILDING 3 A REPLAT
- GREENSPOINTE
- HACIENDA VILLAGE
- HARBOR WINDS
- HERITAGE COMMONS
- HERITAGE PARK TWNHMS
- HICKORY GROVE
- HIGHLAND VILLAGE 1
- HIGHLAND VILLAGE 2
- HIGHLANDS SEC 1
- HIGHLANDS SEC 4
- HIGHLANDS SEC 6
- HIGHLANDS SEC 6 BEDS: 3
- HOLLOWBROOK PH 2
- INDIAN RIDGE
- INDIAN RIDGE PH 2
- JESUPS LANDING
- JESUPS RESERVE TWNHMS REP
- LAKE JESSUP
- LAKE TUSKAWILLA PH 1
- LEW-JIM SUB
- LORI ANNE ACRES
- MOSS COVE
- MOUNT GREENWOOD UNIT 1
- MOUNT GREENWOOD UNIT 2 OF
- MOUNT GREENWOOD UNIT 4
- NORTH ORLANDO
- NORTH ORLANDO 1ST ADD
- NORTH ORLANDO 2ND ADD
- NORTH ORLANDO 5TH ADDITION
- NORTH ORLANDO 8TH ADD
- NORTH ORLANDO RANCHES SEC 01A
- NORTH ORLANDO RANCHES SEC 01B
- NORTH ORLANDO RANCHES SEC 02A
- NORTH ORLANDO RANCHES SEC 08
- NORTH ORLANDO RANCHES SEC 09
- NORTH ORLANDO RANCHES SEC 10
- NORTH ORLANDO TERRACE UNIT 1 SEC 4
- NORTH ORLANDO TERRACE UNIT 2 SEC 9
- NORTH ORLANDO TOWNSITE 4TH ADD REP
- OAK FOREST UNIT 1
- OAK FOREST UNIT 6
- OAK FOREST UNIT 7
- PARKSTONE
- PARKSTONE UNIT 3
- PARKSTONE UNIT 4
- RESERVE AT TUSCAWILLA PH 2
- SEASONS THE
- SEMINOLE CROSSING TWNHMS
- SEVILLE CHASE
- SHEOAH SEC 1
- STERNON PLAZA CONDO
- STONE GABLE
- SUNRISE ESTATES UNIT 5
- SUNRISE UNIT 2-A
- SUNRISE UNIT 2-B
- SUNRISE UNIT 2C
- SUNRISE VILLAGE UNIT 2
- SUNRISE VILLAGE UNIT 5
- SUNRISE VILLAGE UNIT 6
- THE LANDINGS AT PARKSTONE
- TUSCA OAKS
- TUSCANY PLACE PH 1
- TUSCAWILLA PARCEL 90
- TUSCAWILLA PRCL 90
- TUSCAWILLA RIDGE
- TUSCAWILLA UNIT 06
- TUSCAWILLA UNIT 07
- TUSCAWILLA UNIT 14B
- TUSKAWILLA CROSSINGS
- TUSKAWILLA CROSSINGS 60’S
- TUSKAWILLA CROSSINGS PH 1
- WATTS FARMS
- WEDGEWOOD TENNIS VILLAS
- WEDGEWOOD UNIT 1
- WEDGEWOOD UNIT 2
- WILDWOOD
- WINDING HOLLOW
- WINDING HOLLOW UNIT 2
- WINDING HOLLOW UNIT 3
- WINDING HOLLOW UNIT 4
- WINDING HOLLOW UNIT 5
- WINTER SPGS
- WINTER SPGS CENTRE A CONDO
- WINTER SPGS TOWN CENTER A REP
- WINTER SPGS UNIT 3
- WINTER SPGS UNIT 4
- WINTER SPGS VILLAGE PH 2
Market Summary
Current real estate data for Single Family in WINTER SPRINGS as of May 07, 2026
134
Single Family Listed
77
Avg DOM
264
Avg $ / SqFt
$591,316
Avg List Price
Property Summary
- Located in the HIGHLAND VILLAGE 1 subdivision, 335 KIRKCALDY DRIVE WINTER SPRINGS FL is a Single Family for sale in WINTER SPRINGS, FL, 32708. It is listed for $339,900 and features 3 beds, 2 baths, and has approximately 1,178 square feet of living space, and was originally constructed in 1984. The current price per square foot is $289. The average price per square foot for Single Family listings in WINTER SPRINGS is $264. The average listing price for Single Family in WINTER SPRINGS is $591,316. To schedule a showing of MLS#o6400818 at 335 KIRKCALDY DRIVE in WINTER SPRINGS, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.
Similar Listings Nearby
Courtesy of MILLENIUM REALTY GROUP. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than Charles Rutenberg Realty include the name of the listing broker. Neither the listing company nor Charles Rutenberg Realty shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 335 KIRKCALDY DRIVE
WINTER SPRINGS, FL

