Warm and inviting home located in the highly sought-after Highland Village community of Winter Springs—where residents love to live and rarely want to leave. This 2-bedroom, 2-bath home features an open floor plan, abundant natural light, and no carpet throughout. The spacious living and dining areas open a comfortable layout, perfect for everyday living or entertaining. The primary bedroom is generously sized with a large walk-in closet, and the primary bathroom has been updated with a sink, faucet and mirror. The secondary bedroom is also well-sized and versatile. The guest bathroom has been updated with a new vanity and mirror. The kitchen offers ample storage, includes all appliances, and opens directly to the private backyard—complete with a covered patio and ceiling fan, ideal for relaxing outdoors. Seller has recently updated the following: replace all interior doors, all new faux window blinds for all windows and crown molding in living areas. All appliances will stay including the washer and dryer! Enjoy living in a vibrant, well-maintained community with top-rated schools and fantastic amenities including a pool, tennis and pickleball courts, volleyball court, playground, and scenic walking trails and low HOA costs. Conveniently located near SR 434 and Tuskawilla Road, just minutes from Winter Springs Town Center, shopping, dining, and a short walk to Torcaso Park. Schedule your private showing today.
Property Details
Price:
$284,900
MLS #:
O6375532
Status:
Active
Beds:
2
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
HIGHLAND VILLAGE 1
Neighborhood:
32708casselberrrywinterspringstuscawilla
Listed Date:
Jan 31, 2026
Finished Sq Ft:
974
Total Sq Ft:
1,042
Lot Size:
4,716 sqft / 0.11 acres (approx)
Year Built:
1984
See this Listing
Schools
Interior
Appliances
Dishwasher, Electric Water Heater, Microwave, Range, Refrigerator
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Vinyl
Heating
Central, Electric
Interior Features
Ceiling Fan(s), Eating Space In Kitchen, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Walk-In Closet(s)
Laundry Features
Inside
Levels
One
Exterior
Community Features
Clubhouse, Deed Restrictions, Park, Playground, Pool, Sidewalks, Tennis Court(s)
Construction Materials
Vinyl Siding, Wood Frame
Direction Faces
West
Exterior Features
Sliding Doors
Roof
Shingle
Financial
HOA Fee
$72
HOA Fee 2
$425
HOA Fee 2 Frequency
Annually
HOA Fee Frequency
Annually
HOA Name
Highlands Village 1
HOA Name 2
The Highlands HOA
Tax Year
2024
Taxes
$1,428
Map
Community
- Address337 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 Apr 30, 2026
132
Single Family Listed
77
Avg DOM
258
Avg $ / SqFt
$578,277
Avg List Price
Property Summary
- Located in the HIGHLAND VILLAGE 1 subdivision, 337 KIRKCALDY DRIVE WINTER SPRINGS FL is a Single Family for sale in WINTER SPRINGS, FL, 32708. It is listed for $284,900 and features 2 beds, 2 baths, and has approximately 974 square feet of living space, and was originally constructed in 1984. The current price per square foot is $293. The average price per square foot for Single Family listings in WINTER SPRINGS is $258. The average listing price for Single Family in WINTER SPRINGS is $578,277. To schedule a showing of MLS#o6375532 at 337 KIRKCALDY DRIVE in WINTER SPRINGS, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.
Similar Listings Nearby
Courtesy of CHARLES RUTENBERG REALTY ORLANDO. 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. 337 KIRKCALDY DRIVE
WINTER SPRINGS, FL

