Nestled on a tranquil, tree-lined street in the vibrant heart of Winter Park, this reimagined 1960s mid-century modern pool residence beautifully harmonizes timeless architectural soul with stylized contemporary updates.
Bathed in glorious natural sunlight, the open-concept interior unfolds beneath soaring vaulted ceilings, where durable wood-look flooring flows seamlessly across expansive living and dining spaces. At the center of it all lies a true chef’s haven—an exquisitely updated kitchen equipped with solid wood cabinetry, rich granite countertops, a sprawling prep island, sleek stainless steel appliances, and a bold over-range hood.
Thoughtfully arranged along a private bedroom wing, the four spacious bedrooms blend exceptional comfort with versatile living spaces. The fourth bedroom is framed by views of the sun-drenched pool deck—an inspiring backdrop for a home office, creative sanctuary, or private gym. The primary retreat serves as a peaceful haven, complete with an elegant ensuite bath showcasing custom tile work and a glowing vanity mirror.
Step through the doors into your own fully fenced tropical oasis, where quintessential Florida living takes center stage. Spend your afternoons lounging beside the sparkling swimming pool, entertaining guests from the custom Tiki bar, or relaxing with a cool drink under the shade of the gazebo surrounded by fresh, plush, mature landscaping and fresh sod.
Modern convenience and major infrastructure upgrades ensure total peace of mind, featuring updated plumbing, electrical, and windows, along with a brand-new 2026 HVAC heat pump system (complete with a 10-year warranty) and a 2026 water heater. Complete with a two-car carport, dual storage rooms, indoor laundry, and a well-water irrigation system, every practical detail has been addressed.
All of this is situated within top-tier school zones (Brookshire, Glenridge, and Winter Park High), just moments from the boutique shopping and dining on Park Avenue, Rollins College, Baldwin Park, Cady Way Trail, medical hubs, and the energy of downtown Orlando.
Bathed in glorious natural sunlight, the open-concept interior unfolds beneath soaring vaulted ceilings, where durable wood-look flooring flows seamlessly across expansive living and dining spaces. At the center of it all lies a true chef’s haven—an exquisitely updated kitchen equipped with solid wood cabinetry, rich granite countertops, a sprawling prep island, sleek stainless steel appliances, and a bold over-range hood.
Thoughtfully arranged along a private bedroom wing, the four spacious bedrooms blend exceptional comfort with versatile living spaces. The fourth bedroom is framed by views of the sun-drenched pool deck—an inspiring backdrop for a home office, creative sanctuary, or private gym. The primary retreat serves as a peaceful haven, complete with an elegant ensuite bath showcasing custom tile work and a glowing vanity mirror.
Step through the doors into your own fully fenced tropical oasis, where quintessential Florida living takes center stage. Spend your afternoons lounging beside the sparkling swimming pool, entertaining guests from the custom Tiki bar, or relaxing with a cool drink under the shade of the gazebo surrounded by fresh, plush, mature landscaping and fresh sod.
Modern convenience and major infrastructure upgrades ensure total peace of mind, featuring updated plumbing, electrical, and windows, along with a brand-new 2026 HVAC heat pump system (complete with a 10-year warranty) and a 2026 water heater. Complete with a two-car carport, dual storage rooms, indoor laundry, and a well-water irrigation system, every practical detail has been addressed.
All of this is situated within top-tier school zones (Brookshire, Glenridge, and Winter Park High), just moments from the boutique shopping and dining on Park Avenue, Rollins College, Baldwin Park, Cady Way Trail, medical hubs, and the energy of downtown Orlando.
Property Details
Price:
$675,000
MLS #:
O6442348
Status:
Active
Beds:
4
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
KENILWORTH ESTATES 1ST ADD
Neighborhood:
32792winterparkaloma
Listed Date:
Sep 17, 2026
Finished Sq Ft:
1,688
Total Sq Ft:
2,303
Lot Size:
10,667 sqft / 0.24 acres (approx)
Year Built:
1960
See this Listing
Schools
Elementary School:
Brookshire Elem
Middle School:
Glenridge Middle
High School:
Winter Park High
Interior
Appliances
Dishwasher, Dryer, Electric Water Heater, Exhaust Fan, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Engineered Hardwood
Heating
Central, Electric
Interior Features
Ceiling Fan(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Window Treatments
Laundry Features
In Kitchen, Inside
Levels
One
Exterior
Architectural Style
Bungalow
Construction Materials
Block
Covered Spaces
2
Direction Faces
South
Exterior Features
Fire Pit, Garden, Irrigation System, Outdoor Grill, Private Mailbox, Private Yard, Storage
Fencing
Fenced, Wood
Lot Features
Level, Street Dead-End
Open Parking YN
1
Other Structures
Gazebo
Parking Features
Driveway
Roof
Membrane
Spa Features
In Ground
View
Pool
Window Features
Blinds
Financial
Tax Year
2025
Taxes
$4,090
Map
Community
- Address2215 WOODCREST DRIVE WINTER PARK FL
- SubdivisionKENILWORTH ESTATES 1ST ADD
- CityWINTER PARK
- CountyOrange
- Zip Code32792
Subdivisions in WINTER PARK
Market Summary
Current real estate data for Single Family in WINTER PARK as of Oct 18, 2026
281
Single Family Listed
83
Avg DOM
476
Avg $ / SqFt
$1,330,538
Avg List Price
Property Summary
- Located in the KENILWORTH ESTATES 1ST ADD subdivision, 2215 WOODCREST DRIVE WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32792. It is listed for $675,000 and features 4 beds, 2 baths, and has approximately 1,688 square feet of living space, and was originally constructed in 1960. The current price per square foot is $400. The average price per square foot for Single Family listings in WINTER PARK is $476. The average listing price for Single Family in WINTER PARK is $1,330,538. To schedule a showing of MLS#o6442348 at 2215 WOODCREST DRIVE in WINTER PARK, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of KELLER WILLIAMS WINTER PARK. 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 InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. 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. 2215 WOODCREST DRIVE
WINTER PARK, FL
