Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury living. Showcasing his signature aesthetic, the home emphasizes sleek architectural lines, refined finishes, and a seamless connection between indoor and outdoor spaces. Expansive walls of glass flood the interior with natural light and create a striking façade that embodies its contemporary elegance. The main living areas are designed for both entertaining and everyday living. A dramatic two-story living room is anchored by designer furnishings, which extend throughout the home, while the spacious dining area comfortably accommodates large gatherings. The adjacent family room continues the modern aesthetic with a built-in media wall, sleek fireplace, textured design elements, and a triple sliding door connecting the indoor and outdoor spaces. Ready for any caliber of chef, the kitchen boasts Thermador appliances, along with extensive cabinetry and countertop space, soft-close drawers, a waterfall edge island, generously sized pantry, and reverse osmosis water filtration. A private home theater on the main level offers a true cinematic experience with surround sound, custom seating, and blackout shades, along with a stylish wet bar, providing additional space for entertaining. The home’s Crestron automation system is discreetly integrated, allowing full control of lighting, climate, and technology from a single interface. Upstairs, a striking floating staircase leads to a gallery-style landing overlooking the living space below. For those exhausting days, you can instead take a ride on the elevator. The expansive primary suite features a sitting area, a custom closet, and terrace access. The spa-inspired primary bath includes dual rain showers with body sprays, a soaking tub, and dual vanities with elegant finishes. Additional second-floor amenities include a fitness room with steam shower and sauna, an additional en-suite bedroom, one of the two laundry rooms, and access to an upper-level terrace overlooking the landscaped grounds and pool. Two en-suite guest bedrooms are conveniently tucked away on the first floor for maximum privacy. Offering four bedrooms, five full bathrooms, and two half baths, the home delivers both comfort and sophistication at every turn. Thoughtfully integrated automated shades provide effortless privacy, while the advanced air purification systems and whole-home water softener complement the home’s advanced smart features. This residence is offered fully furnished with curated Restoration Hardware pieces, including custom-selected furniture, lighting, rugs, and artwork that enhance its cohesive design. Outdoor living is equally impressive, with covered lanai spaces enhanced by automated roll-down screens, designer furnishings, a summer kitchen with gas grill and ventilation, and tranquil poolside views. The property also includes a split, three-car garage with a large driveway protected by a gated entrance. Completing this extraordinary dwelling is its location in the heart of Winter Park. This lakeside residence sits minutes from Park Ave Shopping, Rollins College, AdventHealth, multiple Botanical Gardens and Museums, well-rated grade schools, and highway access. Schedule your private showing today and experience the Winter Park lifestyle firsthand.
Property Details
Price:
$4,950,000
MLS #:
O6414890
Status:
Active
Beds:
4
Baths:
6
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
FOREST HILLS
Neighborhood:
32789winterpark
Listed Date:
Jun 10, 2026
Finished Sq Ft:
5,550
Total Sq Ft:
8,502
Lot Size:
26,108 sqft / 0.60 acres (approx)
Year Built:
2018
See this Listing
Schools
Elementary School:
Audubon Park K8
Middle School:
Glenridge Middle
High School:
Winter Park High
Interior
Appliances
Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Kitchen Reverse Osmosis System, Microwave, Range Hood, Refrigerator, Washer, Water Softener, Whole House R.O. System, Wine Refrigerator
Bathrooms
5 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air
Flooring
Ceramic Tile
Heating
Central, Electric
Interior Features
Built-in Features, Ceiling Fan(s), Crown Molding, Elevator, High Ceilings, Open Floorplan, PrimaryBedroom Upstairs, Sauna, Smart Home, Solid Surface Counters, Split Bedroom, Thermostat, Tray Ceiling(s), Walk-In Closet(s), Wet Bar
Laundry Features
Corridor Access, Inside, Laundry Room, Upper Level
Levels
Two
Exterior
Architectural Style
Custom
Attached Garage YN
1
Construction Materials
Block, Stucco
Covered Spaces
3
Direction Faces
Southeast
Exterior Features
Balcony, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Yard, Rain Gutters, Sliding Doors
Fencing
Fenced
Garage Spaces
3
Green Energy Efficient
HVAC, Lighting, Thermostat
Lot Features
City Lot, Landscaped, Oversized Lot
Open Parking YN
1
Parking Features
Driveway, Garage Door Opener, Garage Faces Side, Open, Split Garage
Patio And Porch Features
Covered, Deck, Front Porch, Rear Porch, Screened, Wrap Around
Roof
Other
Security Features
Security System
Window Features
Blinds
Financial
Tax Year
2025
Taxes
$56,866
Map
Community
- Address231 CHELTON CIRCLE WINTER PARK FL
- SubdivisionFOREST HILLS
- CityWINTER PARK
- CountyOrange
- Zip Code32789
Subdivisions in WINTER PARK
Market Summary
Current real estate data for Single Family in WINTER PARK as of Aug 29, 2026
302
Single Family Listed
85
Avg DOM
468
Avg $ / SqFt
$1,281,345
Avg List Price
Property Summary
- Located in the FOREST HILLS subdivision, 231 CHELTON CIRCLE WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32789. It is listed for $4,950,000 and features 4 beds, 6 baths, and has approximately 5,550 square feet of living space, and was originally constructed in 2018. The current price per square foot is $892. The average price per square foot for Single Family listings in WINTER PARK is $468. The average listing price for Single Family in WINTER PARK is $1,281,345. To schedule a showing of MLS#o6414890 at 231 CHELTON CIRCLE in WINTER PARK, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY. 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. 231 CHELTON CIRCLE
WINTER PARK, FL
