$4,500,000

231 CHELTON CIRCLE, Winter Park

4

Beds

6

Baths

5,550 ft2

Property Size

O6414890

MLS #

About The Property

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.

Listing updated: 2026-10-28T21:44:36.767Z

Listed by Realtor: Joseph Doher

Listed by office:  BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

Source: Stellar MLS

Property Details

Listing Id: O6414890
Price: $4,500,000
Property Size: 5,550 ft2
Property Lot Size: 1 ft2
Rooms: 10
Bedrooms: 4
Bathrooms: 6
Architectural Style: Custom
Bathrooms Full: 5
Bathrooms Half: 2
Modification Timestamp: 2026-10-28T21:49:47.994Z
Building Area Total: 8502
Construction Materials: Block, Stucco
Cooling: Central Air
CoveredSpaces: 3
CumulativeDaysOnMarket: 140
DaysOnMarket: 140
DirectionFaces: Southeast
ElementarySchool: Audubon Park K8
Fencing: Fenced
FireplaceFeatures: Electric, Family Room
Flooring: Ceramic Tile
FoundationDetails: Slab
Furnished: Furnished
GarageSpaces: 3
GreenEnergyEfficient: HVAC, Lighting, Thermostat
GreenIndoorAirQuality: HVAC UV/Elec. Filtration
GreenWaterConservation: Whole House Water Purification
HighSchool: Winter Park High
Laundry Features: Corridor Access, Inside, Laundry Room, Upper Level
Levels: Two
List AOR: Orlando Regional
List Agent AOR: Orlando Regional
List Agent Email: Joe@JoeDoher.com
List Agent Full Name: Joseph Doher
List Agent MlsId: 272500275
ListOfficeMlsId: 261024791
List Office Name: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
ListOfficePhone: 407-203-0007
Listing Terms: Cash, Conventional
Living Area Source: Public Records
Lot Features: City Lot, Landscaped, Oversized Lot
LotSizeArea: 26108
LotSizeSquareFeet: 26108
MLS Area Major: 32789 - Winter Park
MiddleOrJuniorSchool: Glenridge Middle
MlsStatus: Active
ModificationTimestamp: 2026-10-28T21:44:36.767Z
OnMarketDate: 2026-06-10
Originating System Name: Stellar MLS
Ownership: Fee Simple
Parcel Number: 182230284405170
Parking Features: Driveway, Garage Door Opener, Garage Faces Side, Open, Split Garage
Pets Allowed: Yes
Pool Features: Auto Cleaner, Deck, In Ground
Roof: Other
Security Features: Security System
Sewer: Public Sewer
State Or Province: FL
Status Change Timestamp: 2026-06-10T20:48:42.607Z
Stories Total: 2
Street Name: CHELTON
Street Number: 231
Street Number Numeric: 231
Street Suffix: CIRCLE
Tax Annual Amount: 56865.85
Tax Block: 05
Tax Book Number: K/90
Tax Year: 2025
Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Sewer Connected, Sprinkler Well, Street Lights, Underground Utilities, Water Connected
Water Source: Public
Window Features: Blinds
Year Built: 2018
Zoning: R-1AA
FeedTypes: IDX
Source System Key: 792889532
OriginalEntryTimestamp: 2026-06-10T20:48:42.607Z
OriginalListPrice: 4950000

Amenities and Features

Outdoor Details
Garage Attached
Other Features
Balcony
Bar Fridge
Built-in Features
Built-In Oven
Ceiling Fan(s)
Convection Oven
Cooktop
Crown Molding
Dishwasher
Disposal
Dryer
Electric Water Heater
Elevator
Exhaust Fan
Freezer
Has Cooling System
Has Fireplace
Has Garage
Has Heating System
Has Pool
High Ceilings
Irrigation System
Kitchen Reverse Osmosis System
Lighting
Microwave
Open Floorplan
Open Parking
Outdoor Grill
Outdoor Kitchen
PrimaryBedroom Upstairs
Private Yard
Rain Gutters
Range Hood
Refrigerator
Sauna
Sliding Doors
Smart Home
Solid Surface Counters
Split Bedroom
Thermostat
Tray Ceiling(s)
Walk-In Closet(s)
Washer
Water Softener
Wet Bar
Whole House R.O. System
Wine Refrigerator

Schedule a tour

Sat 14 Nov
Sun 15 Nov
Mon 16 Nov
Tue 17 Nov
Wed 18 Nov
Thu 19 Nov
Fri 20 Nov
Sat 21 Nov
Sun 22 Nov
Mon 23 Nov
In Person
Video Chat
Your information

Map Location

Property Map

Mortgage Calculator

Payment Calculator

$23,072.39
per month
  • Principal and Interest
  • Property Tax
  • HOA fee
  • Private Mortgage Insurance
$ 17,447.39

Image Gallery

Similar Listings

Similar Listings

1640 WALDEMERE STREET, Sarasota
Residential
Active
$5,400,000

1640 WALDEMERE STREET, Sarasota

MLS #
A4701346
Size
5,270 ft2
Beds:
5
Baths:
5.5
mls_logo
206 S WATERWAY DRIVE NW, Port Charlotte
Residential
Active
$825,000

206 S WATERWAY DRIVE NW, Port Charlotte

MLS #
C7529496
Size
2,479 ft2
Beds:
4
Baths:
2
mls_logo
10698 ROYAL CYPRESS WAY, Orlando
Residential
Active
$899,000

10698 ROYAL CYPRESS WAY, Orlando

MLS #
O6443682
Size
2,311 ft2
Beds:
3
Baths:
3
mls_logo

Disclaimer

Property ID - | 876523

All listings featuring of Stellar MLS are provided by Stellar MLS. This information is not verified for authenticity or accuracy and is not guaranteed. Information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by MLS.

©2026 Stellar MLS All rights reserved.

Compare Listings

Janet Richmond
Check Pricing