Under contract-accepting backup offers. Set along a picturesque brick street, 2040 Randall Circle is a beautifully crafted residence that pairs timeless architecture with elevated, designer finishes and a functional floor plan. Framed by manicured landscaping and connected to a detached two-car garage by a covered walkway, the home offers classic curb appeal in an idyllic setting just minutes from vibrant shopping and dining on Park Avenue. Inside, rich hardwood floors run throughout the living spaces, complemented by Restoration Hardware lighting that brings a refined, cohesive feel to every room. The welcoming foyer opens to a gracious formal living room with a gas fireplace and custom built-ins, an elegant yet comfortable space for entertaining or relaxing. Just beyond, the formal dining room is well proportioned for hosting holiday gatherings and dinner parties with ease. The heart of the home is the expansive chef’s kitchen, thoughtfully designed for everyday living and effortless entertaining. An oversized island anchors the space, topped with Carrara marble counters and offering generous seating. A dual Wolf oven with six-burner range plus French cooktop, custom cabinetry, walk-in pantry, and a butler’s pantry complete with under-counter wine refrigerator provide beauty and functionality. A spacious breakfast room filled with natural light overlooks the backyard and flows seamlessly into the family room. Here, a gas fireplace, custom built-ins and three sets of French doors create a warm focal point while inviting in the outdoors. The first-floor primary suite serves as a private retreat, featuring large windows with tranquil views of the pool and direct access to the covered lanai. Dual walk-in closets provide ample storage, and the spa-like primary bath is finished in Carrara marble, offering a large soaking tub and an expansive glass-enclosed shower with dual shower heads. Two powder baths, one thoughtfully designed as a pool bath, along with one of two laundry rooms complete the main level. Upstairs, four additional bedrooms and a dedicated office provide generous space for family and guests. Two of the bedrooms feature private en-suite baths, while the remaining two share a well-appointed Jack & Jill bath. One of these rooms is arranged as a bonus lounge, offering flexibility to serve as a fifth bedroom, media room or additional gathering space if desired. The thoughtful second-floor layout easily adapts to a variety of lifestyle needs, whether accommodating guests, growing families or multi-generational living. A secondary laundry room upstairs adds an added layer of everyday convenience. Outdoor living is equally impressive. The spacious covered lanai with summer kitchen overlooks the saltwater, heated pool and spa, creating an extension of the interior living space. Brick paver flooring continues from the lanai to the open patio, offering multiple areas for lounging, dining and entertaining beneath the Florida sky. Ideally in a desirable location and zoned for sought-after Audubon Park K-8, 2040 Randall Circle offers timeless style, thoughtful design and seamless indoor-outdoor living in one of the area’s charming neighborhoods.
Property Details
Price:
$3,350,000
MLS #:
O6386920
Status:
Pending
Beds:
5
Baths:
5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
CHARMONT
Neighborhood:
32789winterpark
Listed Date:
Mar 5, 2026
Finished Sq Ft:
4,636
Total Sq Ft:
6,085
Lot Size:
11,915 sqft / 0.27 acres (approx)
Year Built:
2017
See this Listing
Schools
Elementary School:
Audubon Park K8
Middle School:
Audubon Park K-8
High School:
Winter Park High
Interior
Appliances
Bar Fridge, Dishwasher, Disposal, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater
Bathrooms
4 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air, Zoned
Flooring
Tile, Hardwood
Heating
Central, Zoned
Interior Features
Built-in Features, Coffered Ceiling(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s), Window Treatments
Laundry Features
Inside, Laundry Room
Levels
Two
Exterior
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
West
Exterior Features
French Doors, Irrigation System, Lighting, Outdoor Kitchen, Rain Gutters, Sidewalk
Fencing
Fenced
Garage Spaces
2
Lot Features
Corner Lot, City Lot, Landscaped, Level
Parking Features
Garage Faces Side
Patio And Porch Features
Covered, Rear Porch
Roof
Shingle
Spa Features
Heated, In Ground
Financial
Tax Year
2024
Taxes
$24,891
Map
Community
- Address2040 RANDALL CIRCLE WINTER PARK FL
- SubdivisionCHARMONT
- CityWINTER PARK
- CountyOrange
- Zip Code32789
Subdivisions in WINTER PARK
- —
- 147 INTERLACHEN PLACE
- ACREAGE & UNREC
- ALABAMA CONDO
- ALBERT LEE RIDGE ADD 02
- ALBERT LEE RIDGE FIRST ADD
- ALLISON OAKES
- ALOMA
- ALOMA BUS CENTER
- ALOMA TRAILS
- ANDALUCIA APTS
- ARAGON CONDO
- ART SYSTEMS CENTER
- AUTUMN GLEN
- BANKS COLONIAL ESTATES
- BEAR GULLY FOREST
- BEL-AIRE PINES, UNIT TWO
- BLDG 6 UNIT 189 THE STRATFORD A WINTER PARK CONDOM
- BLK C PT REP 02
- BROOKSHIRE HEIGHTS
- BROOKSHIRE HEIGHTS 4TH ADD
- CAMPO BELLO
- CAMWOOD SUB
- CAPENS ADD
- CAROLYN ESTATES
- CARVER TOWN
- CARVER TOWN FIRST ADD
- CASA ALOMA
- CEDAR RIDGE UNIT 1
- CEDAR RIDGE UNIT 2
- CEDARWOOD VILLAGE 1
- CHARMONT
- CHATEAUX DU LAC
- CLOISTER GROVE REP
- CLOISTER GROVE SUB
- CLOISTERS CONDO
- COLONIES
- COMSTOCK PARK
- CONWILL ESTATES
- CORONADO TWNHMS
- CORONATION ADD
- CORTLAND PARK
- COUNTRY LANE
- CYPRESS RESERVE
- DIXIE TERRACE
- DUBSDREAD HEIGHTS
- DYER SUSAN RESUB
- EASTBROOK SUB
- EASTBROOK SUB UNIT 05
- EASTBROOK SUB UNIT 06
- EASTBROOK SUB UNIT 06 2ND REP
- EASTBROOK SUB UNIT 06 REP OF PT OF BLK 14
- EASTBROOK SUB UNIT 13
- EASTBROOK SUB UNIT 14
- EASTBROOK SUB UNIT 15
- EASTBROOK SUB UNIT 8
- EASTGATE SUB
- EDGEWOOD SUB
- ENCLAVE AT ALOMA
- ENCLAVE AT HAWKS CREST
- FAIRBANKS PARK
- FAIRBANKS SHORES 5TH ADD
- FERNBROOK TRAILS
- FERNBROOK TRAILS PH 3
- FONTAINEBLEAU
- FOREST HILLS
- FOUR SEASONS CONDO
- GALLERY AT WINTER PARK SEC 01
- GALLOWAY PLACE REP
- GARDEN GROVE
- GARDEN LAKE ESTATES UNIT 3
- GEORGETOWN ESTATES
- GLENCOE SUB
- GLENMOOR
- GOLDEN ROD MANOR
- GOLDENROD VILLAS CONDO
- GOLDENROD VILLAS CONDOMINIUM ASSOCIATES
- GOLFSIDE GOLF COURSE SEC 01
- GOLFSIDE VILLAS CONDO
- GOLFVIEW
- GOLFVIEW HEIGHTS
- GRAYSON SQUARE
- GREEN OAKS REP 02
- GREEN OAKS REP 03
- GREENVIEW AT WINTER PINES
- HENKEL ADD
- HIDDEN OAKS CONDO PH 01
- HIDDEN OAKS CONDO PH 02
- HIDDEN OAKS CONDO PH 03
- HIDDEN OAKS CONDO PH 06
- HIDDEN OAKS CONDO PH 08
- HIDDEN OAKS CONDO PH 10
- HILLS
- HOWELL ESTATES 1ST ADD
- HOWELL ESTATES REP
- HUNTINGTON COURT
- HYDE PARK
- J KRONENBERGER SUB
- KAROLINA ON KILLARNEY
- KENILWORTH ESTATES
- KENILWORTH SHORES
- KENILWORTH SHORES SEC 01
- KENILWORTH SHORES SEC 03
- KENILWORTH SHORES SEC 04
- KENILWORTH SHORES SEC 06
- KENILWORTH SHORES SEC 07
- KILLARNEY BAY CONDO
- KILLARNEY CIRCLE
- KILLARNEY ESTATES
- KILLARNEY SHORES
- LACHEN HOUSE CONDO
- LAKE BELL TERRACE
- LAKE FLORENCE PRESERVE
- LAKE FOREST PARK
- LAKE KILLARNEY CONDO
- LAKE KILLARNEY SHORES
- LAKE KNOWLES TERRACE
- LAKE KNOWLES TERRACE ADD 02
- LAKE MONTE SUB
- LAKE SPIER XING
- LAKE VIRGINIA
- LAKE WAUNATTA VILLAGE
- LAKE WAUNATTA WOODS
- LAKEMONT HEIGHTS
- LAKESIDE ESTATES
- LAKESIDE MANOR APTS CONDO
- LAKESIDE MANOR CONDOMINIUM ASSOCIATION, INC.
- LAKEVIEW TERRACE
- LANCELOT/WINTER PARK
- LANDINGS AT HAWKS CREST
- LAS CASAS DE INDIANA
- LAWNDALE
- LAZY OAKS CONDO
- LORDS SUB
- LOST CREEK
- LUGANO TERRACE
- LYNN HAVEN
- MACCALLUM SUB
- MAGNOLIA GARDENS SUB
- MAGNOLIA SUB
- MAITLAND SHORES
- MAITLAND SHORES FIRST ADD
- MEAD GARDEN
- MEADOWS AT HAWKS CREST
- MORSELAND SUB
- NORTHWOOD TERRACE
- OAKCREST-516
- OAKS CONDO
- OLYMPIA HEIGHTS
- OLYMPIA HEIGHTS ANNEX
- ORANGE GROVE SUB
- ORANGE TERRACE
- ORANGEWOOD PARK
- ORWIN MANOR STRATFORD SEC
- ORWIN MANOR WESTMINSTER SEC
- OSCEOLA COURT
- OSCEOLA PLACE
- OSCEOLA SHORES SEC 1
- OSCEOLA SUMMIT
- PALMER AVE LAKESIDE PROP
- PARK AIRE CONDO
- PARK GREEN
- PARK GROVE
- PARK HILL
- PARK MANOR
- PARK NORTH
- PARK SHORE
- PARKLANDO 03
- PARKVIEW VILLAGE
- PARKVIEW VILLAGE CONDO
- PELICAN BAY
- PENNSYLVANIA STATION 01 CONDO
- PERLE DU LAC
- PERVIS SURVEY FOR R E
- PHILLIPS CIRCLE REP
- PINEWOOD SUB
- PRESERVE AT HAWKS CREST
- QUAIL RUN
- QUARTERS AT WINTER PARK CONDO
- ROBERT DHU MACDONALD PARK
- SANCTUARY AT ALOMA
- SANDLEWOOD CREEK CONDO PH 10
- SEVILLA
- SEVILLE PARK
- SHORES LAKE KILLARNEY
- SLOVAK VILLAGE
- SORENSEN HEIGHTS
- SOUTH LAKEMONT SHORES
- STANSBURY ESTATES
- STRATFORD A WINTER PARK CONDO
- SUBURBAN HOMES
- SUBURBAN HOMES FIRST ADD
- SWOOPE PARK
- SYLVAN HEIGHTS
- SYLVAN LAKE SHORES
- TANGERINE COURT
- TANGLEWOOD SEC 3 REP
- TANGLEWOOD SEC 4
- TEMPLE ESTATES
- TEMPLE HEIGHTS
- TEMPLE TERRACE ANNEX
- TERAZZO DEL SOL CONDO ASSN INC
- THOMAS M HENKELS ADD
- TIMBERLANE SHORES
- TOWNHOMES/HARPER PLACE
- TRINITY BAY PH 2
- TROVILLION CONDO
- TUSCANIA
- TUSCANY TERRACE
- TWIN ACRES
- URBAN GREEN 12
- VALENCIA TERRACE
- VILASA TWNHMS
- VILLAS OF CASSELBERRY PH 1
- VILLAS OF CASSELBERRY PH 2
- VILLAS OF CASSELBERRY PH 3
- VILLAS OF CASSELBERRY PH 4
- VIRGINIA HEIGHTS
- VIRGINIA HEIGHTS REP
- VISTAS AT LAKE HOWELL
- WATERFALL COVE
- WATERFALL COVE AT WINTER PARK
- WATERFALL COVE/WINTER PARK
- WATERS EDGE AT HAWKS CREST
- WHISPERING WATERS
- WHISPERING WATERS/PHILLIPS CIRCLE REP
- WHISPERWOOD 3
- WHISPERWOOD CONDO
- WILLA GROVE
- WINDSONG ELIZABETHS WALK
- WINDSONG ELIZABETHS WALK 43/81
- WINDSONG PRESERVE POINT 43/76
- WINDSONG-KNOWLES PLACE
- WINDSONG-PRESERVE POINT
- WINDWARD SQUARE SEC 1
- WINDWARD SQUARE SEC 2
- WINDWARD SQUARE SEC 3
- WINTER GREEN
- WINTER PARK
- WINTER PARK COMMERCE CENTER
- WINTER PARK ESTATES
- WINTER PARK GARDENS CONDO
- WINTER PARK HEIGHTS
- WINTER PARK OAKS
- WINTER PARK PINES
- WINTER PARK PINES MERRIE OAKS
- WINTER PARK PINES PATIO HOMES
- WINTER PARK PINES REP
- WINTER PARK REP BLK 75
- WINTER PARK VILLAGE
- WINTER PARK VILLAS BLDG 14
- WINTER PARK VILLAS CONDO
- WINTER PARK WOODS CONDO
- WINTER WOODS UNIT 01
- WINTER WOODS UNIT 04
- WOODCREST UNIT 01
- WRENWOOD CONDO
Market Summary
Current real estate data for Single Family in WINTER PARK as of Jun 09, 2026
319
Single Family Listed
87
Avg DOM
464
Avg $ / SqFt
$1,338,110
Avg List Price
Property Summary
- Located in the CHARMONT subdivision, 2040 RANDALL CIRCLE WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32789. It is listed for $3,350,000 and features 5 beds, 5 baths, and has approximately 4,636 square feet of living space, and was originally constructed in 2017. The current price per square foot is $723. The average price per square foot for Single Family listings in WINTER PARK is $464. The average listing price for Single Family in WINTER PARK is $1,338,110. To schedule a showing of MLS#o6386920 at 2040 RANDALL CIRCLE in WINTER PARK, FL, contact your Preferred Real Estate Brokers agent at 4076987254.
Similar Listings Nearby
Courtesy of PREMIER SOTHEBY’S INTL. 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 Preferred Real Estate Brokers include the name of the listing broker. Neither the listing company nor Preferred Real Estate Brokers 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. 2040 RANDALL CIRCLE
WINTER PARK, FL





