Tucked within the prestigious enclave of Windsong Lakeside in Winter Park, this extraordinary estate is a masterclass in refined living—where thoughtful design, cutting-edge technology, and timeless elegance converge. From the moment you arrive, the circular drive and stately presence set a tone of quiet grandeur. Step inside, and the home unfolds with an effortless sense of scale, defined by soaring vaulted ceilings and an abundance of natural light filtering through custom windows. Every detail has been meticulously curated—from the rich new flooring installed in 2025 to the soft glow of Currey & Co. lighting that adds warmth and sophistication to each space. Designed for both comfort and control, the residence is fully integrated with a wireless home automation system, allowing seamless management of lighting, climate, security, and more. Three A/C units ensure optimal comfort, while a new tankless water heater, water softener, and whole-home surround sound system elevate everyday living. A comprehensive security camera system and ADT Home Control provide peace of mind with modern convenience. Each of the four bedrooms is a private sanctuary, complete with its own en-suite bath, offering an elevated sense of privacy for residents and guests alike. The primary suite is a retreat unto itself, featuring custom built-in storage and electric storm shutters with blackout capability. The spa-inspired primary bath showcases a dual Grohe shower system, thermostatic auto tub filler and integrated TV – creating an environment of indulgence and serenity. At the heart of the home lies a newly renovated (2025) chef’s kitchen—an exquisite blend of form and function. Outfitted with premier appliances including a Wolf six-burner gas range, Sub-Zero refrigerator, Monogram built-in microwave, and dual dishwashers, the space is designed for both intimate meals and grand entertaining. Custom cabinetry with integrated lift features, dual sinks, filtered water dispenser, and elegant stone countertops complete this culinary haven. The living room invites relaxation with its newly renovated gas fireplace (2025), while a dedicated office offers bespoke built-in cabinetry with marble surfaces and glass shelving—ideal for sophisticated work-from-home living. Upstairs, the home transforms into an entertainment destination, complete with a projector theatre setup, wet bar, additional powder bath, and extensive storage. A dedicated A/V closet and the potential for an upstairs laundry add both function and flexibility. Outdoors, a private resort-style oasis awaits. The backyard has been completely reimagined, featuring lush turf, a sun deck platform, and even an in-ground trampoline—blending luxury with playfulness. The saltwater pool and spa, enhanced with upgraded LED lighting and a new heater (2025), were fully refinished and redesigned in 2021 to create a serene and visually stunning escape. A fully equipped summer kitchen—complete with a built-in gas grill, dual burners, refrigerator, and screened enclosure—sets the stage for unforgettable gatherings under the Florida sky. The three-car garage is equally impressive, featuring a Wallbox Level 2 electric vehicle charger (2023), seamlessly blending luxury with modern sustainability. This is more than a home—it is a statement of lifestyle, craftsmanship, and elevated living in one of Central Florida’s most sought-after lakefront communities.
Property Details
Price:
$2,795,000
MLS #:
O6395062
Status:
Active
Beds:
4
Baths:
5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINDSONG LAKESIDE SEC 02 43/71
Neighborhood:
32789winterpark
Listed Date:
Apr 1, 2026
Finished Sq Ft:
4,356
Total Sq Ft:
6,601
Lot Size:
16,079 sqft / 0.37 acres (approx)
Year Built:
2005
See this Listing
Schools
Elementary School:
Brookshire Elem
Middle School:
Glenridge Middle
High School:
Winter Park High
Interior
Appliances
Bar Fridge, Dishwasher, Disposal, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Water Softener, Wine Refrigerator
Bathrooms
4 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air, Humidity Control, Zoned
Flooring
Engineered Hardwood, Porcelain Tile, Tile
Heating
Central, Electric, Heat Pump, Zoned
Interior Features
Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Coffered Ceiling(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Pest Guard System, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Tray Ceiling(s), Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar
Laundry Features
Inside, Laundry Room
Levels
Two
Exterior
Association Amenities
Playground, Pool
Attached Garage YN
1
Community Features
Dock, Fishing, Lake, Water Access, Association Recreation – Owned, Deed Restrictions, Gated Community – No Guard, Golf Carts OK, Playground, Pool, Sidewalks, Special Community Restrictions
Construction Materials
Block, Stone, Stucco
Covered Spaces
3
Direction Faces
North
Exterior Features
French Doors, Hurricane Shutters, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Sidewalk
Fencing
Fenced
Garage Spaces
3
Lot Features
Corner Lot, Landscaped, Level, Sidewalk
Open Parking YN
1
Parking Features
Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side, Oversized
Patio And Porch Features
Covered, Enclosed, Patio, Rear Porch, Screened, Side Porch
Roof
Tile
Security Features
Security System, Security System Owned, Smoke Detector(s)
Spa Features
Heated, In Ground
Waterfront Features
Lake
Window Features
Double Pane Windows, Shutters
Financial
HOA Fee
$785
HOA Fee Frequency
Quarterly
HOA Includes
Community Pool, Pool Maintenance, Recreational Facilities
HOA Name
Leland Management/Greg Ashworth
HOA Phone
407-781-1836
Tax Year
2025
Taxes
$21,342
Map
Community
- Address1529 HOLTS GROVE CIRCLE WINTER PARK FL
- SubdivisionWINDSONG LAKESIDE SEC 02 43/71
- CityWINTER PARK
- CountyOrange
- Zip Code32789
Subdivisions in WINTER PARK
- 3223171-3223171
- 4572 PALMETTO CONDO
- ACREAGE
- ACREAGE & UNREC
- ALABAMA CONDO
- ALBERT LEE RIDGE ADD 02
- ALBERT LEE RIDGE FIRST ADD
- ALLISON OAKES
- ALOMA
- ALOMA TRAILS
- ANDALUCIA APTS
- ARAGON CONDO
- ARBORS/ARAGON
- ARROWHEAD COVE
- ARROWHEAD COVE UNIT 02
- ART SYSTEMS CENTER
- AUTUMN GLEN
- AUTUMN GLEN PH 2
- AZALEA LANE
- BANKS COLONIAL ESTATES
- BEAR GULLY BAY
- BEAR GULLY FOREST
- BEAR GULLY POINTE
- BEL AIRE PINES
- BEL-AIRE PINES, UNIT TWO
- BRIDGEWATER
- BROOKSHIRE HEIGHTS
- BROOKSHIRE HEIGHTS 3RD ADD
- BROOKSHIRE HEIGHTS 4TH ADD
- BROOKSHIRE HEIGHTS 4TH ADDITION
- BUNGALOW PARK
- CAMPO BELLO
- CAMWOOD SUB
- CANTON AVE COTTAGES 1
- CAPENS ADD
- CAROLYN ESTATES
- CARVER TOWN
- CARVER TOWN FIRST ADD
- CASA ALOMA
- CASA JARDIN CONDO
- CEDAR RIDGE UNIT 3
- CEDARWOOD VILLAGE 1
- CHARMONT
- CHATEAUX DU LAC
- CLOISTER GROVE SUB
- CLOISTERS CONDO
- COLLEGE PLACE REP
- COLONIES
- COMSTOCK PARK
- CONWILL ESTATES
- CORINTHEAN/WINTER PARK CONDO
- CORONADO TWNHMS
- CORONATION ADD
- CORTLAND PARK
- COUNTRY LANE
- CROSSROADS BUS CNTR CONDP
- CYPRESS RESERVE
- DIXIE TERRACE
- DUBSDREAD HEIGHTS
- DYER SUSAN RESUB
- EASTBROOK SUB UNIT 05
- EASTBROOK SUB UNIT 06
- EASTBROOK SUB UNIT 06 2ND REP
- EASTBROOK SUB UNIT 07
- EASTBROOK SUB UNIT 15
- EASTBROOK SUB UNIT 8
- EASTBROOK SUBD UNIT NO 14
- EASTGATE SUB
- EDEN POINT
- ELLNO WILLO
- ENCLAVE AT ALOMA
- ENCLAVE AT HAWKS CREST
- FAIRBANKS PARK
- FAIRBANKS SHORES 5TH ADD
- FAIRBANKS SHORES FIRST ADD
- FAIRVIEW HEIGHTS REP
- FERNBROOK TRAILS PH 3
- FLAMINGO SHORES
- FLORA PARK FIRST ADD
- FONTAINEBLEAU
- FOREST HILLS
- FOUR SEASONS
- FOUR SEASONS CONDO
- GALLERY AT WINTER PARK SEC 02
- GALLOWAY PLACE REP
- GARDEN ACRES 2ND REP OF BLK E
- GARDEN ACRES REP
- GARDEN LAKE ESTATES UNIT 1
- GEORGEANN HOMES
- GLENCOE SUB
- GOLDENROD VILLAS CONDO
- GOLDENROD VILLAS CONDOMINIUM ASSOCIATES
- GOLFSIDE SEC 03
- GOLFSIDE VILLAS CONDO
- GOLFVIEW
- GOLFVIEW HEIGHTS
- GRAYSON SQUARE
- GREEN OAKS REP 02
- GREEN OAKS REP 03
- GREENS/PK
- GREENVIEW AT WINTER PINES
- HAMILTON PLACE
- HARBOUR RIDGE
- HAWK’S CREST
- HAWKS CREST
- HENKEL ADD
- HIDDEN OAKS CONDO PH 01
- HIDDEN OAKS CONDO PH 02
- HIDDEN OAKS CONDO PH 04
- HIDDEN OAKS CONDO PH 05
- HIDDEN OAKS CONDO PH 07
- HIDDEN OAKS CONDO PH 08
- HIDDEN OAKS CONDO PH 09
- HIDDEN OAKS CONDO PH 10
- HIDDEN OAKS CONDO PH 12
- HILLS
- HOWELL ESTATES 2ND ADD
- HOWELL ESTATES REP
- HUNTINGTON CONDO
- HYDE PARK
- J KRONENBERGER SUB
- JENKINS ADD
- JENKINS SECOND ADD
- JUSTAMERE CAMP REP
- KAROLINA ON KILLARNEY
- KENILWORTH SHORES SEC 01
- KENILWORTH SHORES SEC 02
- KENILWORTH SHORES SEC 04
- KENILWORTH SHORES SEC 06
- KENILWORTH SHORES SEC 07
- KENILWORTH SHORES SEC 1
- KILLARNEY BAY CONDO
- KILLARNEY CIRCLE
- KILLARNEY ESTATES
- KINGS COVE
- KNOWLES MANOR NORTH CONDO
- 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 CROSSING
- LAKE VIRGINIA CONDO
- LAKE WAUNATTA VILLAGE
- LAKE WAUNATTA WOODS
- LAKEMONT HEIGHTS
- LAKESIDE MANOR APTS CONDO
- LAKESIDE MANOR CONDOMINIUM ASSOCIATION, INC.
- LAKEVIEW TERRACE
- LANCELOT/WINTER PARK
- LANDINGS AT HAWKS CREST
- LANDMARK WINTER PARK CONDO
- LAUREL SPGS
- LAWNDALE
- LAWNDALE ANNEX
- LAZY OAKS CONDO
- LORDS SUB
- LORING CHASE
- LOST CREEK
- LOT 59 HYDE PARK PB 34 PGS 38 TO 40
- LUGANO TERRACE
- MAGNOLIA SUB
- MAITLAND SHORES
- MAITLAND SHORES FIRST ADD
- MC INTYRE PLACE CONDO
- MEAD GARDEN
- MEADOWS AT HAWKS CREST
- METZINGERS ADD
- MONDRIAN/WINDER PARK TWNHMS
- MORSELAND SUB
- NORTHWOOD TERRACE
- OAKS CONDO
- OLYMPIA HEIGHTS
- ORANGE GROVE SUB
- ORANGE TERRACE
- ORANGEWOOD PARK
- ORWIN MANOR WESTMINSTER SEC
- OSCEOLA PLACE
- OSCEOLA SHORES SEC 03
- OSCEOLA SUMMIT
- PALMER AVE LAKESIDE PROP
- PALMER PARK
- PARK AIRE CONDO
- PARK GREEN
- PARK GROVE
- PARK HILL
- PARK SHORE
- PARKVIEW VILLAGE
- PARKVIEW VILLAGE CONDO BLDG 2929
- PELICAN BAY
- PHILLIPS CIRCLE REP
- PINES
- PINEWOOD
- PRESERVE AT HAWKS CREST
- QUAIL RUN
- QUARTERS AT WINTER PARK CONDO
- RIDGE HIGH 1ST ADD
- SANCTUARY AT ALOMA
- SANCTUARY AT LAKE ANN
- SANDALWOOD CREEK CONDO PH 09
- SANDALWOOD CREEK CONDO PH 11
- SANDALWOOD CREEK CONDO PH 12
- SANDLEWOOD CREEK CONDO
- SELLS TERRACE
- SEMINOLE COUNTY
- SEMORAN MEDICAL-SURGICAL CENTER CONDO
- SEVILLA
- SHORES LAKE KILLARNEY
- SHORES LAKE KILLARNEY SEC 02
- SICILIAN SHORES REP 02
- SLOVAK VILLAGE
- STANSBURY ESTATES
- STRATFORD A WINTER PARK CONDO
- SUBURBAN HOMES
- SUBURBAN HOMES FIRST ADD
- SUBURBAN HOMES SEC 2
- SWOOPE PARK
- SYLVAN HEIGHTS
- SYLVAN LAKE SHORES
- TAMARAK
- TANGERINE COURT
- TANGLEWOOD SEC 2
- TANGLEWOOD SEC 3 REP
- TANTUM ADD
- TAX EQUITIES INC REP
- TEMPLE ESTATES
- TEMPLE HEIGHTS
- TEMPLE TERRACE
- TEMPLE TERRACE ANNEX
- THE COLONIES CONDO
- TIMBERLANE
- TIMBERLANE SHORES
- TOWNHOMES/HARPER PLACE
- TROTTERS REP
- TUSCANIA
- TUSCANY PLACE FIRST ADD
- TUSCANY TERRACE
- URBAN GREEN 12
- VALENCIA TERRACE
- VIA LAGO/HANGING MOSS PH 1
- VILLAGE WINTERSET INC
- VILLAS OF CASSELBERRY PH 1
- VILLAS OF CASSELBERRY PH 3
- VIRGINIA HEIGHTS
- VIRGINIA HEIGHTS CONDO
- VIRGINIA HEIGHTS REP
- WATERFALL COVE
- WATERFALL COVE AT WINTER PARK
- WATERFALL COVE/WINTER PARK
- WATERS EDGE AT HAWKS CREST
- WHISPERING WATERS
- WHISPERWOOD CONDO
- WILLA GROVE
- WINDSONG
- WINDSONG LAKESIDE
- WINDSONG PRESERVE POINT 43/76
- WINDSONG-KNOWLES PLACE
- WINDWARD SQUARE SEC 1
- WINTER PARK
- WINTER PARK COMMERCE CENTER
- WINTER PARK ESTATES
- WINTER PARK FOREST 1ST ADD
- WINTER PARK GARDENS CONDO
- WINTER PARK HEIGHTS
- WINTER PARK MANOR
- WINTER PARK PINES
- WINTER PARK PINES MERRIE OAKS
- WINTER PARK PINES REP
- WINTER PARK PINES VILLAS
- WINTER PARK RESIDENTIAL
- WINTER PARK VILLAGE
- WINTER PARK VILLAS CONDO
- WINTER PARK VILLAS CONDO BLDG 12
- WINTER PARK WOODS CONDO
- WINTERBROOK
- WOODCREST CONDO
- WOODCREST UNIT 04
- WOODCREST UNIT5
- WRENWOOD CONDO
- WRENWOOD HEIGHTS UNIT 2
- WRENWOOD UNIT 3 2ND ADD
Market Summary
Current real estate data for Single Family in WINTER PARK as of Apr 25, 2026
275
Single Family Listed
84
Avg DOM
486
Avg $ / SqFt
$1,457,623
Avg List Price
Property Summary
- Located in the WINDSONG LAKESIDE SEC 02 43/71 subdivision, 1529 HOLTS GROVE CIRCLE WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32789. It is listed for $2,795,000 and features 4 beds, 5 baths, and has approximately 4,356 square feet of living space, and was originally constructed in 2005. The current price per square foot is $642. The average price per square foot for Single Family listings in WINTER PARK is $486. The average listing price for Single Family in WINTER PARK is $1,457,623. To schedule a showing of MLS#o6395062 at 1529 HOLTS GROVE CIRCLE in WINTER PARK, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
Similar Listings Nearby
Courtesy of KGV REALTY GROUP. 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 CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti 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. 1529 HOLTS GROVE CIRCLE
WINTER PARK, FL
