Home in 1529 Holts Grove Cir Winter Park for sale with MLS# O6395062

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.

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1529 Holts Grove Cir, Winter Park, FL 32789

Price
Price:
$2,850,000.00
Original List Price:
$2,850,000.00
List Price per Sq Ft (Calculated, Approx.):
$654.27
Property Status and Type
Listing Type:
For Sale
Status:
Active
Listing Category:
Residential
Property Type:
Single Family House
MLS Number:
O6395062
Rooms Distribution
Bedrooms:
4
Bathrooms Total:
6
Full Bath:
4
Half Bath:
2
Additional Rooms:
Den/library/office, Inside Utility, Loft, Bonus Room, Media Room, Family Room, Formal Dining Room Separate, Breakfast Room Separate
Measures
Living Area:
4,356 Sqft
Built-Up Area:
6,601 Sqft
Lot Area:
16,079 Sqft
Building Area Source:
Public Records
Living Area Source:
Public Records
Lot Features:
Corner Lot, Paved, Level, Sidewalk, Landscaped
Lot Size Acres:
0.37
Property Features
Waterfront:
No
Private Pool
Swimming Pool Features:
Gunite, Heated, In Ground, Salt Water, Child Safety Fence, Lighting, Tile
Spa
Spa Features:
Heated, In Ground
Security:
Smoke Detector(s), Security System, Security System Owned
Furnished:
Unfurnished
Appliances:
Dishwasher, Disposal, Microwave, Refrigerator, Gas Water Heater, Ice Maker, Water Softener, Range, Range Hood, Tankless Water Heater, Wine Refrigerator, Bar Fridge
Interior:
Eat-in Kitchen, High Ceilings, Walk-In Closet(s), Vaulted Ceiling(s), Built-in Features, Wet Bar, Cathedral Ceiling(s), Ceiling Fans(s), Kitchen/family Room Combo, Living Room/dining Room Combo, Open Floorplan, Split Bedroom, Stone Counters, Thermostat, Solid Surface Counters, Solid Wood Cabinets, Crown Molding, Tray Ceiling(s), Pest Guard System, Coffered Ceiling(s), Primary Bedroom Main Floor
Exterior:
Lighting, Outdoor Grill, Sidewalk, French Doors, Hurricane Shutters, Outdoor Kitchen
Patio and Porch:
Patio, Screened, Covered, Rear Porch, Enclosed, Side Porch
Windows:
Double Pane Windows, Shutters
Laundry:
Inside, Laundry Room
Fireplace
Fireplace:
Gas, Family Room
Air Conditioning System:
Zoned, Central Air, Humidity Control
Heating System:
Central, Electric, Zoned, Heat Pump
Fence:
Fenced
Vegetation and Trees:
Trees/landscaped, Mature Landscaping, Oak Trees
Property Entrance Faces:
North
Other Equipment:
Irrigation Equipment
Water Access
Water Access Features:
Lake
Water Extras
Water Extra Details:
Fishing Pier, Boat Port
Construction
Year Built:
2005
Roof:
Tile
Levels:
Two
Construction Materials:
Block, Stucco, Stone
Flooring:
Tile, Hardwood
Number of stories:
2
Foundation Details:
Slab
Flood Zone Code:
X
Taxes and Expenses
Homestead Property
Tax Annual Amount:
$21,342.45
Tax Year:
2025
Association Fee:
$785.00
Association Fee Frequency:
Quarterly
Total Annual Fees:
$3,140.00
Total Monthly Fees:
$261.67
Parking
Garage
Garage Spaces:
3
Attached Garage
Parking Features:
Driveway, Garage Door Opener, Circular Driveway, Electric Vehicle Charging Station(s), Oversized, Garage Faces Side
Garage Dimensions:
30X10
Utilities
Sewer:
Public Sewer
Utilities Available:
Cable Available, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected, Cable Connected, Sprinkler Meter
Water Source:
Public
Community
Association
Minimum Lease Term:
8-12 Months
Pets Allowed?
Amenities Provided by the Homeowner's Association (HOA):
Pool, Playground
Subdivision Name:
WINDSONG LAKESIDE SEC 02 43/71
Community Features:
Sidewalks, Pool, Playground, Association Recreation - Owned, Deed Restrictions, Golf Carts Ok, Special Community Restrictions, Gated Community - No Guard
Association Fee Includes:
Pool, Recreational Facilities
Senior Community:
No
Association Fee Required:
Required
Association Management:
Leland Management/Greg Ashworth
Association Phone:
407-781-1836
Terms
Listing Terms Considered by Seller:
Cash, Conventional
Occupant Type:
Owner
Lease Considered:
Yes
Zoning and Legal
Tax Legal Description:
WINDSONG - LAKESIDE SECTION 2 43/71 LOT19
Real Estate Folio Number (Parcel Number):
08-22-30-9363-00-190
Zoning:
PURD
Title to the property is held by owner as:
Fee Simple
Public Schools Assigned
Elementary School:
Margate
High School:
Winter Park High
Middle Or Junior School:
Glenridge Middle
Listing History
Originally published on:
April 1, 2026 2:13 pm
Active on the market since:
April 1, 2026
Listing Agreement executed on:
April 1, 2026
Listing Status Last Changed On:
April 1, 2026 2:13 pm
Photos updated on:
April 1, 2026 2:15 pm
Last Modified:
April 9, 2026 8:25 pm
Additional Information
Courtesy of:
KGV REALTY GROUP
Attribution:
407-474-0844
Road Surface Type:
Paved, Asphalt
Location
Street Name:
HOLTS GROVE
Street Number:
1529
City:
WINTER PARK
State:
Florida
Zip Code:
32789
County:
Orange
Latitude:
N28° 35' 41.5''
Longitude:
W82° 40' 3.9''
Property Map

Neighborhood Stats

Source: U.S. Census Bureau, ACS 5-Year Estimates

Median Household Income $100,213
Median Home Value $695,000
Median Rent $1,667/mo
Median Age 44
Population 26,884

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