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$2,495,000
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Property Description
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.
Full Property Details
Full Property Details for 1529 Holts Grove Cir
General
- Sold For: $2,495,000
- HOA FEE: $262/month
- HOA FEE FREQ.: Quarterly
- Taxes: $21,342 (2025)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6395062
- Added to Site: 147 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 9
- Interior Features: Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Coffered Ceiling(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, 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
- Fireplace: Yes
- Fireplace(s): Family Room, Gas
- Appliances: Bar Fridge, Dishwasher, Disposal, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Water Softener, Wine Refrigerator
- Furnishings: Unfurnished
- Flooring: Engineered Hardwood, Porcelain Tile, Tile
Rooms
Bathrooms
- Total Bathrooms: 6
- Full Bathrooms: 4
- Half Bathrooms: 2
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Shared Amenities: Playground, Pool
- Pool: Yes
- Private Pool: Yes
- Pool Description: Child Safety Fence, Gunite, Heated, In Ground, Lighting, Salt Water, Tile
- Spa: Yes
- Spa Description: Heated, In Ground
- Security/Safety: Security System, Security System Owned, Smoke Detector(s)
Exterior
- Exterior Features: French Doors, Hurricane Shutters, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Sidewalk
- Deck/Patio: Covered, Enclosed, Patio, Rear Porch, Screened, Side Porch
- Porch/Patio/Deck: Covered, Enclosed, Patio, Rear Porch, Screened, Side Po
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
- Parking Features: Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side, Oversized
Location
- Area: 32789 - Winter Park
- County: Orange
- Development Name: 32789 - Winter Park
- Subdivision: WINDSONG LAKESIDE SEC 02 43/71
- Driving Directions: From Interstate 4, take Exit 87 for Fairbanks Avenue (State Road 426) and head east toward Winter Park. Continue on Fairbanks Avenue for approximately 2 miles, then turn left onto Pennsylvania Avenue. Follow Pennsylvania Avenue as it becomes Glenridge Way, then continue straight into the Windsong community. Proceed through the neighborhood, then turn onto Holts Grove Circle. Continue along Holts Grove Circle, and 1529 will be located on your right within the Windsong Lakeside community.
- Direction Faces: North
School Information
- Elementary School: Brookshire Elem
- Middle School: Glenridge Middle
- High School: Winter Park High
Community
- Community Name: 32789 - Winter Park
- Community Features: Dock, Fishing, Lake, Water Access, Association Recreation - Owned, Deed Restrictions, Golf Carts OK, Playground, Pool, Sidewalks, Special Community Restrictions
- Optional Amenities: Playground, Pool
- Association: Yes
- Assoc. Name: Leland Management/Greg Ashworth
- Assoc. Fees Include: Community Pool, Pool Maintenance, Recreational Facilities
- Pet Restrictions: Buyer to verify any pet restrictions with the HOA and City.
Heating & Cooling
- Cooling Type: Central Air, Humidity Control, Zoned
- Heating Type: Central, Electric, Heat Pump, Zoned
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable TV Available, Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Sprinkler Meter, Water Connected
Structural Information
- Exterior Const.: Block, Stone, Stucco
- Roof: Tile
- Windows: Double Pane Windows, Shutters
- Stories/Levels: Two
- Square Feet: 4,356
- Sq. Ft. Source: Public Records
- Living Area: 4,356 Sq. Ft.
- Year Built: 2005
Lot Features
- Lot Size (Acres): 0.37
- Lot Size (Sq. Ft.): 16,079
- Lot Size: 16079
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
- Fencing (Description): Fenced
Water Features
- Water Access: Yes
- Water Access Desc: Lake
- Water Extras: Yes
- Water Front Desc.: Lake
Financial Considerations
- Association Fee: $785
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $21,342.45
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: WINDSONG - LAKESIDE SECTION 2 43/71 LOT19
- Flood Zone Info: X
- APN: 82230936300190
- Property ID: 82230936300190
Listed by Kgv Realty Group
Sold by Fannie Hillman & Associates
Get Pre-Approved Today
Schools
Schools serving 1529 Holts Grove Cir
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Brookshire Elementary School 2500 Cady Way, Winter Park, FL 32792 | PK-5 | 0.9 mi |
Glenridge Middle School 2900 Upper Park Road, Orlando, FL 32814 | 6-8 | 1.2 mi |
Winter Park High School 2100 Summerfield Road, Winter Park, FL 32792 | 9-12 | 0.9 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 1529 Holts Grove Cir
Date
Details
Price
Change
Source
8/14/2026
Sold
$2,495,000
-7.56%
MLS
5/18/2026
Price Reduced
$2,699,000
-3.43%
MLS
4/21/2026
Price Reduced
$2,795,000
-1.93%
MLS
4/01/2026
Listed
$2,850,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
1529 Holts Grove Circle, Winter Park, FL 32789 (MLS# O6395062) is a Single Family property that was sold at $2,495,000 on August 14, 2026. Want to learn more about 1529 Holts Grove Circle? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

