$2,699,000
1529 Holts Grove Circle
Winter Park, FL 32789
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history63 days on market
- Status: ActiveApr 1, 2026
- Listed$2,850,000Apr 1, 2026
- Price reduced$2,699,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 63
- Subdivision
- Windsong Lakeside Sec 02 43/71
- County
- Orange
- Year built
- 2005
- Living area
- 4,356 sq ft
- Price/sq ft
- $620
- Building area
- 6,601 sq ft (Public Records)
- Lot size
- 16,079 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- X (12095C0255F)
- Garage
- 3 spaces
- Pool
- Private pool
- Annual taxes
- $21,342 (2025)
- Parcel #
- 08-22-30-9363-00-190
- Zoning
- PURD
- MLS #
- O6395062
Interior Details
- Bedrooms
- 4
- Full bathrooms
- 4
- Half bathrooms
- 2
- Flooring
- Hardwood, Tile
- Appliances
- Bar Fridge, Dishwasher, Disposal, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Water Softener, Wine Refrigerator
- Interior features
- Built-in Features, Cathedral Ceiling(s), Ceiling Fans(s), Coffered Ceiling(s), Crown Molding, Eat-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
- Inside, Laundry Room
- Stories / Levels
- Two
- Direction faces
- North
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central, Electric, Heat Pump, Zoned
- Cooling
- Central Air, Humidity Control, Zoned
Parking
- Garage spaces
- 3
- Attached garage
- Yes
- Parking features
- Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side, Oversized
HOA & Financial
- HOA fee
- $785 / Quarterly
- Monthly HOA
- $262/mo
- Total monthly fees
- $262/mo
- Total annual fees
- $3,140
- HOA name
- Leland Management/Greg Ashworth
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 8-12 Months
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- Buyer to verify any lease restrictions with the HOA and City.
Exterior & Construction
- Exterior features
- French Doors, Hurricane Shutters, Lighting, Outdoor Grill, Outdoor Kitchen, Sidewalk
- Construction materials
- Block, Stone, Stucco
- Roof
- Tile
- Foundation
- Slab
- Pool
- Private pool
- Water access
- Yes
- Road surface
- Asphalt, Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Cable Available, Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Sprinkler Meter, Water Connected
Community
- Pets allowed
- Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Kitchen | First | 16x15 |
| Living Room | First | 23x16 |
| Dining Room | First | 13x12 |
| Den | First | 13x11 |
| Primary Bedroom | First | 18x15 |
| Bedroom 2 | Second | 16x12 |
| Bedroom 3 | Second | 21x14 |
| Bedroom 4 | Second | 14x12 |
| Bonus Room | Second | 21x18 |
Listing Details
- Listing date
- 2026-04-01
- On market date
- 2026-04-01
- Original list price
- $2,850,000
- Occupant type
- Owner
- MLS area
- 32789 - Winter Park
- Listing AOR
- Orlando Regional
- Status changed
- 2026-04-01
- Tax legal description
- WINDSONG - LAKESIDE SECTION 2 43/71 LOT19
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 3, 2026 at 4:45 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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