1529 HOLTS GROVE CIRCLE
Winter Park, FL 32789
$2,495,000
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 ...
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Listing Courtesy of: KGV REALTY GROUP
407-474-0844
Buyer Represented by: FANNIE HILLMAN & ASSOCIATES
| Listing Id: | O6395062 |
|---|---|
| List Price: | $2,699,000 |
| Close Price: | $2,495,000 |
| Close Date: | 2026-08-14 |
| Property Type: | Residential |
| Property Sub Type: | Single Family Residence |
| Status: | Closed |
| Bedrooms Total: | 4 |
| Bathrooms Full: | 4 |
| Bathrooms Half: | 2 |
| Living Area: | 4,356 |
| Tax Annual Amount: | $21,342 |
| Lot Size Square Feet: | 16,079 |
| Lot Size Acres: | 0.37 |
| Waterfront?: | No |
| City: | Winter Park |
| County Or Parish: | Orange |
| Subdivision Name: | Windsong Lakeside Sec 02 43/71 |
| Postal Code: | 32789 |
| Year Built: | 2005 |
| Appliances: | Bar Fridge, Dishwasher, Disposal, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Water Softener, Wine Refrigerator |
| Association Amenities: | Playground, Pool |
| Association Fee: | $785 |
| Association Fee Frequency: | Quarterly |
| Association Fee Includes: | Pool, Recreational Facilities |
| Attached Garage?: | Yes |
| Bathrooms Total Integer: | 6 |
| Building Area Source: | Public Records |
| Building Area Total: | 6601 |
| Building Area Units: | Square Feet |
| Direction Faces: | North |
| Foundation Details: | Slab |
| Construction Materials: | Block, Stone, Stucco |
| Cooling: | Central Air, Humidity Control, Zoned |
| Fireplace Features: | Family Room, Gas |
| 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. |
| Elementary School: | Brookshire Elem |
| Exterior Features: | French Doors, Hurricane Shutters, Lighting, Outdoor Grill, Outdoor Kitchen, Sidewalk |
| Fencing: | Fenced |
| Flooring: | Hardwood, Tile |
| Furnished: | Unfurnished |
| Garage Spaces: | 3 |
| Garage?: | Yes |
| Community Features: | Association Recreation - Owned, Deed Restrictions, Golf Carts OK, Playground, Pool, Sidewalks, Special Community Restrictions |
| Heating: | Central, Electric, Heat Pump, Zoned |
| High School: | Winter Park High |
| 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 Features: | Inside, Laundry Room |
| Levels: | Two |
| Ownership: | Fee Simple |
| Living Area Source: | Public Records |
| Living Area Units: | Square Feet |
| Lot Features: | Corner Lot, Landscaped, Level, Sidewalk, Paved |
| Lot Size Acres: | 0.37 |
| Postal Code Plus4: | 5114 |
| Middle Or Junior School: | Glenridge Middle |
| MLS Area Major: | 32789 - Winter Park |
| MLS Area Major: | 32789 - Winter Park |
| Original List Price: | $2,850,000 |
| Other Equipment: | Irrigation Equipment |
| Parcel Number: | 08-22-30-9363-00-190 |
| 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 |
| Pets Allowed: | Yes |
| Pool Features: | Child Safety Fence, Gunite, Heated, In Ground, Lighting, Salt Water, Tile |
| Stories Total: | 2 |
| Township: | 22 |
| Road Surface Type: | Asphalt, Paved |
| Roof: | Tile |
| Listing Terms: | Cash, Conventional |
| Tax Year: | 2025 |
| Security Features: | Security System, Security System Owned, Smoke Detector(s) |
| Sewer: | Public Sewer |
| Special Listing Conditions: | None |
| State Or Province: | FL |
| Association?: | Yes |
| Utilities: | Cable Available, Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Sprinkler Meter, Water Connected |
| Water Source: | Public |
| Public Survey Range: | 30 |
| Public Survey Section: | 08 |
| Zoning: | PURD |
| Spa Features: | Heated, In Ground |
| Spa?: | Yes |
| Vegetation: | Mature Landscaping, Oak Trees, Trees/Landscaped |
| Window Features: | Double Pane Windows, Shutters |
| Additional Lease Restrictions: | Buyer to verify any lease restrictions with the HOA and City. |
| Additional Rooms: | Bonus Room, Breakfast Room Separate, Den/Library/Office, Family Room, Formal Dining Room Separate, Inside Utility, Loft, Media Room |
| Additional Water Information: | 3 Boat Docks in the Windsong Community. Boat owned by HOA can be rented for a daily charge. |
| Alternate Key Folio Num: | 302208936300190 |
| Amenities Additional Fees: | Boat owned by HOA can be rental daily for an additional charge. |
| Association Approval Required Yn: | No |
| Association Email: | gashworth@lelandmanagement.com |
| Association Fee Requirement: | Required |
| Association Url: | https://www.lelandmanagement.com/community-portal/ |
| Available For Lease Yn: | Yes |
| Building Area Total Srch Sq M: | 613.25 |
| Calculated List Price By Calcula: | 619.61 |
| Cddyn: | No |
| Dprurl: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6395062?w=Agent&skip_sso=true |
| Dprurl 2: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6395062?w=Customer |
| Dpryn: | No |
| Exist Lse Tenant Yn: | No |
| Flood Zone Code: | X |
| Flood Zone Date: | 2009-09-25 |
| Flood Zone Panel: | 12095C0255F |
| Garage Dimensions: | 30X10 |
| Green Verification Count: | 0 |
| Homestead Yn: | Yes |
| Lease Restrictions Yn: | Yes |
| Listing Exclusion Yn: | No |
| Living Area Meters: | 404.69 |
| Lot Size Square Meters: | 1494 |
| Minimum Lease: | 8-12 Months |
| Monthly Hoa Amount: | $262 |
| Pet Restrictions: | Buyer to verify any pet restrictions with the HOA and City. |
| Room Count: | 9 |
| Sdeo yn: | No |
| Total Acreage: | 1/4 to less than 1/2 |
| Total Annual Fees: | $3,140 |
| Total Monthly Fees: | $262 |
| Unit Number Yn: | No |
| Water Access: | Lake |
| Water Access Yn: | Yes |
| Water Extras: | Boat Port, Fishing Pier |
| Water Extras Yn: | Yes |
| Water View: | No |
| Yrs Of Owner Prior To Leasing Re: | 0 |
| Association Name: | Leland Management/Greg Ashworth |
| Association Phone: | 407-781-1836 |
| Association 2 Yn: | 0 |
| Attribution Contact: | 407-474-0844 |
| Originating System Name : | Stellar MLS |
| Community Association Water Features: | Dock, Fishing, Lake, Water Access |
| Dock Yn: | No |
| In Law Suite Yn: | No |
| Green Energy Generation Yn: | No |
| Listing Contract Date: | 2026-04-01 |
| Fireplace?: | Yes |
| Pool Private?: | Yes |
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Property Last Updated: October 21, 2026 08:54 AM - ET
