1529 Holts Grove Circle, FL

$2,699,000

1529 Holts Grove Circle

Winter Park, FL 32789

Active
4
Beds
6
Baths
4,356
Sq Ft
0.37
Acres
2005
Built
Water accessPrivate poolFireplace3-car garage$620/sqft360° tour
Single Family Residence

Property type

2005

Year built

16,079 sqft

Lot size

$620

Price / sq ft

$262/mo

HOA dues

63

Days on market

3

Garage spaces

X

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

Principal & interest$13,648
Property taxes$1,779
Home insurance (est.)$1,237
HOA dues$262

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

  1. Status: Active
    Apr 1, 2026
  2. Listed$2,850,000
    Apr 1, 2026
  3. 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

ElementaryCBrookshire ElemGreatSchools ↗
MiddleAGlenridge MiddleGreatSchools ↗
High SchoolAWinter Park HighGreatSchools ↗

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

RoomLevelDimensions
KitchenFirst16x15
Living RoomFirst23x16
Dining RoomFirst13x12
DenFirst13x11
Primary BedroomFirst18x15
Bedroom 2Second16x12
Bedroom 3Second21x14
Bedroom 4Second14x12
Bonus RoomSecond21x18

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 riskFEMA Zone XPanel 12095C0255F

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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MLS GRID

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.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA