1529 HOLTS GROVE CIRCLE, Winter Park, FL, 32789 | $2,699,000

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 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.

Features

  • Amenities: Playground, Pool
  • Rooms: 9
  • Bedrooms: 4
  • Baths: 4 full / 2 half
  • Laundry: Inside, Laundry Room
  • Year Built: 2005
  • Garage: 3-car Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side, Oversized
  • Heating: Central, Electric, Heat Pump, Zoned
  • Cooling: Central Air, Humidity Control, Zoned
  • Approx Sq. Feet: 4,356
  • Acreage: 0.37
  • Est. Taxes: $21,342
  • HOA Fee: $785 Quarterly
  • Lot Desc: Corner Lot, Landscaped, Level, Sidewalk
  • Elem. School: Brookshire Elem
  • Middle School: Glenridge Middle
  • High School: Winter Park High
  • Pool: Child Safety Fence, Gunite, Heated, In Ground, Lighting, Salt Water, Tile
  • Pet Policy: Yes
  • Appliances: Bar Fridge, Dishwasher, Disposal, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Water Softener, Wine Refrigerator
  • MLS#: O6395062
  • Days on Market: 49 days
  • Website: https://www.raveis.com
    /eprop/O6395062/1529holtsgrovecircle_winterpark_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is 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. (last updated 5/31/2026 5:18:33 PM)
Listing courtesy of KGV REALTY GROUP   Phone: 407-474-0844

William Raveis Family of Services

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Melissa CohnRVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 16953

917.838.7300

Melissa.Cohn@raveis.com

Our Executive Mortgage Banker:

  • Is available to meet with you in our office, your home or office, evenings or weekends
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Our Insurance Division:

  • Will Provide a home insurance quote within 24 hours
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    Encompass, Travelers, Fireman's Fund, Middleoak Mutual, One Beacon and American Reliable

1529 HOLTS GROVE CIRCLE, Winter Park, FL, 32789

$2,699,000

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Melissa Cohn

RVP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 917.838.7300

Melissa.Cohn@raveis.com

NMLS Mortgage Loan Originator ID 16953

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $2,159,200 $2,159,200 $2,159,200
Term 360 months 360 months 180 months
Initial Interest Rate** 6.000% 6.125% 6.000%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.350% 6.259% 6.183%
Monthly Tax Payment $1,779 $1,779 $1,779
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $12,945 $13,120 $18,221
Total Monthly Payment $14,848 $15,023 $20,124

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.  The Total Monthly Payment does not include the estimated HOA/Common Charge payment.