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Under contract
    • Price cut: $96K (5/18)
    $2,699,000

    1529 HOLTS GROVE CIRCLE, WINTER PARK, FL 32789

    4beds
    4,356sqft
    : 
    $18,625/mo
    Get pre-qualified
    Single Family Residence
    Built in 2005
    0.37 Acres Lot
    $-- Zestimate®
    $620/sqft
    $262/mo HOA

    What's special

    Three-car garageAdditional powder bathSun deck platformComprehensive security camera systemExtensive storageWhole-home surround sound systemMonogram built-in microwave
    Under contract-accepting backup offers. 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.
    132 days
    |
    125
    |
    3
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Kristin Vogt PLLC 407-417-7206,

    KGV REALTY GROUP 407-474-0844

    Source: Stellar MLS,MLS#: O6395062MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 6
      • Full bathrooms: 4
      • 1/2 bathrooms: 2
      Rooms
      • Room types: Bonus Room, Breakfast Room Separate, Den/Library/Office, Family Room, Dining Room, Utility Room, Loft, Media Room
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: First
      • Area: 270 Square Feet
      • Dimensions: 18x15
      Bedroom 2
      • Features: Built-in Closet
      • Level: Second
      • Area: 192 Square Feet
      • Dimensions: 16x12
      Bedroom 3
      • Features: Built-in Closet
      • Level: Second
      • Area: 294 Square Feet
      • Dimensions: 21x14
      Bedroom 4
      • Features: Built-in Closet
      • Level: Second
      • Area: 168 Square Feet
      • Dimensions: 14x12
      Bonus room
      • Features: No Closet
      • Level: Second
      • Area: 378 Square Feet
      • Dimensions: 21x18
      Den
      • Level: First
      • Area: 143 Square Feet
      • Dimensions: 13x11
      Dining room
      • Level: First
      • Area: 156 Square Feet
      • Dimensions: 13x12
      Kitchen
      • Features: Granite Counters, Kitchen Island, Pantry
      • Level: First
      • Area: 240 Square Feet
      • Dimensions: 16x15
      Living room
      • Level: First
      • Area: 368 Square Feet
      • Dimensions: 23x16
      Heating
      • Central, Electric, Heat Pump, Zoned
      Cooling
      • Central Air, Humidity Control, Zoned
      Appliances
      • Included: Bar Fridge, Dishwasher, Disposal, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Water Softener, Wine Refrigerator
      • Laundry: Inside, Laundry Room
      Features
      • Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Coffered Ceiling(s), Crown Molding, Eating Space 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
      • Flooring: Engineered Hardwood, Porcelain Tile, Tile
      • Doors: French Doors, Outdoor Grill, Outdoor Kitchen
      • Windows: Hurricane Shutters
      • Has fireplace: Yes
      • Fireplace features: Family Room, Gas
      Interior area
      • Total structure area: 6,601
      • Total interior livable area: 4,356 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 3
      • Parking features: Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side, Oversized
      • Attached garage spaces: 3
      • Has uncovered spaces: Yes
      • Details: Garage Dimensions: 30X10
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Covered, Enclosed, Patio, Rear Porch, Screened, Side Porch
      • Exterior features: Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Sidewalk
      • Has private pool: Yes
      • Pool features: Child Safety Fence, Gunite, Heated, In Ground, Lighting, Salt Water, Tile
      • Has spa: Yes
      • Spa features: Heated, In Ground
      • Fencing: Fenced
      • Waterfront features: Lake, Lake Privileges, Boat Port, Fishing Pier
      Lot
      • Size: 0.37 Acres
      • Features: Corner Lot, Landscaped, Level, Sidewalk
      • Residential vegetation: Mature Landscaping, Oak Trees, Trees/Landscaped
      Details
      • Parcel number: 082230936300190
      • Zoning: PURD
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Block, Stone, Stucco
      • Foundation: Slab
      • Roof: Tile
      Condition
      • New construction: No
      • Year built: 2005

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Available, Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Sprinkler Meter, Water Connected

      Community & HOA

      Community
      • Features: Dock, Fishing, Lake, Water Access, Association Recreation - Owned, Deed Restrictions, Golf Carts OK, Playground, Pool, Sidewalks, Special Community Restrictions
      • Security: Security System, Security System Owned, Smoke Detector(s)
      • Pet fee: $0 monthly
      • Subdivision: WINDSONG LAKESIDE SEC 02 43/71
      HOA
      • Has HOA: Yes
      • Amenities included: Playground, Pool
      • Services included: Community Pool, Pool Maintenance, Recreational Facilities
      • HOA fee: $262 monthly
      • HOA name: Leland Management/Greg Ashworth
      • HOA phone: 407-781-1836
      Location
      • Region: Winter Park

      Financial & listing details

      • Price per square foot: $620/sqft
      • Tax assessed value: $1,562,551
      • Annual tax amount: $21,342
      • Date on market: 4/1/2026
      • Cumulative days on market: 78 days
      • Listing terms: Cash,Conventional
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved, Asphalt

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        7/8/2026Contingent$2,699,000$620/sqft
        Source: Stellar MLS #O6395062 Report a problem
        6/16/2026Pending sale$2,699,000$620/sqft
        Source: Stellar MLS #O6395062 Report a problem
        5/18/2026Price change$2,699,000-3.4%$620/sqft
        Source: Stellar MLS #O6395062 Report a problem
        4/21/2026Price change$2,795,000-1.9%$642/sqft
        Source: Stellar MLS #O6395062 Report a problem
        4/1/2026Listed for sale$2,850,000+115.1%$654/sqft
        Source: Stellar MLS #O6395062 Report a problem
        2/18/2019Sold$1,325,000-11.7%$304/sqft
        Source: Public Record Report a problem
        12/21/2018Pending sale$1,500,000$344/sqft
        Source: Coldwell Banker Residential Real Estate - Winter Park #O5709713 Report a problem
        8/23/2018Price change$1,500,000-6.3%$344/sqft
        Source: Coldwell Banker Residential Real Estate - Winter Park #O5709713 Report a problem
        6/17/2018Price change$1,600,000-5.9%$367/sqft
        Source: Coldwell Banker Residential Real Estate - Winter Park #O5709713 Report a problem
        5/25/2018Listed for sale$1,700,000+28.8%$390/sqft
        Source: COLDWELL BANKER RESIDENTIAL RE #O5709713 Report a problem
        3/17/2014Sold$1,320,000-5.4%$303/sqft
        Source: Stellar MLS #O5174620 Report a problem
        1/25/2014Price change$1,395,000-3.1%$320/sqft
        Source: Kelly Price & Company #O5174620 Report a problem
        1/4/2014Price change$1,440,000-2.4%$331/sqft
        Source: Kelly Price & Company #O5174620 Report a problem
        8/1/2013Listed for sale$1,475,000+28.3%$339/sqft
        Source: Kelly Price & Company #O5174620 Report a problem
        9/3/2010Sold$1,150,000-11.2%$264/sqft
        Source: Public Record Report a problem
        6/26/2010Price change$1,295,000-2.3%$297/sqft
        Source: NRT Florida #O4985760 Report a problem
        6/6/2010Listed for sale$1,325,000-11%$304/sqft
        Source: NRT Florida #O4985760 Report a problem
        8/9/2009Listing removed$1,489,000$342/sqft
        Source: NRT Florida #O4898014 Report a problem
        6/28/2009Price change$1,489,000-6.1%$342/sqft
        Source: NRT Florida #O4898014 Report a problem
        2/20/2009Listed for sale$1,585,000+6%$364/sqft
        Source: NRT Florida #O4898014 Report a problem
        6/24/2005Sold$1,495,000+500.9%$343/sqft
        Source: Public Record Report a problem
        4/2/2001Sold$248,800$57/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$20,706 +3.6%$1,343,664 +3%
        2023$19,988 +5.1%$1,304,528 +3%
        2022$19,013 +1%$1,266,532 +3%
        2021$18,828 -0.3%$1,229,643 +1.4%
        2020$18,877 -5.1%$1,212,666 -0.2%
        2019$19,887 -2.8%$1,215,571 -4.4%
        2018$20,463 $1,271,602 -4%
        2017$20,463 +0.8%$1,324,054 +1.8%
        2016$20,304 +2%$1,300,031 +7.3%
        2015$19,900 +19.6%$1,211,353 +8.3%
        2014$16,646 +2.1%$1,118,620 +6.5%
        2013$16,307 +1%$1,050,160 +7.5%
        2012$16,149 +2.7%$977,130 +6%
        2011$15,719 -3%$921,570 -2%
        2010$16,211 $940,566 -18.9%
        2009-- $1,160,173 -13%
        2008$21,269 -7.4%$1,333,776 -5.2%
        2007$22,958 -3.6%$1,406,948 +5.9%
        2006$23,812 +241%$1,328,387 +254.2%
        2005$6,983 +51.2%$375,000 +50%
        2004$4,618 +3.4%$250,000
        2003$4,466 +0.1%$250,000
        2002$4,464 $250,000
        Find assessor info on the county website

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 32789

        Getting around

        32 / 100
        Car-Dependent
        28 / 100
        Some Transit
        35 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Brookshire Elem
        • Middle: Glenridge Middle
        • High: Winter Park High

        Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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