Skip main navigation
For sale
    • $205,000

    499 CLUB DRIVE, WINTER SPRINGS, FL 32708

    2beds
    1,224sqft
    : 
    $1,993/mo
    Get pre-qualified
    Townhouse
    Built in 1987
    1,294 Square Feet Lot
    $-- Zestimate®
    $167/sqft
    $556/mo HOA

    What's special

    Virtually Staged. As you arrive at this beautiful 2 bedroom + loft, 2 bath residence in a serene townhome community within The Highlands in Winter Springs, you’ll note a feeling of privacy, relaxation, and tranquility among the lush landscaping, fantastic amenities, and peaceful walking trails. TOUR THE HOUSE WITH THE VIRTUAL TOUR AND WALK THRU VIDEO LINKS. Step inside to a spacious open floorplan where light bathes the soaring vaulted ceilings and tile flooring runs throughout the main living areas. The family cook will enjoy preparing meals among the new appliances (2022) in the functional kitchen layout, while overlooking the great room and exterior nature views. Step out to the screened patio to enjoy your morning coffee, where you’ll also find an outside storage closet offering a convenient place for your bikes, tools, or gardening supplies. The layout of this home offers double suites, thoughtfully split between the two levels, each with a full bath with shower/tub combo. Upstairs, a bonus loft provides an ideal flex space for a home office, reading nook, or more! Life here is stress-free with a new roof (2026) and A/C (2023), and 2 reserved parking spaces, side-by-side, right outside your front door. Beyond the home itself, this community provides you a carefree lifestyle with the HOA taking care of exterior maintenance and landscaping, leaving you plenty of time to meet up with friendly neighbors to enjoy the private community pool within the neighborhood, as well as the Highlands’ exceptional amenities -- including a junior Olympic-size lap pool, tennis/pickleball courts, clubhouse, playground, and picnic areas, perfect for relaxing moments or social gatherings. Conveniently located with easy access to main thoroughfares, everyday conveniences are close by -- groceries, restaurants, shopping, banks, fitness centers, etc. – as well as top-rated Seminole County schools. Come see why your new neighbors already love to call the area home and are enjoying the care-free lifestyle you deserve!!
    5 days
    201
    19

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Chris Winn 407-970-6776,

    BLOOM HOME GROUP REALTY LLC 407-434-9408

    Source: Stellar MLS,MLS#: O6447987MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 2
      • Bathrooms: 2
      • Full bathrooms: 2
      Rooms
      • Room types: Loft
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: Second
      • Area: 182 Square Feet
      • Dimensions: 14x13
      Bedroom 1
      • Features: Built-in Closet
      • Level: First
      • Area: 130 Square Feet
      • Dimensions: 13x10
      Bathroom 1
      • Level: First
      • Area: 50 Square Feet
      • Dimensions: 10x5
      Bathroom 2
      • Level: Second
      • Area: 50 Square Feet
      • Dimensions: 10x5
      Kitchen
      • Level: First
      • Area: 80 Square Feet
      • Dimensions: 10x8
      Living room
      • Level: First
      • Area: 323 Square Feet
      • Dimensions: 19x17
      Loft
      • Level: Second
      • Area: 110 Square Feet
      • Dimensions: 11x10
      Heating
      • Central, Electric
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
      • Laundry: Laundry Closet, Upper Level
      Features
      • Cathedral Ceiling(s), Ceiling Fan(s), High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Vaulted Ceiling(s)
      • Flooring: Carpet, Laminate, Tile
      • Doors: Sliding Doors
      • Has fireplace: No
      Interior area
      • Total structure area: 1,280
      • Total interior livable area: 1,224 sqft
      Video & virtual tour

      Property

      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Covered, Patio, Screened
      Lot
      • Size: 1,294 Square Feet
      Details
      • Parcel number: 3320305HY00000720
      • Zoning: PUD
      • Special conditions: None

      Construction

      Type & style
      • Home type: Townhouse
      • Property subtype: Townhouse
      Materials
      • Block, Stucco
      • Foundation: Slab
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 1987

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Public

      Community & HOA

      Community
      • Features: Clubhouse, Community Mailbox, Deed Restrictions, Park, Playground, Pool, Tennis Court(s)
      • Pet fee: $0 monthly
      • Subdivision: CYPRESS CLUB
      HOA
      • Has HOA: Yes
      • Amenities included: Clubhouse, Park, Pickleball Court(s), Playground, Pool, Tennis Court(s)
      • Services included: Community Pool, Maintenance Structure, Maintenance Grounds
      • HOA fee: $556 monthly
      • HOA name: Michelle Pogue
      • HOA phone: 407-788-6700
      • Second HOA name: The Highlands
      • Second HOA phone: 407-770-1748
      Location
      • Region: Winter Springs

      Financial & listing details

      • Price per square foot: $167/sqft
      • Tax assessed value: $205,350
      • Annual tax amount: $2,064
      • Date on market: 10/13/2026
      • Cumulative days on market: 198 days
      • Listing terms: Cash,Conventional,FHA,VA Loan
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Road surface type: Asphalt

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        10/14/2026Listed for sale$205,000-2.4%$167/sqft
        Source: Stellar MLS #O6447987 Report a problem
        10/1/2026Listing removed$210,000$172/sqft
        Source: Stellar MLS #O6391855 Report a problem
        8/10/2026Price change$210,000-4.3%$172/sqft
        Source: Stellar MLS #O6391855 Report a problem
        7/14/2026Price change$219,500-6.6%$179/sqft
        Source: Stellar MLS #O6391855 Report a problem
        5/12/2026Price change$235,000-5.1%$192/sqft
        Source: Stellar MLS #O6391855 Report a problem
        4/8/2026Price change$247,500-2.9%$202/sqft
        Source: Stellar MLS #O6391855 Report a problem
        3/20/2026Listed for sale$255,000-5.6%$208/sqft
        Source: Stellar MLS #O6391855 Report a problem
        8/1/2022Sold$270,000+8.4%$221/sqft
        Source: Public Record Report a problem
        7/5/2022Pending sale$249,000$203/sqft
        Source: Stellar MLS #O6038322 Report a problem
        6/27/2022Listed for sale$249,000+49.1%$203/sqft
        Source: Stellar MLS #O6038322 Report a problem
        6/8/2020Sold$167,000-1.1%$136/sqft
        Source: Public Record Report a problem
        4/27/2020Pending sale$168,900$138/sqft
        Source: RE/MAX PRIME PROPERTIES #O5858896 Report a problem
        4/22/2020Listed for sale$168,900+50.8%$138/sqft
        Source: RE/MAX PRIME PROPERTIES #O5858896 Report a problem
        3/2/2015Sold$112,000+85.1%$92/sqft
        Source: Stellar MLS #O5328935 Report a problem
        3/29/2011Sold$60,500+2.5%$49/sqft
        Source: Public Record Report a problem
        2/11/2011Listed for sale$59,000$48/sqft
        Source: Stirling Sotheby's International Realty Heathrow Gallery #o4968506 Report a problem
        12/5/2010Listing removed$59,000$48/sqft
        Source: Stirling Sotheby's International Realty Heathrow Gallery #o4968506 Report a problem
        9/15/2010Price change$59,000-30.6%$48/sqft
        Source: Stirling Sotheby's International Realty #O4968506 Report a problem
        6/23/2010Price change$85,000-10.5%$69/sqft
        Source: Stirling Sotheby's International Realty Heathrow Gallery #o4968506 Report a problem
        6/5/2010Listed for sale$95,000+72.7%$78/sqft
        Source: Stirling Sotheby's International Realty Heathrow Gallery #o4968506 Report a problem
        10/5/1993Sold$55,000$45/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$1,987 +6.3%$165,128 +2.9%
        2024$1,868 +4.6%$160,474 +3%
        2023$1,786 -29.8%$155,800 +1%
        2022$2,543 +12.6%$154,310 +10%
        2021$2,258 +106.5%$140,282 +29.6%
        2020$1,093 +2%$108,271 +2.3%
        2019$1,072 $105,837 +1.9%
        2018$1,072 +1.4%$103,864 +2.1%
        2017$1,057 +1.4%$101,728 +3%
        2016$1,042 -37.9%$98,728 +27.6%
        2015$1,677 $77,400 +3.5%
        2014$1,677 +34.2%$74,799 +10.4%
        2013$1,249 +8.7%$67,767 +4.9%
        2012$1,150 +50.8%$64,585 -20.9%
        2011$762 -21%$81,643 -11.6%
        2010$965 -13.7%$92,348 -8.7%
        2009$1,118 -16.4%$101,110 -12.5%
        2008$1,338 -2.2%$115,558 +3%
        2007$1,367 -8.8%$112,192 +2.5%
        2006$1,500 +0.4%$109,456 +3%
        2005$1,494 +101.7%$106,268 +64.5%
        2004$741 +1.8%$64,612 +1.9%
        2003$727 +4.6%$63,407 +2.4%
        2002$695 +10.2%$61,921 +4.6%
        2000$631 $59,171
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        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.
        See how much you could borrow to make a competitive offer.
        Get pre-qualified

        Climate risks

        Neighborhood: 32708

        Getting around

        7 / 100
        Car-Dependent
        27 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

        A local agent can set up tours, give advice and negotiate with sellers.

        Browse local experts

        Similar homes

                Nearby cities

                Nearby zip codes

                Other Winter Springs Topics

                  Search
                  Updates
                  Favorites
                  Plan
                  Inbox