Skip main navigation
For sale
    • Price cut: $16K (6/9)
    $495,500

    2248 HILLSHIRE DRIVE, ORLANDO, FL 32828

    4beds
    1,877sqft
    : 
    $3,530/mo
    Get pre-qualified
    Single Family Residence
    Built in 2001
    6,212 Square Feet Lot
    $-- Zestimate®
    $264/sqft
    $251/mo HOA

    What's special

    Beautiful viewsNew patio door
    Beautifully maintained 4-bedroom, 2-bath pool home nestled on a serene pond and conservation lot — truly your own little piece of paradise in Southeast Orlando. The backyard is a private retreat featuring elegant cast iron fencing draped in fragrant jasmine, creating a peaceful setting perfect for relaxing, entertaining, or enjoying the water views and fishing right from your backyard. This move-in ready home has been thoughtfully updated throughout. Exterior was freshly painted in 2020, roof replaced in December 2019, and the entire interior was repainted in 2022 with cheerful coastal-inspired “Key West” colors and beach-themed charm. The covered lanai features brand new screens installed in 2023 along with a new patio door, while the pool deck and porches have been freshly refinished with Sherwin-Williams pool deck paint. Located within a gated, guard-monitored community offering added privacy and security, with driver’s license verification and owner approval required for entry. Conveniently situated just 30 minutes to Downtown Orlando, Disney, and countless Central Florida attractions, plus only 30–45 minutes to the beaches via SR 528 and I-95. Waterford Lakes shopping, dining, and entertainment are just 15 minutes away. Enjoy Florida living at its finest with beautiful views, thoughtful updates, and an unbeatable location.
    93 days
    |
    1,133
    |
    72
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Diane Molaka 407-222-4270,

    CHARLES RUTENBERG REALTY ORLANDO 407-622-2122

    Source: Stellar MLS,MLS#: O6408756MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 2
      • Full bathrooms: 2
      Rooms
      • Room types: Family Room
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: First
      • Area: 225 Square Feet
      • Dimensions: 15x15
      Bathroom 2
      • Features: Built-in Closet
      • Level: First
      • Area: 110 Square Feet
      • Dimensions: 11x10
      Bathroom 3
      • Features: Built-in Closet
      • Level: Basement
      • Area: 110 Square Feet
      • Dimensions: 11x10
      Bathroom 4
      • Features: Built-in Closet
      • Level: First
      • Area: 110 Square Feet
      • Dimensions: 11x10
      Dining room
      • Level: First
      • Area: 110 Square Feet
      • Dimensions: 11x10
      Family room
      • Level: First
      • Area: 336 Square Feet
      • Dimensions: 24x14
      Kitchen
      • Level: First
      • Area: 108 Square Feet
      • Dimensions: 12x9
      Living room
      • Level: First
      • Area: 110 Square Feet
      • Dimensions: 11x10
      Heating
      • Electric
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Range Hood
      • Laundry: Laundry Room
      Features
      • Cathedral Ceiling(s), Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Walk-In Closet(s)
      • Flooring: Ceramic Tile, Laminate
      • Windows: Window Treatments
      • Has fireplace: No
      Interior area
      • Total structure area: 2,419
      • Total interior livable area: 1,877 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage - Attached
      • Attached garage spaces: 2
      Features
      • Levels: One
      • Stories: 1
      • Exterior features: Lighting, Sidewalk
      • Has private pool: Yes
      • Pool features: Gunite, In Ground, Lighting
      • Has view: Yes
      • View description: Pond
      • Has water view: Yes
      • Water view: Pond
      • Waterfront features: Pond, Pond Access
      Lot
      • Size: 6,212 Square Feet
      Details
      • Parcel number: 012331198615069
      • Zoning: P-D
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Block, Stucco
      • Foundation: Concrete Perimeter
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 2001

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Connected, Electricity Connected, Phone Available, Public, Sprinkler Recycled, Water Connected

      Community & HOA

      Community
      • Features: Association Recreation - Owned, Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf Carts OK, Golf, Park, Playground, Pool, Sidewalks, Tennis Court(s)
      • Security: Gated Community
      • Pet fee: $0 monthly
      • Subdivision: STONEYBROOK
      HOA
      • Has HOA: Yes
      • Amenities included: Basketball Court, Cable TV, Clubhouse, Fence Restrictions, Fitness Center, Gated, Golf Course, Maintenance, Pickleball Court(s), Playground, Pool, Sauna, Tennis Court(s), Trail(s)
      • Services included: 24-Hour Guard, Cable TV, Community Pool, Reserve Fund, Maintenance Grounds, Manager, Pool Maintenance, Private Road, Recreational Facilities
      • HOA fee: $251 monthly
      • HOA name: Debra Zimmerman
      • HOA phone: 407-249-7930
      Location
      • Region: Orlando

      Financial & listing details

      • Price per square foot: $264/sqft
      • Tax assessed value: $416,035
      • Annual tax amount: $4,017
      • Date on market: 5/18/2026
      • Cumulative days on market: 86 days
      • Listing terms: Cash,Conventional,FHA,VA Loan
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Asphalt

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        6/9/2026Price change$495,500-3.1%$264/sqft
        Source: Stellar MLS #O6408756 Report a problem
        5/18/2026Listed for sale$511,500+96.7%$273/sqft
        Source: Stellar MLS #O6408756 Report a problem
        6/30/2015Sold$260,000-1.9%$139/sqft
        Source: Stellar MLS #O5369718 Report a problem
        6/4/2015Pending sale$265,000$141/sqft
        Source: KELLER WILLIAMS ADVANTAGE RLTY #O5369718 Report a problem
        5/29/2015Listed for sale$265,000+56.8%$141/sqft
        Source: KELLER WILLIAMS ADVANTAGE RLTY #O5369718 Report a problem
        4/18/2015Listing removed$1,900$1/sqft
        Source: Owner Report a problem
        3/19/2015Listed for rent$1,900-2.6%$1/sqft
        Source: Owner Report a problem
        4/8/2014Listing removed$1,950$1/sqft
        Source: N/A Report a problem
        1/15/2014Listed for rent$1,950$1/sqft
        Source: N/A Report a problem
        10/1/2001Sold$169,000$90/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$3,807 +7.4%$257,786 +3%
        2023$3,546 +3.8%$250,278 +3%
        2022$3,416 +1.7%$242,988 +3%
        2021$3,358 +0.9%$235,911 +1.4%
        2020$3,329 +1.4%$232,654 +2.3%
        2019$3,283 +0.9%$227,423 +1.9%
        2018$3,255 $223,183 -0.1%
        2017$3,255 +1.5%$223,493 +4.4%
        2016$3,205 +0.9%$214,097 +5.2%
        2015$3,178 -9.2%$203,477 +7.8%
        2014$3,500 +10.6%$188,766 +11.7%
        2013$3,165 +9.7%$169,044 +12.7%
        2012$2,886 -4.3%$150,041 -4.3%
        2011$3,014 +1.7%$156,702 -1.4%
        2010$2,964 $158,943 -20%
        2009-- $198,602 -21.7%
        2008$4,394 -9.6%$253,752 -11.4%
        2007$4,862 +76.4%$286,345 +7.4%
        2006$2,756 +0.7%$266,718 +50.3%
        2005$2,735 +4.7%$177,493 +1.6%
        2004$2,612 +0.4%$174,615 +9.7%
        2003$2,602 +12.5%$159,235 +12.8%
        2002$2,314 $141,214
        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: Alafaya

        Getting around

        2 / 100
        Car-Dependent
        0 / 100
        No Nearby Transit
        34 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Stone Lake Elem
        • Middle: Avalon Middle
        • High: Timber Creek High

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

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

        A local lender can help you make sure your offer is ready when you are.

        Browse local experts

        Similar homes

              Nearby cities

              Nearby neighborhoods

              Nearby zip codes

              Other Orlando Topics

                Search
                Updates
                Favorites
                Plan
                Inbox