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Single family home for sale at 2248 Hillshire Dr, Orlando, FL 32828 | MLS# O6408756 | Listing updated on 2026-09-01
Photo 1 of Single family home for sale at 2248 Hillshire Dr, Orlando, FL 32828 | MLS# O6408756 | Listing updated on 2026-09-01
Photo 2 of Single family home for sale at 2248 Hillshire Dr, Orlando, FL 32828 | MLS# O6408756 | Listing updated on 2026-09-01
Photo 3 of Single family home for sale at 2248 Hillshire Dr, Orlando, FL 32828 | MLS# O6408756 | Listing updated on 2026-09-01
Photo 4 of Single family home for sale at 2248 Hillshire Dr, Orlando, FL 32828 | MLS# O6408756 | Listing updated on 2026-09-01
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$495,500

Monthly Est:$2,466

  • Beds Icon4 Beds
  • Beds Icon
    2 Baths
  • Beds Icon1,877sqft

2248 Hillshire Dr, Orlando, FL 32828

$2,466/moEst:

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  • Single Family Residence

  • Built in 2001

  • $250.67/mo HOA

  • 6,212 sqft lot

  • $264/sq.ft

Description

Under contract-accepting backup offers. 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 ch
arm. 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.

  • Houzeo last checked: 4 minutes ago
  • Listing updated: September 1, 2026 at 11:52 pm
  • Listing Provided by: Diane Molaka (407) 222-4270 | CHARLES RUTENBERG REALTY ORLANDO (407) 622-2122
  • Source: Stellar MLS-FL | MLS#: O6408756 Stellar MLS-FL

Property Details

  • Status

    Active Under Contract

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Orange County

  • City

    Orlando

  • Neighborhood

    --

  • Year Built

    2001

  • HOA Fees

    $250.67/mo

  • Finished Area

    1,877 sqft

  • Lot Size

    6,212 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Stellar MLS

  • MLS Number

    O6408756

  • MLS Status

    Pending

  • Days on Market

    145

  • Cumulative Days on Market

    106

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Location

HOA Management

Debra Zimmerman

HOA Fees

$752/ Quarterly

Amenities

Amenities and services may be covered by one or multiple associations and service providers.

Cable TV Cable TV

Club House Club House

Pool Pool

Gym Gym

Golf Golf

Security Gate Security Gate

Maintenance Maintenance

Security Guard Security Guard

Bike Trails Bike Trails

Basket Ball Basket Ball

Spa Spa

Park Playground Park Playground

Tennis Tennis

Sports Court Sports Court

Recreational Facilities Recreational Facilities

Management Management

Escrow Reserves Fund Escrow Reserves Fund

Private Road Private Road

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 2

  • Primary Bedroom

    Level: First

    Area: 225.00 Square Feet

    Dimensions: 15x15

  • Bathroom 2

    Level: First

    Area: 110.00 Square Feet

    Dimensions: 11x10

  • Bathroom 3

    Level: Basement

    Area: 110.00 Square Feet

    Dimensions: 11x10

  • Bathroom 4

    Level: First

    Area: 110.00 Square Feet

    Dimensions: 11x10

  • Living Room

    Level: First

    Area: 110.00 Square Feet

    Dimensions: 11x10

  • Dining Room

    Level: First

    Area: 110.00 Square Feet

    Dimensions: 11x10

  • Kitchen

    Level: First

    Area: 108.00 Square Feet

    Dimensions: 12x9

  • Family Room

    Level: First

    Area: 336.00 Square Feet

    Dimensions: 24x14

Interior

  • Appliances

    Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Range Hood

  • Flooring

    Ceramic Tile, Laminate

  • Sewer

    Public Sewer

  • Heating

    Electric

  • Exterior Features

    Lighting, Sidewalk

  • Interior Features

    Cathedral Ceiling(s), Ceiling Fans(s), Eat In Kitchen, High Ceilings, Kitchen/family Room Combo, Walk In Closet(s), Window Treatments

  • Cooling

    Central Air

Construction

  • Year Built

    Year Built: 2001

  • Home type

    Single Family Residence

  • Foundation Details

    Concrete Perimeter

  • Roof

    Shingle

  • Construction Materials

    Block, Stucco

Utilities & Energy

  • Association Amenities

    Basketball Court, Cable Tv, Clubhouse, Fence Restrictions, Fitness Center, Gated, Golf Course, Maintenance, Pickleball Court(s), Playground, Pool, Sauna, Tennis Court(s), Trail(s)

  • Laundry Features

    Laundry Room

  • Utilities

    Cable Connected, Electricity Connected, Phone Available, Public, Sprinkler Recycled, Water Connected

  • Security Features

    Gated Community

  • Water Source

    Public

  • Pool Features

    Gunite, In Ground, Lighting

Other Features

  • Subdivision Name

    Stoneybrook

  • Community Features

    Association Recreation Owned, Clubhouse, Deed Restrictions, Fitness Center, Gated Community Guard, Golf Carts Ok, Golf, Park, Playground, Pool, Sidewalks, Tennis Court(s)

Price History

DateEventPrice

09/01/2026

Source: mls_logoStellar MLS-FL #MFRO6408756

Contingent (Active Under Contract)

$495,500

$264/sqft

06/09/2026

Source: mls_logoStellar MLS-FL #MFRO6408756

Price Decreased

$495,500 -3.13%

$264/sqft

05/18/2026

Source: mls_logoStellar MLS-FL #MFRO6408756

Listed for Sale

$511,500

$273/sqft

05/18/2026

Source: mls_logoStellar MLS-FL #MFRO6408756

Price Increased

$511,500 +96.73%

$273/sqft

06/30/2015

Source: mls_logoStellar MLS-FL #MFRO5369718

Price Decreased

$260,000 -1.89%

$139/sqft

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Nearby Homes

Based on information from Stellar MLS® through Oct 11, 2026, 05:15AM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the 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. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.

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