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$511,500 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1,877 Sq. Ft.
  • Updated 5 days ago
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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.

Full Property Details for 2248 Hillshire Dr

General

  • Price: $511,500
  • HOA FEE: $251/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $4,017 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6408756
  • Updated: 5/19/2026
  • Added to Site: 6 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 8
  • Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Walk-In Closet(s), Window Treatments
  • Appliances: Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Range Hood
  • Furnishings: Unfurnished
  • Flooring: Ceramic Tile, Laminate

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Shared 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)
  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Gunite, In Ground, Lighting
  • Security/Safety: Gated Community

Exterior

  • Exterior Features: Lighting, Sidewalk

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 32828 - Orlando/Alafaya/Waterford Lakes
  • County: Orange
  • Development Name: 32828 - Orlando/Alafaya/Waterford Lakes
  • Subdivision: STONEYBROOK
  • Driving Directions: From SR 408 go south on Alafaya Trail past Eastwood and turn left into the Stoneybrook community and stay in left lane for the guard to call the owner and see your license and for Realtors their Real Estate License.
  • Direction Faces: North

School Information

  • Elementary School: Stone Lake Elem
  • Middle School: Avalon Middle
  • High School: Timber Creek High

Community

  • Community Name: 32828 - Orlando/Alafaya/Waterford Lakes
  • Community Features: Association Recreation - Owned, Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf Carts OK, Golf, Park, Playground, Pool, Sidewalks, Tennis Court(s)
  • Optional Amenities: Basketball Court, Cable TV, Clubhouse, Fence Restrictions, Fitness Center, Gated, Golf Course, Maintenance,
  • Association: Yes
  • Assoc. Name: Debra Zimmerman
  • Assoc. Fees Include: 24-Hour Guard, Cable TV, Community Pool, Escrow Reserves Fund, Maintenance Grounds, Manager, Pool Maintenance, Private Road, Recreational Facilities
  • Pet Restrictions: check with the HOA

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable Connected, Electricity Connected, Phone Available, Public, Sprinkler Recycled, Water Connected

Structural Information

  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 1,877
  • Sq. Ft. Source: Public Records
  • Year Built: 2001

Lot Features

  • Lot Size (Acres): 0.14
  • Lot Size (Sq. Ft.): 6,212
  • Lot Size: 6212
  • Street/Road Desc.: Asphalt

Water Features

  • Water Front: Yes
  • Water Access: Yes
  • Water Access Desc: Pond
  • Water Front Desc.: Pond

Financial Considerations

  • Association Fee: $752
  • Assoc Fee Freq.: Quarterly
  • Assoc Fee Desc.: Required
  • Tax Amount: $4,017
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: STONEYBROOK UNIT 5 42/33 LOT 69 BLK 15
  • Flood Zone Info: X
  • APN: 12331198615069
  • Property ID: 12331198615069
  • Block/Lot/Section: 15

Listed by Charles Rutenberg Realty Orlando

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Listing agent

— 2248 Hillshire Dr —

  • Charles Rutenberg Realty Orlando

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 2248 Hillshire Dr

School District:Orange County School District
NameGradesDistance
Stone Lakes Elementary School
15200 Stoneybrook Boulevard, Orlando, FL 32828
K-50.7 mi
Timber Creek High School
1001 Avalon Park Boulevard, Orlando, FL 32828
9-121 mi
Avalon Middle School, Orlando, FL
13914 Mailer Boulevard, Orlando, FL 32828
6-81.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2248 Hillshire Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/18/2026
Listed
$511,500
96.73%
MLS
6/30/2015
Sold
$260,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2248 Hillshire Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,017
6%
$272,424
6%
2024
$3,807
7%
$257,786
3%
2023
$3,546
6%
$250,278
6%
2021
$3,358
-2%
$235,911
-3%
2022
$3,416
2%
$242,988
4%
2021
$3,358
2%
$232,654
2%
2019
$3,283
1%
$227,423
2%
2018
$3,255
2%
$223,183
2%
2017
$3,205
1%
$218,593
2%
2016
$3,178
-14%
$214,097
7%
2015
$3,701
6%
$199,705
10%
2014
$3,500
11%
$181,550
10%
2013
$3,165
—
$165,045
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Charles Rutenberg Realty Orlando

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2248 Hillshire Drive, Orlando, FL 32828 (MLS# O6408756) is a Single Family property with 4 bedrooms and 2 full bathrooms. 2248 Hillshire Drive is currently listed for $511,500 and was received on May 18, 2026. Want to learn more about 2248 Hillshire Drive? Do you have questions about finding other Single Family real estate for sale in Orlando? You can browse all Orlando real estate or contact a Coldwell Banker agent to request more information.

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