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.
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.
Property Details
Price:
$495,500
MLS #:
O6408756
Status:
Active
Beds:
4
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
STONEYBROOK
Neighborhood:
32828orlandoalafayawaterfordlakes
Listed Date:
May 18, 2026
Finished Sq Ft:
1,877
Total Sq Ft:
2,419
Lot Size:
6,212 sqft / 0.14 acres (approx)
Year Built:
2001
See this Listing
Schools
Elementary School:
Stone Lake Elem
Middle School:
Avalon Middle
High School:
Timber Creek High
Interior
Appliances
Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Range Hood
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Ceramic Tile, Laminate
Heating
Electric
Interior Features
Cathedral Ceiling(s), Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Walk-In Closet(s), Window Treatments
Laundry Features
Laundry Room
Levels
One
Exterior
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)
Attached Garage YN
1
Community Features
Association Recreation – Owned, Clubhouse, Deed Restrictions, Fitness Center, Gated Community – Guard, Golf Carts OK, Golf, Park, Playground, Pool, Sidewalks, Tennis Court(s)
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
North
Exterior Features
Lighting, Sidewalk
Garage Spaces
2
Roof
Shingle
Security Features
Gated Community
Waterfront Features
Pond
Financial
HOA Fee
$752
HOA Fee Frequency
Quarterly
HOA Includes
24-Hour Guard, Cable TV, Community Pool, Escrow Reserves Fund, Maintenance Grounds, Manager, Pool Maintenance, Private Road, Recreational Facilities
HOA Name
Debra Zimmerman
HOA Phone
4072497930
Tax Year
2025
Taxes
$4,017
Map
Community
- Address2248 HILLSHIRE DRIVE ORLANDO FL
- SubdivisionSTONEYBROOK
- CityORLANDO
- CountyOrange
- Zip Code32828
Market Summary
Current real estate data for Single Family in ORLANDO as of Jul 23, 2026
3,105
Single Family Listed
99
Avg DOM
287
Avg $ / SqFt
$680,223
Avg List Price
Property Summary
- Located in the STONEYBROOK subdivision, 2248 HILLSHIRE DRIVE ORLANDO FL is a Single Family for sale in ORLANDO, FL, 32828. It is listed for $495,500 and features 4 beds, 2 baths, and has approximately 1,877 square feet of living space, and was originally constructed in 2001. The current price per square foot is $264. The average price per square foot for Single Family listings in ORLANDO is $287. The average listing price for Single Family in ORLANDO is $680,223. To schedule a showing of MLS#o6408756 at 2248 HILLSHIRE DRIVE in ORLANDO, FL, contact your agent at 407-583-9870.
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Courtesy of CHARLES RUTENBERG REALTY ORLANDO. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than include the name of the listing broker. Neither the listing company nor shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 2248 HILLSHIRE DRIVE
ORLANDO, FL