Listings

ORLANDO, FL 32828 2248 HILLSHIRE DRIVE

2248 HILLSHIRE DRIVE ORLANDO, FL - Image 12248 HILLSHIRE DRIVE ORLANDO, FL - Image 22248 HILLSHIRE DRIVE ORLANDO, FL - Image 3
25 more
2248 HILLSHIRE DRIVE ORLANDO, FL - Image 42248 HILLSHIRE DRIVE ORLANDO, FL - Image 52248 HILLSHIRE DRIVE ORLANDO, FL - Image 62248 HILLSHIRE DRIVE ORLANDO, FL - Image 72248 HILLSHIRE DRIVE ORLANDO, FL - Image 82248 HILLSHIRE DRIVE ORLANDO, FL - Image 92248 HILLSHIRE DRIVE ORLANDO, FL - Image 102248 HILLSHIRE DRIVE ORLANDO, FL - Image 112248 HILLSHIRE DRIVE ORLANDO, FL - Image 122248 HILLSHIRE DRIVE ORLANDO, FL - Image 132248 HILLSHIRE DRIVE ORLANDO, FL - Image 142248 HILLSHIRE DRIVE ORLANDO, FL - Image 152248 HILLSHIRE DRIVE ORLANDO, FL - Image 162248 HILLSHIRE DRIVE ORLANDO, FL - Image 172248 HILLSHIRE DRIVE ORLANDO, FL - Image 182248 HILLSHIRE DRIVE ORLANDO, FL - Image 192248 HILLSHIRE DRIVE ORLANDO, FL - Image 202248 HILLSHIRE DRIVE ORLANDO, FL - Image 212248 HILLSHIRE DRIVE ORLANDO, FL - Image 222248 HILLSHIRE DRIVE ORLANDO, FL - Image 232248 HILLSHIRE DRIVE ORLANDO, FL - Image 242248 HILLSHIRE DRIVE ORLANDO, FL - Image 252248 HILLSHIRE DRIVE ORLANDO, FL - Image 262248 HILLSHIRE DRIVE ORLANDO, FL - Image 272248 HILLSHIRE DRIVE ORLANDO, FL - Image 282248 HILLSHIRE DRIVE ORLANDO, FL - Image 29
Presented By: CHARLES RUTENBERG REALTY ORLANDO with 407-622-2122. - 407-622-2122
  • MLS# O6408756
  • 05/18/2026
  • Request Tour
  • Request Info
  • Beds • 4
  • Baths • 2
  • SQFT • 1,877
  • Garage • 2

Home Details

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. Seller is contributing $5,500. towards buyers closing cost & or prepaids at closing with an acceptable sales price.
Presented By: CHARLES RUTENBERG REALTY ORLANDO with 407-622-2122. - 407-622-2122

Interior Features for 2248 HILLSHIRE DRIVE

Bedrooms

Total Bedrooms4

Bathrooms

Half Baths0
Total Baths2

Other Interior Features

LivingAreaSourcePublic Records
Air Conditioning Y/NYes
Fireplace Y/NNo
FlooringCeramic Tile, Laminate
Furnished Y/NUnfurnished
Heating Y/NYes
Interior AmenitiesCathedral Ceiling(s), Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Walk-In Closet(s), Window Treatments
Laundry FeaturesLaundry Room

General for 2248 HILLSHIRE DRIVE

Additional Parcels Y/NNo
Additional RoomsFamily Room
AppliancesDishwasher, Disposal, Electric Water Heater, Microwave, Range, Range Hood
Assoc Fee Paid PerQuarterly
Association AmenitiesBasketball Court, Cable TV, Clubhouse, Fence Restrictions, Fitness Center, Gated, Golf Course, Maintenance, Pickleball Court(s), Playground, Pool, Sauna, Tennis Court(s), Trail(s)
Association Fee Includes24-Hour Guard, Cable TV, Community Pool, Escrow Reserves Fund, Maintenance Grounds, Manager, Pool Maintenance, Private Road, Recreational Facilities
Association NameDebra Zimmerman
Attached Garage Yes
Building Area UnitsSquare Feet
Carport Y/NNo
CityORLANDO
Community FeaturesAssociation Recreation - Owned, Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf Carts OK, Golf, Park, Playground, Pool, Sidewalks, Tennis Court(s)
Construction MaterialsBlock, Stucco
CoolingCentral Air
CountyOrange
DirectionsFrom 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.
Elementary SchoolStone Lake Elem
Facing DirectionNorth
Flood Zone CodeX
Flood Zone Code XY
Full Baths2
Garage Spaces2
Garage Y/NYes
HOA Fee$752
HeatingElectric
High SchoolTimber Creek High
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionSTONEYBROOK UNIT 5 42/33 LOT 69 BLK 15
LevelsOne
Listing TermsCash, Conventional, FHA, VA Loan
Living Area UnitsSquare Feet
Lot Size Square Feet6212
Lot Size UnitsSquare Feet
MLS Area32828 - Orlando/Alafaya/Waterford Lakes
Middle/Junior High SchoolAvalon Middle
Minimum Lease8-12 Months
Monthly HOA Amount250.67
New ConstructionNo
Occupancy TypeOwner
OwnershipFee Simple
Pets AllowedBreed Restrictions, Cats OK
Pool FeaturesGunite, In Ground, Lighting
Property SubtypeSingle Family Residence
Property TypeResidential
RoofShingle
STELLAR_InLawSuiteYNNo
Security FeaturesGated Community
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive
StatusActive
Subdivision NameSTONEYBROOK
Tax Annual Amount4017
Tax Lot69
Tax Year2025
Total Rooms8
UtilitiesCable Connected, Electricity Connected, Phone Available, Public, Sprinkler Recycled, Water Connected
Virtual TourClick here
Water Access TypePond
Water Access Y/NYes
Water ViewPond
Water View Y/NYes
Waterfront FeaturesPond
Year Built2001
ZoningP-D

Exterior for 2248 HILLSHIRE DRIVE

Building Area Total2419
Covered Spaces2
Exterior AmenitiesLighting, Sidewalk
Foundation DetailsConcrete Perimeter
Lot Size Acres0.14
Lot Size Area6212
Private PoolYes
Road Surface TypeAsphalt
Water SourcePublic
Waterfront Y/NYes

Additional Details

Price History

Cindy Gonzalez

Price $511,500
MLS#O6408756
List Date 05/18/2026
Property Type Single Family
Phone 239.243.2743
Request Tour
Request Info
Visit My Website

Similar Properties to 2248 HILLSHIRE DRIVE