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$495,500

2248 Hillshire Dr

Orlando, FL
Pending
4
Bedrooms
2
Bathrooms
2,419
Square Feet
0.14
Lot Size (acres)
2001
Year Built
138
Days On Market

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 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.

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Listing Information

Listing Updated
09/01/2026
Listed By
Diane Molaka, 4072224270 · CHARLES RUTENBERG REALTY ORLANDO, 4076222122
MLS#
O6408756
Source
Stellar MLS
Status
Pending

Facts & Features

Location

Community Information

Address
2248 Hillshire Dr, Orlando, FL 32828
City
Orlando
County
Orange
Neighborhood
STONEYBROOK
Zip Code
32828

Architecture

Bedrooms
4
Bathrooms
2
Year Built
2001
Construction Materials
Stucco, Block
Building Area
2,419 sq. ft.
Foundation
Concrete Perimeter
Roof
Shingle
Levels
One
Garage
Yes
Garage Spaces
2
Parking Features
Attached

Features & Amenities

Interior Features
Cathedral Ceiling(s), Eat-in Kitchen, Walk-In Closet(s), High Ceilings
Appliances
Dishwasher, Electric Water Heater, Microwave, Range, Disposal, Range Hood
Flooring
Laminate, Ceramic Tile
Exterior Features
Lighting
Community Features
Clubhouse, Gated, Golf, Pool, Sidewalks, Playground, Tennis Court(s), Park, Fitness Center
Cooling
Central Air
Heating
Electric

Property Features

Lot Size
0.14 Acres
Lot Features
Waterfront
View
Water, Pond
Water
Public
Sewer
Public Sewer
Utilities
Cable Available, Cable Connected, Electricity Connected, Water Connected, Phone Available

Square Footage

Total
1,877 sq. ft.

Tax & Financial Information

List Price
$495,500
Annual Taxes
$4,017
Association Fee
$752 (paid Quarterly)
Fee Includes
Maintenance Grounds, Cable TV
Association Amenities
Playground, Clubhouse, Fitness Center, Maintenance, Pool, Gated, Sauna, Tennis Court(s), Trail(s), Basketball Court, Cable TV, Golf Course

Schools

78/100
Avalon Middle
Middle · Grades 06–08 · 1.6 mi
Assigned school for this home
City
Orlando
Students
911
Parent reviews
5.0★ avg · 1 review
Student body
42% White · 36% Hispanic / Latino · 9% Asian
Free/reduced lunch
29%
Phone
(407) 207-7839
99/100
Timber Creek High
High · Grades 08–12 · 1.1 mi
Assigned school for this home
City
Orlando
Students
3,030
Parent reviews
5.0★ avg · 2 reviews
Student body
44% White · 36% Hispanic / Latino · 11% Black
Free/reduced lunch
31%
Phone
(321) 235-7800
100/100
East River High
High · Grades 09–12 · 3.1 mi
City
Orlando
Students
1,831
Parent reviews
5.0★ avg · 2 reviews
Student body
43% White · 41% Hispanic / Latino · 10% Black
Free/reduced lunch
57%
Phone
(407) 956-8550
78/100
Stone Lakes Elementary
Elementary · Grades KG–05 · 0.7 mi
City
Orlando
Students
773
Parent reviews
5.0★ avg · 2 reviews
Student body
40% White · 37% Hispanic / Latino · 11% Asian
Free/reduced lunch
30%
Phone
(407) 207-7793
77/100
Timber Springs Middle
Middle · Grades 06–08 · 1.8 mi
City
Orlando
Students
969
Parent reviews
5.0★ avg · 1 review
Student body
46% Hispanic / Latino · 30% White · 13% Black
Free/reduced lunch
37%
Phone
(321) 413-2201
77/100
Castle Creek Elementary
Elementary · Grades PK–05 · 2.2 mi
City
Orlando
Students
579
Parent reviews
5.0★ avg · 2 reviews
Student body
56% Hispanic / Latino · 19% White · 15% Black
Free/reduced lunch
60%
Phone
(407) 207-7428
77/100
Discovery Middle
Middle · Grades 06–08 · 2.3 mi
City
Orlando
Students
812
Parent reviews
5.0★ avg · 1 review
Student body
52% Hispanic / Latino · 31% White · 9% Black
Free/reduced lunch
53%
Phone
(407) 384-1555
56/100
Avalon Elementary
Elementary · Grades PK–05 · 1.1 mi
City
Orlando
Students
741
Student body
49% White · 33% Hispanic / Latino · 7% Black
Free/reduced lunch
26%
Phone
(407) 207-3825

School ratings are provided for informational purposes only and are subject to change. Attendance boundaries are for reference only — contact the school or district directly to verify enrollment eligibility.

Historical Data

Price History

DateEventPrice
06/10/2026Price change$495,500
05/18/2026Listed for sale$511,500

Listed by Diane Molaka · CHARLES RUTENBERG REALTY ORLANDO · 4076222122

Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. Copyright 2026, Stellar MLS. All rights reserved.

Last Updated: September 1, 2026 at 11:53 PM | Source: Stellar MLS | MLS#: O6408756

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