2248 Hillshire Dr, ORLANDO, FL
$495,500
4
Beds
2
Baths
1,877
Square feet
0.14
Acres
About 2248 Hillshire Dr
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.
Features of 2248 Hillshire Dr
| MLS® # | O6408756 |
|---|---|
| Price | $495,500 |
| Bedrooms | 4 |
| Bathrooms | 2.00 |
| Full Baths | 2 |
| Square Footage | 1,877 |
| Acres | 0.14 |
| Year Built | 2001 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Status | Active |
Community Information
| Address | 2248 Hillshire Dr |
|---|---|
| Area | Orlando/Alafaya/Waterford Lakes |
| Subdivision | STONEYBROOK |
| City | ORLANDO |
| County | Orange |
| State | FL |
| Zip Code | 32828-7504 |
Amenities
| 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) |
|---|---|
| # of Garages | 2 |
| Is Waterfront | Yes |
| Waterfront | Pond |
| Has Pool | Yes |
Interior
| Interior Features | Cathedral Ceiling(s), Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Walk-In Closet(s), Window Treatments |
|---|---|
| Appliances | Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Range Hood |
| Heating | Electric |
| Cooling | Central Air |
| Fireplace | No |
Exterior
| Exterior Features | Lighting, Sidewalk |
|---|---|
| Roof | Shingle |
| Foundation | Concrete Perimeter |
School Information
| Elementary | Stone Lake Elem |
|---|---|
| Middle | Avalon Middle |
| High | Timber Creek High |
Taxes & HOA Fees
| Taxes | $4,017 |
|---|---|
| Has HOA | Yes |
| HOA Fee Requirement | Required |
| HOA Fee | $752 |
| HOA Payment Schedule | Quarterly |
Additional Information
| Date Listed | May 18th, 2026 |
|---|---|
| Days on Market | 105 |
| Zoning | P-D |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Office | CHARLES RUTENBERG REALTY ORLANDO |
|---|