5561 CYPRESS HILL ROAD WINTER GARDEN FL 34787 MLS #O6383015

5561 CYPRESS HILL ROAD
WINTER GARDEN, FL, 34787
$595,000
3 Beds
2.5 Baths
2,470 SqFt
0.1 Acres
Add
MLS #O6383015 image #0
Under contract-accepting backup offers. Welcome home to this truly exceptional, move-in ready two-story gem in the highly desirable Orchard Hills community of Winter Garden—showing like a brand-new model home! Meticulously maintained by the owners, this nine-year-old home feels fresh, modern, and beautifully cared for from the moment you arrive. Step inside to an inviting open-concept design featuring stylish wood-look tile throughout the first floor, a bright and spacious living area, and a stunning, modern kitchen complete with a large center island, stainless steel appliances, quartz countertops, and abundant cabinetry—perfect for entertaining or everyday living. A versatile bonus room near the rear of the home offers the ideal space for a home office or guest retreat, along with a convenient half bath and extra storage. Enjoy Florida living with the charming, enclosed patio that connects to the rear-entry two-car garage with additional storage. Upstairs, a generous loft leads to three bedrooms, including a serene primary suite with a private balcony overlooking tranquil pond views. The spa-like ensuite bath features a walk-in shower, soaking tub, and private water closet. Additional upgrades include a full home fire sprinkler system, helping reduce homeowners’ insurance costs, and rain gutters. Residents of Orchard Hills enjoy an amenity-rich lifestyle, including a pool, clubhouse, fitness center, playgrounds, dog park, grilling area, and frequent events. The HOA covers exterior maintenance, lawn care, landscaping, and outdoor pest prevention—making life truly low-maintenance. Just minutes from Disney World, major highways, shopping and dining, this home is a rare opportunity you won’t want to miss!

Property Details

Price:
$595,000
MLS #:
O6383015
Status:
Pending
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ORCHARD HILLS PHASE 2
Neighborhood:
34787wintergardenoakland
Listed Date:
Feb 16, 2026
Finished Sq Ft:
2,470
Total Sq Ft:
3,698
Lot Size:
4,563 sqft / 0.10 acres (approx)
Year Built:
2016
34787 – Winter Garden/oakland34787wintergardenoaklandOrchard Hills Phase 2Keene Crossing ElementaryBridgewater MiddleWindermere High SchoolWaterNone8-12 MonthsPets Allowed

Ask a Question

See this Listing

Send
  

Schools

Elementary School:
Keene Crossing Elementary
Middle School:
Bridgewater Middle
High School:
Windermere High School

Interior

Appliances
Microwave, Range, Refrigerator, Dishwasher, Disposal, Electric Water Heater
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Tile, Carpet
Heating
Central, Electric
Interior Features
Open Floorplan, PrimaryBedroom Upstairs, Stone Counters, Walk-In Closet(s), Ceiling Fan(s)
Laundry Features
Laundry Room, Electric Dryer Hookup, Inside, Upper Level, Washer Hookup
Levels
Two

Exterior

Attached Garage YN
1
Construction Materials
Stucco, Block, Concrete
Covered Spaces
2
Direction Faces
South
Exterior Features
Balcony, Sidewalk, Rain Gutters
Garage Spaces
2
Open Parking YN
1
Parking Features
Driveway
Patio And Porch Features
Screened, Front Porch, Rear Porch
Roof
Shingle
Security Features
Fire Sprinkler System
View
Water

Financial

HOA Fee
$565
HOA Fee Frequency
Quarterly
HOA Name
Paul Clark
HOA Name 2
First Service Residential
HOA Phone
407-347-9923
HOA Phone 2
407-347-9923
Tax Year
2025
Taxes
$5,339

Map

Community

Subdivisions in WINTER GARDEN

Market Summary

Current real estate data for Single Family in WINTER GARDEN as of Apr 24, 2026
780
Single Family Listed
109
Avg DOM
282
Avg $ / SqFt
$749,764
Avg List Price

Property Summary

    Located in the ORCHARD HILLS PHASE 2 subdivision, 5561 CYPRESS HILL ROAD WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $595,000 and features 3 beds, 3 baths, and has approximately 2,470 square feet of living space, and was originally constructed in 2016. The current price per square foot is $241. The average price per square foot for Single Family listings in WINTER GARDEN is $282. The average listing price for Single Family in WINTER GARDEN is $749,764. To schedule a showing of MLS#o6383015 at 5561 CYPRESS HILL ROAD in WINTER GARDEN, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

Similar Listings Nearby

broker reciprocity
MLS# O6397847broker reciprocity
910 LASCALA DRIVE
WINDERMERE, FL

$770,000

4.8 miles away

broker reciprocity
MLS# O6320456broker reciprocity
7409 FAIRGROVE AVENUE
WINDERMERE, FL

$769,000

2.9 miles away

broker reciprocity
MLS# O6393857broker reciprocity
17326 BAL HARBOUR DRIVE
WINTER GARDEN, FL

$769,000

2.8 miles away

broker reciprocity
MLS# G5109739broker reciprocity
17066 HAGGERTY HOLLOW DRIVE
WINTER GARDEN, FL

$765,377

3.1 miles away

broker reciprocity
MLS# O6370025broker reciprocity
2015 SANDY GARDEN LANE
WINTER GARDEN, FL

$765,000

1.6 miles away

broker reciprocity
MLS# O6265256broker reciprocity
11410 RAPALLO LANE
WINDERMERE, FL

$760,000

4.7 miles away

5561 CYPRESS HILL ROAD
WINTER GARDEN, FL