5561 CYPRESS HILL ROAD Winter Garden, FL $ 595,000
5561 CYPRESS HILL ROAD
$ 595,000
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5561 CYPRESS HILL ROAD

Winter Garden, FL, 34787
$ 595,000
Bedrooms3 Baths2.1 Sq 2,470

Monthly Estimate*

$ 3,664

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Single Family Home for sale in Winter Garden, FL

for $595,000 with 3 bedrooms and 2 full baths, 1 half bath. This 2,470 square foot home was built in 2016 on a lot size of 0.1.

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!

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Single Family Active

Price

$ 595,000

Bedrooms

3

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 5,338

Style

Single Family Residence

Lot Size

0.1

Year Built

2016

Town/City

Winter Garden

County/Region

Orange

MLS | Web ID

O6383015

Features
General
Sewer Public Sewer
Heating Central Electric
Cooling Central Air
Utilities Cable Available Water Available Electricity Available Electricity Connected
Possession Close Of Escrow
Roof Shingle
Appliances Microwave Range Refrigerator Dishwasher Disposal Electric Water Heater
Zoning ORG-P-D
HOA Fee 565
Garage Spaces 2
Patio/Porch Features Screened Front Porch Rear Porch
Security Features Fire Sprinkler System
Construction Materials Stucco Block Concrete
Pets Allowed Cats OK Dogs OK Yes
Year Built 2016
View Water
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Assoc Fee Paid Per Quarterly
County Orange
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name ORCHARD HILLS PHASE 2
Facing Direction South
Garage Y/N true
Total Rooms 13
Full Baths 2
Status Active
Directions FL 429 to Winter Garden Vineland Rd and 535; turn left on 535 then right on Tilden Rd. and left on Tiny Rd then left on Cypress Hill Rd. House is on the left.
High School Windermere High School
City WINTER GARDEN
Association Name Paul Clark
Senior Community Y/N false
MLS Area 34787 - Winter Garden/Oakland
Lot Size Units Square Feet
Lot Size Square Feet 4563
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Elementary School Keene Crossing Elementary
Property Attached Y/N false
Land Lease Y/N false
Tax Annual Amount 5338.72
Middle/Junior High School Bridgewater Middle
Property Condition Completed
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6383015
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 358
Legal Description ORCHARD HILLS PHASE 2 85/35 LOT 358
Water View Pond
Minimum Lease 8-12 Months
Water Access Y/N false
Monthly HOA Amount 188.33
Additional Rooms Inside Utility Loft Den/Library/Office Storage Rooms
Water View Y/N true
Flood Zone Code X
DockY/N false
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Interior
Interior Amenities Open Floorplan PrimaryBedroom Upstairs Stone Counters Walk-In Closet(s) Ceiling Fan(s)
Flooring Tile Carpet
Furnished Y/N Unfurnished
Total Stories 2
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N false
Half Baths 1
Laundry Features Laundry Room Electric Dryer Hookup Inside Upper Level Washer Hookup
Total Bedrooms 3
Total Baths 3
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Exterior
Exterior Amenities Balcony Sidewalk Rain Gutters
Parking Features Driveway
Water Source Public
Lot Size Area 4563
Foundation Details Slab
Building Area Total 3698
Lot Size Acres 0.1
Road Surface Type Asphalt
Private Pool false
Waterfront Y/N false
Covered Spaces 2
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* Excluded Features
List By
Watson Realty Corp

Broker

kathymcdonald4026@gmail.com

Email

Affordability Calculator

$4,108
Per Month
89%
11%
0%
Monthly Principal & Interest
$3,664
Monthly Property Taxes
$445
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Windermere High School High School High School
Pricing History
DatePricePrice ChangeDescription
2/17/2026$595,000 Listed Price

Map


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5561 CYPRESS HILL ROAD, Winter Garden, FL, 34787 is a Single Family Home for sale at $595,000 with 2,470 sqft and a lot size of 0.1. 5561 CYPRESS HILL ROAD has 3 bedrooms, 2.1 baths, and was built in 2016. The property's zip code is 34787 which is in Winter Garden, FL