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WINTER GARDEN, FL 34787 5561 CYPRESS HILL ROAD

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Presented By: WATSON REALTY CORP with 407-332-6000. - 407-332-6000
  • MLS# O6383015
  • 02/16/2026
  • Request Tour
  • Request Info
  • Beds • 3
  • Full/Half Baths • 2 / 1
  • SQFT • 2,470
  • Garage • 2

Home Details

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!
Presented By: WATSON REALTY CORP with 407-332-6000. - 407-332-6000

Interior Features for 5561 CYPRESS HILL ROAD

Bedrooms

Total Bedrooms3

Bathrooms

Half Baths1
Total Baths3

Other Interior Features

LivingAreaSourcePublic Records
Air Conditioning Y/NYes
Fireplace Y/NNo
FlooringTile, Carpet
Furnished Y/NUnfurnished
Heating Y/NYes
Interior AmenitiesOpen Floorplan, PrimaryBedroom Upstairs, Stone Counters, Walk-In Closet(s), Ceiling Fan(s)
Laundry FeaturesLaundry Room, Electric Dryer Hookup, Inside, Upper Level, Washer Hookup
Total Stories2

General for 5561 CYPRESS HILL ROAD

Additional Parcels Y/NNo
Additional RoomsInside Utility, Loft, Den/Library/Office, Storage Rooms
AppliancesMicrowave, Range, Refrigerator, Dishwasher, Disposal, Electric Water Heater
Assoc Fee Paid PerQuarterly
Association NamePaul Clark
AssociationName2First Service Residential
Attached Garage Yes
Building Area UnitsSquare Feet
Carport Y/NNo
CityWINTER GARDEN
Construction MaterialsStucco, Block, Concrete
CoolingCentral Air
CountyOrange
DirectionsFL 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.
DockY/NNo
Elementary SchoolKeene Crossing Elementary
Facing DirectionSouth
Flood Zone CodeX
Flood Zone Code XY
Full Baths2
Garage Spaces2
Garage Y/NYes
HOA Fee$565
HeatingCentral, Electric
High SchoolWindermere High School
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionORCHARD HILLS PHASE 2 85/35 LOT 358
LevelsTwo
Listing TermsCash, Conventional, FHA, VA Loan
Living Area UnitsSquare Feet
Lot Size Square Feet4563
Lot Size UnitsSquare Feet
MLS Area34787 - Winter Garden/Oakland
Middle/Junior High SchoolBridgewater Middle
Minimum Lease8-12 Months
Monthly HOA Amount188.33
New ConstructionNo
Occupancy TypeOwner
OwnershipFee Simple
Patio/Porch FeaturesScreened, Front Porch, Rear Porch
Pets AllowedCats OK, Dogs OK, Yes
PossessionClose Of Escrow
Property Attached Y/NNo
Property ConditionCompleted
Property SubtypeSingle Family Residence
Property TypeResidential
RoofShingle
STELLAR_InLawSuiteYNNo
Security FeaturesFire Sprinkler System
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive
StatusActive
Subdivision NameORCHARD HILLS PHASE 2
Tax Annual Amount5338.72
Tax Lot358
Tax Year2025
Total Rooms13
UtilitiesCable Available, Water Available, Electricity Available, Electricity Connected
ViewWater
Virtual TourClick here
Water Access Y/NNo
Water ViewPond
Water View Y/NYes
Year Built2016
ZoningORG-P-D

Exterior for 5561 CYPRESS HILL ROAD

Building Area Total3698
Covered Spaces2
Exterior AmenitiesBalcony, Sidewalk, Rain Gutters
Foundation DetailsSlab
Lot Size Acres0.1
Lot Size Area4563
Parking FeaturesDriveway
Private PoolNo
Road Surface TypeAsphalt
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

Steven Silcock

Broker Owner
Price $595,000
MLS#O6383015
List Date 02/16/2026
Property Type Single Family
Phone 407.574.0218
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