5887 CYPRESS HILL ROAD Winter Garden, FL $ 475,000
5887 CYPRESS HILL ROAD
$ 475,000
Recently Listed
Open House 9/5 1pm - 4pm
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5887 CYPRESS HILL ROAD

Winter Garden, FL, 34787
$ 475,000
Bedrooms3 Baths2.1 Sq 1,810

Monthly Estimate*

$ 2,999

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Single Family Home for sale in Winter Garden, FL

for $475,000 with 3 bedrooms and 2 full baths, 1 half bath. This 1,810 square foot home was built in 2017 on a lot size of 0.1.

Welcome to 5887 Cypress Hill Rd, a beautifully maintained 3-bedroom, 2.5-bath home located in the highly desirable Orchard Hills community of Winter Garden. Built in 2017, this spacious 1,810-square-foot home offers an inviting open floor plan with high ceilings, modern finishes, and plenty of natural light. The kitchen features granite countertops and opens seamlessly to the main living and dining areas, making it ideal for both everyday living and entertaining. The primary suite offers a comfortable retreat with a walk-in closet, while the additional bedrooms provide plenty of space for family, guests, or a home office. Enjoy the convenience of a 2-car garage, low-maintenance living, and a location just minutes from Winter Garden Village, shopping, dining, entertainment, and major roadways including the 429. Orchard Hills residents enjoy fantastic amenities including a community pool, clubhouse, fitness center, playground, dog park, sidewalks, and lawn maintenance included with the HOA. With its combination of comfort, convenience, and an exceptional Winter Garden location, this home is a must-see!

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Open House

9/5/2026 1:00 PM - 4:00 PM
5887 CYPRESS HILL ROAD Winter Garden, FL
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 475,000

Bedrooms

3

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 7,251

Style

Single Family Residence

Lot Size

0.1

Year Built

2017

Town/City

Winter Garden

County/Region

Orange

MLS | Web ID

O6438059

Features
General
Sewer Public Sewer
Heating Central
Cooling Central Air
Utilities Electricity Available
Roof Shingle
Appliances Dishwasher Dryer Microwave Range Refrigerator Washer
Zoning P-D
HOA Fee 565
Garage Spaces 2
Construction Materials Block Stucco
Pets Allowed Breed Restrictions Cats OK Dogs OK Number Limit Yes
Year Built 2017
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Community Features Clubhouse Dog Park Fitness Center Pool
Assoc Fee Paid Per Quarterly
County Orange
New Construction false
Property Type Residential
Attached Garage false
Subdivision Name ORCHARD HILLS PH 4
Facing Direction North
Garage Y/N true
Total Rooms 8
Full Baths 2
Status Active
Directions FL-408 W to Winter Garden. Take exit 19 from FL-429 S. Follow Winter Garden Vineland Rd Tilden Rd and Tiny Rd to Cypress Hill Rd in Horizon West. Merge onto Stoneybrook W Pkwy. Use the left 2 lanes to turn left onto Winter Garden Vineland Rd. Turn right onto Tilden Rd. Turn left onto Tiny Rd. Turn left onto Cypress Hill Rd. Turn right onto Chestnut Chase Rd. Turn left onto Cypress Hill Rd. Destination will be on the rigHT.
High School Windermere High School
City WINTER GARDEN
Association Name Edward Clark
Senior Community Y/N false
MLS Area 34787 - Winter Garden/Oakland
Lot Size Units Square Feet
Lot Size Square Feet 4347
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Elementary School Keene Crossing Elementary
Land Lease Y/N false
Tax Annual Amount 7251.64
Middle/Junior High School Bridgewater Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://visithome.ai/JH4RGdHa6QzA9ogioJKG3x?mu=ft https://homes.mythicframestudio.com/dashboard/listings/xNZQeOamDNE4IMap1nX5#8soJbNAcVXaWHn0pm1eG_b3aa2423-f54f-4d98-9f26-149b719eee1c
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 584
Legal Description ORCHARD HILLS PHASE 4 91/129 LOT 584
Minimum Lease 7 Months
Water Access Y/N false
Monthly HOA Amount 188.33
Water View Y/N false
Flood Zone Code X
In Law Suite YN false
Flood Zone Code X Y
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Interior
Interior Amenities Ceiling Fan(s) Eating Space In Kitchen Kitchen/Family Room Combo Stone Counters Thermostat
Flooring Carpet Tile Vinyl
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 Inside Laundry Closet Upper Level
Total Bedrooms 3
Total Baths 3
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Exterior
Exterior Amenities Courtyard
Parking Features Other
Water Source Public
Lot Size Area 4347
Foundation Details Slab
Building Area Total 2615
Lot Size Acres 0.1
Road Surface Type Paved
Private Pool false
Waterfront Y/N false
Covered Spaces 2
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* Excluded Features
List By
Keller Williams Elite Partners Iii Realty

Broker

trevor@trusttrevor.com

Email

Affordability Calculator

$3,603
Per Month
83%
17%
0%
Monthly Principal & Interest
$2,999
Monthly Property Taxes
$604
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% 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
9/1/2026$475,000 Listed Price

Map


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5887 CYPRESS HILL ROAD, Winter Garden, FL, 34787 is a Single Family Home for sale at $475,000 with 1,810 sqft and a lot size of 0.1. 5887 CYPRESS HILL ROAD has 3 bedrooms, 2.1 baths, and was built in 2017. The property's zip code is 34787 which is in Winter Garden, FL