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$475,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,810 Sq. Ft.
  • Updated 11 hours ago

Next open house:

Open House: 1:00 PM - 4:00 PM

Saturday 9/5 1:00 PM - 4:00 PM

5887 Cypress Hill Road,Winter Garden, FL 34787

5887 Cypress Hill RoadWinter GardenFL34787

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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!

Full Property Details for 5887 Cypress Hill Rd

General

  • Price: $475,000
  • HOA FEE: $188/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $7,251 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6438059
  • Updated: Today (9/1/2026)
  • Added to Site: Today

Rental Information

  • Min. Lease: 7 Months

Interior

  • Number of Rooms: 8
  • Interior Features: Ceiling Fan(s), Eating Space In Kitchen, Kitchen and Family Room Combination, Stone Counters, Thermostat
  • Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Carpet, Tile, Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Inside, Laundry Closet, Upper Level

Exterior

  • Exterior Features: Courtyard

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Other

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: ORCHARD HILLS PH 4
  • Driving 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.
  • Direction Faces: North

School Information

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

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Community Features: Clubhouse, Dog Park, Fitness Center, Pool
  • Association: Yes
  • Assoc. Name: Edward Clark
  • Number of Pets: 3
  • Pet Restrictions: Buyer and buyer's agent must verify with the association.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Electricity Available

Structural Information

  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 1,810
  • Sq. Ft. Source: Public Records
  • Year Built: 2017

Lot Features

  • Lot Size (Acres): 0.1
  • Lot Size (Sq. Ft.): 4,347
  • Lot Size: 4347
  • Street/Road Desc.: Paved

Financial Considerations

  • Association Fee: $565
  • Assoc Fee Freq.: Quarterly
  • Assoc Fee Desc.: Required
  • Tax Amount: $7,251.64
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: ORCHARD HILLS PHASE 4 91/129 LOT 584
  • Flood Zone Info: X
  • APN: 152327585605840
  • Property ID: 152327585605840
  • Block/Lot/Section: 5

Listed by Keller Williams Elite Partners Iii Realty

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Listing agent

— 5887 Cypress Hill Rd —

  • Keller Williams Elite Partners Iii Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5887 Cypress Hill Rd

School District:Orange County School District
NameGradesDistance
Keenes Crossing Elementary School
5240 Keenes Pheasant Drive, Windermere, FL 34786
PK-50.6 mi
Bridgewater Middle School
5600 Tiny Road, Winter Garden, FL 34787
6-80.5 mi
Windermere High School
5523 Winter Garden Vineland Road, Windermere, FL 34786
9-121.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5887 Cypress Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/01/2026
Listed
$475,000
50.79%
MLS
6/21/2019
Sold
$315,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5887 Cypress Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$7,252
—
$396,140
-1%
2025
$7,252
8%
$400,520
-5%
2024
$6,696
15%
$420,253
14%
2023
$5,813
24%
$369,106
40%
2021
$4,674
-11%
$264,528
-19%
2022
$5,231
12%
$326,608
30%
2021
$4,674
34%
$250,919
11%
2019
$3,493
1%
$225,818
2%
2018
$3,464
495%
$221,607
533%
2017
$582
—
$35,000
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 5887 Cypress Hill Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Keller Williams Elite Partners Iii Realty

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5887 Cypress Hill Road, Winter Garden, FL 34787 (MLS# O6438059) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 5887 Cypress Hill Road is currently listed for $475,000 and was received on September 01, 2026. Want to learn more about 5887 Cypress Hill Road? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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