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$595,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,470 Sq. Ft.
  • Updated 2 days ago
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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!

Full Property Details for 5561 Cypress Hill Rd

General

  • Price: $595,000
  • HOA FEE: $188/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $5,338 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6383015
  • Updated: 2/17/2026
  • Added to Site: 4 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 13
  • Interior Features: Open Floorplan, PrimaryBedroom Upstairs, Stone Counters, Walk-In Closet(s), Ceiling Fan(s)
  • Appliances: Microwave, Range, Refrigerator, Dishwasher, Disposal, Electric Water Heater
  • Furnishings: Unfurnished
  • Flooring: Tile, Carpet

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Laundry Room, Electric Dryer Hookup, Inside, Upper Level, Washer Hookup

Additional Information

  • Security/Safety: Fire Sprinkler System

Exterior

  • Exterior Features: Balcony, Sidewalk, Rain Gutters
  • Deck/Patio: Screened, Front Porch, Rear Porch
  • Porch/Patio/Deck: Screened, Front Porch, Rear Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: ORCHARD HILLS PHASE 2
  • Driving 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.
  • Direction Faces: South

School Information

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

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Association: Yes
  • Assoc. Name: Paul Clark

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV Available, Water Available, Electricity Available, Electricity Connected

Structural Information

  • Exterior Const.: Stucco, Block, Concrete
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 2,470
  • Sq. Ft. Source: Public Records
  • Year Built: 2016

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.1
  • Lot Size (Sq. Ft.): 4,563
  • Lot Size: 4563
  • Street/Road Desc.: Asphalt

Water Features

  • Water View: Yes

Financial Considerations

  • Association Fee: $565
  • Assoc Fee Freq.: Quarterly
  • Assoc Fee Desc.: Required
  • Tax Amount: $5,338.72
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: ORCHARD HILLS PHASE 2 85/35 LOT 358
  • Flood Zone Info: X
  • APN: 152327584903580
  • Property ID: 152327584903580
  • Block/Lot/Section: 3

Listed by Watson Realty Corp

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Listing agent

— 5561 Cypress Hill Rd —

  • Watson Realty Corp

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 5561 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
6-80.6 mi
Windermere High School
5523 Winter Garden Vineland Road, Windermere, FL 34786
9-121.7 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5561 Cypress Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/16/2026
Listed
$595,000
112.13%
MLS
6/15/2016
Sold
$280,490
—
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 5561 Cypress Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$5,080
—
$328,606
3%
2024
$5,080
7%
$319,345
3%
2023
$4,728
5%
$310,044
6%
2021
$4,489
-1%
$292,247
-3%
2022
$4,541
1%
$301,014
4%
2021
$4,489
2%
$288,212
2%
2019
$4,401
1%
$281,732
2%
2018
$4,367
1%
$276,479
2%
2017
$4,309
318%
$270,792
674%
2016
$1,031
97%
$35,000
17%
2015
$523
—
$30,000
—
View All
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 5561 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 Watson Realty Corp

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5561 Cypress Hill Road, Winter Garden, FL 34787 (MLS# O6383015) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 5561 Cypress Hill Road is currently listed for $595,000 and was received on February 16, 2026. Want to learn more about 5561 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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