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$3,400

  • Sold
  • Closed
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,350 Sq. Ft.
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See This Home
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Meticulously maintained 3-bedroom, 2.5-bath home with bonus room in the desirable Orchard Hills community. Stylish upgrades throughout, including ceiling beams with integrated lighting, electric fireplace, quartz countertops, 42" kitchen cabinets, new stainless steel dishwasher, and a smart thermostat. Bonus room with French doors can function as a home office or optional 4th bedroom. Upstairs loft and private master suite balcony offers additional living space and views of Disney fireworks. Located on a large corner lot with abundant natural light and a screened-in patio. Home includes a brand-new high-end washer and dryer, EV charger in the garage, and a custom built-in closet system in the master bedroom closet. Zoned for best schools: Keene's Crossing Elementary, Bridgewater Middle, and Windermere High. Community features resort-style pool, clubhouse, fitness center, playground. Rent: $3,400/month. First month, last month, and security deposit required. No pets allowed. Tenants pays utilities. Lawncare included in rent. Appointments only. Must fill pre showing form at link below: https://forms.gle/FmoCnnuzkWyKzi786 .

Full Property Details for 5555 Cypress Hill Rd

General

  • Rent: $3,400
  • Status: Closed
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6320473
  • Added to Site: 212 day(s) ago

Rental Information

  • Lease/Rent Term: 12 Months
  • Min. Lease: 1-2 Years

Interior

  • Number of Rooms: 9
  • Interior Features: Ceiling Fan(s), Crown Molding, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Thermostat, Walk-In Closet(s)
  • Appliances: Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Range, Range Hood, Refrigerator, Washer
  • Furnishings: Unfurnished

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Shared Amenities: Clubhouse, Fitness Center, Pool, Spa/Hot Tub

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: ORCHARD HILLS PH 2
  • Driving Directions: 429 S exit 19, turn left Winter Garden Rd. Follow Winter Garden Vineland Rd, Tilden Rd and Tiny Rd to Cypress Hill Rd

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Optional Amenities: Clubhouse, Fitness Center, Pool, Spa/Hot Tub

Heating & Cooling

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

Structural Information

  • Stories/Levels: Two
  • Square Feet: 2,350
  • Sq. Ft. Source: Public Records
  • Living Area: 2,350 Sq. Ft.
  • Year Built: 2016

Lot Features

  • Lot Size (Acres): 0.15
  • Lot Size (Sq. Ft.): 6,548
  • Lot Size: 6548
  • Street/Road Desc.: Asphalt

Financial Considerations

  • Lease Price: $3,400
  • Application Fee: $85
  • Security Deposit: $3,300

Disclosures and Reports

  • APN: 152327584903590
  • Property ID: 152327584903590

Listed and Sold by Charles Rutenberg Realty Orlando

Listing agent

— 5555 Cypress Hill Rd —

  • Charles Rutenberg Realty Orlando

Schools serving 5555 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 History for 5555 Cypress Hill Rd

Date
Details
Price
Change
Source
7/08/2025
Sold
$3,400
—
MLS
7/07/2025
Price Increased
$3,400
3.03%
MLS
6/20/2025
Listed
$3,300
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed and Sold by Charles Rutenberg Realty Orlando

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5555 Cypress Hill Road, Winter Garden, FL 34787 (MLS# O6320473) is a Single Family property that was sold at $3,400 on July 08, 2025. Want to learn more about 5555 Cypress Hill Road? Do you have questions about finding other real estate for sale or rent in Winter Garden? You can browse all Winter Garden rentals or contact a Coldwell Banker agent to request more information.