Date
Details
Price
Change
Source
1/14/2026
Listed
$2,795
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/11
$2,795 Just Listed
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1/11
Property Description
Welcome to this stunning 3-bedroom, 2-bathroom home located in the beautiful and desirable Orchard Hills subdivision of Winter Garden, FL. This home boasts a split bedroom plan, offering privacy and space, with carpeted bedrooms for added comfort. The master suite features a garden tub, perfect for unwinding after a long day. The open floor-plan is ideal for entertaining, with wood look tiled living areas and modern fixtures adding a touch of elegance. The kitchen is equipped with stainless steel appliances, ready for your culinary adventures. The interior has been freshly painted, giving the home a clean and bright feel. Step outside to a manicured lawn and a fence enclosed backyard, perfect for outdoor activities. Not to mention LAWN SERVICE IS INCLUDED in the rent! The screen enclosed rear patio is a great spot for relaxation, while the front porch offers a scenic pond view, adding to the home's charm. The property also includes a large interior laundry room and a two-car garage for your convenience. As part of a vibrant community, you'll have access to a community pool, fitness center, and clubhouse. This home is not just a place to live, but a lifestyle to enjoy. Come and experience the comfort and convenience this home provides. ** RENTERS INSURANCE REQUIRED ** Washer and Dryer are in AS-IS condition. All residents are enrolled in the Resident Benefits Package (RBP) for $35.00/month which includes credit building to help boost the resident's credit score with timely rent payments, up to $1M Identity Theft Protection, HVAC air filter delivery, move-in concierge service making utility connection and home service setup a breeze during your move-in, our best-in-class resident rewards program, and much more! More details upon application. If approved for this home, new tenants must pay a $200.00 lease coordination fee due at the same time as the security deposit payment.
Full Property Details
Full Property Details for 5567 Cypress Hill Rd
General
- Rent: $2,795
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6368103
- Updated: 1/14/2026
- Added to Site: 3 day(s) ago
Rental Information
- Lease/Rent Term: 12 Months
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 7
- Interior Features: Ceiling Fan(s), Open Floorplan, Solid Surface Counters, Thermostat, Walk-In Closet(s)
- Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
- Furnishings: Unfurnished
- Flooring: Carpet, Tile
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Shared Amenities: Clubhouse, Fitness Center, Pool
- Security/Safety: Smoke Detector(s)
Exterior
- Exterior Features: Irrigation System, Lighting, Rain Gutters, Sidewalk, Sliding Doors
- Deck/Patio: Covered, Front Porch, Patio, Rear Porch
- Porch/Patio/Deck: Covered, Front Porch, Patio, Rear Porch
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Driveway, Garage Door Opener, Garage Faces Rear
Location
- Area: 34787 - Winter Garden/Oakland
- County: Orange
- Development Name: 34787 - Winter Garden/Oakland
- Subdivision: ORCHARD HILLS PH 2
- Driving Directions: From FL-429 south, take exit 19 toward CR-535/Winter Garden Vineland Rd, 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. 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
- Community Features: Clubhouse, Fitness Center, Pool, Sidewalks
- Optional Amenities: Clubhouse, Fitness Center, Pool
- Association: Yes
- Assoc. Name: Edward "Paul" Clark
- Number of Pets: 2
- Pet Restrictions: Please review our full pet policy here: https://rentcare.petscreening.com/, / 40lbs.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Fiber Optics, Sewer Connected, Sprinkler Recycled, Street Lights, Underground Utilities, Water Connected
Structural Information
- Windows: Blinds
- Stories/Levels: One
- Square Feet: 1,650
- Sq. Ft. Source: Public Records
- Year Built: 2017
Lot Features
- Property View: Water
- Lot Size (Acres): 0.13
- Lot Size (Sq. Ft.): 5,767
- Lot Size: 5767
- Frontage: Street Paved
- Street/Road Desc.: Paved
- Fencing (Description): Partial
Water Features
- Water View: Yes
Financial Considerations
- Lease Price: $2,795
- Assoc Fee Desc.: None
- Application Fee: $100
- Security Deposit: $2,795
- Pet Deposit: $250
Disclosures and Reports
- APN: 152327584903570
- Property ID: 152327584903570
Listed by Ct Homes Realty Corporation
Schools
Schools serving 5567 Cypress Hill Rd
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Keenes Crossing Elementary School 5240 Keenes Pheasant Drive, Windermere, FL 34786 | PK-5 | 0.6 mi |
Bridgewater Middle School 5600 Tiny Road, Winter Garden, FL 34787 | 6-8 | 0.6 mi |
Windermere High School 5523 Winter Garden Vineland Road, Windermere, FL 34786 | 9-12 | 1.7 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 5567 Cypress Hill Rd
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- Single Family
- Active
- 3Beds
- 2Total Baths
- 2,094Sq. Ft.
Listed by Sunny 365 Realty Group
- Single Family
- Active
- Updated 8 days ago
- 3Beds
- 2Total Baths
- 1,664Sq. Ft.
Listed by Trusthome Properties Inc
- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 2Total Baths
- 1,710Sq. Ft.
Listed by Premier Management Group Inc
- Single Family
- Active
- 3Beds
- 2Total Baths
- 2,026Sq. Ft.
Listed by La Rosa Realty Orlando Llc
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![[Address not provided], Minneola, FL 34715 - Photo 1](https://m.cbhomes.com/p/646/TB8465324/E2E0edEA7f324Cd/s23cc.webp)
- Single Family
- Active
- Updated 23 hours ago
- 3Beds
- 2Total Baths
- 1,357Sq. Ft.
Listed by Tah Florida Llc
- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 2Total Baths
- 1,402Sq. Ft.
Listed by Scates Realty & Investment Pro
- Single Family
- Active
- Updated 5 days ago
- 4Beds
- 4Total Baths
- 2,843Sq. Ft.
Listed by Wra Business & Real Estate
- Townhouse
- Active
- Updated 2 days ago
- 4Beds
- 3Total Baths
- 2,056Sq. Ft.
Listed by Mariela Alvarez De Van Adelberg (407) 283-8853
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- Single Family
- Active
- Updated 5 days ago
- 2Beds
- 1Total Bath
- 1,492Sq. Ft.
Listed by Engel & Volkers Clermont
- Single Family
- Active
- Updated 3 days ago
- 3Beds
- 2Total Baths
- 1,587Sq. Ft.
Listed by Wheatley Realty Group
- Single Family
- Active
- Updated 3 days ago
- 4Beds
- 4Total Baths
- 3,401Sq. Ft.
Listed by Agent Group Realty
- Single Family
- Active
- Updated 1 day ago
- 5Beds
- 3Total Baths
- 2,580Sq. Ft.
Listed by McO Realty Group Llc
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- Single Family
- Closed
- 4Beds
- 4Total Baths
- 2,573Sq. Ft.
Listed and Sold by Multi Choice Realty Llc
- Single Family
- Closed
- 4Beds
- 4Total Baths
- 2,853Sq. Ft.
Listed by Jc Florida Realty Llc
Sold by Jc Florida Realty Llc
Sold by Jc Florida Realty Llc
- Single Family
- Closed
- 4Beds
- 4Total Baths
- 2,426Sq. Ft.
Listed and Sold by Multi Choice Realty Llc
- Townhouse
- Closed
- 3Beds
- 3Total Baths
- 1,617Sq. Ft.
Listed and Sold by Fusilier Management Group
5567 Cypress Hill Road, Winter Garden, FL 34787 (MLS# O6368103) is a Single Family property with 3 bedrooms and 2 full bathrooms. 5567 Cypress Hill Road is currently listed for rent at $2,795 and was received on January 14, 2026. Want to learn more about 5567 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.