![Property at 14755 Masthead Landing Cir, Winter Garden, FL, 34787, 4 beds, 2 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/c4ea649d-4d8e-41bc-9d2c-3d4a537c0849/islphoto/genIsl.0_2.webp)
14755 Masthead Landing Cir, Winter Garden, FL, 34787
![Property at 173 Donner Dr, Winter Garden, FL, 34787, 5 beds, 4 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/1dcabb2a-1725-441d-9fdc-85f06861b35c/islphoto/genIsl.0_2.webp)
173 Donner Dr, Winter Garden, FL, 34787![Property at 669 Groves End Ln, Winter Garden, FL, 34787, 4 beds, 2.5 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/b0020e76-aa0b-49e5-8bcb-c0d5de773756/islphoto/genIsl.0_1.webp)
669 Groves End Ln, Winter Garden, FL, 34787![Property at 643 Willett Dr, Winter Garden, FL, 34787, 4 beds, 2.5 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/808867b8-a3a8-41c3-b856-af85ff0fe7ad/islphoto/genIsl.0_3.webp)
643 Willett Dr, Winter Garden, FL, 34787![Property at 14423 Hampshire Bay Cir, Winter Garden, FL, 34787, 4 beds, 3.5 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/14adaa46-1188-4471-a7f5-496f1f554547/islphoto/genIsl.0_1.webp)
14423 Hampshire Bay Cir, Winter Garden, FL, 34787![Property at 625 Willett Dr, Winter Garden, FL, 34787, 2 beds, 1 bath, [object Object]](https://ssl.cdn-redfin.com/photo/rent/f867b5ef-b8b7-4ca3-9d40-83e92c7938f6/islphoto/genIsl.0_1.webp)
625 Willett Dr, Winter Garden, FL, 34787![Property at 545 First Cape Coral Dr, Winter Garden, FL, 34787, 4 beds, 2.5 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/1a939fec-07c4-4646-9936-4a93fda26427/islphoto/genIsl.0_1.webp)
545 First Cape Coral Dr, Winter Garden, FL, 34787![Property at 1000 Araminta St, Winter Garden, FL, 34787, 4 beds, 2.5 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/37cc9fa9-c083-493e-97df-1a591b848f5e/islphoto/genIsl.0_2.webp)
1000 Araminta St, Winter Garden, FL, 34787![Property at 207 Black Springs Ln, Winter Garden, FL, 34787, 4 beds, 2.5 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/beff2678-f3da-4e9e-93bd-ab62d3df2478/islphoto/genIsl.0_1.webp)
207 Black Springs Ln, Winter Garden, FL, 34787![Property at 902 Lost Grove Cir, Winter Garden, FL, 34787, 5 beds, 3 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/7d078883-e039-4e3f-9356-60b6484389b3/islphoto/genIsl.0_1.webp)
902 Lost Grove Cir, Winter Garden, FL, 34787![Property at 944 Lost Grove Cir, Winter Garden, FL, 34787, 5 beds, 3 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/eb39eca8-2e48-45fa-92f8-e5f13874abf9/islphoto/genIsl.0_1.webp)
944 Lost Grove Cir, Winter Garden, FL, 34787![Property at 813 Grande Regal Pt, Winter Garden, FL, 34787, 4 beds, 2.5 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/31d3aa80-5f3f-466a-88f8-abf4a9601a26/islphoto/genIsl.0_1.webp)
813 Grande Regal Pt, Winter Garden, FL, 34787![Property at 14281 Lagoon Cove Ln, Winter Garden, FL, 34787, 4 beds, 2.5 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/33d9750d-b247-4f24-a0ec-1ecaa80bc1b3/islphoto/genIsl.0_1.webp)
14281 Lagoon Cove Ln, Winter Garden, FL, 34787![Property at 604 Bending Oak Trl, Winter Garden, FL, 34787, 4 beds, 2 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/b4fa79d9-be35-45f4-8de3-a0de6a2ddbc8/islphoto/genIsl.0_1.webp)
604 Bending Oak Trl, Winter Garden, FL, 34787
Based on information submitted to the MLS GRID as of Mon Sep 15 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
More to explore in Oakland, FL
- Property Types
- Bedrooms
- Amenities
- Price
Rentals near Oakland, FL
Apartments for rent near Oakland, FL
Popular rental markets in Florida
- Rentals
- Apartments
About us
Find us
Subsidiaries
United States
CanadaCopyright: © 2025 Redfin. All rights reserved.
Updated January 2023: By searching, you agree to the Terms of Use, and Privacy Policy.
Do not sell or share my personal information.
REDFIN and all REDFIN variants, TITLE FORWARD, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.
California DRE #01521930
Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures
New Mexico Real Estate Licenses
TREC: Info About Brokerage Services, Consumer Protection Notice
Rocket Mortgage is an affiliated business of Redfin. All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York. For additional information on Rocket Mortgage or to receive lending services in the State of New York, please visit RocketMortgage.com.
Rocket Mortgage, LLC, Rocket Homes Real Estate LLC, Rocket Card, LLC, RockLoans Marketplace LLC (doing business as Rocket Loans), and Rocket Money, Inc., are separate operating subsidiaries of Rocket Limited Partnership. Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company is a separate legal entity operated and managed through its own management and governance structure. Rocket Limited Partnership is an indirect, wholly owned subsidiary of Rocket Companies, Inc. (NYSE: RKT).
If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.
REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.