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Preserving the look and feel of Historic Winter Garden for years to come

The Charm of Oakland Hills

Introducing Oakland Hills  - Winter Garden's premier luxury new home community. Oakland Hills is an enclave of only 17 over-sized home sites nestled among grand oak trees reminiscent of old Florida rural estates.

These brand new custom homes  feature  modern farmhouse architectural style and  are designed to maximize the natural attributes of each specific lot. No two homes will be alike ensuring individuality and unique curb appeal throughout the community.

Unlike most new communities, Oakland Hills is designed to respect the natural condition by preserving mature trees and winding a narrow roadway through the community without the use of curb and gutter. This low-impact design respects the natural lay of the land and is a key component in the overall look and feel of the development. Oakland Hills will truly evoke the sense of old Florida with its careful planning of details from the homes to the natural landscaping.

Availability is limited and subject to change.

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A location that can't be beat.

Oakland Hills is located within a two-minute bike ride from the West Orange Trail. From there it’s just another 7-minute bike ride to The Plant Street Marketand the Farmers Market in downtown Winter Garden. By motor vehicle, all of Central Florida’s major commuter corridors are easily accessible including the FL-429 which is just 4 miles away.

• West Orange Trail - 2 minutes

• Downtown Winter Garden - 4 minutes

• Walt Disney World Resort - 25 minutes

• Downtown Orlando - 29 minutes

• Orlando International - 35 minutes

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Oakland Hills Area Map

Homes For Sale

Basil  |  Clare


The Basil

685 Large Oak Lane (Lot 5)

Price: Sold

5 Bedrooms  |  4/1 Bathrooms  |  4,170 SqFt

Fall head-over-heels for this modern farmhouse custom masterpiece situated within Winter Garden’s premier luxury new home community, Oakland Hills. Combining sleek contemporary design elements with cozy, yet chic farmhouse aesthetics, this 5BR, 4/1BA home is timelessly fresh with the most sought-after architectural style in years! Expertly designed for this 1/3-acre lot, the home embraces modern trends while still exuding warm, rustic charm.

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Floor Plans

Download Floor Plan

The Basil - Floor Plan

The Clare

15210 E. Oakland Avenue (Lot 2)

Price: Sold

4 Bedrooms  |  3  Bathrooms  |  3,640 SqFt

Expertly designed for this 0.47-acre lot, this home embraces modern trends while still exuding warm, rustic charm. Keeping true to the farmhouse style, the home will feature a large covered rear porch with an optional summer kitchen that overlooks the spacious backyard and grand oak tree. The home is complete with a study, an upstairs bonus room, a smart home system, energy-efficient appliances, and energy-saving construction features.

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Floor Plans

Download Floor Plan

The Clare - Floor Plan

Lots For Sale



Lot 1 - $ 310,000

Lot 2 - Sold

 Lot 3 - Sold

 Lot 4 - the "Gabriel"

 Lot 5 - Sold

 Lot 6 - Sold

 Lot 7 - Sold

 Lot 8 - Sold

Lot 9 - Sold

Lot 10 - Sold

 Lot 11 - Sold

Lot 12 - Sold 

Lot 13 - Sold

Lot 14 - Sold

 Lot 15 - Sold

Lot 16 - Sold

Lot 17 - Sold

Pricing and Availability Subject to Change

Floor Plans

Buy one of our existing homes built by our custom builders or let us work with you to design and build your dream home styled to fit your unique tastes. We are also happy to sell you a lot today and then let you decide whether to build your new home now or later. Either way, draw inspiration from floor plans created especially for Oakland Hills by our Winter Park based architects. Feel free to call us at any time with any questions you may have.   We will be delighted to help guide you through the process of becoming a new home owner in Winter Garden’s newest and most stylish community! 

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About Us

Project Finance and Development

PFD creates inspiring and compelling communities that change the trajectory of more typical, generally unimaginative development concepts. The team at PFD is constantly testing and measuring their ideas against the company’s mission of only doing projects where the team would themselves like to live or shop. PFD takes on a new project only when it believes that its vision for the site will result in a development that has a positive impact on the surrounding area. This approach creates value not only for PFD but also for its neighbors. 

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The Julie Bettosini Team at Stockworth

Julie Bettosini is a luxury property specialist and co-founder of Stockworth Realty Group. With more than 19 years of Real Estate experience, and backed by a full team of licensed real estate professionals, she provides client-centered service and personalized corporate relocation for major companies, professional athletes and executives moving to Orlando. Julie  holds a bachelor’s degree in communications from the University of Central Florida and is a Winter Garden Resident. 

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Contact Us

Contact Julie Bettosini at Stockworth Realty Group for more information or to schedule your private tour.


15188 E Oakland Avenue

Winter Garden, FL 34787


(407) 909-5903