
John’s Landing Community | Oakland, Florida
Welcome Homeowners and Residents to John’s Landing Homeowners Association
John’s Landing is a premier single-family residential community, ideally situated along the scenic shores of John’s Lake. Its location offers convenient access to the Florida Turnpike, the West Orange Trail, and Oakland Town Hall, blending natural beauty with everyday accessibility.
Surrounded by a canopy of mature oak trees, the community features 273 homes, many of which are thoughtfully positioned around tranquil ponds. Along the southern boundary, a collection of 58 luxurious custom homes, known as John’s Landing Estates, offers exclusive lakefront and adjacent residences, enhancing the community’s upscale character.
This private, upscale, gated community provides residents with a peaceful and refined living environment while remaining close to Central Florida’s many attractions. As a deed-restricted neighborhood, John’s Landing upholds a high standard of living, complemented by amenities such as a multi-purpose court for tennis, pickleball, and basketball, a children’s playground, and a scenic boat dock with direct access to John’s Lake.
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Board Meetings
For a list of the board meetings for this year – click here. All board meetings are held at the Oakland Meeting Hall, 221 N Arrington Street | Oakland, FL 34760.
All homeowners are welcome to attend the board meetings. (Meetings are restricted to homeowners ONLY). This is a valuable opportunity to meet your Board of Directors and connect with your neighbors, while staying informed about important updates and activities within your community.
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Architectural Review Board (ARB) Committee Meetings
When needed, ARB Committee Meetings are held virtually on Wednesdays at 7:00pm. Meetings are restricted to homeowners ONLY.
ARB committee meetings are NOT held during holiday periods.
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Association Assessments
Association Assessments are due on January 1st and July 1st

The current Association Assessments are $1,150 a year due bi-annually for the amount of $575 on January 1st and July 1st. Non-paid dues will be placed into delinquency and subject to fines, penalties and a lien placed against the property until paid in full.
To set-up recurring payments, make a payment, see your ledger in detail, or respond to a violation – log-in to the Southwest Homeowner Portal. Pro-Tip: If you set-up recurring payments using ACH or e-check…there is no processing fee for homeowners! Other payment methods have processing fees charged by the software – that includes debit cards with CC logos. Southwest accepts credit cards, checks, and even Apple Pay.
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Community News
Residents please refer to the News Page for all the latest Community News, Notices and Updates.
Latest News:
Association Assessments for July 1st 2025
Upgrading to ButterflyMX Entry System at the Community Gate
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ButterflyMX System for Gate Access

IMPORTANT ButterflyMX Information:
Important Reminder – ButterflyMX Registration | Gate Clickers Still Work
Important Notice – Old Gate Codes No Longer Valid | ButterflyMX Access Instructions
Immediate Action Required – Register Now for ButterflyMX Gate Access
Resident Contact Info for ButterflyMX Gate Access
Upgrading to ButterflyMX Entry System at the Community Gate
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Friendly Reminders
It’s the responsibility of all John’s Landing HOA members to maintain their property in accordance with the community’s Covenants and Restrictions.
Violations

Violations not cured will result in Fines and Liens
READ MORE
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Architectural Review Board Approval

If you are planning to complete external property maintenance or make any exterior changes to your home including exterior painting, roofing, windows, doors, landscaping (including sod and trees), mailboxes etc. an Architectural Review Board (ARB) Application must be submitted for approval. Any work performed without Architectural Review Board (ARB) Committee approval, which is required pursuant to the Johns Landing Declaration of Covenants, Conditions, Easements & Restrictions Article XV, may be subject to a fine.
NOTE: You will require prior Architectural Review Board (ARB) approval when painting the same color or using the same materials for maintenance, repairs or replacement.
Work may not commence until your request is approved by the Architectural Review Board (ARB).
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Golf Cart Ordinance – Town of Oakland
- All town streets within Town subdivisions or streets in subdivisions which traffic is enforceable providing they are approved for use by the subdivisions Homeowners Association and a written agreement has been entered with the Town for traffic enforcement on subdivision streets. Any notice to rescind this use will be provided in writing.
- No golf cart is permitted to ride on private property except that property owned by the same individual as the golf cart or without written consent of the owner. If the owner is present on properly where a golf cart is being used, they are permitted to give verbal consent.
- *The Town of Oakland shall provide signage designating streets or other areas where golf carts may be operated.
- Full Town of Oakland Golf Cart Ordinance READ MORE
