55+ communities in Winter Garden: costs, fees and amenities compared

55+ communities within reach of Winter Garden

Builder prices were checked on builder sites in September 2026. Resale price ranges, home counts and HOA ranges come from 55places, which notes that dues vary by home and section. Confirm every figure with the builder or HOA.

Each community in brief

Del Webb Oasis, Winter Garden

Del Webb Oasis is a gated 55+ community at 13055 Sand Castle Drive, Winter Garden. Del Webb began building in 2020 with 422 homes planned, according to 55places. Single-family homes in the Distinctive and Echelon series run from about 1,670 to 3,453 square feet, and one-story attached villas are about 1,579 square feet. The 12,000-square-foot clubhouse has a fitness center and gathering rooms, with a pool, spa and pickleball courts outside.

55places lists HOA dues on current listings of roughly $474 to $712 a month, the highest of the communities in our table. Ask what the dues include and whether the community is in a CDD.

Del Webb Lakehaven, Clermont

Del Webb Lakehaven, at 6852 Willow Bank Drive, Clermont 34714, listed homes from $404,990 in September 2026. 55places describes 11 single-family plans from 1,405 to more than 3,453 square feet, two clubhouses, indoor and outdoor pickleball and lake-view trails, with more lakeside amenities planned.

Sanctuary at Wellness Ridge, Clermont

Lennar describes this section of Wellness Ridge as exclusively for active adults ages 55 and over, with plans from about $429,000. The Wellness Ridge CDD's FY2027 budget sets operations assessments of $506.93 to $1,382.54 a home by lot type, plus debt assessments.

Palms at Serenoa, Clermont

D.R. Horton's Palms at Serenoa has 570 single-level homes planned, from 1,402 to 1,707 square feet for single-family models, according to 55places, which lists prices from the high $200,000s to the low $400,000s and HOA dues of about $105 to $333 a month.

Del Webb Minneola

Del Webb Minneola, at 1411 Sunset Crest Way, listed homes from $373,990 in September 2026. 55places describes a two-story clubhouse, fitness center, tavern and zero-entry pool, with dues of about $206 to $434 a month.

Kings Ridge, Clermont

Kings Ridge is the largest resale option, with 2,088 homes built by Lennar between 1995 and 2000 and two golf courses. See our Kings Ridge page for older-home checks.

Trilogy Orlando, Groveland

Trilogy Orlando has about 1,500 homes and a 57,000-square-foot clubhouse called Magnolia House. It is a resale community, with homes built from 2005 to 2022 according to 55places.

Four Seasons at Orlando, Kissimmee

To the south, K. Hovnanian's Four Seasons at Orlando is a gated 55+ community of 557 homes off SR 429 and I-4, built from 2017, with a 12,000-square-foot clubhouse. 55places lists prices from the high $300,000s to the low $600,000s and dues of about $236 to $480 a month. It is in Osceola County, so taxes and services differ again.

Legal 55+ rules: the 80/20 test

The 80% occupancy test

Under the federal Fair Housing Act exemption and Florida's matching statute, a 55+ community must have at least 80% of occupied units with at least one resident aged 55 or older, publish and follow policies showing that intent, and verify ages using reliable surveys and affidavits.

What the other 20% allows

Florida's statute says a community still qualifies if a long-time resident who moved in on or before 1 October 1989 does not meet the age test, or if empty units are reserved for qualifying buyers. Beyond that, each community's documents set its own rules on younger residents, guests and rentals, so read them before you buy.

A 55+ label is a legal designation about who can live in the community. It says nothing about amenities, fees or the condition of the homes, which is why the cost comparison below matters as much as the age rule.

What it costs: dues, CDD, tax and insurance

HOA dues

Ask what the dues include: lawn care, cable or internet, gate staffing and clubhouse programming. Del Webb Oasis's range of about $474 to $712 a month may include services that a lower-fee community bills separately.

CDD assessments

New communities in Lake County often sit in a CDD. The Wellness Ridge CDD, for example, adopted FY2027 operations assessments of $506.93 to $1,382.54 a home by product type, with separate debt assessments on top. Florida law requires a bold CDD disclosure in the first sale contract.

Property tax by county

Winter Garden is in Orange County and the Clermont-area options are in Lake County, which have different millage. See our Orange County and Lake County tax pages. If the home will be your permanent residence on 1 January, apply for homestead, which can cut taxable value by up to $50,000.

Insurance

Get a homeowners quote for the exact address before you commit. For older resale homes, insurers may ask for four-point and wind mitigation reports.

New construction or resale 55+

Most 55+ choices near Winter Garden fall into two groups. Newer Del Webb and Lennar communities offer current floor plans, builder warranties and amenities that may still be under construction. Older resale communities such as Kings Ridge, where 55places says all 2,088 homes were built between 1995 and 2000, offer established amenities and mature landscaping, and often lower prices, but the homes may need updates to roofs, HVAC and windows.

For resale homes, ask for the age of the roof and major systems and order a full inspection. For new homes, ask which amenities are finished, what the builder still controls, and when the HOA will pass to resident control.

How to choose: questions to ask any 55+ community

1. How does the community verify ages, and how often does it update records?
2. Can a resident under 55 live in the home, and under what conditions?
3. Are rentals allowed, and for what minimum term?
4. What is the current HOA budget and reserve balance?
5. Is there a CDD, and what are the O&M and debt amounts for this lot?
6. Which amenities are finished, and which are still planned?

If you are selling a larger home to move, our downsizing in Florida guide covers timing both sales.

Common questions

Sources

• Cornell LII: 42 U.S. Code 3607, religious organization or private club exemption (housing for older persons)
• Pulte: New homes in Winter Garden, Florida
• 55places: Del Webb Oasis, Winter Garden
• Del Webb: New homes in Clermont, Florida
• Del Webb: 55+ communities in Minneola
• Lennar: Sanctuary at Wellness Ridge, Clermont
• Lennar: New homes in Clermont, FL
• 55places: Kings Ridge, Clermont
• 55places: Trilogy Orlando, Groveland
• 55places: Del Webb Lakehaven, Clermont
• Wellness Ridge CDD: FY2027 adopted budget (PDF)
• Florida Department of Revenue: Property tax exemptions for homeowners
• 55places: Four Seasons at Orlando, Kissimmee
• 55places: Palms at Serenoa, Clermont
• Florida Statutes: Section 760.29, housing for older persons
• Florida Statutes: Section 190.048, sale of real estate within a district
• 55places: Cresswind at Lake Harris, Tavares