Winter Park, FL 55+ active adult communities & homes for sale - Page 5

2,702 homes near Winter Park

Sort by:

Relevance

4 rating (17 reviews)

The Villages®

$100ks - $1Ms

The Villages®, The Villages, FL

New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

New and Resale | Age-targeted | Built 2004 - present | 1,561 homes

4.5 rating (11 reviews)

Spruce Creek Country Club

$100ks - $400ks

Spruce Creek Country Club, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes

5 rating (2 reviews)

Plantation at Leesburg

$100ks - $300ks

Plantation at Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes

4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

3.6 rating (48 reviews)

Latitude Margaritaville

$300ks - $800ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes

5 rating (1 reviews)

Plantation Bay Golf &...

$400ks - $2Ms

Plantation Bay Golf &..., Ormond Beach, FL

New and Resale | Age-targeted | Built 1988 - present | 3,500 homes

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 homes

5 rating (3 reviews)

Twin Lakes

$200ks - $600ks

Twin Lakes, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes

Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

Grand Haven

$200ks - $800ks

Grand Haven, Palm Coast, FL

New and Resale | Age-targeted | Built 1997 - present | 1,901 homes

5 rating (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes

3.8 rating (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes

5 rating (3 reviews)

Lake Ashton

$200ks - $500ks

Lake Ashton, Lake Wales, FL

Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes

4 rating (4 reviews)

Lakes of Mount Dora

$300ks - $900ks

Lakes of Mount Dora, Mount Dora, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes

5 rating (1 reviews)

Sandpiper Golf & Coun...

$100ks - $300ks

Sandpiper Golf & Coun..., Lakeland, FL

New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

New and Resale | Age-targeted | Built 1980 - present | 1,000 homes

3.8 rating (4 reviews)

Spruce Creek South

$100ks - $200ks

Spruce Creek South, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes

4 rating (2 reviews)

Harbor Hills Country Club

$300ks - $900ks

Harbor Hills Country Club, Lady Lake, FL

New and Resale | Age-targeted | Built 1989 - present | 940 homes

5 rating (1 reviews)

Cresswind at Victoria Gar...

$300ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 homes

The Country Club of Mount...

$200ks - $1Ms

The Country Club of Mount..., Mount Dora, FL

Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes

3.6 rating (5 reviews)

Heritage Hills

$200ks - $400ks

Heritage Hills, Clermont, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes

5 rating (1 reviews)

Del Webb Sunbridge

$400ks - $800ks

Del Webb Sunbridge, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes

Heritage - The Cottages o...

$300ks

Heritage - The Cottages o..., Okahumpka, FL

New Construction | 55+ age-restricted | Built 2022 - present | 179 homes

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes

4.4 rating (16 reviews)

Del Webb Orlando

$200ks - $500ks

Del Webb Orlando, Davenport, FL

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes

5 rating (1 reviews)

Legacy of Leesburg

$200ks - $400ks

Legacy of Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes

The Timbers at Everlands

$200ks - $500ks

The Timbers at Everlands, Palm Bay, FL

New Construction | 55+ age-restricted | Built 2023 - present | 450 homes

5 rating (1 reviews)

VillageWalk at Lake Nona

$300ks - $700ks

VillageWalk at Lake Nona, Orlando, FL

Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2017 - present | 557 homes

Colonnades

$100ks - $200ks

Colonnades, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1985 - 1994 | 360 homes

1 2...3

Latitude Margaritaville

422 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$678,000

2 beds

2 baths

1,922 sq ft

House

422 CORAL REEF WAY, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

Cresswind at Hammock Oaks

533 HAMMOCK OAKS BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159

$475,990

3 beds

3 baths

2,129 sq ft

House

533 HAMMOCK OAKS BLVD, LADY LAKE, FL, 32...

Community: Cresswind at Hammock Oaks

Cresswind at Hammock Oaks

545 HAMMOCK OAKS BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159

$495,990

3 beds

3 baths

2,289 sq ft

House

545 HAMMOCK OAKS BLVD, LADY LAKE, FL, 32...

Community: Cresswind at Hammock Oaks

Highland Fairways

2227 GRAND CYPRESS DR, LAKELAND, FL, 338..., Lakeland, FL 33810

$205,000

2 beds

2 baths

1,363 sq ft

House

2227 GRAND CYPRESS DR, LAKELAND, FL, 338...

Community: Highland Fairways

The Villages®

$217,000

2 beds

2 baths

1,149 sq ft

Manufactured Home

1001 MATTHEW AVE, THE VILLAGES, FL, 3215...

Community: The Villages®

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Cresswind at Hammock Oaks

419 VERONA WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$371,990

2 beds

2 baths

1,434 sq ft

House

419 VERONA WAY, LADY LAKE, FL, 32159

Community: Cresswind at Hammock Oaks

The Villages®

$529,000

3 beds

2 baths

1,943 sq ft

House

3578 OBRIEN PL, THE VILLAGES, FL, 32163

Community: The Villages®

Cresswind at Hammock Oaks

423 VERONA WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$394,990

3 beds

2 baths

1,724 sq ft

House

423 VERONA WAY, LADY LAKE, FL, 32159

Community: Cresswind at Hammock Oaks

Grand Haven

22 IBIS CT, PALM COAST, FL, 32137, Palm Coast, FL 32137

$525,000

4 beds

2 baths

2,670 sq ft

House

22 IBIS CT, PALM COAST, FL, 32137

Community: Grand Haven

The Villages®

$349,500

3 beds

2 baths

1,497 sq ft

House

16947 SE 93RD CUTHBERT CIR, THE VILLAGES...

Community: The Villages®

The Villages®

$245,000

2 beds

2 baths

1,121 sq ft

Villa

214 MONTOYA DR, THE VILLAGES, FL, 32159

Community: The Villages®

Solivita

205 BELL TOWER XING, POINCIANA, FL, 3475..., Poinciana, FL 34759

$257,500

2 beds

2 baths

1,405 sq ft

House

205 BELL TOWER XING, POINCIANA, FL, 3475...

Community: Solivita

Del Webb Oasis

15084 CANOPY COVER DR, WINTER GARDEN, FL..., Winter Garden, FL 34787

$910,000

3 beds

3 baths

2,270 sq ft

House

15084 CANOPY COVER DR, WINTER GARDEN, FL...

Community: Del Webb Oasis

Cresswind at Lake Harris

1732 POINT GRACE RD, TAVARES, FL, 32778, Tavares, FL 32778

$516,990

3 beds

3 baths

2,129 sq ft

House

1732 POINT GRACE RD, TAVARES, FL, 32778

Community: Cresswind at Lake Harris

Cindy Certified

12523 GOLD HONEYSUCKLE ST, WINTER GARDEN..., Winter Garden, FL 34787

$834,990

4 beds

3 baths

2,552 sq ft

House

12523 GOLD HONEYSUCKLE ST, WINTER GARDEN...

Cresswind DeLand

1242 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724

$593,990

3 beds

3 baths

2,490 sq ft

House

1242 CRESSWIND BLVD, DELAND, FL, 32724

Community: Cresswind DeLand

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

The Villages®

$525,000

3 beds

2 baths

1,926 sq ft

House

3984 MCDOWELL DR, THE VILLAGES, FL, 3216...

Community: The Villages®

Cindy Certified

870 BALLANTYNE DR, LAKE WALES, FL, 33898, Lake Wales, FL 33898

$320,000

4 beds

2 baths

1,822 sq ft

House

870 BALLANTYNE DR, LAKE WALES, FL, 33898

The Villages®

$415,000

3 beds

2 baths

1,902 sq ft

House

16573 SE 77TH NORTHRIDGE CT, THE VILLAGE...

364 ACADIA DR, POINCIANA, FL, 34759

Community: Solivita

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Cresswind DeLand

1246 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724

$618,990

3 beds

4 baths

2,776 sq ft

House

1246 CRESSWIND BLVD, DELAND, FL, 32724

Community: Cresswind DeLand

Venetian Bay

3118 BORASSUS DR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$349,000

3 beds

2 baths

1,610 sq ft

House

3118 BORASSUS DR, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Cresswind DeLand

1197 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724

$443,990

2 beds

2 baths

1,668 sq ft

House

1197 CRESSWIND BLVD, DELAND, FL, 32724

Community: Cresswind DeLand

Cindy Certified

4826 RIVER BIRCH BND, LAKELAND, FL, 3381..., Lakeland, FL 33811

$282,990

3 beds

2 baths

1,302 sq ft

House

4826 RIVER BIRCH BND, LAKELAND, FL, 3381...

Cindy Certified

495 TAFT DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$299,900

2 baths

963 sq ft

Villa

737 LOUISE LN, THE VILLAGES, FL, 32163

Community: The Villages®

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Cindy Certified

3277 WHOLENESS WAY, CLERMONT, FL, 34714, Clermont, FL 34714

$612,990

4 beds

4 baths

2,911 sq ft

House

3277 WHOLENESS WAY, CLERMONT, FL, 34714

Cindy Certified

3156 NAMASTE DR, CLERMONT, FL, 34714, Clermont, FL 34714

$584,940

4 beds

2 baths

2,532 sq ft

House

3156 NAMASTE DR, CLERMONT, FL, 34714

1 2 3 4 5 6 7 8 9 10 11 12 13 14…68

Frequently Asked Questions

What size 55+ communities are there in Winter Park?

In Winter Park, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winter Park?

The smallest 55+ community in Winter Park has 178 homes, the largest has 178 homes, and the average community consists of 178 homes.

Are there new 55+ homes available in Winter Park?

Yes, there is new 55+ home available in Winter Park. The most recent community started in Winter Park include Rosalia Winter Park. There is also 1 community in Winter Park that offers new construction homes, including Rosalia Winter Park.

Are there gated 55+ communities in Winter Park?

Yes, there is gated 55+ community in Winter Park. The only 55+ community in Winter Park is gated. For instance, Rosalia Winter Park is a gated community with 178 homes.

Want more information about active adult communities around Winter Park?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting optout@55places.com. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Winter Park?

Call us: (888) 625-4885

2,702 homes

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Aug 25, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

Winter Park, FL 55+ active adult communities & homes for sale - Page 5

98 communities near Winter Park

2,702 homes near Winter Park

2 beds

2 baths

1,922 sq ft

House

3 beds

3 baths

2,129 sq ft

House

3 beds

3 baths

2,289 sq ft

House

2 beds

2 baths

1,363 sq ft

House

2 beds

2 baths

1,149 sq ft

Manufactured Home

2 beds

2 baths

1,434 sq ft

House

3 beds

2 baths

1,943 sq ft

House

3 beds

2 baths

1,724 sq ft

House

4 beds

2 baths

2,670 sq ft

House

3 beds

2 baths

1,497 sq ft

House

2 beds

2 baths

1,121 sq ft

Villa

2 beds

2 baths

1,405 sq ft

House

3 beds

3 baths

2,270 sq ft

House

3 beds

3 baths

2,129 sq ft

House

4 beds

3 baths

2,552 sq ft

House

3 beds

3 baths

2,490 sq ft

House

3 beds

2 baths

1,926 sq ft

House

4 beds

2 baths

1,822 sq ft

House

3 beds

2 baths

1,902 sq ft

House

2 beds