Winter Park, FL 55+ active adult communities & homes for sale - Page 22

2,698 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

4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

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

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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

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

Questions? Call us: (888) 625-4885

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

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

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

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.

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

5 rating (3 reviews)

Lake Ashton

$200ks - $500ks

Lake Ashton, Lake Wales, FL

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

Grand Haven

$200ks - $800ks

Grand Haven, Palm Coast, FL

New and Resale | Age-targeted | Built 1997 - present | 1,901 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 (8 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

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

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

Questions? Call us: (888) 625-4885

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

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

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)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

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

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

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

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

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

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes

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

Questions? Call us: (888) 625-4885

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)

Del Webb Sunbridge

$400ks - $800ks

Del Webb Sunbridge, St. Cloud, FL

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

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

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

Heritage - The Cottages o...

$300ks

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

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

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

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

Del Webb at Viera

$400ks - $1Ms

Del Webb at Viera, Melbourne, FL

New Construction | 55+ age-restricted | Built 2021 - present | 1,300 homes

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

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

Lakeside Landings

$100ks - $300ks

Lakeside Landings, Oxford, FL

New and Resale | Age-targeted | Built 2005 - present | 700 homes

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

Questions? Call us: (888) 625-4885

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

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

1 2...3

Cindy Certified

2259 CANYON OAK DR DR, DAVENPORT, FL, 33..., Davenport, FL 33837

$275,000

3 beds

2 baths

1,420 sq ft

House

2259 CANYON OAK DR DR, DAVENPORT, FL, 33...

The Villages®

$525,000

3 beds

2 baths

2,125 sq ft

House

2120 CALLAWAY DR, THE VILLAGES, FL, 3216...

Community: The Villages®

Sandpiper Golf & Country Club

6218 CRANE DR, LAKELAND, FL, 33809, Lakeland, FL 33809

$332,000

3 beds

2 baths

1,598 sq ft

House

6218 CRANE DR, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

Pelican Bay Daytona Beach

568 PELICAN BAY DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119

$700,000

4 beds

4 baths

3,393 sq ft

House

568 PELICAN BAY DR, DAYTONA BEACH, FL, 3...

Community: Pelican Bay Daytona Beach

Venetian Bay

2817 S ASCIANO CT, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168

$689,900

3 beds

3 baths

2,299 sq ft

House

2817 S ASCIANO CT, NEW SMYRNA BEACH, FL,...

Community: Venetian Bay

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

Questions? Call us: (888) 625-4885

The Villages®

$450,000

2 beds

2 baths

2,296 sq ft

House

1641 CARRERA DR, THE VILLAGES, FL, 32159

Community: The Villages®

Grand Haven

10 VILLAGE VIEW WAY, PALM COAST, FL, 321..., Palm Coast, FL 32137

$499,000

3 beds

3 baths

2,096 sq ft

House

10 VILLAGE VIEW WAY, PALM COAST, FL, 321...

Community: Grand Haven

Cindy Certified

1405 E VOORHIS AVE, DELAND, FL, 32724, Deland, FL 32724

$325,000

3 beds

2 baths

1,386 sq ft

3951 KENNEBUNK LOOP, MOUNT DORA, FL, 327...

Community: Lakes of Mount Dora

Cindy Certified

1717 DALROY ST, PALM BAY, FL, 32907, Palm Bay, FL 32907

$427,000

2 baths

1,840 sq ft

House

26045 OLIVE ROSE WAY, GROVELAND, FL, 347...

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

Questions? Call us: (888) 625-4885

Cindy Certified

26136 AZALEA OAK CIR, GROVELAND, FL, 347..., Groveland, FL 34736

$390,090

1,198 sq ft

Villa

8214 SE 169TH PALOWNIA LOOP, THE VILLAGE...

Community: The Villages®

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

Questions? Call us: (888) 625-4885

The Villages®

702 TURNBERRY LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$250,000

2 beds

2 baths

1,748 sq ft

Manufactured Home

702 TURNBERRY LN, LADY LAKE, FL, 32159

Community: The Villages®

Scottish Highlands

1607 SELKIRK DR, LEESBURG, FL, 34788, Leesburg, FL 34788

$248,500

3 beds

2 baths

1,510 sq ft

House

1607 SELKIRK DR, LEESBURG, FL, 34788

Community: Scottish Highlands

The Villages®

$398,000

3 beds

2 baths

1,430 sq ft

Villa

1521 TRENTON LN, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

$575,000

3 beds

2 baths

1,926 sq ft

House

1349 PATRICK PL, THE VILLAGES, FL, 32162

Community: The Villages®

Grand Haven

7 OASIS CIR, PALM COAST, FL, 32137, Palm Coast, FL 32137

$489,000

3 beds

2 baths

2,018 sq ft

House

7 OASIS CIR, PALM COAST, FL, 32137

Community: Grand Haven

Lakeside Landings

10038 KETCH KAY LN, OXFORD, FL, 34484, Oxford, FL 34484

$338,900

3 beds

2 baths

1,619 sq ft

House

10038 KETCH KAY LN, OXFORD, FL, 34484

Community: Lakeside Landings

Lakes of Mount Dora

8595 HEMPSTEAD WAY, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757

$496,990

4 beds

3 baths

2,107 sq ft

House

8595 HEMPSTEAD WAY, MOUNT DORA, FL, 3275...

Community: Lakes of Mount Dora

The Villages®

$399,000

3 beds

2 baths

1,564 sq ft

House

3305 FINK ST, THE VILLAGES, FL, 32163

Community: The Villages®

Lake James

$429,900

2 beds

2 baths

1,931 sq ft

House

2309 LAKE JAMES WAY, LAKELAND, FL, 33810

Community: Lake James

Venetian Bay

3072 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$317,000

3 beds

3 baths

1,672 sq ft

House

3072 MELETO BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Venetian Bay

527 LUNA BELLA LN, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168

$675,000

3 beds

2 baths

2,416 sq ft

House

527 LUNA BELLA LN, NEW SMYRNA BEACH, FL,...

Community: Venetian Bay

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

Questions? Call us: (888) 625-4885

The Villages®

$329,000

3 beds

2 baths

1,497 sq ft

House

1506 AQUINO LN, THE VILLAGES, FL, 32159

Community: The Villages®

Spruce Creek South

17655 SE 102ND CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$190,000

2 beds

2 baths

1,008 sq ft

House

17655 SE 102ND CIR, SUMMERFIELD, FL, 344...

Community: Spruce Creek South

1…16 17 18 19 20 21 22 23 24 25 26 27 28…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

2,698 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: Oct 10, 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 22

98 communities near Winter Park

2,698 homes near Winter Park

3 beds

2 baths

1,420 sq ft

House

3 beds

2 baths

2,125 sq ft

House

3 beds

2 baths

1,598 sq ft

House

4 beds

4 baths

3,393 sq ft

House

3 beds

3 baths

2,299 sq ft

House

2 beds

2 baths

2,296 sq ft

House

3 beds

3 baths

2,096 sq ft

House

3 beds

2 baths

1,386 sq ft

House

3 beds

2 baths

2,000 sq ft

House

2 beds

2 baths

1,452 sq ft

House

3 beds

2 baths

2,202 sq ft

House

3 beds

2 baths

2,180 sq ft

House

4 beds

3 baths

2,365 sq ft

House

3 beds

2 baths

1,718 sq ft

House

2 beds

2 baths

1,840 sq ft

House

4 beds

2 baths

1,840 sq ft

House

5 beds

3 baths

2,133 sq ft

House

3 beds

3 baths

2,203 sq ft

Townhouse

3 beds

2 baths

2,202 sq ft

House

2 beds