Winter Park, FL 55+ active adult communities & homes for sale - Page 19

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

The Villages®

$279,900

2 beds

1 baths

978 sq ft

Villa

2913 PANCHOS WAY, THE VILLAGES, FL, 3216...

Community: The Villages®

Pelican Bay Daytona Beach

108 BLACK DUCK CIR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119

$239,500

3 beds

3 baths

1,627 sq ft

Townhouse

108 BLACK DUCK CIR, DAYTONA BEACH, FL, 3...

Community: Pelican Bay Daytona Beach

The Villages®

$319,000

2 beds

2 baths

1,248 sq ft

House

672 SAN PEDRO DR, THE VILLAGES, FL, 3215...

Community: The Villages®

The Villages®

$550,000

3 beds

2 baths

1,930 sq ft

House

591 BAKER LN, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$525,000

3 beds

2 baths

1,755 sq ft

House

652 SAN PEDRO DR, 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

Halifax Plantation

1416 KILRUSH DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$575,000

4 beds

2 baths

2,540 sq ft

House

1416 KILRUSH DR, ORMOND BEACH, FL, 32174

Community: Halifax Plantation

Venetian Bay

3338 TORRE BLVD, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168

$345,900

2 beds

2 baths

1,529 sq ft

Townhouse

3338 TORRE BLVD, NEW SMYRNA BEACH, FL, 3...

Community: Venetian Bay

Plantation Bay Golf & Country Club

13 BAY POINT DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$839,000

3 beds

4 baths

3,596 sq ft

House

13 BAY POINT DR, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Latitude Margaritaville

318 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$374,900

2 beds

2 baths

1,160 sq ft

House

318 GYPSY PALACE LN, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

Cindy Certified

3133 ROCKWOOD WAY, MINNEOLA, FL, 34715, Minneola, FL 34715

$513,490

4 beds

3 baths

2,366 sq ft

5271 HAVEN VIEW DR, CLERMONT, FL, 34714

Spruce Creek Country Club

9345 SE 136TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$439,900

2 beds

2 baths

1,989 sq ft

House

9345 SE 136TH PL, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

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

Questions? Call us: (888) 625-4885

Latitude Margaritaville

677 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$620,000

3 beds

3 baths

2,116 sq ft

House

677 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

The Villages®

$899,000

3 beds

3 baths

2,453 sq ft

House

1555 COPE PL, THE VILLAGES, FL, 32162

Community: The Villages®

Solivita

861 BELLA VIANA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$395,000

2 beds

3 baths

2,379 sq ft

House

861 BELLA VIANA RD, KISSIMMEE, FL, 34759

Community: Solivita

Latitude Margaritaville

664 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$595,000

2 beds

2 baths

1,922 sq ft

House

664 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

Latitude Margaritaville

214 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124

$384,900

2 beds

2 baths

1,308 sq ft

House

214 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...

Community: Latitude Margaritaville

Del Webb Sunbridge

6100 SANDY SPRINGS CT, ST CLOUD, FL, 347..., St Cloud, FL 34771

$1,050,000

4 beds

4 baths

3,559 sq ft

House

6100 SANDY SPRINGS CT, ST CLOUD, FL, 347...

Community: Del Webb Sunbridge

The Villages®

$319,900

2 beds

2 baths

1,415 sq ft

House

2713 DE LA ROSA ST, THE VILLAGES, FL, 32...

Community: The Villages®

Palms at Serenoa

17558 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714

$425,000

3 beds

2 baths

1,822 sq ft

House

17558 BLAZING STAR CIR, CLERMONT, FL, 34...

Community: Palms at Serenoa

Cindy Certified

1520 CONGAREE ST, DAVENPORT, FL, 33837, Davenport, FL 33837

$329,000

3 beds

2 baths

1,734 sq ft

House

1520 CONGAREE ST, DAVENPORT, FL, 33837

Del Webb at Viera

8974 BLISSFUL BREEZE TRL, MELBOURNE, FL,..., Melbourne, FL 32940

$420,620

2 beds

2 baths

1,579 sq ft

Villa

8974 BLISSFUL BREEZE TRL, MELBOURNE, FL,...

Community: Del Webb at Viera

Arlington Ridge

27001 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748

$275,500

2 beds

2 baths

1,330 sq ft

Villa

27001 WHITE PLAINS WAY, LEESBURG, FL, 34...

Community: Arlington Ridge

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

Questions? Call us: (888) 625-4885

Cresswind at Lake Harris

1463 SANTORINI WAY, TAVARES, FL, 32778, Tavares, FL 32778

$399,999

2 beds

2 baths

1,434 sq ft

House

1463 SANTORINI WAY, TAVARES, FL, 32778

Community: Cresswind at Lake Harris

Cindy Certified

6939 HIGGS ALY, ORLANDO, FL, 32827, Orlando, FL 32827

$545,000

2 baths

2,035 sq ft

House

4195 MUIRFIELD LOOP, LAKE WALES, FL, 338...

4465 RIVER BIRCH BND, LAKELAND, FL, 3381...

Trilogy® Orlando

264 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736

$635,000

2 beds

3 baths

2,315 sq ft

House

264 SILVER MAPLE RD, GROVELAND, FL, 3473...

Community: Trilogy® Orlando

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

Questions? Call us: (888) 625-4885

Trilogy® Orlando

145 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736

$600,000

3 beds

2 baths

2,876 sq ft

House

145 BAYOU BEND RD, GROVELAND, FL, 34736

Community: Trilogy® Orlando

Cindy Certified

33611 SKY BLOSSOM CIR, LEESBURG, FL, 347..., Leesburg, FL 34788

$325,000

4 beds

2 baths

1,850 sq ft

House

33611 SKY BLOSSOM CIR, LEESBURG, FL, 347...

1…13 14 15 16 17 18 19 20 21 22 23 24 25…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 19

98 communities near Winter Park

2,698 homes near Winter Park

2 beds

1 baths

978 sq ft

Villa

3 beds

3 baths

1,627 sq ft

Townhouse

2 beds

2 baths

1,248 sq ft

House

3 beds

2 baths

1,930 sq ft

House

3 beds

2 baths

1,755 sq ft

House

4 beds

2 baths

2,540 sq ft

House

2 beds

2 baths

1,529 sq ft

Townhouse

3 beds

4 baths

3,596 sq ft

House

2 beds

2 baths

1,160 sq ft

House

4 beds

3 baths

2,366 sq ft

House

3 beds

2 baths

1,919 sq ft

House

2 beds

2 baths

1,272 sq ft

House

3 beds

2 baths

1,224 sq ft

House

2 beds

2 baths

1,545 sq ft

House

2 beds

2 baths

1,580 sq ft

House

2 beds

2 baths

1,989 sq ft

House

3 beds

3 baths

2,116 sq ft

House

3 beds

3 baths

2,453 sq ft

House

2 beds

3 baths

2,379 sq ft

House

2 beds