not an image

Call us at (888) 625-4885 to learn more about active adult communities in Winter Park

Winter Park, FL 55+ active adult communities & homes for sale - Page 59

2,513 homes near Winter Park

Sort by:

Relevance

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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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
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 (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 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) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 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.
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 (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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
5 rating (7 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
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 (3 reviews) Twin Lakes
$200ks - $600ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 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 (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
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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
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
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 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 (2 reviews) Heritage Isle
$300ks - $500ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 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.
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 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
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$200ks - $600ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes
3.8 rating (5 reviews) Traditions at Lake Ruby
$200ks - $300ks
Traditions at Lake Ruby, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 552 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
4.1 rating (9 reviews) Indian River Colony Club
$200ks - $400ks
Indian River Colony Club, Melbourne, FL
New and Resale | 55+ age-restricted | Built 1986 - present | 777 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.
Tohoqua Reserve
$300ks - $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2021 - present | 258 homes
The Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes
12...3
Grand Haven 67 LAGARE ST, PALM COAST, FL, 32137, Palm Coast, FL 32137
$499,000

3 beds

|

3 baths

|

2,446 sq ft

|

House

67 LAGARE ST, PALM COAST, FL, 32137
Community: Grand Haven
Ridgehaven 457 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$459,990

4 beds

|

3 baths

|

2,487 sq ft

|

House

457 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
The Villages® 4216 BALCHARAN TER, THE VILLAGES, FL, 32..., The Villages, FL 32163
$534,900

3 beds

|

2 baths

|

1,924 sq ft

|

House

4216 BALCHARAN TER, THE VILLAGES, FL, 32...
Community: The Villages®
Heritage Isle 3029 VALLEJO WAY, MELBOURNE, FL, 32940, Melbourne, FL 32940
$309,000

2 beds

|

2 baths

|

1,532 sq ft

|

Townhouse

3029 VALLEJO WAY, MELBOURNE, FL, 32940
Community: Heritage Isle
Royal Highlands 4738 ST ANDREWS ARC, LEESBURG, FL, 34748, Leesburg, FL 34748
$294,999

3 beds

|

2 baths

|

1,892 sq ft

|

House

4738 ST ANDREWS ARC, LEESBURG, FL, 34748
Community: Royal Highlands
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Arlington Ridge 3507 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$309,900

2 beds

|

2 baths

|

1,476 sq ft

|

House

3507 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
The Villages® 1722 BUGLE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$424,500

3 beds

|

2 baths

|

1,667 sq ft

|

House

1722 BUGLE TER, THE VILLAGES, FL, 32162
Community: The Villages®
Lake Ashton 5200 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884
$510,000

3 beds

|

2 baths

|

2,443 sq ft

|

House

5200 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
Summer Trees 79 CYPRESS POND RD 79, PORT ORANGE, FL, ..., Port Orange, FL 32128
$220,000

2 beds

|

2 baths

|

888 sq ft

|

Condo

79 CYPRESS POND RD 79, PORT ORANGE, FL, ...
Community: Summer Trees
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.
Summer Trees 79 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$220,000

2 beds

|

2 baths

|

1,300 sq ft

|

House

79 CYPRESS POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
The Lakes at Harmony 3184 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773
$469,800

3 beds

|

2 baths

|

1,852 sq ft

|

House

3184 SONGBIRD CIR, HARMONY, FL, 34773
Del Webb Sunbridge 2698 RIVER CREEK LN, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771
$595,000

3 beds

|

3 baths

|

2,080 sq ft

|

House

2698 RIVER CREEK LN, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
Spruce Creek Country Club 12855 SE 92ND COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$339,000

2 beds

|

2 baths

|

1,995 sq ft

|

House

12855 SE 92ND COURT RD, SUMMERFIELD, FL,...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Harbor Hills Country Club 5235 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$1,200,000

4 beds

|

4 baths

|

3,836 sq ft

|

House

5235 GREENS DR, LADY LAKE, FL, 32159
The Villages® 902 ROSE LN, THE VILLAGES, FL, 32159, The Villages, FL 32159
$159,900

2 beds

|

2 baths

|

1,036 sq ft

|

Manufactured Home

902 ROSE LN, THE VILLAGES, FL, 32159
Community: The Villages®
Carlsberg Estates on Lake Suzanne 464 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$350,000

3 beds

|

2 baths

|

1,429 sq ft

|

House

464 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Arlington Ridge 26917 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$229,000

2 beds

|

2 baths

|

1,251 sq ft

|

House

26917 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
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.
The Villages® 1725 HILTON HEAD BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$159,000

2 beds

|

2 baths

|

1,092 sq ft

|

Manufactured Home

1725 HILTON HEAD BLVD, LADY LAKE, FL, 32...
Community: The Villages®
Solivita 418 TREVISO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$615,000

3 beds

|

3 baths

|

2,427 sq ft

|

House

418 TREVISO DR, KISSIMMEE, FL, 34759
Community: Solivita
Pelican Bay Daytona Beach 133 BLUE HERON DR D, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$188,000

2 beds

|

2 baths

|

1,242 sq ft

|

Condo

133 BLUE HERON DR D, DAYTONA BEACH, FL, ...
Sullivan Ranch 30308 CHEVAL ST, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$396,890

3 beds

|

2 baths

|

1,851 sq ft

|

House

30308 CHEVAL ST, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Venetian Bay 349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$374,900

3 beds

|

2 baths

|

1,520 sq ft

|

House

349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
The Villages® 362 ARBELLA LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$339,000

2 beds

|

2 baths

|

1,393 sq ft

|

House

362 ARBELLA LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Cresswind at Victoria Gardens 600 GARDEN CLUB DR, DELAND, FL, 32724, Deland, FL 32724
$549,900

4 beds

|

3 baths

|

2,569 sq ft

|

House

600 GARDEN CLUB DR, DELAND, FL, 32724
The Savannahs 4464 CALADIUM CIR, WEST MELBOURNE, FL, 3..., West Melbourne, FL 32904
$399,900

4 beds

|

2 baths

|

2,051 sq ft

|

House

4464 CALADIUM CIR, WEST MELBOURNE, FL, 3...
Community: The Savannahs
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.
Del Webb Minneola 2759 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715
$465,000

2 beds

|

2 baths

|

1,405 sq ft

|

House

2759 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
Legacy of Leesburg 27328 PINE STRAW RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$365,000

3 beds

|

2 baths

|

1,894 sq ft

|

House

27328 PINE STRAW RD, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Halifax Plantation 3132 CONNEMARA DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$319,900

3 beds

|

2 baths

|

1,670 sq ft

|

Townhouse

3132 CONNEMARA DR, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
Highland Lakes 5507 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$219,990

2 beds

|

2 baths

|

1,160 sq ft

|

House

5507 LAVER ST, LEESBURG, FL, 34748
Community: Highland Lakes
Lake James 7770 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$449,000

2 beds

|

2 baths

|

1,990 sq ft

|

House

7770 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Lakes at Laurel Highlands 2062 BLUE HIGHLANDS DR, LAKELAND, FL, 33..., Lakeland, FL 33811
$370,000

5 beds

|

3 baths

|

2,696 sq ft

|

House

2062 BLUE HIGHLANDS DR, LAKELAND, FL, 33...
Lake Ashton 4188 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$275,000

2 beds

|

2 baths

|

1,520 sq ft

|

House

4188 MUIRFIELD LOOP, LAKE WALES, FL, 338...
Community: Lake Ashton
Trilogy® Orlando 101 FLAME VINE WAY, GROVELAND, FL, 34736, Groveland, FL 34736
$300,000

3 beds

|

2 baths

|

1,794 sq ft

|

House

101 FLAME VINE WAY, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Plantation Bay Golf & Country Club 829 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$375,000

3 beds

|

3 baths

|

2,101 sq ft

|

Townhouse

829 PINEWOOD DR, ORMOND BEACH, FL, 32174
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.
Spruce Creek South 17533 SE 96TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$249,000

2 beds

|

2 baths

|

1,534 sq ft

|

House

17533 SE 96TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Harbor Hills Country Club 6008 APEX WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$700,000

4 beds

|

3 baths

|

3,432 sq ft

|

House

6008 APEX WAY, LADY LAKE, FL, 32159
Spruce Creek Country Club 9588 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$329,000

2 beds

|

2 baths

|

1,979 sq ft

|

House

9588 SE 124TH LOOP, SUMMERFIELD, FL, 344...
Arlington Ridge 4110 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$374,900

3 beds

|

2 baths

|

1,857 sq ft

|

House

4110 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Spruce Creek South 9499 SE 174TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$229,900

2 beds

|

2 baths

|

1,678 sq ft

|

House

9499 SE 174TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Solivita 516 MILLIFIORA LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$262,000

2 beds

|

2 baths

|

1,240 sq ft

|

House

516 MILLIFIORA LN, KISSIMMEE, FL, 34759
Community: Solivita

Want more information about active adult communities around Winter Park?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
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 [email protected]. 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
2,513 homes
Remove Boundaries ×
Map Satellite

Reinmlsx

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: Apr 10, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top