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 62

2,553 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 (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
4.7 rating (3 reviews) Spruce Creek South
$100ks - $200ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 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) Plantation Bay Golf &...
$400ks - $2Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale | Age-targeted | Built 1988 - present | 3,500 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 (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 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
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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 (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
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.
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 (3 reviews) Twin Lakes
$200ks - $600ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
5 rating (2 reviews) Heritage Isle
$300ks - $500ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 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
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
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 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...
$200ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 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.
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 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
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
Colonnades
$100ks - $200ks
Colonnades, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1985 - 1994 | 360 homes
Ridgehaven
$300ks - $600ks
Ridgehaven, Ormond Beach, FL
New Construction | 55+ age-restricted
The Country Club of Mount...
$200ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 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.
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 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
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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
12...3
The Villages® 2142 MARGARITA DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$380,000

3 beds

|

2 baths

|

1,904 sq ft

|

House

2142 MARGARITA DR, THE VILLAGES, FL, 321...
Community: The Villages®
Lake Ashton 5325 NICKLAUS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$279,900

2 beds

|

2 baths

|

1,319 sq ft

|

House

5325 NICKLAUS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
Solivita 2502 PALM TREE DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$308,000

2 beds

|

2 baths

|

1,539 sq ft

|

Townhouse

2502 PALM TREE DR, POINCIANA, FL, 34759
Community: Solivita
Solivita 702 TORREY PINES WAY WAY, POINCIANA, FL,..., Poinciana, FL 34759
$419,500

3 beds

|

3 baths

|

2,190 sq ft

|

House

702 TORREY PINES WAY WAY, POINCIANA, FL,...
Community: Solivita
Lake Ashton 4168 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$349,900

3 beds

|

2 baths

|

1,756 sq ft

|

House

4168 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Trilogy® Orlando 228 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736
$425,000

2 beds

|

2 baths

|

2,197 sq ft

|

House

228 BAYOU BEND RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Cresswind at Victoria Gardens 1079 LINCOLNSHIRE DR, DELAND, FL, 32724, Deland, FL 32724
$369,900

2 beds

|

2 baths

|

1,651 sq ft

|

House

1079 LINCOLNSHIRE DR, DELAND, FL, 32724
The Villages® 1007 ALOHA WAY, THE VILLAGES, FL, 32159, The Villages, FL 32159
$143,500

2 beds

|

2 baths

|

1,152 sq ft

|

Mobile Home

1007 ALOHA WAY, THE VILLAGES, FL, 32159
Community: The Villages®
Spruce Creek South 17807 SE 97TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$217,999

3 beds

|

2 baths

|

1,450 sq ft

|

House

17807 SE 97TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
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.
Harbor Hills Country Club 6200 TOPSAIL RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$260,000

2 beds

|

2 baths

|

1,537 sq ft

|

Villa

6200 TOPSAIL RD, LADY LAKE, FL, 32159
The Villages® 3441 POSSEHL PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$254,900

2 beds

|

2 baths

|

1,148 sq ft

|

Villa

3441 POSSEHL PL, THE VILLAGES, FL, 32163
Community: The Villages®
Solivita 188 OLYMPUS WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$299,999

2 beds

|

2 baths

|

1,250 sq ft

|

House

188 OLYMPUS WAY, KISSIMMEE, FL, 34759
Community: Solivita
Royal Highlands 20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748
$389,000

3 beds

|

3 baths

|

2,224 sq ft

|

House

20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Solivita 555 PRESIDO PARK PL, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$299,900

3 beds

|

2 baths

|

1,610 sq ft

|

House

555 PRESIDO PARK PL, KISSIMMEE, FL, 3475...
Community: Solivita
The Villages® 610 ESPANA ST, THE VILLAGES, FL, 32159, The Villages, FL 32159
$640,000

3 beds

|

3 baths

|

2,086 sq ft

|

House

610 ESPANA ST, THE VILLAGES, FL, 32159
Community: The Villages®
Plantation at Leesburg 3909 RIVER CREST CIR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$299,000

3 beds

|

2 baths

|

1,690 sq ft

|

House

3909 RIVER CREST CIR, LEESBURG, FL, 3474...
Plantation at Leesburg 4822 SAWGRASS LAKE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$394,900

3 beds

|

3 baths

|

2,780 sq ft

|

House

4822 SAWGRASS LAKE CIR, LEESBURG, FL, 34...
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.
Plantation at Leesburg 25527 OAK ALY, LEESBURG, FL, 34748, Leesburg, FL 34748
$264,900

2 beds

|

2 baths

|

1,518 sq ft

|

House

25527 OAK ALY, LEESBURG, FL, 34748
The Villages® 2935 CEDAR GROVE LOOP, THE VILLAGES, FL,..., The Villages, FL 32163
$799,000

3 beds

|

2 baths

|

3,466 sq ft

|

House

2935 CEDAR GROVE LOOP, THE VILLAGES, FL,...
Community: The Villages®
Carmel Condominium 1420 HUNTINGTON LN 2304, ROCKLEDGE, FL, ..., Rockledge, FL 32955
$169,900

2 beds

|

2 baths

|

1,008 sq ft

|

Condo

1420 HUNTINGTON LN 2304, ROCKLEDGE, FL, ...
Community: Carmel Condominium
Huntington at Hunter's Ridge 34 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$330,000

3 beds

|

2 baths

|

1,523 sq ft

|

House

34 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Summit Greens 993 EVEREST ST, CLERMONT, FL, 34711, Clermont, FL 34711
$399,900

3 beds

|

2 baths

|

2,078 sq ft

|

House

993 EVEREST ST, CLERMONT, FL, 34711
Community: Summit Greens
Spruce Creek Country Club 13751 SE 88TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$259,000

2 beds

|

2 baths

|

1,364 sq ft

|

House

13751 SE 88TH CT, SUMMERFIELD, FL, 34491
Carmel Condominium 1420 HUNTINGTON LN 2101, ROCKLEDGE, FL, ..., Rockledge, FL 32955
$209,000

2 beds

|

2 baths

|

1,228 sq ft

|

Condo

1420 HUNTINGTON LN 2101, ROCKLEDGE, FL, ...
Community: Carmel Condominium
Lake Ashton 4232 ROEBELENII DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$339,900

3 beds

|

2 baths

|

1,941 sq ft

|

House

4232 ROEBELENII DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
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.
Pennbrooke Fairways 321 RANCHWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$325,000

3 beds

|

2 baths

|

1,894 sq ft

|

House

321 RANCHWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Stonecrest 12225 SE 173RD PL, SUMMERFIELD,, FL, 344..., Summerfield,, FL 34491
$309,000

3 beds

|

2 baths

|

1,475 sq ft

|

House

12225 SE 173RD PL, SUMMERFIELD,, FL, 344...
Community: Stonecrest
Plantation Bay Golf & Country Club 842 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$358,500

2 beds

|

2 baths

|

1,562 sq ft

|

Townhouse

842 ALDENHAM LN, ORMOND BEACH, FL, 32174
Trilogy® Orlando 112 FLAME VINE WAY, GROVELAND, FL, 34736, Groveland, FL 34736
$299,000

2 beds

|

2 baths

|

1,556 sq ft

|

House

112 FLAME VINE WAY, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Gatherings of Lake Nona 7545 LAUREATE BLVD 7203, ORLANDO, FL, 32..., Orlando, FL 32827
$458,990

2 beds

|

2 baths

|

1,549 sq ft

|

Condo

7545 LAUREATE BLVD 7203, ORLANDO, FL, 32...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Stonecrest 17728 SE 115TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$365,000

3 beds

|

3 baths

|

1,658 sq ft

|

House

17728 SE 115TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Vienna Square 1703 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$259,000

2 beds

|

2 baths

|

1,164 sq ft

|

Villa

1703 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
Lakes of Mount Dora 3969 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$374,990

2 beds

|

2 baths

|

1,402 sq ft

|

House

3969 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
The Villages® 1532 W SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$249,999

2 beds

|

2 baths

|

1,092 sq ft

|

Manufactured Home

1532 W SCHWARTZ BLVD, LADY LAKE, FL, 321...
Community: The Villages®
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.
Heritage Isle 3140 LE CONTE ST, MELBOURNE, FL, 32940, Melbourne, FL 32940
$294,560

2 beds

|

2 baths

|

1,407 sq ft

|

Townhouse

3140 LE CONTE ST, MELBOURNE, FL, 32940
Community: Heritage Isle
Solivita 159 VENTANA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$325,000

3 beds

|

2 baths

|

1,813 sq ft

|

House

159 VENTANA DR, KISSIMMEE, FL, 34759
Community: Solivita
Heritage Isle 7174 EGBERT ST, MELBOURNE, FL, 32940, Melbourne, FL 32940
$414,900

3 beds

|

2 baths

|

1,770 sq ft

|

House

7174 EGBERT ST, MELBOURNE, FL, 32940
Community: Heritage Isle
Sullivan Ranch 22004 BELGIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$309,699

3 beds

|

2 baths

|

1,437 sq ft

|

House

22004 BELGIAN CT, 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
Del Webb Orlando 280 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$474,000

3 beds

|

2 baths

|

2,365 sq ft

|

House

280 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
The Villages® 2866 JUDAH ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$314,000

2 beds

|

2 baths

|

1,257 sq ft

|

House

2866 JUDAH ST, THE VILLAGES, FL, 32163
Community: The Villages®

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
2,553 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: Feb 24, 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