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 38

2,398 homes near Winter Park

Sort by:

Relevance

Relevance

4 rating (17 reviews) The Villages®
<$100k - $2Ms
The Villages®, The Villages, FL
New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes
4.7 rating (18 reviews) Solivita
$100Ks - $600Ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
3.6 rating (48 reviews) Latitude Margaritaville
$300Ks - $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
5 rating (1 reviews) Plantation Bay Golf &...
$200Ks - $3Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale | Age-targeted | Built 1988 - present | 3,500 homes
4.5 rating (11 reviews) Spruce Creek Country Club
$200Ks - $500Ks
Spruce Creek Country Club, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 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 - $500Ks
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
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes
5 rating (7 reviews) Kings Ridge
$200Ks - $400Ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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
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
$300Ks - $1Ms
Grand Haven, Palm Coast, FL
New and Resale | Age-targeted | Built 1997 - present | 1,901 homes
Pelican Bay Daytona Beach
$100Ks - $400Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $400Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
5 rating (1 reviews) Cypress Lakes
$100Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
Venetian Bay
$200Ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
5 rating (2 reviews) Heritage Isle
$200Ks - $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.
5 rating (8 reviews) Royal Highlands
$200Ks - $400Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
Del Webb at Viera
$400Ks - $1Ms
Del Webb at Viera, Melbourne, FL
New Construction | 55+ age-restricted | Built 2021 - present | 1,300 homes
5 rating (1 reviews) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$300Ks - $1Ms
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
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) Sandpiper Golf & Coun...
$200Ks - $400Ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
3.6 rating (5 reviews) Heritage Hills
$200Ks - $500Ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$300Ks - $600Ks
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.
Halifax Plantation
$200Ks - $700Ks
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 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
Breakaway Trails
$400Ks - $800Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$400Ks - $900Ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
4 rating (2 reviews) Harbor Hills Country Club
$200Ks - $1Ms
Harbor Hills Country Club, Lady Lake, FL
New and Resale | Age-targeted | Built 1989 - present | 940 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 - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
5 rating (2 reviews) Bridgewater at Viera
$300Ks - $800Ks
Bridgewater at Viera, Melbourne, FL
Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 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
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.
4.1 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
3.9 rating (7 reviews) Summit Greens
$300Ks - $400Ks
Summit Greens, Clermont, FL
Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 homes
5 rating (1 reviews) Royal Harbor
$200Ks - $400Ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
Lakeside Landings
$200Ks - $500Ks
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
1 rating (1 reviews) Sullivan Ranch
$200Ks - $700Ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
Highland Fairways
$100Ks - $300Ks
Highland Fairways, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes
Huntington at Hunter's Ridge 6 FOX LAIR CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$359,000

3 beds

|

2 baths

|

1,637 sq ft

|

House

6 FOX LAIR CT, ORMOND BEACH, FL, 32174
Solivita 670 CARMEL LN, POINCIANA, FL, 34759, Poinciana, FL 34759
$420,000

2 beds

|

3 baths

|

2,343 sq ft

|

House

670 CARMEL LN, POINCIANA, FL, 34759
Community: Solivita
The Villages® 1605 CHAVEZ CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$350,000

2 beds

|

2 baths

|

1,638 sq ft

|

House

1605 CHAVEZ CT, THE VILLAGES, FL, 32159
Community: The Villages®
Solivita 3390 FALLBROOK DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$265,000

2 beds

|

2 baths

|

1,353 sq ft

|

Villa

3390 FALLBROOK DR, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 3233 LOWE CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$515,000

3 beds

|

3 baths

|

2,056 sq ft

|

House

3233 LOWE CT, 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
Solivita 502 MONTEREY ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$319,900

2 beds

|

2 baths

|

1,655 sq ft

|

House

502 MONTEREY ST, KISSIMMEE, FL, 34759
Community: Solivita
Royal Highlands 21636 KING HENRY AVE, LEESBURG, FL, 3474..., Leesburg, FL 34748
$229,900

3 beds

|

2 baths

|

1,642 sq ft

|

House

21636 KING HENRY AVE, LEESBURG, FL, 3474...
Community: Royal Highlands
Solivita 537 MONTAGE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$549,900

3 beds

|

3 baths

|

2,441 sq ft

|

House

537 MONTAGE LN, KISSIMMEE, FL, 34759
Community: Solivita
Spruce Creek Country Club 13709 SE 86TH TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$299,900

2 beds

|

2 baths

|

1,537 sq ft

|

House

13709 SE 86TH TER, SUMMERFIELD, FL, 3449...
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.
Halifax Plantation 3231 GALTY CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$399,000

2 beds

|

2 baths

|

1,943 sq ft

|

House

3231 GALTY CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
Halifax Plantation 3227 GALTY CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$399,000

3 beds

|

2 baths

|

2,059 sq ft

|

House

3227 GALTY CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
The Villages® 1133 DEL TORO DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$329,900

2 beds

|

2 baths

|

1,332 sq ft

|

House

1133 DEL TORO DR, THE VILLAGES, FL, 3215...
Community: The Villages®
The Villages® 12347 NE 52ND LOOP, OXFORD, FL, 34484, Oxford, FL 34484
$349,000

4 beds

|

4 baths

|

2,092 sq ft

|

House

12347 NE 52ND LOOP, OXFORD, FL, 34484
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 1638 DURAN DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$265,000

2 beds

|

2 baths

|

1,179 sq ft

|

House

1638 DURAN DR, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1411 JUAREZ PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$465,000

3 beds

|

2 baths

|

1,388 sq ft

|

House

1411 JUAREZ PL, THE VILLAGES, FL, 32159
Community: The Villages®
Stonecrest 17645 SE 117TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$299,900

3 beds

|

3 baths

|

1,686 sq ft

|

House

17645 SE 117TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
Enclave at VillageWalk 11741 SAVONA WAY, ORLANDO, FL, 32827, Orlando, FL 32827
$1,100,000

4 beds

|

4 baths

|

3,197 sq ft

|

House

11741 SAVONA WAY, ORLANDO, FL, 32827
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 15913 SE 101ST CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$269,990

4 beds

|

2 baths

|

1,498 sq ft

|

House

15913 SE 101ST CIR, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Spruce Creek South 15919 SE 101ST CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$266,990

3 beds

|

2 baths

|

1,328 sq ft

|

House

15919 SE 101ST CIR, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Latitude Margaritaville 422 LIME AVE, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124
$379,900

2 beds

|

2 baths

|

1,466 sq ft

|

House

422 LIME AVE, DAYTONA BEACH, FL, 32124
Solivita 417 LAKE BUTLER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$324,900

3 beds

|

2 baths

|

2,728 sq ft

|

House

417 LAKE BUTLER DR, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Hills 3201 SONESTA CT A, CLERMONT, FL, 34711, Clermont, FL 34711
$335,000

2 beds

|

2 baths

|

1,503 sq ft

|

Villa

3201 SONESTA CT A, CLERMONT, FL, 34711
Community: Heritage Hills
Four Seasons at Orlando 7661 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747
$449,000

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

7661 SAND PIERRE CT, KISSIMMEE, FL, 3474...
Four Seasons at Orlando 1825 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$369,000

2 beds

|

2 baths

|

1,557 sq ft

|

Villa

1825 FLORA PASS PL, KISSIMMEE, FL, 34747
Carmel Condominium 1420 HUNTINGTON LN 2502, ROCKLEDGE, FL, ..., Rockledge, FL 32955
$125,000

2 beds

|

2 baths

|

1,008 sq ft

|

Condo

1420 HUNTINGTON LN 2502, ROCKLEDGE, FL, ...
Community: Carmel Condominium
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® 1639 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$279,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

1639 CAMPOS DR, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 458 JUNGLE PLUM WAY, THE VILLAGES, FL, 3..., The Villages, FL 32163
$479,500

3 beds

|

2 baths

|

1,830 sq ft

|

House

458 JUNGLE PLUM WAY, THE VILLAGES, FL, 3...
Community: The Villages®
Plantation Bay Golf & Country Club 48 TREETOP CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$315,000

2 beds

|

3 baths

|

2,079 sq ft

|

House

48 TREETOP CIR, ORMOND BEACH, FL, 32174
The Villages® 14202 SANDALWOOD DR # 202, WILDWOOD, FL,..., Wildwood, FL 34785
$119,900

2 beds

|

2 baths

|

1,085 sq ft

|

Condo

14202 SANDALWOOD DR # 202, WILDWOOD, FL,...
Community: The Villages®
Plantation Bay Golf & Country Club 715 COBBLESTONE DR, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$380,000

2 beds

|

3 baths

|

1,875 sq ft

|

Townhouse

715 COBBLESTONE DR, ORMOND BEACH, FL, 32...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 2369 TRAVIS PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$250,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2369 TRAVIS PL, THE VILLAGES, FL, 32162
Community: The Villages®
Lakes at Laurel Highlands 2651 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$399,900

6 beds

|

3 baths

|

2,696 sq ft

|

House

2651 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Heritage Landings 2651 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$399,900

6 beds

|

3 baths

|

2,696 sq ft

|

House

2651 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Heritage Landings
Solivita 151 BELL TOWER XING W, KISSIMMEE, FL, 34..., Kissimmee, FL 34759
$228,900

2 beds

|

2 baths

|

1,356 sq ft

|

House

151 BELL TOWER XING W, KISSIMMEE, FL, 34...
Community: Solivita
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® 528 CARRERA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$334,500

3 beds

|

2 baths

|

1,624 sq ft

|

House

528 CARRERA DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 802 MIRANDA WAY, THE VILLAGES, FL, 32159, The Villages, FL 32159
$349,000

2 beds

|

2 baths

|

1,471 sq ft

|

House

802 MIRANDA WAY, THE VILLAGES, FL, 32159
Community: The Villages®
The Country Club of Mount Dora 5061 GREENBRIAR TRL, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$849,000

4 beds

|

3 baths

|

2,922 sq ft

|

House

5061 GREENBRIAR TRL, MOUNT DORA, FL, 327...
Royal Harbor 5151 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778
$409,000

4 beds

|

2 baths

|

2,091 sq ft

|

House

5151 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 2845 CHARITY LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163
$329,900

2 beds

|

2 baths

|

1,206 sq ft

|

House

2845 CHARITY LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
Colonnades 4823 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811
$215,000

2 beds

|

2 baths

|

1,196 sq ft

|

House

4823 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades

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
2,398 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: Jan 11, 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