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 9

2,414 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
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
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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 homes
Grand Haven
$200ks - $800ks
Grand Haven, Palm Coast, FL
New and Resale | Age-targeted | Built 1997 - present | 1,901 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
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
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
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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 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
4 rating (4 reviews) Lakes of Mount Dora
$300ks - $1Ms
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 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 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
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 (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 (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
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes
The Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
5 rating (2 reviews) Heritage Isle
$300ks - $500ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 homes
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 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
Ridgehaven
$300ks - $600ks
Ridgehaven, Ormond Beach, FL
New Construction | 55+ age-restricted
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 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) VillageWalk at Lake Nona
$300ks - $700ks
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 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
5 rating (2 reviews) Bridgewater at Viera
$300ks - $800ks
Bridgewater at Viera, Melbourne, FL
Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 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.
12...3
Sullivan Ranch 20831 SULLIVAN RANCH BLVD, MOUNT DORA, F..., Mount Dora, FL 32757
$349,900

3 beds

|

2 baths

|

1,440 sq ft

|

House

20831 SULLIVAN RANCH BLVD, MOUNT DORA, F...
Community: Sullivan Ranch
Pelican Bay Daytona Beach 103 MORNING DOVE CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$456,000

3 beds

|

2 baths

|

1,921 sq ft

|

House

103 MORNING DOVE CT, DAYTONA BEACH, FL, ...
Palms at Serenoa 3790 MYRTLE OAK CT, CLERMONT, FL, 34714, Clermont, FL 34714
$349,900

2 beds

|

2 baths

|

1,646 sq ft

|

House

3790 MYRTLE OAK CT, CLERMONT, FL, 34714
Community: Palms at Serenoa
The Country Club of Mount Dora 8011 PINE HOLLOW DR, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$465,000

3 beds

|

2 baths

|

2,016 sq ft

|

House

8011 PINE HOLLOW DR, MOUNT DORA, FL, 327...
Kings Ridge 2160 ADDISON AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$284,900

2 beds

|

2 baths

|

1,334 sq ft

|

House

2160 ADDISON AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Plantation Bay Golf & Country Club 30 LANDINGS LN 30, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$250,000

2 beds

|

2 baths

|

1,173 sq ft

|

Townhouse

30 LANDINGS LN 30, ORMOND BEACH, FL, 321...
The Villages® 7631 SE 170TH LONGVIEW LN, THE VILLAGES,..., The Villages, FL 32162
$315,000

2 beds

|

2 baths

|

1,186 sq ft

|

Villa

7631 SE 170TH LONGVIEW LN, THE VILLAGES,...
Community: The Villages®
Plantation Bay Golf & Country Club 30 LANDINGS LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$250,000

2 beds

|

2 baths

|

1,173 sq ft

|

Townhouse

30 LANDINGS LN, ORMOND BEACH, FL, 32174
Grand Haven 19 RIVER LANDING DR, PALM COAST, FL, 321..., Palm Coast, FL 32137
$550,000

2 beds

|

3 baths

|

2,201 sq ft

|

Townhouse

19 RIVER LANDING DR, PALM COAST, FL, 321...
Community: Grand Haven
Solivita 276 BELL TOWER XING, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$445,000

3 beds

|

3 baths

|

2,561 sq ft

|

House

276 BELL TOWER XING, KISSIMMEE, FL, 3475...
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.
Del Webb at Viera 8842 STORMY SKY CT, MELBOURNE, FL, 32940, Melbourne, FL 32940
$444,900

3 beds

|

2 baths

|

1,454 sq ft

|

House

8842 STORMY SKY CT, MELBOURNE, FL, 32940
Community: Del Webb at Viera
The Villages® 2306 NACKMAN PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$410,000

3 beds

|

2 baths

|

1,397 sq ft

|

Villa

2306 NACKMAN PL, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1936 NEEDLEWOOD LN, THE VILLAGES, FL, 32..., The Villages, FL 32162
$600,000

3 beds

|

2 baths

|

1,602 sq ft

|

Villa

1936 NEEDLEWOOD LN, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 1089 BERG CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$430,000

3 beds

|

2 baths

|

1,685 sq ft

|

Villa

1089 BERG CT, THE VILLAGES, FL, 32162
Community: The Villages®
Halifax Plantation 3513 KILGALLEN CT, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$1,125,000

4 beds

|

5 baths

|

5,040 sq ft

|

House

3513 KILGALLEN CT, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
The Villages® 3285 DRESSENDORFER DR, THE VILLAGES, FL,..., The Villages, FL 32163
$669,000

3 beds

|

2 baths

|

1,903 sq ft

|

House

3285 DRESSENDORFER DR, THE VILLAGES, FL,...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 17705 SE 93RD HAWTHORNE AVE, THE VILLAGE..., The Villages, FL 32162
$315,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

17705 SE 93RD HAWTHORNE AVE, THE VILLAGE...
Community: The Villages®
Heritage Isle 6828 TOLAND DR 306, MELBOURNE, FL, 32940, Melbourne, FL 32940
$300,000

2 beds

|

2 baths

|

1,232 sq ft

|

Condo

6828 TOLAND DR 306, MELBOURNE, FL, 32940
Community: Heritage Isle
Traditions at Lake Ruby 3023 CANEEL ST, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$235,000

2 beds

|

2 baths

|

1,385 sq ft

|

Townhouse

3023 CANEEL ST, WINTER HAVEN, FL, 33884
Foxwood Lake Estates 5027 FOREST CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33810
$190,000

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

5027 FOREST CREST DR, LAKELAND, FL, 3381...
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 Oasis 15157 AQUA SOL LN, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$455,900

2 beds

|

2 baths

|

1,574 sq ft

|

Villa

15157 AQUA SOL LN, WINTER GARDEN, FL, 34...
Community: Del Webb Oasis
Solivita 294 ADDISON DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$450,000

3 beds

|

3 baths

|

2,711 sq ft

|

House

294 ADDISON DR, POINCIANA, FL, 34759
Community: Solivita
The Villages® 1202 FERNANDO LN, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$315,000

2 beds

|

1 baths

|

1,040 sq ft

|

Villa

1202 FERNANDO LN, THE VILLAGES, FL, 3215...
Community: The Villages®
Sullivan Ranch 30030 MESSARA CV, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$499,900

6 beds

|

4 baths

|

3,499 sq ft

|

House

30030 MESSARA CV, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
The Villages® 3948 MUNFORD TER, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$325,000

2 beds

|

2 baths

|

979 sq ft

|

Villa

3948 MUNFORD TER, THE VILLAGES, FL, 3216...
Community: The Villages®
Arlington Ridge 26709 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748
$375,000

2 beds

|

2 baths

|

2,235 sq ft

|

House

26709 AUGUSTA SPRINGS CIR, LEESBURG, FL,...
Community: Arlington Ridge
Del Webb at Viera 8953 BLISSFUL BREEZE TRL, MELBOURNE, FL,..., Melbourne, FL 32940
$454,920

2 beds

|

2 baths

|

1,579 sq ft

|

Villa

8953 BLISSFUL BREEZE TRL, MELBOURNE, FL,...
Community: Del Webb at Viera
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Plantation at Leesburg 24511 BOCAGE WAY, LEESBURG, FL, 34748, Leesburg, FL 34748
$415,000

3 beds

|

3 baths

|

2,684 sq ft

|

House

24511 BOCAGE WAY, LEESBURG, FL, 34748
The Villages® 16689 SE 78TH LIVE OAK AVE, THE VILLAGES..., The Villages, FL 32162
$364,900

3 beds

|

2 baths

|

1,478 sq ft

|

House

16689 SE 78TH LIVE OAK AVE, THE VILLAGES...
Community: The Villages®
Lake Ashton 1108 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$422,999

2 beds

|

2 baths

|

1,533 sq ft

|

House

1108 SAWGRASS DR, WINTER HAVEN, FL, 3388...
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.
Del Webb at Viera 9043 BLISSFUL BREEZE TRL, MELBOURNE, FL,..., Melbourne, FL 32940
$433,110

2 beds

|

2 baths

|

1,579 sq ft

|

Villa

9043 BLISSFUL BREEZE TRL, MELBOURNE, FL,...
Community: Del Webb at Viera
Arlington Ridge 4025 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$415,000

3 beds

|

2 baths

|

1,719 sq ft

|

House

4025 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
The Villages® 1060 GOLDEN GROVE DR, THE VILLAGES, FL, ..., The Villages, FL 32162
$299,900

2 beds

|

2 baths

|

1,142 sq ft

|

House

1060 GOLDEN GROVE DR, THE VILLAGES, FL, ...
Community: The Villages®
Solivita 268 ACADIA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$292,000

2 beds

|

2 baths

|

1,387 sq ft

|

House

268 ACADIA DR, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 805 HUBBARD LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$425,000

3 beds

|

2 baths

|

1,419 sq ft

|

House

805 HUBBARD LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Heritage Isle 3664 GURRERO DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$529,000

3 beds

|

2 baths

|

2,061 sq ft

|

House

3664 GURRERO DR, MELBOURNE, FL, 32940
Community: Heritage Isle
Pelican Bay Daytona Beach 108 BLACK DUCK CIR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119
$249,900

3 beds

|

3 baths

|

1,627 sq ft

|

House

108 BLACK DUCK CIR, DAYTONA BEACH, FL, 3...
The Villages® 4348 TUSCALOOSA PATH, THE VILLAGES, FL, ..., The Villages, FL 32163
$559,000

3 beds

|

3 baths

|

1,905 sq ft

|

House

4348 TUSCALOOSA PATH, THE VILLAGES, FL, ...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Plantation at Leesburg 25212 CLIFFORD HL, LEESBURG, FL, 34748, Leesburg, FL 34748
$259,000

2 beds

|

2 baths

|

1,407 sq ft

|

House

25212 CLIFFORD HL, LEESBURG, FL, 34748
The Villages® 5991 BARLEY PATH, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$851,248

3 beds

|

2 baths

|

2,016 sq ft

|

House

5991 BARLEY PATH, THE VILLAGES, FL, 3216...
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.

Frequently Asked Questions


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
2,414 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: May 25, 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