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 10

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
The Villages® 1563 EASTOVER TER, THE VILLAGES, FL, 321..., The Villages, FL 32162
$399,900

3 beds

|

2 baths

|

1,667 sq ft

|

House

1563 EASTOVER TER, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 415 S TIMBER TRL, WILDWOOD, FL, 34785, Wildwood, FL 34785
$109,900

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

415 S TIMBER TRL, WILDWOOD, FL, 34785
Community: The Villages®
The Villages® 3389 LUTY LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$349,900

3 beds

|

2 baths

|

1,547 sq ft

|

House

3389 LUTY LN, THE VILLAGES, FL, 32163
Community: The Villages®
Stonecrest 10948 SE 167TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$405,000

3 beds

|

2 baths

|

1,891 sq ft

|

House

10948 SE 167TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Villages® 3090 RANCHWOOD TER, THE VILLAGES, FL, 32..., The Villages, FL 32163
$759,000

3 beds

|

2 baths

|

2,060 sq ft

|

House

3090 RANCHWOOD TER, THE VILLAGES, FL, 32...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Del Webb Orlando 109 MONTORO LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$479,900

3 beds

|

3 baths

|

2,607 sq ft

|

House

109 MONTORO LN, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Stonecrest 11217 SE 170TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$315,000

3 beds

|

2 baths

|

1,472 sq ft

|

House

11217 SE 170TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Twin Lakes 2373 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772
$380,000

2 beds

|

2 baths

|

1,624 sq ft

|

Villa

2373 DATURA LOOP, ST CLOUD, FL, 34772
Community: Twin Lakes
Indian River Colony Club 1453 PATRIOT DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$350,000

4 beds

|

2 baths

|

2,293 sq ft

|

House

1453 PATRIOT DR, MELBOURNE, FL, 32940
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® 3074 BRINE WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163
$379,900

3 beds

|

2 baths

|

1,846 sq ft

|

House

3074 BRINE WAY, THE VILLAGES, FL, 32163
Community: The Villages®
Pennbrooke Fairways 844 EAGLES LNDG, LEESBURG, FL, 34748, Leesburg, FL 34748
$319,500

2 beds

|

2 baths

|

1,766 sq ft

|

House

844 EAGLES LNDG, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Lake Henry Estates 601 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844
$339,000

3 beds

|

2 baths

|

1,994 sq ft

|

House

601 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
Stonecrest 11614 SE 172ND LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$375,000

3 beds

|

2 baths

|

1,919 sq ft

|

House

11614 SE 172ND LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 1840 W SCHWARTZ BLVD, THE VILLAGES, FL, ..., The Villages, FL 32159
$230,000

2 beds

|

2 baths

|

1,277 sq ft

|

Manufactured Home

1840 W SCHWARTZ BLVD, THE VILLAGES, FL, ...
Community: The Villages®
VillageWalk at Lake Nona 12017 KAJETAN LN, ORLANDO, FL, 32827, Orlando, FL 32827
$455,000

2 beds

|

2 baths

|

1,512 sq ft

|

Halfplex

12017 KAJETAN LN, ORLANDO, FL, 32827
Lake Ashton 4243 DORNOCH DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$264,000

3 beds

|

2 baths

|

1,503 sq ft

|

House

4243 DORNOCH DR, LAKE WALES, FL, 33859
Community: Lake Ashton
The Villages® 9230 SE 179TH WESLEY ST, THE VILLAGES, F..., The Villages, FL 32162
$259,900

2 beds

|

2 baths

|

1,148 sq ft

|

House

9230 SE 179TH WESLEY ST, THE VILLAGES, F...
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.
Plantation Bay Golf & Country Club 685 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$685,000

4 beds

|

3 baths

|

2,496 sq ft

|

House

685 ALDENHAM LN, ORMOND BEACH, FL, 32174
The Villages® 1866 KYRLE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$500,000

4 beds

|

2 baths

|

2,222 sq ft

|

House

1866 KYRLE TER, THE VILLAGES, FL, 32162
Community: The Villages®
Gatherings of Lake Nona 7545 LAUREATE BLVD 7404, ORLANDO, FL, 32..., Orlando, FL 32827
$471,990

2 beds

|

2 baths

|

1,486 sq ft

|

Condo

7545 LAUREATE BLVD 7404, ORLANDO, FL, 32...
Spruce Creek Country Club 9049 SE 119TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$429,900

3 beds

|

2 baths

|

2,134 sq ft

|

House

9049 SE 119TH ST, SUMMERFIELD, FL, 34491
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Gatherings of Lake Nona 7545 LAUREATE BLVD 7303, ORLANDO, FL, 32..., Orlando, FL 32827
$469,990

2 beds

|

2 baths

|

1,549 sq ft

|

Condo

7545 LAUREATE BLVD 7303, ORLANDO, FL, 32...
Kings Ridge 3721 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711
$380,000

3 beds

|

2 baths

|

1,871 sq ft

|

House

3721 DOUNE WAY, CLERMONT, FL, 34711
Community: Kings Ridge
Del Webb Sunbridge 6129 BLUE POND WAY, ST CLOUD, FL, 34771, St Cloud, FL 34771
$675,000

3 beds

|

3 baths

|

2,283 sq ft

|

House

6129 BLUE POND WAY, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
The Villages® 7574 SE 171ST SUN VALLEY PL, THE VILLAGE..., The Villages, FL 32162
$270,000

2 beds

|

2 baths

|

1,172 sq ft

|

Villa

7574 SE 171ST SUN VALLEY PL, THE VILLAGE...
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.
The Timbers at Everlands 2732 ANTARUS DR, PALM BAY, FL, 32907, Palm Bay, FL 32907
$347,383

3 beds

|

3 baths

|

1,963 sq ft

|

House

2732 ANTARUS DR, PALM BAY, FL, 32907
Halifax Plantation 1424 KILRUSH DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$619,000

4 beds

|

3 baths

|

2,280 sq ft

|

House

1424 KILRUSH DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
Stonecrest 17380 SE 111TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$299,900

2 beds

|

2 baths

|

1,359 sq ft

|

House

17380 SE 111TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Timbers at Everlands 2743 ANTARUS DR, PALM BAY, FL, 32907, Palm Bay, FL 32907
$347,383

3 beds

|

3 baths

|

1,831 sq ft

|

House

2743 ANTARUS DR, PALM BAY, FL, 32907
Heritage Hills 3651 LIMESTONE ST, CLERMONT, FL, 34711, Clermont, FL 34711
$409,000

3 beds

|

2 baths

|

1,845 sq ft

|

House

3651 LIMESTONE ST, CLERMONT, FL, 34711
Community: Heritage Hills
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Del Webb Orlando 545 CANTABRIA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$304,924

2 beds

|

2 baths

|

1,433 sq ft

|

House

545 CANTABRIA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
The Villages® 2378 YOUNGMANN LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163
$399,900

3 beds

|

2 baths

|

1,611 sq ft

|

House

2378 YOUNGMANN LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
Del Webb Sunbridge 2808 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ..., St Cloud, FL 34771
$899,000

3 beds

|

3 baths

|

2,321 sq ft

|

House

2808 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ...
Community: Del Webb Sunbridge
The Villages® 2134 TALLSMAN CT, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$1,200,000

4 beds

|

2 baths

|

3,883 sq ft

|

House

2134 TALLSMAN CT, 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.
Lake Ashton 4201 BERWICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$229,900

2 beds

|

2 baths

|

1,109 sq ft

|

House

4201 BERWICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
The Villages® 16913 SE 88TH TRUMBULL TER, THE VILLAGES..., The Villages, FL 32162
$575,250

3 beds

|

2 baths

|

1,924 sq ft

|

House

16913 SE 88TH TRUMBULL TER, THE VILLAGES...
Community: The Villages®
The Villages® 2056 PALO ALTO AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159
$650,000

3 beds

|

2 baths

|

2,477 sq ft

|

House

2056 PALO ALTO AVE, THE VILLAGES, FL, 32...
Community: The Villages®
Solivita 144 SORRENTO RD, POINCIANA, FL, 34759, Poinciana, FL 34759
$270,000

2 beds

|

2 baths

|

1,467 sq ft

|

House

144 SORRENTO RD, POINCIANA, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Venetian Bay 3011 ARECA AVE, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$675,000

4 beds

|

2 baths

|

2,003 sq ft

|

House

3011 ARECA AVE, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
The Villages® 2415 MORVEN PARK WAY, THE VILLAGES, FL, ..., The Villages, FL 32162
$449,500

3 beds

|

2 baths

|

1,979 sq ft

|

House

2415 MORVEN PARK WAY, THE VILLAGES, FL, ...
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
2,513 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