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 53

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
Arlington Ridge 26812 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748
$475,000

4 beds

|

3 baths

|

2,318 sq ft

|

House

26812 AUGUSTA SPRINGS CIR, LEESBURG, FL,...
Community: Arlington Ridge
Trilogy® Orlando 251 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$399,000

2 beds

|

2 baths

|

1,900 sq ft

|

House

251 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Solivita 915 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759
$590,000

4 beds

|

3 baths

|

3,110 sq ft

|

House

915 SAN RAPHAEL ST, POINCIANA, FL, 34759
Community: Solivita
Scottish Highlands 803 DUNDEE CIR, LEESBURG, FL, 34788, Leesburg, FL 34788
$249,900

2 beds

|

2 baths

|

1,436 sq ft

|

House

803 DUNDEE CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
The Villages® 16946 SE 93RD CUTHBERT CIR, THE VILLAGES..., The Villages, FL 32162
$429,000

3 beds

|

2 baths

|

2,002 sq ft

|

House

16946 SE 93RD CUTHBERT CIR, THE VILLAGES...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Royal Highlands 20504 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748
$339,900

2 beds

|

2 baths

|

1,722 sq ft

|

House

20504 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
Plantation at Leesburg 24841 PINE HL, LEESBURG, FL, 34748, Leesburg, FL 34748
$136,000

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

24841 PINE HL, LEESBURG, FL, 34748
The Villages® 17602 SE 82ND WOODLAWN AVE, THE VILLAGES..., The Villages, FL 32162
$379,900

3 beds

|

2 baths

|

1,924 sq ft

|

House

17602 SE 82ND WOODLAWN AVE, THE VILLAGES...
Community: The Villages®
Sullivan Ranch 30101 BRETTON LOOP, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$669,900

4 beds

|

3 baths

|

3,452 sq ft

|

House

30101 BRETTON LOOP, MOUNT DORA, FL, 3275...
Community: Sullivan Ranch
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 16 LAGARE ST, PALM COAST, FL, 32137, Palm Coast, FL 32137
$550,000

3 beds

|

2 baths

|

2,154 sq ft

|

House

16 LAGARE ST, PALM COAST, FL, 32137
Community: Grand Haven
Del Webb Sunbridge 3122 VANGUARD CT, ST CLOUD, FL, 34771, St Cloud, FL 34771
$1,175,000

5 beds

|

4 baths

|

3,460 sq ft

|

House

3122 VANGUARD CT, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
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
Royal Highlands 4528 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$399,500

2 beds

|

2 baths

|

2,200 sq ft

|

House

4528 GLEN COE ST, 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
Plantation Bay Golf & Country Club 1117 OXBRIDGE LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$1,897,000

4 beds

|

5 baths

|

5,352 sq ft

|

House

1117 OXBRIDGE LN, ORMOND BEACH, FL, 3217...
Grand Haven 455 RIVERFRONT DR A104, PALM COAST, FL, ..., Palm Coast, FL 32137
$974,000

3 beds

|

3 baths

|

2,167 sq ft

|

Condo

455 RIVERFRONT DR A104, PALM COAST, FL, ...
Community: Grand Haven
American Village 31 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164
$374,885

4 beds

|

2 baths

|

1,986 sq ft

|

House

31 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
The Villages® 1130 AVENIDA DE LAS CASAS, LADY LAKE, FL..., Lady Lake, FL 32159
$450,000

2 beds

|

3 baths

|

1,780 sq ft

|

Condo

1130 AVENIDA DE LAS CASAS, LADY LAKE, FL...
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.
Highland Fairways 2137 GRAND CYPRESS DR, LAKELAND, FL, 338..., Lakeland, FL 33810
$284,900

3 beds

|

2 baths

|

1,808 sq ft

|

House

2137 GRAND CYPRESS DR, LAKELAND, FL, 338...
Community: Highland Fairways
Spruce Creek Country Club 12176 SE 91ST AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$318,000

3 beds

|

2 baths

|

2,120 sq ft

|

House

12176 SE 91ST AVE, SUMMERFIELD, FL, 3449...
The Villages® 1092 INCORVAIA WAY, THE VILLAGES, FL, 32..., The Villages, FL 32163
$619,900

3 beds

|

3 baths

|

2,409 sq ft

|

House

1092 INCORVAIA WAY, THE VILLAGES, FL, 32...
Community: The Villages®
Plantation at Leesburg 3606 MULBERRY GROVE LOOP, LEESBURG, FL, ..., Leesburg, FL 34748
$449,500

3 beds

|

3 baths

|

2,664 sq ft

|

House

3606 MULBERRY GROVE LOOP, LEESBURG, FL, ...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Lakes at Harmony 3436 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$289,900

2 beds

|

2 baths

|

1,637 sq ft

|

House

3436 SAGEBRUSH ST, HARMONY, FL, 34773
The Villages® 939 KOLLER CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$465,000

3 beds

|

2 baths

|

1,880 sq ft

|

House

939 KOLLER CT, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 6052 CHASE CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$319,900

2 beds

|

2 baths

|

1,227 sq ft

|

Villa

6052 CHASE CT, THE VILLAGES, FL, 32163
Community: The Villages®
Highland Lakes 5606 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$269,900

3 beds

|

2 baths

|

1,919 sq ft

|

House

5606 LAVER ST, LEESBURG, FL, 34748
Community: Highland Lakes
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 615 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$93,900

1 beds

|

1 baths

|

490 sq ft

|

Manufactured Home

615 COTTAGE PARK LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
The Villages® 2573 CARIBE DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$334,900

3 beds

|

2 baths

|

1,472 sq ft

|

House

2573 CARIBE DR, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 712 JASON DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$215,000

2 beds

|

2 baths

|

1,292 sq ft

|

Manufactured Home

712 JASON DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Country Club of Mount Dora 3016 ANDOVER CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$315,000

2 beds

|

2 baths

|

1,522 sq ft

|

House

3016 ANDOVER CT, MOUNT DORA, FL, 32757
Royal Harbor 5138 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778
$359,900

3 beds

|

2 baths

|

1,889 sq ft

|

House

5138 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® 1258 WEATON CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$339,900

3 beds

|

2 baths

|

1,477 sq ft

|

House

1258 WEATON CT, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 870 HENDERSON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$319,900

3 beds

|

2 baths

|

1,375 sq ft

|

House

870 HENDERSON LN, THE VILLAGES, FL, 3216...
Community: The Villages®
Plantation Bay Golf & Country Club 875 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$388,000

3 beds

|

3 baths

|

2,101 sq ft

|

Townhouse

875 PINEWOOD DR, ORMOND BEACH, FL, 32174
Sandpiper Golf & Country Club 6096 KITTIWAKE DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$299,900

3 beds

|

2 baths

|

1,489 sq ft

|

House

6096 KITTIWAKE DR, LAKELAND, FL, 33809
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.
Royal Highlands 5401 ESSEX CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$380,000

2 beds

|

3 baths

|

2,009 sq ft

|

House

5401 ESSEX CT, LEESBURG, FL, 34748
Community: Royal Highlands
Twin Lakes 2606 MEADOWEDGE LOOP, ST CLOUD, FL, 3477..., St Cloud, FL 34772
$549,000

3 beds

|

3 baths

|

2,365 sq ft

|

House

2606 MEADOWEDGE LOOP, ST CLOUD, FL, 3477...
Community: Twin Lakes
Summer Trees 130 CYPRESS POND RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$264,500

3 beds

|

2 baths

|

1,363 sq ft

|

House

130 CYPRESS POND RD, PORT ORANGE, FL, 32...
Community: Summer Trees
Plantation at Leesburg 25273 LOST OAK CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,000

3 beds

|

2 baths

|

1,702 sq ft

|

House

25273 LOST OAK CIR, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Breakaway Trails 94 SHADOWCREEK WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$599,900

4 beds

|

3 baths

|

3,261 sq ft

|

House

94 SHADOWCREEK WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
Kings Ridge 3572 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$357,500

2 beds

|

2 baths

|

1,745 sq ft

|

House

3572 CAPLAND AVE, CLERMONT, FL, 34711
Community: Kings Ridge

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