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 31

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 (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 (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
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
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 (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.
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
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
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
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
Tohoqua Reserve
$300ks - $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2021 - present | 258 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
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 (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
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
Heritage Hills 2823 MAYPORT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$520,000

3 beds

|

3 baths

|

2,573 sq ft

|

House

2823 MAYPORT ST, CLERMONT, FL, 34711
Community: Heritage Hills
The Villages® 2223 WESTCHESTER WAY, THE VILLAGES, FL, ..., The Villages, FL 32162
$649,000

3 beds

|

2 baths

|

2,004 sq ft

|

House

2223 WESTCHESTER WAY, THE VILLAGES, FL, ...
Community: The Villages®
Venetian Bay 3074 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$600,000

4 beds

|

4 baths

|

2,092 sq ft

|

Townhouse

3074 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Indian River Colony Club 1741 FREEDOM DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$300,000

3 beds

|

2 baths

|

1,995 sq ft

|

House

1741 FREEDOM DR, MELBOURNE, FL, 32940
Heritage Isle 6858 TOLAND DR 104, MELBOURNE, FL, 32940, Melbourne, FL 32940
$277,500

2 beds

|

2 baths

|

1,194 sq ft

|

Condo

6858 TOLAND DR 104, MELBOURNE, FL, 32940
Community: Heritage Isle
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 3258 SYLEWOOD AVE, THE VILLAGES, FL, 321..., The Villages, FL 32163
$430,000

3 beds

|

2 baths

|

1,956 sq ft

|

House

3258 SYLEWOOD AVE, THE VILLAGES, FL, 321...
Community: The Villages®
Solivita 786 CIELO TRL, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$413,000

2 beds

|

2 baths

|

2,170 sq ft

|

House

786 CIELO TRL, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 444 MAYWOOD WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$299,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

444 MAYWOOD WAY, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 13811 COUNTY RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$300,000

4 beds

|

2 baths

|

2,280 sq ft

|

Manufactured Home

13811 COUNTY RD, LADY LAKE, FL, 32159
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 Lakes 6514 WILANDER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$349,900

3 beds

|

3 baths

|

2,546 sq ft

|

House

6514 WILANDER ST, LEESBURG, FL, 34748
Community: Highland Lakes
Summit Greens 2833 FALCON RDG, CLERMONT, FL, 34711, Clermont, FL 34711
$599,000

3 beds

|

3 baths

|

2,804 sq ft

|

House

2833 FALCON RDG, CLERMONT, FL, 34711
Community: Summit Greens
The Country Club of Mount Dora 8013 PINE HOLLOW DR, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$459,000

3 beds

|

2 baths

|

2,256 sq ft

|

House

8013 PINE HOLLOW DR, MOUNT DORA, FL, 327...
Lake Ashton 6216 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$459,000

3 beds

|

2 baths

|

2,045 sq ft

|

House

6216 PINEHURST LOOP, WINTER HAVEN, FL, 3...
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Spruce Creek Country Club 13700 SE 90TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$285,000

3 beds

|

2 baths

|

2,054 sq ft

|

House

13700 SE 90TH CT, SUMMERFIELD, FL, 34491
Lake Ashton 4424 WATERFORD DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$289,000

2 beds

|

2 baths

|

1,530 sq ft

|

House

4424 WATERFORD DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Traditions at Lake Ruby 3008 CANEEL ST, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$210,000

2 beds

|

2 baths

|

1,385 sq ft

|

Villa

3008 CANEEL ST, WINTER HAVEN, FL, 33884
Heritage Isle 6963 KEPLAR DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$549,000

4 beds

|

3 baths

|

2,271 sq ft

|

House

6963 KEPLAR DR, MELBOURNE, FL, 32940
Community: Heritage Isle
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 Hills 4027 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711
$425,000

3 beds

|

2 baths

|

1,866 sq ft

|

House

4027 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
Del Webb Minneola 2750 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715
$514,900

2 beds

|

2 baths

|

1,409 sq ft

|

House

2750 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
Plantation at Leesburg 24239 BELLE MEDE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$379,973

3 beds

|

2 baths

|

2,289 sq ft

|

House

24239 BELLE MEDE DR, LEESBURG, FL, 34748
The Villages® 8371 SE 168TH TRINITY PL, THE VILLAGES, ..., The Villages, FL 32162
$315,000

3 beds

|

2 baths

|

1,496 sq ft

|

House

8371 SE 168TH TRINITY PL, THE VILLAGES, ...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 885 IRON OAK WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$2,500,000

4 beds

|

3 baths

|

3,340 sq ft

|

House

885 IRON OAK WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
Halifax Plantation 3763 CARRICK DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$529,000

3 beds

|

2 baths

|

2,264 sq ft

|

House

3763 CARRICK DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
The Villages® 1601 CHAVEZ CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$325,000

2 beds

|

2 baths

|

1,332 sq ft

|

House

1601 CHAVEZ CT, THE VILLAGES, FL, 32159
Community: The Villages®
Plantation at Leesburg 25607 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748
$256,000

2 beds

|

2 baths

|

1,345 sq ft

|

House

25607 BELLE HELENE, LEESBURG, FL, 34748
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® 1106 BERKSHIRE PL, THE VILLAGES, FL, 321..., The Villages, FL 32162
$324,900

2 beds

|

2 baths

|

1,100 sq ft

|

House

1106 BERKSHIRE PL, THE VILLAGES, FL, 321...
Community: The Villages®
Pelican Bay Daytona Beach 126 BLUE HERON DR B, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$179,900

2 beds

|

2 baths

|

1,237 sq ft

|

Condo

126 BLUE HERON DR B, DAYTONA BEACH, FL, ...
Royal Harbor 5685 GULF STREAM ST, TAVARES, FL, 32778, Tavares, FL 32778
$349,000

3 beds

|

2 baths

|

1,823 sq ft

|

House

5685 GULF STREAM ST, TAVARES, FL, 32778
Community: Royal Harbor
The Villages® 17411 SE 74TH NETHERCLIFT TER, THE VILLA..., The Villages, FL 32162
$235,000

2 beds

|

2 baths

|

1,148 sq ft

|

House

17411 SE 74TH NETHERCLIFT TER, THE VILLA...
Community: The Villages®
Breakaway Trails 27 LAKE VISTA WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$825,000

4 beds

|

4 baths

|

3,505 sq ft

|

House

27 LAKE VISTA WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Solivita 884 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$264,000

2 beds

|

2 baths

|

1,507 sq ft

|

House

884 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
Alhambra Villas Condominiums 183 N HILL AVE 90, DELAND, FL, 32724, Deland, FL 32724
$175,000

2 beds

|

2 baths

|

979 sq ft

|

Condo

183 N HILL AVE 90, DELAND, FL, 32724
The Villages® 17645 SE 93RD CARSON TER, THE VILLAGES, ..., The Villages, FL 32162
$390,000

3 beds

|

2 baths

|

1,640 sq ft

|

House

17645 SE 93RD CARSON TER, THE VILLAGES, ...
Community: The Villages®
Solivita 172 ACADIA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$253,900

2 beds

|

2 baths

|

1,392 sq ft

|

House

172 ACADIA DR, KISSIMMEE, FL, 34759
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.
Spruce Creek Country Club 13146 SE 93RD TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$309,900

2 beds

|

2 baths

|

1,425 sq ft

|

House

13146 SE 93RD TERRACE RD, SUMMERFIELD, F...
Heritage Isle 2670 CAMBERLY CIR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$275,000

2 beds

|

2 baths

|

1,407 sq ft

|

Townhouse

2670 CAMBERLY CIR, MELBOURNE, FL, 32940
Community: Heritage Isle
Highland Lakes 5500 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$280,000

3 beds

|

2 baths

|

1,591 sq ft

|

House

5500 LAVER ST, LEESBURG, FL, 34748
Community: Highland Lakes
Pennbrooke Fairways 1145 MEADOWBEND DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$307,900

3 beds

|

2 baths

|

1,641 sq ft

|

House

1145 MEADOWBEND DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Solivita 501 PALERMO BLVD, POINCIANA, FL, 34759, Poinciana, FL 34759
$509,999

3 beds

|

3 baths

|

2,580 sq ft

|

House

501 PALERMO BLVD, POINCIANA, FL, 34759
Community: Solivita
Breakaway Trails 8 TROPIC LAKE WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$542,000

3 beds

|

3 baths

|

2,073 sq ft

|

House

8 TROPIC LAKE WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails

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