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 48

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
The Villages® 5967 FREITAG AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$559,000

3 beds

|

2 baths

|

1,633 sq ft

|

Villa

5967 FREITAG AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
Del Webb Orlando 540 PAMPLONA PL, DAVENPORT, FL, 33837, Davenport, FL 33837
$329,900

2 beds

|

3 baths

|

1,772 sq ft

|

House

540 PAMPLONA PL, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Plantation Bay Golf & Country Club 823 CREEKWOOD DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$560,000

3 beds

|

2 baths

|

1,762 sq ft

|

House

823 CREEKWOOD DR, ORMOND BEACH, FL, 3217...
Grand Haven 2 GLENEAGLES PL, PALM COAST, FL, 32137, Palm Coast, FL 32137
$438,900

3 beds

|

2 baths

|

1,785 sq ft

|

House

2 GLENEAGLES PL, PALM COAST, FL, 32137
Community: Grand Haven
The Villages® 931 OLEANDER ST, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$295,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

931 OLEANDER ST, LADY LAKE, FL, 32159
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 2865 JUDAH ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$329,000

2 beds

|

2 baths

|

1,286 sq ft

|

Villa

2865 JUDAH ST, THE VILLAGES, FL, 32163
Community: The Villages®
Enclave at VillageWalk 11675 SAVONA WAY, ORLANDO, FL, 32827, Orlando, FL 32827
$1,385,000

4 beds

|

5 baths

|

4,622 sq ft

|

House

11675 SAVONA WAY, ORLANDO, FL, 32827
The Villages® 1067 CARVER CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$352,829

2 beds

|

2 baths

|

1,270 sq ft

|

Villa

1067 CARVER CT, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 442 PACE LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$289,900

2 beds

|

2 baths

|

1,100 sq ft

|

House

442 PACE LN, THE VILLAGES, FL, 32162
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 26209 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$249,900

2 beds

|

2 baths

|

1,514 sq ft

|

House

26209 NEWCOMBE CIR, LEESBURG, FL, 34748
Community: Highland Lakes
The Villages® 17985 SE 92ND AMORY AVE, THE VILLAGES, F..., The Villages, FL 32162
$319,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

17985 SE 92ND AMORY AVE, THE VILLAGES, F...
Community: The Villages®
Spruce Creek South 10035 SE 175TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$229,000

2 beds

|

2 baths

|

1,359 sq ft

|

Villa

10035 SE 175TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Royal Highlands 21122 LIONHEART DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$259,900

3 beds

|

2 baths

|

1,453 sq ft

|

House

21122 LIONHEART DR, 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
Lake James 7929 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$510,000

3 beds

|

2 baths

|

2,653 sq ft

|

House

7929 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Lake Ashton 4040 BIRKDALE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$289,900

2 beds

|

2 baths

|

1,530 sq ft

|

House

4040 BIRKDALE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Plantation at Leesburg 4712 BELLE GRV, LEESBURG, FL, 34748, Leesburg, FL 34748
$189,000

3 beds

|

2 baths

|

1,524 sq ft

|

Manufactured Home

4712 BELLE GRV, LEESBURG, FL, 34748
The Villages® 8143 SE 175TH COLUMBIA PL, THE VILLAGES,..., The Villages, FL 32162
$299,750

3 beds

|

2 baths

|

1,231 sq ft

|

House

8143 SE 175TH COLUMBIA PL, THE VILLAGES,...
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 Villages® 2109 HARSTON TRL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$299,000

2 beds

|

2 baths

|

1,142 sq ft

|

House

2109 HARSTON TRL, THE VILLAGES, FL, 3216...
Community: The Villages®
Spruce Creek Country Club 13235 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$365,000

2 beds

|

2 baths

|

2,149 sq ft

|

House

13235 SE 97TH TERRACE RD, SUMMERFIELD, F...
Colonnades 1635 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811
$265,000

2 beds

|

2 baths

|

1,751 sq ft

|

House

1635 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
Ridgehaven 1340 OAKHAVEN AVE, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$393,750

4 beds

|

3 baths

|

2,190 sq ft

|

House

1340 OAKHAVEN AVE, ORMOND BEACH, FL, 321...
Community: Ridgehaven
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Colonnades 4908 DAWNVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$229,695

2 beds

|

2 baths

|

1,338 sq ft

|

House

4908 DAWNVIEW LN, LAKELAND, FL, 33811
Community: Colonnades
Lake Ashton 4497 STRATHMORE DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$393,000

3 beds

|

2 baths

|

2,312 sq ft

|

House

4497 STRATHMORE DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
Plantation at Leesburg 25504 BELLE ALLIANCE, LEESBURG, FL, 3474..., Leesburg, FL 34748
$169,900

2 beds

|

2 baths

|

1,674 sq ft

|

Manufactured Home

25504 BELLE ALLIANCE, LEESBURG, FL, 3474...
Plantation at Leesburg 25327 TEMPLE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$275,000

2 beds

|

2 baths

|

1,433 sq ft

|

House

25327 TEMPLE CT, 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.
Venetian Bay 3507 CASALTA CIR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$419,900

3 beds

|

3 baths

|

2,644 sq ft

|

House

3507 CASALTA CIR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Venetian Bay 3020 KING PALM DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$612,000

4 beds

|

3 baths

|

2,179 sq ft

|

House

3020 KING PALM DR, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
The Villages® 9191 SE 166TH SPRUNG LN, THE VILLAGES, F..., The Villages, FL 32162
$330,000

2 beds

|

2 baths

|

1,152 sq ft

|

Villa

9191 SE 166TH SPRUNG LN, THE VILLAGES, F...
Community: The Villages®
The Villages® 2282 SHEEHAN ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$280,000

2 beds

|

2 baths

|

1,227 sq ft

|

Villa

2282 SHEEHAN ST, THE VILLAGES, FL, 32163
Community: The Villages®
Royal Highlands 21202 BRAVEHEART DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$305,000

3 beds

|

2 baths

|

1,588 sq ft

|

House

21202 BRAVEHEART DR, 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
Ridgehaven 1332 OAKHAVEN AVE, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$449,990

5 beds

|

4 baths

|

3,232 sq ft

|

House

1332 OAKHAVEN AVE, ORMOND BEACH, FL, 321...
Community: Ridgehaven
Huntington at Hunter's Ridge 13 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$399,900

4 beds

|

3 baths

|

2,156 sq ft

|

House

13 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Lake Ashton 4249 BERWICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$389,900

3 beds

|

2 baths

|

1,847 sq ft

|

House

4249 BERWICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Grand Haven 14 EGRET DR, PALM COAST, FL, 32137, Palm Coast, FL 32137
$550,000

3 beds

|

2 baths

|

2,456 sq ft

|

House

14 EGRET DR, PALM COAST, FL, 32137
Community: Grand Haven
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.
Venetian Bay 3566 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$675,000

5 beds

|

3 baths

|

2,405 sq ft

|

House

3566 MARIBELLA DR, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
Tohoqua Reserve 1991 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$479,900

3 beds

|

2 baths

|

2,056 sq ft

|

House

1991 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Plantation at Leesburg 4849 SABLE RIDGE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$395,000

3 beds

|

3 baths

|

2,607 sq ft

|

House

4849 SABLE RIDGE CT, LEESBURG, FL, 34748
Spruce Creek Country Club 9910 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$393,000

3 beds

|

2 baths

|

2,025 sq ft

|

House

9910 SE 138TH LOOP, SUMMERFIELD, FL, 344...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Venetian Bay 552 CARO CT, NEW SMYRNA BEACH, FL, 32168, New Smyrna Beach, FL 32168
$464,500

3 beds

|

2 baths

|

1,728 sq ft

|

House

552 CARO CT, NEW SMYRNA BEACH, FL, 32168
Community: Venetian Bay
Plantation Bay Golf & Country Club 55 BAY POINTE DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$425,000

2 beds

|

3 baths

|

2,790 sq ft

|

House

55 BAY POINTE DR, ORMOND BEACH, FL, 3217...

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