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 24

2,259 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
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
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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
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) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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
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.
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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
3.8 rating (6 reviews) Trilogy® Orlando
$200ks - $500ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
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
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
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
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 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) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 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
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 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) Legacy of Leesburg
$200ks - $400ks
Legacy of Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 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
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 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
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 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
The Timbers at Everlands
$200ks - $500ks
The Timbers at Everlands, Palm Bay, FL
New Construction | 55+ age-restricted | Built 2023 - present | 450 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 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
The Villages® 600 AUDREY LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$409,000

3 beds

|

2 baths

|

1,397 sq ft

|

Villa

600 AUDREY LN, THE VILLAGES, FL, 32162
Community: The Villages®
Del Webb Minneola 1552 SKYLINE HEIGHTS CIR, MINNEOLA, FL, ..., Minneola, FL 34715
$864,900

3 beds

|

4 baths

|

2,844 sq ft

|

House

1552 SKYLINE HEIGHTS CIR, MINNEOLA, FL, ...
Community: Del Webb Minneola
Latitude Margaritaville 132 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$409,900

2 beds

|

2 baths

|

1,464 sq ft

|

House

132 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
The Villages® 8142 SE 175TH COLUMBIA PL, THE VILLAGES,..., The Villages, FL 32162
$340,000

3 beds

|

2 baths

|

1,265 sq ft

|

House

8142 SE 175TH COLUMBIA PL, THE VILLAGES,...
Community: The Villages®
Latitude Margaritaville 275 POP TOP LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124
$414,000

2 beds

|

2 baths

|

1,464 sq ft

|

House

275 POP TOP LN, DAYTONA BEACH, FL, 32124
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 2255 PATRICIA PL, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$429,900

3 beds

|

2 baths

|

1,642 sq ft

|

Villa

2255 PATRICIA PL, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 1710 ROSALES RD, THE VILLAGES, FL, 32162, The Villages, FL 32162
$249,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

1710 ROSALES RD, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 951 OLEANDER ST, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$223,850

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

951 OLEANDER ST, LADY LAKE, FL, 32159
Community: The Villages®
Halifax Plantation 3753 MAYO CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$664,900

4 beds

|

4 baths

|

2,863 sq ft

|

House

3753 MAYO CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
The Country Club of Mount Dora 9035 LAUREL RIDGE DR, MOUNT DORA, FL, 32..., Mount Dora, FL 32757
$544,900

2 beds

|

3 baths

|

2,477 sq ft

|

House

9035 LAUREL RIDGE DR, MOUNT DORA, FL, 32...
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 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...
Pelican Bay Daytona Beach 128 SPOONBILL CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32119
$349,900

3 beds

|

2 baths

|

2,056 sq ft

|

House

128 SPOONBILL CT, DAYTONA BEACH, FL, 321...
High Vista at Ridgewood Lakes 237 GOLF VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$399,000

3 beds

|

3 baths

|

2,611 sq ft

|

House

237 GOLF VISTA DR, DAVENPORT, FL, 33837
Four Seasons at Orlando 1691 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$355,000

2 beds

|

2 baths

|

1,557 sq ft

|

Villa

1691 KEY BAY TRL, KISSIMMEE, FL, 34747
Spruce Creek South 17814 SE 107TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$249,900

3 beds

|

2 baths

|

1,450 sq ft

|

House

17814 SE 107TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Latitude Margaritaville 396 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$389,900

2 beds

|

2 baths

|

1,466 sq ft

|

House

396 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 1304 GUADALUPE CT, THE VILLAGES, FL, 321..., The Villages, FL 32159
$335,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

1304 GUADALUPE CT, THE VILLAGES, FL, 321...
Community: The Villages®
Latitude Margaritaville 244 POP TOP LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124
$479,900

3 beds

|

2 baths

|

1,563 sq ft

|

House

244 POP TOP LN, DAYTONA BEACH, FL, 32124
Grand Haven 200 RIVERFRONT DR D304, PALM COAST, FL, ..., Palm Coast, FL 32137
$499,000

3 beds

|

3 baths

|

2,015 sq ft

|

Condo

200 RIVERFRONT DR D304, PALM COAST, FL, ...
Community: Grand Haven
The Villages® 3541 ROANOKE ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$270,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

3541 ROANOKE ST, 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.
The Villages® 1008 VENTURA DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$319,000

3 beds

|

2 baths

|

1,344 sq ft

|

House

1008 VENTURA DR, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 2426 SAFFRON LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$319,900

2 beds

|

2 baths

|

1,196 sq ft

|

Villa

2426 SAFFRON LN, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1795 HAGOOD LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$489,900

3 beds

|

2 baths

|

1,770 sq ft

|

House

1795 HAGOOD LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Kings Ridge 4390 SAMBOURNE ST, CLERMONT, FL, 34711, Clermont, FL 34711
$317,500

2 beds

|

2 baths

|

1,363 sq ft

|

House

4390 SAMBOURNE ST, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 2696 MIDLAND TER, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$899,000

3 beds

|

2 baths

|

2,133 sq ft

|

House

2696 MIDLAND TER, THE VILLAGES, FL, 3216...
Community: The Villages®
Plantation Bay Golf & Country Club 420 WINGSPAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$4,450,000

5 beds

|

7 baths

|

5,151 sq ft

|

House

420 WINGSPAN DR, ORMOND BEACH, FL, 32174
The Villages® 1035 BLYTHE WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$415,000

2 beds

|

2 baths

|

1,670 sq ft

|

House

1035 BLYTHE WAY, THE VILLAGES, FL, 32162
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Plantation Bay Golf & Country Club 708 WOODBRIDGE CT, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$850,000

3 beds

|

2 baths

|

2,434 sq ft

|

House

708 WOODBRIDGE CT, ORMOND BEACH, FL, 321...
Royal Highlands 20634 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748
$305,000

2 beds

|

2 baths

|

1,858 sq ft

|

House

20634 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
Twin Lakes 2486 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772
$320,000

2 beds

|

2 baths

|

1,464 sq ft

|

Villa

2486 DATURA LOOP, ST CLOUD, FL, 34772
Community: Twin 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.
Halifax Plantation 3505 TORY CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$575,000

3 beds

|

2 baths

|

2,184 sq ft

|

House

3505 TORY CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
The Villages® 2039 TYNTE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$585,000

3 beds

|

3 baths

|

2,473 sq ft

|

House

2039 TYNTE TER, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1969 HAGOOD LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$419,500

3 beds

|

2 baths

|

2,000 sq ft

|

House

1969 HAGOOD LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 1648 ABASCO CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$329,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

1648 ABASCO CT, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 447 FOSTER PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$449,999

3 beds

|

2 baths

|

1,872 sq ft

|

House

447 FOSTER PL, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 991 BARRYMOORE LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32162
$429,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

991 BARRYMOORE LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
Venetian Bay 3604 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$698,000

4 beds

|

2 baths

|

2,050 sq ft

|

House

3604 MARIBELLA DR, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
The Villages® 17167 SE 76TH BOXBURY CT, THE VILLAGES, ..., The Villages, FL 32162
$257,500

2 beds

|

2 baths

|

1,194 sq ft

|

House

17167 SE 76TH BOXBURY CT, THE VILLAGES, ...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Trilogy® Orlando 115 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736
$330,000

3 beds

|

2 baths

|

1,856 sq ft

|

House

115 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
The Villages® 4106 VICTORY DR, THE VILLAGES, FL, 32163, The Villages, FL 32163
$479,000

3 beds

|

2 baths

|

1,904 sq ft

|

House

4106 VICTORY DR, THE VILLAGES, FL, 32163
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
2,259 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: Jul 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