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 15

2,414 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
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
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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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.
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 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
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
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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 homes
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
4 rating (4 reviews) Lakes of Mount Dora
$300ks - $1Ms
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 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
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) Cresswind at Victoria Gar...
$200ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes
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) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
5 rating (2 reviews) Heritage Isle
$300ks - $500ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 homes
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 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.
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
Ridgehaven
$300ks - $600ks
Ridgehaven, Ormond Beach, FL
New Construction | 55+ age-restricted
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 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
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
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
5 rating (2 reviews) Bridgewater at Viera
$300ks - $800ks
Bridgewater at Viera, Melbourne, FL
Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 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
Latitude Margaritaville 703 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$639,900

2 beds

|

3 baths

|

2,139 sq ft

|

House

703 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
The Villages® 24104 SANDALWOOD DR 104, WILDWOOD, FL, 3..., Wildwood, FL 34785
$115,000

1 beds

|

1 baths

|

900 sq ft

|

Condo

24104 SANDALWOOD DR 104, WILDWOOD, FL, 3...
Community: The Villages®
Indian River Colony Club 1375 MAYFLOWER AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940
$330,000

3 beds

|

2 baths

|

2,010 sq ft

|

House

1375 MAYFLOWER AVE, MELBOURNE, FL, 32940
Harbor Hills Country Club 5013 HARBOR HEIGHTS, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$352,000

3 beds

|

2 baths

|

1,954 sq ft

|

House

5013 HARBOR HEIGHTS, LADY LAKE, FL, 3215...
The Villages® 2427 SOUTHERN OAK ST, THE VILLAGES, FL, ..., The Villages, FL 32162
$309,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2427 SOUTHERN OAK ST, THE VILLAGES, FL, ...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Spruce Creek Country Club 13828 SE 85TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$249,900

2 beds

|

2 baths

|

1,315 sq ft

|

House

13828 SE 85TH CIR, SUMMERFIELD, FL, 3449...
The Villages® 2820 CHRISTOPHER CT, THE VILLAGES, FL, 3..., The Villages, FL 32163
$389,000

3 beds

|

2 baths

|

1,485 sq ft

|

House

2820 CHRISTOPHER CT, THE VILLAGES, FL, 3...
Community: The Villages®
Plantation at Leesburg 25073 RIVERWALK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$300,000

3 beds

|

2 baths

|

1,814 sq ft

|

House

25073 RIVERWALK DR, LEESBURG, FL, 34748
The Villages® 3076 GULFPORT CT, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$349,999

2 beds

|

2 baths

|

1,161 sq ft

|

Villa

3076 GULFPORT CT, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 1407 FIGUEROA ST, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$305,000

3 beds

|

2 baths

|

1,687 sq ft

|

House

1407 FIGUEROA ST, 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.
Sullivan Ranch 22024 BELGIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$320,000

3 beds

|

2 baths

|

1,437 sq ft

|

House

22024 BELGIAN CT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
The Villages® 930 TARRSON BLVD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$139,800

2 beds

|

2 baths

|

960 sq ft

|

Manufactured Home

930 TARRSON BLVD, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 17869 SE 86TH AUBURN AVE, THE VILLAGES, ..., The Villages, FL 32162
$339,000

3 beds

|

2 baths

|

1,498 sq ft

|

House

17869 SE 86TH AUBURN AVE, THE VILLAGES, ...
Community: The Villages®
The Villages® 208 DESOTA CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$369,000

2 beds

|

2 baths

|

1,504 sq ft

|

House

208 DESOTA CT, LADY LAKE, FL, 32159
Community: The Villages®
Heritage - The Cottages of Sanders Grove 6358 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762
$305,000

3 beds

|

2 baths

|

1,690 sq ft

|

House

6358 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
Grand Haven 1 GLENEAGLES PL, PALM COAST, FL, 32137, Palm Coast, FL 32137
$399,000

3 beds

|

2 baths

|

1,488 sq ft

|

House

1 GLENEAGLES PL, PALM COAST, FL, 32137
Community: Grand Haven
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Stonecrest 17552 SE 119TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$325,000

3 beds

|

3 baths

|

1,676 sq ft

|

House

17552 SE 119TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 580 GOUGH PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$574,000

3 beds

|

2 baths

|

1,918 sq ft

|

House

580 GOUGH PL, THE VILLAGES, FL, 32163
Community: The Villages®
Harbor Hills Country Club 39654 GROVE HEIGHTS, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$799,900

4 beds

|

4 baths

|

2,761 sq ft

|

House

39654 GROVE HEIGHTS, LADY LAKE, FL, 3215...
Halifax Plantation 3013 GLIN CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$315,000

3 beds

|

2 baths

|

1,684 sq ft

|

House

3013 GLIN CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
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.
Solivita 516 MILLIFIORA LN, POINCIANA, FL, 34759, Poinciana, FL 34759
$260,000

2 beds

|

2 baths

|

1,240 sq ft

|

House

516 MILLIFIORA LN, POINCIANA, FL, 34759
Community: Solivita
Harbor Hills Country Club 5084 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$711,150

4 beds

|

3 baths

|

2,586 sq ft

|

House

5084 GREENS DR, LADY LAKE, FL, 32159
Arlington Ridge 4562 ANTIETAM CREEK TRL, LEESBURG, FL, 3..., Leesburg, FL 34748
$360,000

3 beds

|

2 baths

|

2,207 sq ft

|

House

4562 ANTIETAM CREEK TRL, LEESBURG, FL, 3...
Community: Arlington Ridge
Sandpiper Golf & Country Club 6101 MAGPIE DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$325,000

2 beds

|

2 baths

|

1,242 sq ft

|

House

6101 MAGPIE DR, LAKELAND, FL, 33809
Royal Harbor 5277 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778
$365,000

3 beds

|

2 baths

|

2,086 sq ft

|

House

5277 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
Halifax Plantation 3722 LONGFORD CIR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$625,000

4 beds

|

3 baths

|

2,580 sq ft

|

House

3722 LONGFORD CIR, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
Indian River Colony Club 1537 TIPPICANOE CT, MELBOURNE, FL, 32940, Melbourne, FL 32940
$330,000

4 beds

|

3 baths

|

2,351 sq ft

|

House

1537 TIPPICANOE CT, MELBOURNE, FL, 32940
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Lakes at Harmony 3415 FEATHERGRASS CT, ST CLOUD, FL, 3477..., St Cloud, FL 34773
$599,900

5 beds

|

4 baths

|

3,300 sq ft

|

House

3415 FEATHERGRASS CT, ST CLOUD, FL, 3477...
The Villages® 5554 MILLICAN AVE, THE VILLAGES, FL, 321..., The Villages, FL 32163
$479,000

3 beds

|

2 baths

|

1,696 sq ft

|

Villa

5554 MILLICAN AVE, THE VILLAGES, FL, 321...
Community: The Villages®
High Vista at Ridgewood Lakes 322 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$318,000

3 beds

|

2 baths

|

1,776 sq ft

|

House

322 HIGH VISTA DR, DAVENPORT, FL, 33837
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® 1215 WESTMORELAND LOOP, THE VILLAGES, FL..., The Villages, FL 32162
$419,000

3 beds

|

2 baths

|

1,747 sq ft

|

House

1215 WESTMORELAND LOOP, THE VILLAGES, FL...
Community: The Villages®
The Villages® 2430 MERIDA CIR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$255,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

2430 MERIDA CIR, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 661 SHERWOOD ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$389,500

2 beds

|

2 baths

|

1,182 sq ft

|

Villa

661 SHERWOOD ST, THE VILLAGES, FL, 32162
Community: The Villages®
The Timbers at Everlands 2322 NW ANTARUS DR DR, PALM BAY, FL, 329..., Palm Bay, FL 32907
$384,900

3 beds

|

3 baths

|

2,070 sq ft

|

House

2322 NW ANTARUS DR DR, PALM BAY, FL, 329...
Plantation at Leesburg 25143 BARROW HL, LEESBURG, FL, 34748, Leesburg, FL 34748
$185,000

2 beds

|

2 baths

|

1,108 sq ft

|

Manufactured Home

25143 BARROW HL, LEESBURG, FL, 34748
Summit Chase Villas 12532 ORANGEWOOD CT, TAVARES, FL, 32778, Tavares, FL 32778
$199,800

2 beds

|

2 baths

|

918 sq ft

|

Condo

12532 ORANGEWOOD CT, TAVARES, FL, 32778
Community: Summit Chase Villas
The Villages® 2234 KERSHAW RD, THE VILLAGES, FL, 32162, The Villages, FL 32162
$475,000

3 beds

|

2 baths

|

2,000 sq ft

|

House

2234 KERSHAW RD, THE VILLAGES, FL, 32162
Community: The Villages®
Summer Trees 114 RUSTIC POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$282,406

2 beds

|

2 baths

|

1,481 sq ft

|

House

114 RUSTIC POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Latitude Margaritaville 328 CHEESEBURGER DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$874,900

3 beds

|

3 baths

|

2,430 sq ft

|

House

328 CHEESEBURGER DR, DAYTONA BEACH, FL, ...
The Villages® 1797 PAMPLICO CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$474,900

3 beds

|

2 baths

|

1,887 sq ft

|

House

1797 PAMPLICO 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.

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
2,414 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: May 25, 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