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

2,513 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® 8645 SE 177TH GRASSMERE ST, THE VILLAGES..., The Villages, FL 32162
$1,350,000

3 beds

|

2 baths

|

3,085 sq ft

|

House

8645 SE 177TH GRASSMERE ST, THE VILLAGES...
Community: The Villages®
Gatherings of Lake Nona 7545 LAUREATE BLVD 7301, ORLANDO, FL, 32..., Orlando, FL 32827
$426,990

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

7545 LAUREATE BLVD 7301, ORLANDO, FL, 32...
Gatherings of Lake Nona 7557 LAUREATE BLVD 6401, ORLANDO, FL, 32..., Orlando, FL 32827
$379,990

2 beds

|

2 baths

|

1,368 sq ft

|

Condo

7557 LAUREATE BLVD 6401, ORLANDO, FL, 32...
Sandpiper Golf & Country Club 6260 CRANE DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$349,900

3 beds

|

2 baths

|

1,830 sq ft

|

House

6260 CRANE DR, LAKELAND, FL, 33809
The Villages® 1305 LA ESTRELLITA WAY, THE VILLAGES, FL..., The Villages, FL 32162
$320,000

3 beds

|

2 baths

|

1,817 sq ft

|

House

1305 LA ESTRELLITA WAY, 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
The Country Club of Mount Dora 1500 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$665,000

4 beds

|

3 baths

|

2,484 sq ft

|

House

1500 EDGEWATER DR, MOUNT DORA, FL, 32757
The Villages® 1462 PELICAN PATH, THE VILLAGES, FL, 321..., The Villages, FL 32162
$429,900

3 beds

|

2 baths

|

1,715 sq ft

|

House

1462 PELICAN PATH, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 242 JUAREZ WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$225,000

2 beds

|

2 baths

|

1,066 sq ft

|

House

242 JUAREZ WAY, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 5546 COTTRELL CT, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$662,900

3 beds

|

2 baths

|

1,809 sq ft

|

Villa

5546 COTTRELL 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.
Sullivan Ranch 20900 OLDENBURG LOOP, MOUNT DORA, FL, 32..., Mount Dora, FL 32757
$409,300

4 beds

|

2 baths

|

2,110 sq ft

|

House

20900 OLDENBURG LOOP, MOUNT DORA, FL, 32...
Community: Sullivan Ranch
Scottish Highlands 2003 TWEED CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$199,500

2 beds

|

2 baths

|

1,360 sq ft

|

House

2003 TWEED CT, LEESBURG, FL, 34788
Community: Scottish Highlands
Summer Trees 73 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$180,000

2 beds

|

2 baths

|

1,228 sq ft

|

Townhouse

73 CYPRESS POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
Twin Lakes 2461 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772
$289,900

2 beds

|

2 baths

|

1,464 sq ft

|

Halfplex

2461 DATURA LOOP, ST CLOUD, FL, 34772
Community: Twin Lakes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Isle 2700 CAMBERLY CIR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$295,000

2 beds

|

2 baths

|

1,394 sq ft

|

Townhouse

2700 CAMBERLY CIR, MELBOURNE, FL, 32940
Community: Heritage Isle
Oakview 1581 OAKVIEW CIR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33880
$214,900

2 beds

|

2 baths

|

1,220 sq ft

|

House

1581 OAKVIEW CIR, WINTER HAVEN, FL, 3388...
Community: Oakview
Venetian Bay 3102 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$412,900

3 beds

|

3 baths

|

1,916 sq ft

|

House

3102 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Spruce Creek South 17587 SE 96TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$339,900

3 beds

|

2 baths

|

1,652 sq ft

|

House

17587 SE 96TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
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® 17283 SE 94TH COULTS CIR, THE VILLAGES, ..., The Villages, FL 32162
$324,900

3 beds

|

2 baths

|

1,640 sq ft

|

House

17283 SE 94TH COULTS CIR, THE VILLAGES, ...
Community: The Villages®
Park Place 107 PARK PLACE CIR, PALM COAST, FL, 3216..., Palm Coast, FL 32164
$385,800

3 beds

|

2 baths

|

1,759 sq ft

|

House

107 PARK PLACE CIR, PALM COAST, FL, 3216...
Community: Park Place
The Villages® 16715 SE 80TH CLOVERWOOD TER, THE VILLAG..., The Villages, FL 32162
$308,000

3 beds

|

2 baths

|

1,477 sq ft

|

House

16715 SE 80TH CLOVERWOOD TER, THE VILLAG...
Community: The Villages®
Alamanda Key 4220 ALAMANDA KEY DR DRIVE, MELBOURNE, F..., Melbourne, FL 32901
$315,000

3 beds

|

2 baths

|

1,551 sq ft

|

House

4220 ALAMANDA KEY DR DRIVE, MELBOURNE, F...
Community: Alamanda Key
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 2726 MONCAYO AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$219,900

2 beds

|

1 baths

|

1,034 sq ft

|

Villa

2726 MONCAYO AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 1134 SALIDO AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$385,000

3 beds

|

2 baths

|

1,542 sq ft

|

House

1134 SALIDO AVE, LADY LAKE, FL, 32159
Community: The Villages®
Venetian Bay 3131 PORTOFINO BLVD, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168
$540,000

4 beds

|

4 baths

|

2,338 sq ft

|

House

3131 PORTOFINO BLVD, NEW SMYRNA BEACH, F...
Community: Venetian Bay
Lake Ashton 5264 GREEN DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$335,000

3 beds

|

2 baths

|

2,011 sq ft

|

House

5264 GREEN DR, WINTER HAVEN, FL, 33884
Community: Lake Ashton
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.
Scottish Highlands 1605 SELKIRK DR, LEESBURG, FL, 34788, Leesburg, FL 34788
$210,000

2 beds

|

2 baths

|

1,284 sq ft

|

House

1605 SELKIRK DR, LEESBURG, FL, 34788
Community: Scottish Highlands
Cresswind at Victoria Gardens 304 STONINGTON WAY, DELAND, FL, 32724, Deland, FL 32724
$310,000

3 beds

|

2 baths

|

1,480 sq ft

|

House

304 STONINGTON WAY, DELAND, FL, 32724
The Villages® 16905 SE 93RD CUTHBERT CIR, THE VILLAGES..., The Villages, FL 32162
$450,000

3 beds

|

2 baths

|

1,924 sq ft

|

House

16905 SE 93RD CUTHBERT CIR, THE VILLAGES...
Community: The Villages®
Grand Haven 10 RIVER PARK DR N, PALM COAST, FL, 3213..., Palm Coast, FL 32137
$499,000

2 beds

|

2 baths

|

1,828 sq ft

|

Townhouse

10 RIVER PARK DR N, PALM COAST, FL, 3213...
Community: Grand Haven
The Lakes at Harmony 3204 OXBOW CT, HARMONY, FL, 34773, Harmony, FL 34773
$469,000

4 beds

|

3 baths

|

2,361 sq ft

|

House

3204 OXBOW CT, HARMONY, FL, 34773
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 3500 COUNTRYSIDE PATH, THE VILLAGES, FL,..., The Villages, FL 32163
$349,900

3 beds

|

2 baths

|

1,531 sq ft

|

House

3500 COUNTRYSIDE PATH, THE VILLAGES, FL,...
Community: The Villages®
The Villages® 1994 ORANGEBURG TER, THE VILLAGES, FL, 3..., The Villages, FL 32162
$267,500

2 beds

|

2 baths

|

1,142 sq ft

|

House

1994 ORANGEBURG TER, THE VILLAGES, FL, 3...
Community: The Villages®
The Villages® 1776 WAX BERRY CT, THE VILLAGES, FL, 321..., The Villages, FL 32163
$599,000

3 beds

|

2 baths

|

1,944 sq ft

|

House

1776 WAX BERRY CT, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 1469 SOTHELL ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$290,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

1469 SOTHELL 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.
Royal Harbor 5279 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778
$345,000

3 beds

|

2 baths

|

1,713 sq ft

|

House

5279 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
Plantation at Leesburg 25045 PINE HL, LEESBURG, FL, 34748, Leesburg, FL 34748
$159,900

2 beds

|

2 baths

|

1,188 sq ft

|

Manufactured Home

25045 PINE HL, LEESBURG, FL, 34748
Twin Lakes 2682 MIDSWEET AVE, ST CLOUD, FL, 34772, St Cloud, FL 34772
$514,900

2 beds

|

2 baths

|

1,707 sq ft

|

House

2682 MIDSWEET AVE, ST CLOUD, FL, 34772
Community: Twin Lakes
Plantation Bay Golf & Country Club 848 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$434,900

4 beds

|

3 baths

|

2,101 sq ft

|

Townhouse

848 PINEWOOD DR, ORMOND BEACH, FL, 32174
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Lake Ashton 4648 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$359,000

3 beds

|

2 baths

|

1,847 sq ft

|

House

4648 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
The Villages® 17835 SE 88TH GRIMBALL AVE, THE VILLAGES..., The Villages, FL 32162
$344,900

3 beds

|

2 baths

|

1,608 sq ft

|

House

17835 SE 88TH GRIMBALL AVE, THE VILLAGES...
Community: The Villages®

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