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 44

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
VillageWalk at Lake Nona 11932 LORENZA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$450,000

3 beds

|

3 baths

|

1,830 sq ft

|

Townhouse

11932 LORENZA LN, ORLANDO, FL, 32827
Foxwood Lake Estates 4910 LOCH NESS DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$200,000

2 beds

|

2 baths

|

1,404 sq ft

|

Manufactured Home

4910 LOCH NESS DR, LAKELAND, FL, 33810
The Villages® 3942 ZENITH LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$490,910

3 beds

|

2 baths

|

1,922 sq ft

|

House

3942 ZENITH LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Spruce Creek South 9900 SE 175TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$380,000

3 beds

|

2 baths

|

2,349 sq ft

|

House

9900 SE 175TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Lakes of Mount Dora 8683 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$414,000

3 beds

|

2 baths

|

1,968 sq ft

|

House

8683 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Sullivan Ranch 20930 SULLIVAN RANCH BLVD, MOUNT DORA, F..., Mount Dora, FL 32757
$625,000

6 beds

|

4 baths

|

3,499 sq ft

|

House

20930 SULLIVAN RANCH BLVD, MOUNT DORA, F...
Community: Sullivan Ranch
Plantation at Leesburg 25720 BELLE ALLIANCE, LEESBURG, FL, 3474..., Leesburg, FL 34748
$249,000

2 beds

|

2 baths

|

1,478 sq ft

|

House

25720 BELLE ALLIANCE, LEESBURG, FL, 3474...
Foxwood Lake Estates 1819 SHERWOOD HILL DR, LAKELAND, FL, 338..., Lakeland, FL 33810
$151,000

2 beds

|

2 baths

|

1,568 sq ft

|

Manufactured Home

1819 SHERWOOD HILL DR, LAKELAND, FL, 338...
Spruce Creek Country Club 13766 SE 89TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$328,950

3 beds

|

2 baths

|

2,025 sq ft

|

House

13766 SE 89TH AVE, SUMMERFIELD, FL, 3449...
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 3371 PINTELLO AVE, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$415,000

4 beds

|

2 baths

|

2,162 sq ft

|

House

3371 PINTELLO AVE, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
Four Seasons at Orlando 2051 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$489,000

3 beds

|

2 baths

|

1,964 sq ft

|

House

2051 FLORA PASS PL, KISSIMMEE, FL, 34747
Plantation at Leesburg 3605 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748
$319,000

2 beds

|

2 baths

|

1,868 sq ft

|

House

3605 MOUNT HOPE LOOP, LEESBURG, FL, 3474...
Del Webb Sunbridge 6515 QUEST ST, ST CLOUD, FL, 34771, St Cloud, FL 34771
$650,000

4 beds

|

3 baths

|

2,904 sq ft

|

House

6515 QUEST ST, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Legacy of Leesburg 5510 CELEBRATION WAY, LEESBURG, FL, 3474..., Leesburg, FL 34748
$386,500

3 beds

|

3 baths

|

2,044 sq ft

|

House

5510 CELEBRATION WAY, LEESBURG, FL, 3474...
Community: Legacy of Leesburg
Spruce Creek Country Club 14280 SE 85TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$259,900

2 beds

|

2 baths

|

1,556 sq ft

|

House

14280 SE 85TH AVE, SUMMERFIELD, FL, 3449...
Trilogy® Orlando 107 BALMY COAST RD, GROVELAND, FL, 34736, Groveland, FL 34736
$625,000

4 beds

|

3 baths

|

2,756 sq ft

|

House

107 BALMY COAST RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
The Villages® 2737 AVA ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$715,000

3 beds

|

2 baths

|

1,630 sq ft

|

House

2737 AVA ST, 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.
The Villages® 802 MIRANDA WAY, THE VILLAGES, FL, 32159, The Villages, FL 32159
$339,000

2 beds

|

2 baths

|

1,471 sq ft

|

House

802 MIRANDA WAY, THE VILLAGES, FL, 32159
Community: The Villages®
Stonecrest 11041 SE 169TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$289,900

3 beds

|

2 baths

|

1,417 sq ft

|

House

11041 SE 169TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Plantation Bay Golf & Country Club 1321 SUNNINGDALE LN, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174
$469,000

3 beds

|

2 baths

|

1,930 sq ft

|

House

1321 SUNNINGDALE LN, ORMOND BEACH, FL, 3...
Gatherings of Lake Nona 7565 LAUREATE BLVD 3304, ORLANDO, FL, 32..., Orlando, FL 32827
$425,000

2 beds

|

2 baths

|

1,486 sq ft

|

Condo

7565 LAUREATE BLVD 3304, ORLANDO, FL, 32...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 3229 KILLINGTON LOOP, THE VILLAGES, FL, ..., The Villages, FL 32163
$499,000

3 beds

|

3 baths

|

2,072 sq ft

|

House

3229 KILLINGTON LOOP, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 17035 SE 94TH BERRIEN CT, THE VILLAGES, ..., The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,731 sq ft

|

House

17035 SE 94TH BERRIEN CT, THE VILLAGES, ...
Community: The Villages®
The Villages® 2016 PEACEFUL PL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$299,900

2 beds

|

2 baths

|

1,188 sq ft

|

Villa

2016 PEACEFUL PL, THE VILLAGES, FL, 3216...
Community: The Villages®
Grand Haven 79 SOUTHLAKE DR, PALM COAST, FL, 32137, Palm Coast, FL 32137
$499,900

3 beds

|

3 baths

|

2,020 sq ft

|

House

79 SOUTHLAKE 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.
Huntington at Hunter's Ridge 3 HAWK ROOST CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$339,000

2 beds

|

2 baths

|

1,593 sq ft

|

House

3 HAWK ROOST CT, ORMOND BEACH, FL, 32174
The Villages® 108 WINTERBERRY AVE, WILDWOOD, FL, 34785, Wildwood, FL 34785
$99,999

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

108 WINTERBERRY AVE, WILDWOOD, FL, 34785
Community: The Villages®
Stonecrest 11019 SE 170TH LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$269,900

3 beds

|

2 baths

|

1,324 sq ft

|

House

11019 SE 170TH LANE RD, SUMMERFIELD, FL,...
Community: Stonecrest
Venetian Bay 664 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$757,248

4 beds

|

4 baths

|

3,221 sq ft

|

House

664 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Breakaway Trails 7 LAKE VISTA WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$750,000

5 beds

|

4 baths

|

4,379 sq ft

|

House

7 LAKE VISTA WAY, ORMOND BEACH, FL, 3217...
Community: Breakaway Trails
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Bridgewater at Viera 1393 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940
$815,000

3 beds

|

4 baths

|

2,784 sq ft

|

House

1393 GREAT BELT CIR, MELBOURNE, FL, 3294...
Ridgehaven 1138 CLIFFHAVEN CT, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$520,526

3 beds

|

3 baths

|

2,183 sq ft

|

House

1138 CLIFFHAVEN CT, ORMOND BEACH, FL, 32...
Community: Ridgehaven
Ridgehaven 1130 CLIFFHAVEN CT, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$490,990

4 beds

|

3 baths

|

2,275 sq ft

|

House

1130 CLIFFHAVEN CT, ORMOND BEACH, FL, 32...
Community: Ridgehaven
Ridgehaven 1134 CLIFFHAVEN CT, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$490,137

4 beds

|

2 baths

|

1,945 sq ft

|

House

1134 CLIFFHAVEN CT, ORMOND BEACH, FL, 32...
Community: Ridgehaven
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.
Ridgehaven 1126 CLIFFHAVEN CT, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$486,990

3 beds

|

3 baths

|

2,344 sq ft

|

House

1126 CLIFFHAVEN CT, ORMOND BEACH, FL, 32...
Community: Ridgehaven
Stonecrest 12095 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$299,000

3 beds

|

2 baths

|

1,663 sq ft

|

House

12095 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Villages® 17659 SE 92ND GRANTHAM TER, THE VILLAGES..., The Villages, FL 32162
$249,900

3 beds

|

2 baths

|

1,253 sq ft

|

House

17659 SE 92ND GRANTHAM TER, THE VILLAGES...
Community: The Villages®
Spruce Creek South 17960 SE 108TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$234,900

2 beds

|

2 baths

|

1,570 sq ft

|

House

17960 SE 108TH CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Plantation Bay Golf & Country Club 24 BAY POINTE DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$698,000

5 beds

|

4 baths

|

4,274 sq ft

|

House

24 BAY POINTE DR, ORMOND BEACH, FL, 3217...
High Vista at Ridgewood Lakes 642 VISTA OAKS WAY, DAVENPORT, FL, 33837, Davenport, FL 33837
$324,000

3 beds

|

2 baths

|

1,781 sq ft

|

House

642 VISTA OAKS WAY, DAVENPORT, FL, 33837

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