not an image

Call us at (689) 407-5757 to learn more about active adult communities in Winter Garden

Winter Garden, FL 55+ active adult communities & homes for sale - Page 69

3,218 homes near Winter Garden

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
3.8 rating (14 reviews) Sun City Center
$100ks - $800ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4 rating (57 reviews) On Top of the World
$100ks - $600ks
On Top of the World, Ocala, FL
New and Resale | 55+ age-restricted | Built 1981 - present | 10,000 homes
4.2 rating (10 reviews) Stone Creek
$200ks - $500ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.7 rating (18 reviews) Solivita
$300ks - $700ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
4.1 rating (29 reviews) Oak Run
$100ks - $300ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 homes
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
4.6 rating (5 reviews) Ocala Preserve
$100ks - $500ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 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 (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 (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
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
4 rating (7 reviews) Tampa Bay Golf and Countr...
$200ks - $500ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
5 rating (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 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
5 rating (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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
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
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
Lake Jovita Golf and Coun...
$400ks - $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale | Age-targeted | Built 1999 - present | 875 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.
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4.7 rating (11 reviews) Valencia Lakes
$200ks - $700ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 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
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 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
Mirada
$300ks - $500ks
Mirada, San Antonio, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 858 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 Garden? 55places can help!
Questions? Call us: (689) 407-5757
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 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.
12...3
Venetian Bay 3362 MARSILI AVE, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$350,000

3 beds

|

2 baths

|

1,952 sq ft

|

House

3362 MARSILI AVE, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Plantation at Leesburg 4900 HERON RUN CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$234,900

2 beds

|

2 baths

|

1,289 sq ft

|

House

4900 HERON RUN CIR, LEESBURG, FL, 34748
Pine Run Estates 10041 SW 97TH CT, OCALA, FL, 34481, Ocala, FL 34481
$230,000

3 beds

|

2 baths

|

1,456 sq ft

|

House

10041 SW 97TH CT, OCALA, FL, 34481
Community: Pine Run Estates
Venetian Bay 3070 TIGER PALM WAY, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168
$536,990

5 beds

|

5 baths

|

3,349 sq ft

|

House

3070 TIGER PALM WAY, NEW SMYRNA BEACH, F...
Community: Venetian Bay
Venetian Bay 3143 TIGER PALM WAY, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168
$536,990

4 beds

|

4 baths

|

3,136 sq ft

|

House

3143 TIGER PALM WAY, NEW SMYRNA BEACH, F...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 125 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$461,990

4 beds

|

3 baths

|

2,208 sq ft

|

House

125 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
Venetian Bay 3139 TIGER PALM WAY, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168
$449,990

4 beds

|

3 baths

|

2,208 sq ft

|

House

3139 TIGER PALM WAY, NEW SMYRNA BEACH, F...
Community: Venetian Bay
Venetian Bay 3147 TIGER PALM WAY, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168
$494,990

5 beds

|

3 baths

|

3,184 sq ft

|

House

3147 TIGER PALM WAY, NEW SMYRNA BEACH, F...
Community: Venetian Bay
Latitude Margaritaville 237 SAND BAR LN, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124
$509,900

2 beds

|

2 baths

|

1,681 sq ft

|

House

237 SAND BAR LN, DAYTONA BEACH, FL, 3212...
Breakaway Trails 15 CIRCLE CREEK WAY, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174
$495,000

3 beds

|

2 baths

|

1,875 sq ft

|

House

15 CIRCLE CREEK WAY, ORMOND BEACH, FL, 3...
Community: Breakaway Trails
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® 518 SAINT ANDREWS BLVD, LADY LAKE, FL, 3..., Lady Lake, FL 32159
$225,000

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

518 SAINT ANDREWS BLVD, LADY LAKE, FL, 3...
Community: The Villages®
Valencia del Sol 4717 AVILA LAKES DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$350,000

2 beds

|

2 baths

|

1,648 sq ft

|

Villa

4717 AVILA LAKES DR, WIMAUMA, FL, 33598
Community: Valencia del Sol
Sun City Center 332 CLUB MANOR DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$165,900

2 beds

|

2 baths

|

1,516 sq ft

|

Condo

332 CLUB MANOR DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Solivita 405 BALBOA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$365,000

3 beds

|

3 baths

|

2,350 sq ft

|

House

405 BALBOA DR, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 1433 ARBOR TRL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$358,000

3 beds

|

2 baths

|

1,490 sq ft

|

House

1433 ARBOR TRL, THE VILLAGES, FL, 32162
Community: The Villages®
Traditions at Lake Ruby 2733 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$359,500

3 beds

|

3 baths

|

2,032 sq ft

|

House

2733 ATTWATER LOOP, WINTER HAVEN, FL, 33...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stonecrest 11193 SE 173RD PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$340,000

3 beds

|

2 baths

|

1,974 sq ft

|

House

11193 SE 173RD PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
On Top of the World 10453 SW 99TH LN, OCALA, FL, 34481, Ocala, FL 34481
$489,900

2 beds

|

2 baths

|

2,097 sq ft

|

House

10453 SW 99TH LN, OCALA, FL, 34481
Community: On Top of the World
Valencia del Sol 15433 SANTA POLA DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$340,000

2 beds

|

2 baths

|

1,599 sq ft

|

House

15433 SANTA POLA DR, WIMAUMA, FL, 33598
Community: Valencia del Sol
Arlington Ridge 27143 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$349,000

3 beds

|

2 baths

|

1,699 sq ft

|

House

27143 ROANOKE DR, LEESBURG, FL, 34748
Community: Arlington Ridge
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.
Tampa Bay Golf and Country Club 29146 PRINCEVILLE DR, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$339,000

2 beds

|

2 baths

|

1,777 sq ft

|

House

29146 PRINCEVILLE DR, SAN ANTONIO, FL, 3...
The Villages® 4515 BIGGS PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$1,299,000

3 beds

|

3 baths

|

2,837 sq ft

|

House

4515 BIGGS PL, THE VILLAGES, FL, 32163
Community: The Villages®
Stone Creek 7639 SW 94TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$299,900

2 beds

|

2 baths

|

1,432 sq ft

|

House

7639 SW 94TH CIR, OCALA, FL, 34481
Community: Stone Creek
Solivita 141 MARABELLA LOOP, POINCIANA, FL, 34759, Poinciana, FL 34759
$299,999

3 beds

|

2 baths

|

1,786 sq ft

|

House

141 MARABELLA LOOP, POINCIANA, FL, 34759
Community: Solivita
Spruce Creek Country Club 9479 SE 130TH STREET RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$449,900

3 beds

|

3 baths

|

2,346 sq ft

|

House

9479 SE 130TH STREET RD, SUMMERFIELD, FL...
Lake Ashton 4081 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$390,500

3 beds

|

2 baths

|

2,027 sq ft

|

House

4081 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Encore at Fishhawk Ranch 6036 PLOVER MEADOW ST, LITHIA, FL, 33547, Lithia, FL 33547
$435,000

2 beds

|

3 baths

|

2,049 sq ft

|

House

6036 PLOVER MEADOW ST, LITHIA, FL, 33547
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8637 SW 88TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$230,000

2 beds

|

2 baths

|

1,578 sq ft

|

House

8637 SW 88TH LOOP, OCALA, FL, 34481
Community: On Top of the World
The Villages® 5107 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484
$414,900

4 beds

|

3 baths

|

1,910 sq ft

|

House

5107 NE 122ND BLVD, OXFORD, FL, 34484
Community: The Villages®
Valencia Lakes 15767 CRYSTAL WATERS DR, WIMAUMA, FL, 33..., Wimauma, FL 33598
$334,900

3 beds

|

2 baths

|

2,152 sq ft

|

House

15767 CRYSTAL WATERS DR, WIMAUMA, FL, 33...
Community: Valencia 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.
Lake Ashton 4577 BACK NINE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33884
$349,600

3 beds

|

2 baths

|

1,918 sq ft

|

House

4577 BACK NINE DR, WINTER HAVEN, FL, 338...
Community: Lake Ashton
Summer Trees 49 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$240,000

2 beds

|

2 baths

|

1,048 sq ft

|

House

49 CYPRESS POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
Solivita 699 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$430,000

3 beds

|

3 baths

|

2,450 sq ft

|

House

699 GLENDORA RD, KISSIMMEE, FL, 34759
Community: Solivita
Latitude Margaritaville 562 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$340,000

2 beds

|

2 baths

|

1,160 sq ft

|

Villa

562 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Pine Run Estates 9940 SW 103RD PL, OCALA, FL, 34481, Ocala, FL 34481
$145,000

2 beds

|

2 baths

|

1,270 sq ft

|

House

9940 SW 103RD PL, OCALA, FL, 34481
Community: Pine Run Estates
Quail Meadow 3061 NW 49TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$259,900

3 beds

|

2 baths

|

1,495 sq ft

|

House

3061 NW 49TH AVE, OCALA, FL, 34482
Community: Quail Meadow
SummerGlen 15312 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$290,000

3 beds

|

3 baths

|

2,360 sq ft

|

House

15312 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
VillageWalk at Lake Nona 8681 LOWER VILLAGEWALK CIR, ORLANDO, FL,..., Orlando, FL 32827
$474,950

3 beds

|

3 baths

|

1,830 sq ft

|

Townhouse

8681 LOWER VILLAGEWALK CIR, ORLANDO, FL,...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 18101 SANDALWOOD DR, WILDWOOD, FL, 34785, Wildwood, FL 34785
$89,900

1 beds

|

1 baths

|

872 sq ft

|

Condo

18101 SANDALWOOD DR, WILDWOOD, FL, 34785
Community: The Villages®
Ocala Preserve 5575 NW 43RD LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$435,000

2 beds

|

2 baths

|

1,856 sq ft

|

House

5575 NW 43RD LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
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 Garden?

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 Garden?

Call us: (689) 407-5757
3,218 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