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Winter Garden, FL 55+ active adult communities & homes for sale - Page 3

109 communities near Winter Garden

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5 rating (1 reviews) Esplanade at Highland Ran...
$300ks - $600ks
Esplanade at Highland Ran..., Clermont, FL
Resale Only | 55+ age-restricted | Built 2014 - 2022 | 475 homes
5 rating (2 reviews) Palms at Serenoa
$200ks - $400ks
Palms at Serenoa, Clermont, FL
New Construction | 55+ age-restricted | Built 2018 - present | 570 homes
2 rating (1 reviews) Heritage Landings
$200ks - $300ks
Heritage Landings, Lakeland, FL
New Construction | 55+ age-restricted | Built 2017 - 2020 | 65 homes
Thunderbird Hill
$100ks - $200ks
Thunderbird Hill, Sebring, FL
Resale Only | 55+ age-restricted | Built 1984 - 2000 | 103 homes
Valencia Ridge
$400ks - $800ks
Valencia Ridge, Wesley Chapel, FL
New Construction | 55+ age-restricted | Built 2023 - present | 395 homes
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1 rating (1 reviews) Windermere
$100ks - $200ks
Windermere, Inverness, FL
Resale Only | Age-targeted | Built 1989 - present | 180 homes
Lake Henry Estates
$100ks - $300ks
Lake Henry Estates, Haines City, FL
Resale Only | 55+ age-restricted | Built 1992 - 2004 | 280 homes
Alhambra Villas Condomini...
$100ks - $200ks
Alhambra Villas Condomini..., DeLand, FL
Resale Only | 55+ age-restricted | Built 1970 - 1972 | 60 homes
Royal Palm
$200ks - $300ks
Royal Palm, Port Orange, FL
Resale Only | 55+ age-restricted | Built 2002 - 2016 | 458 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.
Baytree
$100ks - $300ks
Baytree, Tavares, FL
Resale Only | 55+ age-restricted | Built 1990 - 2003 | 221 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
El Dorado
$400ks - $600ks
El Dorado, Ocala, FL
Resale Only | Age-targeted | Built 1978 - 2003 | 56 homes
Archers Mill
$300ks - $500ks
Archers Mill, Ormond Beach, FL
New Construction | Age-targeted | 94 homes
Enclave at VillageWalk
$700ks - $1Ms
Enclave at VillageWalk, Orlando, FL
Resale Only | Age-targeted | Built 2015 - 2021 | 144 homes
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Questions? Call us: (689) 407-5757
Tarawood
$200ks
Tarawood, Floral City, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 150 homes
Spring Lake Towers
$100ks
Spring Lake Towers, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1970 - 1970 | 79 homes
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Questions? Call us: (689) 407-5757
5 rating (1 reviews) Silver Lakes
$100ks - $300ks
Silver Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1996 - 2001 | 148 homes
5 rating (1 reviews) Cypress Lakes
$100ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 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.
Heritage - The Cottages o...
$300ks
Heritage - The Cottages o..., Okahumpka, FL
New Construction | 55+ age-restricted | Built 2022 - present | 179 homes
Oakview
$100ks - $200ks
Oakview, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 homes
Hidden Creek
$100ks - $200ks
Hidden Creek, Sebring, FL
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 55 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Ormond Renaissance
$300ks - $400ks
Ormond Renaissance, Ormond Beach, FL
New Construction | 55+ age-restricted | Built 2016 - present | 280 homes
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Questions? Call us: (689) 407-5757
Villas On The Green
$200ks - $300ks
Villas On The Green, Riverview, FL
Resale Only | 55+ age-restricted | Built 1989 - 1992 | 105 homes
Preserve at Lakeside Land...
$200ks - $300ks
Preserve at Lakeside Land..., Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 44 homes
Fountain View
$300ks - $400ks
Fountain View, Ormond Beach, FL
New Construction | 55+ age-restricted | Built 2023 - present | 100 homes
Bridgewater Landing
$200ks - $300ks
Bridgewater Landing, Riverview, FL
Resale Only | 55+ age-restricted | Built 2017 - 2024 | 64 homes
Want to learn more about 55+ rental communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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.
Serenity Reserve
$400ks
Serenity Reserve, St. Cloud, FL
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 85 homes
The Wellington
$100ks - $200ks
The Wellington, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1969 - 1981 | 77 homes
Summit Chase Villas
$100ks
Summit Chase Villas, Tavares, FL
Resale Only | 55+ age-restricted | Built 1982 - 1989 | 60 homes
Poinsettia Heights
$100ks - $200ks
Poinsettia Heights, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1978 - 2000 | 49 homes
New Lakeside Landings 5415 ADMIRAL WAY # H5-102, OXFORD, FL, 3..., Oxford, FL 34484
$239,900

2 beds

|

2 baths

|

1,281 sq ft

|

Condo

5415 ADMIRAL WAY # H5-102, OXFORD, FL, 3...
Community: Lakeside Landings
New On Top of the World 9729 SW 97TH ST, OCALA, FL, 34481, Ocala, FL 34481
$189,900

2 beds

|

2 baths

|

1,230 sq ft

|

House

9729 SW 97TH ST, OCALA, FL, 34481
Community: On Top of the World
New The Villages® 2903 LARRANAGA DR, THE VILLAGES, FL, 321..., The Villages, FL 32162
$795,000

3 beds

|

2 baths

|

2,449 sq ft

|

House

2903 LARRANAGA DR, THE VILLAGES, FL, 321...
Community: The Villages®
New Sun City Center 2169 ACADIA GREENS DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$210,000

2 beds

|

2 baths

|

1,093 sq ft

|

Villa

2169 ACADIA GREENS DR, SUN CITY CENTER, ...
Community: Sun City Center
New Pennbrooke Fairways 33012 PENNBROOKE PKWY, LEESBURG, FL, 347..., Leesburg, FL 34748
$289,000

3 beds

|

2 baths

|

1,718 sq ft

|

House

33012 PENNBROOKE PKWY, LEESBURG, FL, 347...
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Want to learn more about 55+ rental communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New On Top of the World 8830 SW 98TH PL L, OCALA, FL, 34481, Ocala, FL 34481
$182,000

2 beds

|

3 baths

|

1,764 sq ft

|

Condo

8830 SW 98TH PL L, OCALA, FL, 34481
Community: On Top of the World
New Lakeside Landings 5105 JAREDS LANDING WAY, OXFORD, FL, 344..., Oxford, FL 34484
$629,900

3 beds

|

2 baths

|

2,326 sq ft

|

House

5105 JAREDS LANDING WAY, OXFORD, FL, 344...
Community: Lakeside Landings
New The Villages® 2351 PINE RIDGE ST, THE VILLAGES, FL, 32..., The Villages, FL 32162
$282,500

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2351 PINE RIDGE ST, THE VILLAGES, FL, 32...
Community: The Villages®
New Pine Run Estates 10061 SW 100TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$172,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

10061 SW 100TH AVE, OCALA, FL, 34481
Community: Pine Run Estates
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.
New Latitude Margaritaville 426 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$609,900

3 beds

|

2 baths

|

1,848 sq ft

|

House

426 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
New Latitude Margaritaville 298 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$599,900

2 beds

|

3 baths

|

2,139 sq ft

|

House

298 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
New Latitude Margaritaville 904 BARNACLE BAY CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$760,000

2 beds

|

3 baths

|

2,160 sq ft

|

House

904 BARNACLE BAY CT, DAYTONA BEACH, FL, ...
New The Lakes at Harmony 3470 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$295,000

2 beds

|

2 baths

|

1,426 sq ft

|

House

3470 SAGEBRUSH ST, HARMONY, FL, 34773
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Plantation at Leesburg 4721 TARA VIEW RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$314,900

3 beds

|

2 baths

|

1,979 sq ft

|

House

4721 TARA VIEW RD, LEESBURG, FL, 34748
New The Villages® 2839 LARRANAGA DR, THE VILLAGES, FL, 321..., The Villages, FL 32162
$825,000

4 beds

|

3 baths

|

2,602 sq ft

|

House

2839 LARRANAGA DR, THE VILLAGES, FL, 321...
Community: The Villages®
Want to learn more about 55+ rental communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Sun City Center 1021 AUGUSTA DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$288,500

3 beds

|

2 baths

|

1,757 sq ft

|

House

1021 AUGUSTA DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
New The Villages® 7814 SE 166TH SMALLWOOD PL, THE VILLAGES..., The Villages, FL 32162
$410,000

3 beds

|

2 baths

|

2,237 sq ft

|

House

7814 SE 166TH SMALLWOOD PL, THE VILLAGES...
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.
New Heritage Hills 3538 FAIRWATERS CT B, CLERMONT, FL, 3471..., Clermont, FL 34711
$315,000

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3538 FAIRWATERS CT B, CLERMONT, FL, 3471...
Community: Heritage Hills
New Sun City Center 1102 HAREFIELD CIR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$135,000

2 beds

|

2 baths

|

1,390 sq ft

|

Condo

1102 HAREFIELD CIR, SUN CITY CENTER, FL,...
Community: Sun City Center
New The Villages® 2713 CASTILLO DR, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$310,000

2 beds

|

2 baths

|

1,534 sq ft

|

House

2713 CASTILLO DR, THE VILLAGES, FL, 3216...
Community: The Villages®
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
New Valencia Ridge 32623 NEROLI ST, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$719,900

3 beds

|

3 baths

|

2,209 sq ft

|

House

32623 NEROLI ST, WESLEY CHAPEL, FL, 3354...
Community: Valencia Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New SummerGlen 15050 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$349,900

3 beds

|

2 baths

|

2,324 sq ft

|

House

15050 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
New Royal Highlands 4741 INVERNESS DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$364,999

3 beds

|

2 baths

|

1,902 sq ft

|

House

4741 INVERNESS DR, LEESBURG, FL, 34748
Community: Royal Highlands
New Foxwood Lake Estates 1631 FOXWAY DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$224,900

3 beds

|

2 baths

|

1,456 sq ft

|

Manufactured Home

1631 FOXWAY DR, LAKELAND, FL, 33810
New The Villages® 670 WOODBRIDGE WAY, THE VILLAGES, FL, 32..., The Villages, FL 32163
$884,900

3 beds

|

2 baths

|

2,299 sq ft

|

House

670 WOODBRIDGE WAY, THE VILLAGES, FL, 32...
Community: The Villages®
Want to learn more about 55+ rental communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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.
New The Villages® 1020 DUSTIN DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$162,900

2 beds

|

2 baths

|

1,240 sq ft

|

Manufactured Home

1020 DUSTIN DR, LADY LAKE, FL, 32159
Community: The Villages®
New Stone Creek 5362 SW 86TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$324,960

2 beds

|

2 baths

|

1,405 sq ft

|

House

5362 SW 86TH COURT RD, OCALA, FL, 34481
Community: Stone Creek
New Valencia Ridge 32616 NEROLI ST, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$676,900

3 beds

|

3 baths

|

2,450 sq ft

|

House

32616 NEROLI ST, WESLEY CHAPEL, FL, 3354...
Community: Valencia Ridge
New Kings Ridge 2302 EDMONTON CT, CLERMONT, FL, 34711, Clermont, FL 34711
$330,000

3 beds

|

2 baths

|

1,705 sq ft

|

House

2302 EDMONTON CT, CLERMONT, FL, 34711
Community: Kings Ridge
New Foxwood Lake Estates 1679 FOXWAY DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$165,000

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

1679 FOXWAY DR, LAKELAND, FL, 33810
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
New Lake Jovita Golf and Country Club 13235 LEGENDS TRL, DADE CITY, FL, 33525, Dade City, FL 33525
$579,000

4 beds

|

3 baths

|

1,945 sq ft

|

House

13235 LEGENDS TRL, DADE CITY, FL, 33525
New Arlington Ridge 26725 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748
$335,000

2 beds

|

2 baths

|

2,203 sq ft

|

House

26725 AUGUSTA SPRINGS CIR, LEESBURG, FL,...
Community: Arlington Ridge
New Sun City Center 222 LINGER LN, SUN CITY CENTER, FL, 3357..., Sun City Center, FL 33573
$299,900

2 beds

|

2 baths

|

1,587 sq ft

|

House

222 LINGER LN, SUN CITY CENTER, FL, 3357...
Community: Sun City Center
New Lake James 8107 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$370,000

2 beds

|

2 baths

|

1,557 sq ft

|

House

8107 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
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.
New The Villages® 3040 BATALLY CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$365,000

3 beds

|

2 baths

|

1,512 sq ft

|

House

3040 BATALLY CT, THE VILLAGES, FL, 32162
Community: The Villages®
Want to learn more about 55+ rental communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Oak Run 5706 SW 71ST AVE, OCALA, FL, 34474, Ocala, FL 34474
$409,915

4 beds

|

3 baths

|

2,420 sq ft

|

House

5706 SW 71ST AVE, OCALA, FL, 34474
Community: Oak Run
New Pelican Bay Daytona Beach 636 BROWN PELICAN DR, DAYTONA BEACH, FL,..., Daytona Beach, FL 32119
$239,900

3 beds

|

2 baths

|

1,628 sq ft

|

Townhouse

636 BROWN PELICAN DR, DAYTONA BEACH, FL,...
New On Top of the World 8681 SW 93RD PL B, OCALA, FL, 34481, Ocala, FL 34481
$179,900

2 beds

|

2 baths

|

1,409 sq ft

|

Villa

8681 SW 93RD PL B, OCALA, FL, 34481
Community: On Top of the World
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New On Top of the World 8641 SW 99TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$585,665

3 beds

|

2 baths

|

2,678 sq ft

|

House

8641 SW 99TH CIR, OCALA, FL, 34481
Community: On Top of the World
New Palm Cay 8172 SW 107TH PL, OCALA, FL, 34481, Ocala, FL 34481
$189,900

2 beds

|

2 baths

|

864 sq ft

|

House

8172 SW 107TH PL, OCALA, FL, 34481
Community: Palm Cay

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© 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: Feb 16, 2026.
This application does not include information on all of the properties available for sale at this time.

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