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Winter Garden, FL 55+ active adult communities & homes for sale - Page 67

3,497 homes near Winter Garden

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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 (56 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
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
4.1 rating (29 reviews) Oak Run
$100ks - $300ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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.
4.6 rating (5 reviews) Ocala Preserve
$100ks - $500ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 homes
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 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
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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 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
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 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 (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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
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
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 (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
4.7 rating (11 reviews) Valencia Lakes
$200ks - $700ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 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
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
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
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.
3.6 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) Cresswind at Victoria Gar...
$200ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
Mirada
$300ks - $500ks
Mirada, San Antonio, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 858 homes
3.8 rating (5 reviews) Marion Landing
$100ks - $300ks
Marion Landing, Ocala, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 600 homes
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes
Quail Meadow
$200ks - $400ks
Quail Meadow, Ocala, FL
Resale Only | 55+ age-restricted | Built 1988 - 2006 | 460 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 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
Lake Henry Estates 656 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844
$259,900

2 beds

|

2 baths

|

1,681 sq ft

|

House

656 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
Spruce Creek Country Club 9479 SE 130TH STREET RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$469,000

3 beds

|

3 baths

|

2,346 sq ft

|

House

9479 SE 130TH STREET RD, SUMMERFIELD, FL...
Spruce Creek Country Club 9345 SE 136TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$464,900

2 beds

|

2 baths

|

1,989 sq ft

|

House

9345 SE 136TH PL, SUMMERFIELD, FL, 34491
Solivita 2316 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$289,900

2 beds

|

2 baths

|

1,539 sq ft

|

Villa

2316 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
Thunderbird Hill 3718 THUNDERBIRD HILL CIR, SEBRING, FL, ..., Sebring, FL 33872
$185,000

2 beds

|

2 baths

|

1,242 sq ft

|

Halfplex

3718 THUNDERBIRD HILL CIR, SEBRING, FL, ...
Community: Thunderbird Hill
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Preserve 3545 NW 56TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$565,000

2 beds

|

3 baths

|

2,563 sq ft

|

House

3545 NW 56TH AVE, OCALA, FL, 34482
Community: Ocala Preserve
Spruce Creek Country Club 13185 SE 93RD TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$269,000

2 beds

|

2 baths

|

1,244 sq ft

|

House

13185 SE 93RD TERRACE RD, SUMMERFIELD, F...
Lake Ashton 4189 LIMERICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$539,000

2 beds

|

2 baths

|

2,227 sq ft

|

House

4189 LIMERICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Lake Ashton 4081 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$399,500

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
$450,000

2 beds

|

3 baths

|

2,049 sq ft

|

House

6036 PLOVER MEADOW ST, LITHIA, FL, 33547
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.
Ocala Palms 2171 NW 50TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$259,900

2 beds

|

2 baths

|

1,343 sq ft

|

House

2171 NW 50TH AVE, OCALA, FL, 34482
Community: Ocala Palms
Valencia Lakes 16251 DIAMOND BAY DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$495,000

3 beds

|

3 baths

|

2,465 sq ft

|

House

16251 DIAMOND BAY DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Sun City Center 1338 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$415,000

3 beds

|

2 baths

|

2,482 sq ft

|

Condo

1338 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
The Villages® 3079 NUTWOOD AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$295,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

3079 NUTWOOD AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
Highland Lakes 26707 CASH CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$215,000

2 beds

|

2 baths

|

1,293 sq ft

|

Villa

26707 CASH CT, LEESBURG, FL, 34748
Community: Highland Lakes
Spruce Creek Country Club 13820 SE 86TH TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$259,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

13820 SE 86TH TER, SUMMERFIELD, FL, 3449...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stonecrest 17787 SE 114TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$349,900

3 beds

|

2 baths

|

1,867 sq ft

|

House

17787 SE 114TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
Arlington Ridge 26822 BULL RUN, LEESBURG, FL, 34748, Leesburg, FL 34748
$324,000

3 beds

|

2 baths

|

1,602 sq ft

|

House

26822 BULL RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
On Top of the World 8637 SW 88TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$239,500

2 beds

|

2 baths

|

1,578 sq ft

|

House

8637 SW 88TH LOOP, OCALA, FL, 34481
Community: On Top of the World
The Villages® 5885 FLINT LOOP, THE VILLAGES, FL, 32163, The Villages, FL 32163
$799,900

3 beds

|

3 baths

|

1,977 sq ft

|

House

5885 FLINT LOOP, 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.
Del Webb Sunbridge 2575 PINE PRESERVE CT, ST CLOUD, FL, 347..., St Cloud, FL 34771
$699,000

3 beds

|

3 baths

|

2,483 sq ft

|

House

2575 PINE PRESERVE CT, ST CLOUD, FL, 347...
Community: Del Webb Sunbridge
Spruce Creek North 10780 SW 62ND AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34476
$159,900

2 beds

|

2 baths

|

960 sq ft

|

House

10780 SW 62ND AVENUE RD, OCALA, FL, 3447...
Community: Spruce Creek North
The Villages® 5107 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484
$419,900

4 beds

|

3 baths

|

1,910 sq ft

|

House

5107 NE 122ND BLVD, OXFORD, FL, 34484
Community: The Villages®
Lake Ashton 4577 BACK NINE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33884
$359,900

3 beds

|

2 baths

|

1,918 sq ft

|

House

4577 BACK NINE DR, WINTER HAVEN, FL, 338...
Community: Lake Ashton
On Top of the World 9614 SW 93RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$219,900

2 beds

|

2 baths

|

1,683 sq ft

|

House

9614 SW 93RD LOOP, OCALA, FL, 34481
Community: On Top of the World
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
Highlands Ridge 4028 CARTER CREEK DR, AVON PARK, FL, 338..., Avon Park, FL 33825
$354,900

3 beds

|

2 baths

|

2,671 sq ft

|

House

4028 CARTER CREEK DR, AVON PARK, FL, 338...
Community: Highlands Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 251 ROCK SPRINGS DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$325,000

2 beds

|

2 baths

|

2,050 sq ft

|

House

251 ROCK SPRINGS DR, KISSIMMEE, FL, 3475...
Community: Solivita
Sun City Center 1148 CORINTH GREENS DR 12, SUN CITY CENT..., Sun City Center, FL 33573
$299,000

2 beds

|

2 baths

|

1,610 sq ft

|

Condo

1148 CORINTH GREENS DR 12, SUN CITY CENT...
Community: Sun City Center
Plantation at Leesburg 25300 HIBISCUS ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$249,000

2 beds

|

2 baths

|

1,908 sq ft

|

House

25300 HIBISCUS ST, LEESBURG, FL, 34748
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.
Southshore Bay 16938 SCUBA CREST ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$599,999

3 beds

|

4 baths

|

2,778 sq ft

|

House

16938 SCUBA CREST ST, WIMAUMA, FL, 33598
Community: Southshore Bay
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
$345,000

2 beds

|

2 baths

|

1,160 sq ft

|

Villa

562 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
The Villages® 8089 SE 174TH BELHAVEN LOOP, THE VILLAGE..., The Villages, FL 32162
$370,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

8089 SE 174TH BELHAVEN LOOP, THE VILLAGE...
Community: The Villages®
Solivita 513 VINEYARD WAY, POINCIANA, FL, 34759, Poinciana, FL 34759
$259,900

2 beds

|

2 baths

|

1,240 sq ft

|

House

513 VINEYARD WAY, POINCIANA, FL, 34759
Community: Solivita
On Top of the World 9196 SW 106TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$425,000

3 beds

|

2 baths

|

1,651 sq ft

|

House

9196 SW 106TH AVE, OCALA, FL, 34481
Community: On Top of the World
The Villages® 9239 SE 171ST COOPER LOOP, THE VILLAGES,..., The Villages, FL 32162
$349,500

3 beds

|

2 baths

|

1,993 sq ft

|

House

9239 SE 171ST COOPER LOOP, THE VILLAGES,...
Community: The Villages®
Quail Meadow 4972 NW 31ST ST, OCALA, FL, 34482, Ocala, FL 34482
$274,900

3 beds

|

2 baths

|

1,476 sq ft

|

House

4972 NW 31ST ST, OCALA, FL, 34482
Community: Quail Meadow
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Quail Meadow 3061 NW 49TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$269,900

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
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.

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3,497 homes
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