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Winter Garden, FL 55+ active adult communities & homes for sale - Page 43

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
On Top of the World 9629 SW 95TH TER D, OCALA, FL, 34481, Ocala, FL 34481
$154,975

2 beds

|

2 baths

|

1,412 sq ft

|

Villa

9629 SW 95TH TER D, OCALA, FL, 34481
Community: On Top of the World
Trilogy® Orlando 125 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$374,999

3 beds

|

2 baths

|

1,680 sq ft

|

House

125 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Del Webb Sunbridge 2555 PINE PRESERVE CT, ST CLOUD, FL, 347..., St Cloud, FL 34771
$895,000

3 beds

|

4 baths

|

2,866 sq ft

|

House

2555 PINE PRESERVE CT, ST CLOUD, FL, 347...
Community: Del Webb Sunbridge
Latitude Margaritaville 338 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$635,000

3 beds

|

3 baths

|

2,393 sq ft

|

House

338 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Kings Ridge 3635 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711
$388,800

2 beds

|

2 baths

|

1,661 sq ft

|

House

3635 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lakeside Landings 10144 LAKE MIONA WAY, OXFORD, FL, 34484, Oxford, FL 34484
$529,000

4 beds

|

2 baths

|

2,319 sq ft

|

House

10144 LAKE MIONA WAY, OXFORD, FL, 34484
Community: Lakeside Landings
The Villages® 2525 FIVE FORKS TRL, THE VILLAGES, FL, 3..., The Villages, FL 32162
$435,000

3 beds

|

2 baths

|

2,160 sq ft

|

House

2525 FIVE FORKS TRL, THE VILLAGES, FL, 3...
Community: The Villages®
The Villages® 17559 SE 81ST PARNASSUS CT, THE VILLAGES..., The Villages, FL 32162
$389,900

3 beds

|

2 baths

|

1,597 sq ft

|

House

17559 SE 81ST PARNASSUS CT, THE VILLAGES...
Community: The Villages®
Traditions at Lake Ruby 4019 CARTERET DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$269,999

2 beds

|

2 baths

|

1,719 sq ft

|

House

4019 CARTERET DR, WINTER HAVEN, FL, 3388...
Quail Meadow 4572 NW 32ND ST, OCALA, FL, 34482, Ocala, FL 34482
$330,000

3 beds

|

2 baths

|

2,108 sq ft

|

House

4572 NW 32ND ST, OCALA, FL, 34482
Community: Quail Meadow
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.
Latitude Margaritaville 673 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$379,000

2 beds

|

2 baths

|

1,308 sq ft

|

House

673 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Kings Ridge 3622 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$369,900

2 beds

|

2 baths

|

1,792 sq ft

|

House

3622 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
Royal Harbor 6105 DORY WAY, TAVARES, FL, 32778, Tavares, FL 32778
$310,000

3 beds

|

2 baths

|

1,556 sq ft

|

House

6105 DORY WAY, TAVARES, FL, 32778
Community: Royal Harbor
The Villages® 17369 SE 75TH COACHMAN CT, THE VILLAGES,..., The Villages, FL 32162
$264,900

2 beds

|

2 baths

|

1,213 sq ft

|

House

17369 SE 75TH COACHMAN CT, THE VILLAGES,...
Community: The Villages®
Harbor Hills Country Club 5312 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$450,000

3 beds

|

2 baths

|

2,029 sq ft

|

House

5312 GREENS DR, LADY LAKE, FL, 32159
On Top of the World 9686 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$215,000

2 beds

|

2 baths

|

1,515 sq ft

|

House

9686 SW 92ND PLACE RD, 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
On Top of the World 9922 SW 97TH LN, OCALA, FL, 34481, Ocala, FL 34481
$365,000

3 beds

|

2 baths

|

2,118 sq ft

|

House

9922 SW 97TH LN, OCALA, FL, 34481
Community: On Top of the World
Stone Creek 5882 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$294,900

2 beds

|

2 baths

|

1,469 sq ft

|

House

5882 SW 93RD CIR, OCALA, FL, 34481
Community: Stone Creek
The Villages® 2303 NAUTILUS LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$325,000

2 beds

|

2 baths

|

1,196 sq ft

|

Villa

2303 NAUTILUS LN, THE VILLAGES, FL, 3216...
Community: The Villages®
Stone Creek 9299 SW 66TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$434,900

2 beds

|

2 baths

|

1,904 sq ft

|

House

9299 SW 66TH LOOP, OCALA, FL, 34481
Community: Stone Creek
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.
Sun City Center 2215 WORTHINGTON GREENS DR 20, SUN CITY ..., Sun City Center, FL 33573
$249,500

2 beds

|

2 baths

|

1,617 sq ft

|

Condo

2215 WORTHINGTON GREENS DR 20, SUN CITY ...
Community: Sun City Center
Stonecrest 11102 SE 168TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$539,000

3 beds

|

2 baths

|

1,807 sq ft

|

House

11102 SE 168TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Kings Ridge 2219 CAXTON AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$380,000

3 beds

|

2 baths

|

2,031 sq ft

|

House

2219 CAXTON AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Solivita 162 TALL PINES PASS, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$325,000

2 beds

|

2 baths

|

2,038 sq ft

|

House

162 TALL PINES PASS, KISSIMMEE, FL, 3475...
Community: Solivita
Solivita 813 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$499,000

3 beds

|

3 baths

|

2,454 sq ft

|

House

813 GLENDORA RD, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 17470 SE 93RD VINE AVE, THE VILLAGES, FL..., The Villages, FL 32162
$250,000

2 beds

|

2 baths

|

1,172 sq ft

|

Villa

17470 SE 93RD VINE AVE, THE VILLAGES, FL...
Community: The Villages®
The Villages® 624 FAYETTE CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$405,999

3 beds

|

2 baths

|

1,502 sq ft

|

House

624 FAYETTE CT, THE VILLAGES, FL, 32162
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stone Creek 5294 SW 87TH TER, OCALA, FL, 34481, Ocala, FL 34481
$499,000

3 beds

|

3 baths

|

2,110 sq ft

|

House

5294 SW 87TH TER, OCALA, FL, 34481
Community: Stone Creek
Highland Lakes 27217 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$244,900

3 beds

|

2 baths

|

1,756 sq ft

|

House

27217 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
Sun City Center 1435 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$415,000

3 beds

|

2 baths

|

2,482 sq ft

|

Condo

1435 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
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 3049 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$315,000

3 beds

|

3 baths

|

1,614 sq ft

|

House

3049 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
The Villages® 1988 DOVE HOLLOW RUN, THE VILLAGES, FL, ..., The Villages, FL 32162
$814,900

4 beds

|

2 baths

|

2,544 sq ft

|

House

1988 DOVE HOLLOW RUN, THE VILLAGES, FL, ...
Community: The Villages®
Venetian Bay 3057 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$545,000

4 beds

|

4 baths

|

2,086 sq ft

|

Townhouse

3057 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Sun City Center 2111 W VIEW DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$439,900

2 beds

|

2 baths

|

2,149 sq ft

|

House

2111 W VIEW DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Trilogy® Orlando 334 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$460,000

2 beds

|

2 baths

|

1,967 sq ft

|

House

334 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Harbor Hills Country Club 39125 TACOMA DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$499,000

3 beds

|

3 baths

|

2,584 sq ft

|

House

39125 TACOMA DR, LADY LAKE, FL, 32159
Stone Creek 6776 SW 95TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$474,800

2 beds

|

2 baths

|

2,031 sq ft

|

House

6776 SW 95TH CIR, OCALA, FL, 34481
Community: Stone Creek
Kings Ridge 3734 HASTING LN, CLERMONT, FL, 34711, Clermont, FL 34711
$369,900

2 beds

|

2 baths

|

1,985 sq ft

|

House

3734 HASTING LN, CLERMONT, FL, 34711
Community: Kings Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Trilogy® Orlando 371 SALT MARSH LN, GROVELAND, FL, 34736, Groveland, FL 34736
$379,000

2 beds

|

2 baths

|

1,624 sq ft

|

House

371 SALT MARSH LN, GROVELAND, FL, 34736
Community: Trilogy® Orlando
The Villages® 5716 MELVIN DR, THE VILLAGES, FL, 32163, The Villages, FL 32163
$529,900

3 beds

|

3 baths

|

1,901 sq ft

|

House

5716 MELVIN DR, 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.

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3,497 homes
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