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Winter Garden, FL 55+ active adult communities & homes for sale - Page 34

3,517 homes near Winter Garden

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5 rating (1 reviews) Del Webb Oasis
$400Ks - $900Ks
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
4 rating (17 reviews) The Villages®
<$100k - $2Ms
The Villages®, The Villages, FL
New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes
4.1 rating (55 reviews) On Top of the World
$100Ks - $700Ks
On Top of the World, Ocala, FL
New and Resale | 55+ age-restricted | Built 1981 - present | 10,000 homes
3.8 rating (14 reviews) Sun City Center
<$100k - $500Ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4.7 rating (18 reviews) Solivita
$100Ks - $600Ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
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3.6 rating (48 reviews) Latitude Margaritaville
$300Ks - $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
4.2 rating (10 reviews) Stone Creek
$200Ks - $900Ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.1 rating (29 reviews) Oak Run
$100Ks - $500Ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 homes
4.5 rating (11 reviews) Spruce Creek Country Club
$200Ks - $500Ks
Spruce Creek Country Club, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 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 - $500Ks
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
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 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 (3 reviews) Twin Lakes
$200Ks - $600Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
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Pelican Bay Daytona Beach
$100Ks - $400Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4.6 rating (5 reviews) Ocala Preserve
$200Ks - $600Ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 homes
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $400Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $600Ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 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) Cypress Lakes
$100Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
Venetian Bay
$200Ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
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Questions? Call us: (689) 407-5757
5 rating (8 reviews) Royal Highlands
$200Ks - $400Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
4 rating (7 reviews) Tampa Bay Golf and Countr...
$200Ks - $400Ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes
5 rating (1 reviews) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$300Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 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.
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
5 rating (1 reviews) Sandpiper Golf & Coun...
$200Ks - $400Ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
3.6 rating (5 reviews) Heritage Hills
$200Ks - $500Ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
5 rating (1 reviews) Ocala Palms
$100Ks - $400Ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$300Ks - $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 Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (5 reviews) SummerGlen
$100Ks - $400Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
5 rating (1 reviews) Legacy of Leesburg
$200Ks - $400Ks
Legacy of Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes
Breakaway Trails
$400Ks - $800Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$400Ks - $900Ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 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 rating (2 reviews) Harbor Hills Country Club
$200Ks - $1Ms
Harbor Hills Country Club, Lady Lake, FL
New and Resale | Age-targeted | Built 1989 - present | 940 homes
4.8 rating (6 reviews) Highland Lakes
$100Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
Pine Run Estates
<$100k - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lake Jovita Golf and Coun...
$300Ks - $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale | Age-targeted | Built 1999 - present | 875 homes
Esplanade at Wiregrass Ra...
$400Ks - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
The Villages® 937 KAUSKA WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163
$369,000

3 beds

|

2 baths

|

1,558 sq ft

|

House

937 KAUSKA WAY, THE VILLAGES, FL, 32163
Community: The Villages®
Stonecrest 11961 SE 176TH PLACE RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$339,000

3 beds

|

2 baths

|

1,723 sq ft

|

House

11961 SE 176TH PLACE RD, SUMMERFIELD, FL...
Community: Stonecrest
Stonecrest 17577 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$365,900

3 beds

|

2 baths

|

1,543 sq ft

|

House

17577 SE 112TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 1923 USEPPA OAKS LN, THE VILLAGES, FL, 3..., The Villages, FL 32163
$455,000

3 beds

|

2 baths

|

1,875 sq ft

|

House

1923 USEPPA OAKS LN, THE VILLAGES, FL, 3...
Community: The Villages®
Summit Greens 1180 MESA VERDE CT, CLERMONT, FL, 34711, Clermont, FL 34711
$344,900

2 beds

|

2 baths

|

1,508 sq ft

|

House

1180 MESA VERDE CT, CLERMONT, FL, 34711
Community: Summit Greens
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 611 FOX HILLS DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$276,999

2 beds

|

2 baths

|

1,271 sq ft

|

House

611 FOX HILLS DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Spruce Creek North 11215 SW 63RD TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$175,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

11215 SW 63RD TERRACE RD, OCALA, FL, 344...
Community: Spruce Creek North
Sun City Center 1817 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$374,000

2 beds

|

2 baths

|

1,857 sq ft

|

House

1817 NEW BEDFORD DR, SUN CITY CENTER, FL...
Community: Sun City Center
New Arlington Ridge 26822 BULL RUN, LEESBURG, FL, 34748, Leesburg, FL 34748
$329,000

3 beds

|

2 baths

|

1,599 sq ft

|

House

26822 BULL RUN, 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.
Stonecrest 17563 SE 122ND TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$550,000

3 beds

|

3 baths

|

2,071 sq ft

|

House

17563 SE 122ND TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 2544 ASHVILLE AVE, THE VILLAGES, FL, 321..., The Villages, FL 32162
$625,000

3 beds

|

2 baths

|

2,485 sq ft

|

House

2544 ASHVILLE AVE, THE VILLAGES, FL, 321...
Community: The Villages®
Sun City Center 1723 WOLF LAUREL DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$355,000

2 beds

|

2 baths

|

2,031 sq ft

|

House

1723 WOLF LAUREL DR, SUN CITY CENTER, FL...
Community: Sun City Center
Legacy of Leesburg 5313 TREASURE VIEW WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$279,990

3 beds

|

2 baths

|

1,479 sq ft

|

House

5313 TREASURE VIEW WAY, LEESBURG, FL, 34...
Community: Legacy of Leesburg
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 2530 SAFFRON LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$405,000

3 beds

|

2 baths

|

1,512 sq ft

|

House

2530 SAFFRON LN, THE VILLAGES, FL, 32162
Community: The Villages®
Cresswind at Victoria Gardens 1128 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724
$558,600

2 beds

|

3 baths

|

2,670 sq ft

|

House

1128 HERON POINT WAY, DELAND, FL, 32724
Carillon Lakes 3413 WATERLUTE WAY, LAKELAND, FL, 33811, Lakeland, FL 33811
$294,900

3 beds

|

2 baths

|

1,811 sq ft

|

House

3413 WATERLUTE WAY, LAKELAND, FL, 33811
Community: Carillon Lakes
JB Ranch 9149 SW 62ND TERRACE RD, OCALA, FL, 3447..., Ocala, FL 34476
$299,900

3 beds

|

2 baths

|

1,641 sq ft

|

House

9149 SW 62ND TERRACE RD, OCALA, FL, 3447...
Community: JB Ranch
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.
Stone Creek 9423 SW 60TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$419,000

2 beds

|

2 baths

|

1,891 sq ft

|

House

9423 SW 60TH LANE RD, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 7262 SW 94TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$385,900

3 beds

|

2 baths

|

2,122 sq ft

|

House

7262 SW 94TH AVE, OCALA, FL, 34481
Community: Stone Creek
On Top of the World 8678 SW 83RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$323,000

3 beds

|

2 baths

|

1,695 sq ft

|

House

8678 SW 83RD CIR, OCALA, FL, 34481
Community: On Top of the World
Oak Run 9021 SW 108TH PL, OCALA, FL, 34481, Ocala, FL 34481
$189,000

2 beds

|

2 baths

|

1,224 sq ft

|

House

9021 SW 108TH PL, OCALA, FL, 34481
Community: Oak Run
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Liberty Village 7930 SW 74TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$350,000

4 beds

|

3 baths

|

2,292 sq ft

|

House

7930 SW 74TH LOOP, OCALA, FL, 34481
Community: Liberty Village
The Villages® 1751 BRANDENBURG CT, THE VILLAGES, FL, 3..., The Villages, FL 32163
$334,900

2 beds

|

2 baths

|

1,220 sq ft

|

Villa

1751 BRANDENBURG CT, THE VILLAGES, FL, 3...
Community: The Villages®
Spruce Creek Preserve 14117 SW 115TH CIR, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$199,900

2 beds

|

2 baths

|

1,296 sq ft

|

House

14117 SW 115TH CIR, DUNNELLON, FL, 34432
The Villages® 1818 TRIMARCHE TER, THE VILLAGES, FL, 32..., The Villages, FL 32163
$474,900

3 beds

|

2 baths

|

1,630 sq ft

|

House

1818 TRIMARCHE TER, THE VILLAGES, FL, 32...
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® 2973 KRAMER CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$335,000

3 beds

|

2 baths

|

1,403 sq ft

|

House

2973 KRAMER CT, THE VILLAGES, FL, 32163
Community: The Villages®
Oak Run 11558 SW 74TH CT, OCALA, FL, 34476, Ocala, FL 34476
$344,900

3 beds

|

2 baths

|

1,548 sq ft

|

House

11558 SW 74TH CT, OCALA, FL, 34476
Community: Oak Run
Pennbrooke Fairways 131 WILLOW BROOK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$242,900

3 beds

|

2 baths

|

1,720 sq ft

|

House

131 WILLOW BROOK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
The Villages® 1617 HILTON HEAD BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$169,900

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

1617 HILTON HEAD BLVD, LADY LAKE, FL, 32...
Community: The Villages®
Del Webb Sunbridge 2458 CLIFF WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$402,900

2 beds

|

2 baths

|

1,584 sq ft

|

Villa

2458 CLIFF WAY, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek South 10767 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$239,000

3 beds

|

2 baths

|

1,690 sq ft

|

House

10767 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Spruce Creek South
Stonecrest 11735 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$439,000

3 beds

|

2 baths

|

1,777 sq ft

|

House

11735 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Stonecrest 17739 SE 121ST TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491
$314,900

2 beds

|

2 baths

|

1,572 sq ft

|

House

17739 SE 121ST TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
On Top of the World 9855 SW 85TH TERRACE RD A, OCALA, FL, 34..., Ocala, FL 34481
$162,900

2 beds

|

2 baths

|

1,338 sq ft

|

Villa

9855 SW 85TH TERRACE RD A, OCALA, FL, 34...
Community: On Top of the World
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.
Plantation at Leesburg 4849 SABLE RIDGE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$419,000

3 beds

|

3 baths

|

2,607 sq ft

|

House

4849 SABLE RIDGE CT, LEESBURG, FL, 34748
New Spruce Creek South 17973 SE 104TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$255,000

3 beds

|

2 baths

|

1,526 sq ft

|

House

17973 SE 104TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Ocala Palms 2459 NW 55TH AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$245,900

3 beds

|

2 baths

|

1,514 sq ft

|

House

2459 NW 55TH AVENUE RD, OCALA, FL, 34482
Community: Ocala Palms
Sun City Center 1715 DANBURY DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$319,900

3 beds

|

2 baths

|

1,662 sq ft

|

House

1715 DANBURY DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Marco Polo Village 4910 SW 114TH STREET RD, OCALA, FL, 3447..., Ocala, FL 34476
$299,900

4 beds

|

2 baths

|

1,716 sq ft

|

House

4910 SW 114TH STREET RD, OCALA, FL, 3447...
Community: Marco Polo Village
Oak Run 11222 SW 73RD CIR, OCALA, FL, 34476, Ocala, FL 34476
$210,000

2 beds

|

2 baths

|

1,420 sq ft

|

House

11222 SW 73RD CIR, OCALA, FL, 34476
Community: Oak Run

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