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

3,958 homes near Winter Garden

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No reviews yet Del Webb Oasis
$400Ks - $1Ms
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
4 rating (17 reviews) The Villages®
<$100k - $1Ms
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
<$100k - $600Ks
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 - $600Ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4.7 rating (18 reviews) Solivita
$200Ks - $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 (46 reviews) Latitude Margaritaville
$300Ks - $700Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
4.2 rating (10 reviews) Stone Creek
$200Ks - $800Ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 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
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
5 rating (2 reviews) Plantation at Leesburg
$100Ks - $400Ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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 (3 reviews) Stonecrest
$200Ks - $600Ks
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 - $1Ms
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
<$100k - $600Ks
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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.7 rating (3 reviews) Spruce Creek South
$200Ks - $300Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $900Ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
5 rating (1 reviews) Cypress Lakes
$200Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $900Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
No reviews yet Venetian Bay
$200Ks - $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.
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
5 rating (8 reviews) Royal Highlands
$200Ks - $400Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
3.8 rating (6 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) VillageWalk at Lake Nona
$400Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (8 reviews) Pennbrooke Fairways
$100Ks - $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 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
3.6 rating (5 reviews) Heritage Hills
$300Ks - $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
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 (5 reviews) SummerGlen
$200Ks - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 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
No reviews yet Breakaway Trails
$400Ks - $700Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$200Ks - $800Ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
4 rating (2 reviews) Harbor Hills Country Club
$200Ks - $800Ks
Harbor Hills Country Club, Lady Lake, FL
New and Resale | Age-targeted | Built 1989 - present | 940 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.8 rating (6 reviews) Highland Lakes
$100Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $500Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
$100Ks - $400Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet 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
No reviews yet Esplanade at Wiregrass Ra...
$400Ks - $900Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
The Villages® 502 SAN MARINO DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$310,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

502 SAN MARINO DR, LADY LAKE, FL, 32159
Community: The Villages®
Sun City Center 1929 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$369,995

2 beds

|

2 baths

|

2,044 sq ft

|

House

1929 NEW BEDFORD DR, SUN CITY CENTER, FL...
Community: Sun City Center
The Villages® 2549 BUTTONWOOD RUN, THE VILLAGES, FL, 3..., The Villages, FL 32162
$359,900

3 beds

|

2 baths

|

1,488 sq ft

|

House

2549 BUTTONWOOD RUN, THE VILLAGES, FL, 3...
Community: The Villages®
The Lakes at Harmony 3397 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$493,000

3 beds

|

3 baths

|

2,355 sq ft

|

House

3397 SAGEBRUSH ST, HARMONY, FL, 34773
JB Ranch 4690 SW 88TH LN, OCALA, FL, 34476, Ocala, FL 34476
$321,215

4 beds

|

2 baths

|

1,828 sq ft

|

House

4690 SW 88TH LN, OCALA, FL, 34476
Community: JB Ranch
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
JB Ranch 4698 SW 88TH LN, OCALA, FL, 34476, Ocala, FL 34476
$304,990

3 beds

|

2 baths

|

1,672 sq ft

|

House

4698 SW 88TH LN, OCALA, FL, 34476
Community: JB Ranch
JB Ranch 4683 SW 88TH LN, OCALA, FL, 34476, Ocala, FL 34476
$324,990

4 beds

|

2 baths

|

1,828 sq ft

|

House

4683 SW 88TH LN, OCALA, FL, 34476
Community: JB Ranch
Sun City Center 1809 HAVERFORD AVE, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$275,000

2 beds

|

2 baths

|

1,402 sq ft

|

House

1809 HAVERFORD AVE, SUN CITY CENTER, FL,...
Community: Sun City Center
Marco Polo Village 5365 SW 111TH LANE RD, OCALA, FL, 34476, Ocala, FL 34476
$345,000

3 beds

|

2 baths

|

1,884 sq ft

|

House

5365 SW 111TH LANE RD, OCALA, FL, 34476
Community: Marco Polo Village
JB Ranch 4699 SW 88TH LN, OCALA, FL, 34476, Ocala, FL 34476
$305,990

3 beds

|

2 baths

|

1,672 sq ft

|

House

4699 SW 88TH LN, OCALA, FL, 34476
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.
JB Ranch 4746 SW 88TH LN, OCALA, FL, 34476, Ocala, FL 34476
$319,990

4 beds

|

2 baths

|

1,828 sq ft

|

House

4746 SW 88TH LN, OCALA, FL, 34476
Community: JB Ranch
The Villages® 604 JUANITA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$299,900

3 beds

|

2 baths

|

1,437 sq ft

|

House

604 JUANITA CT, THE VILLAGES, FL, 32159
Community: The Villages®
JB Ranch 4706 SW 88TH LN, OCALA, FL, 34476, Ocala, FL 34476
$305,990

3 beds

|

2 baths

|

1,672 sq ft

|

House

4706 SW 88TH LN, OCALA, FL, 34476
Community: JB Ranch
The Villages® 612 LISBON LN, THE VILLAGES, FL, 32159, The Villages, FL 32159
$349,000

2 beds

|

2 baths

|

1,383 sq ft

|

House

612 LISBON LN, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 3008 BRIDGEFIELD CT, THE VILLAGES, FL, 3..., The Villages, FL 32162
$435,000

3 beds

|

2 baths

|

2,122 sq ft

|

House

3008 BRIDGEFIELD CT, THE VILLAGES, FL, 3...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 412 HILDALGO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$269,900

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

412 HILDALGO DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1972 PALO ALTO AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159
$749,000

3 beds

|

2 baths

|

2,215 sq ft

|

House

1972 PALO ALTO AVE, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 1526 BLUEBERRY WAY, THE VILLAGES, FL, 32..., The Villages, FL 32162
$385,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

1526 BLUEBERRY WAY, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 2120 CALLAWAY DR, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$525,000

3 beds

|

2 baths

|

2,125 sq ft

|

House

2120 CALLAWAY DR, THE VILLAGES, FL, 3216...
Community: The Villages®
Twin Lakes 2810 WINDSONG LN, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$530,000

3 beds

|

2 baths

|

1,582 sq ft

|

House

2810 WINDSONG LN, SAINT CLOUD, FL, 34772
Community: Twin 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.
The Villages® 3432 FAIRFIELD ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$415,000

3 beds

|

2 baths

|

1,477 sq ft

|

House

3432 FAIRFIELD ST, THE VILLAGES, FL, 321...
Community: The Villages®
Spruce Creek South 10783 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$219,500

2 beds

|

2 baths

|

1,144 sq ft

|

House

10783 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Stonecrest 17471 SE 110TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$379,000

3 beds

|

2 baths

|

1,768 sq ft

|

House

17471 SE 110TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 2433 TAMARINDO DR, THE VILLAGES, FL, 321..., The Villages, FL 32162
$399,999

3 beds

|

2 baths

|

1,858 sq ft

|

House

2433 TAMARINDO DR, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 3407 MELBOURNE LN, THE VILLAGES, FL, 321..., The Villages, FL 32163
$420,000

3 beds

|

2 baths

|

1,559 sq ft

|

House

3407 MELBOURNE LN, THE VILLAGES, FL, 321...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 3403 RABBIT RUN PATH, THE VILLAGES, FL, ..., The Villages, FL 32163
$625,000

3 beds

|

2 baths

|

2,035 sq ft

|

House

3403 RABBIT RUN PATH, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 9199 SE 171ST COOPER LOOP, THE VILLAGES,..., The Villages, FL 32162
$425,000

3 beds

|

2 baths

|

1,850 sq ft

|

House

9199 SE 171ST COOPER LOOP, THE VILLAGES,...
Community: The Villages®
The Villages® 17478 SE 77TH SYCAMORE AVE, THE VILLAGES..., The Villages, FL 32162
$249,900

2 beds

|

2 baths

|

1,160 sq ft

|

House

17478 SE 77TH SYCAMORE AVE, THE VILLAGES...
Community: The Villages®
The Villages® 520 SAINT ANDREWS BLVD, THE VILLAGES, FL..., The Villages, FL 32159
$234,900

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

520 SAINT ANDREWS BLVD, THE VILLAGES, FL...
Community: The Villages®
The Villages® 3381 HARRIS CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$346,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

3381 HARRIS CT, 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.
The Villages® 3213 ARCHER AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$389,000

2 beds

|

2 baths

|

1,196 sq ft

|

Villa

3213 ARCHER AVE, THE VILLAGES, FL, 32162
Community: The Villages®
Royal Harbor 6122 SAILBOAT AVE, TAVARES, FL, 32778, Tavares, FL 32778
$299,000

3 beds

|

3 baths

|

2,350 sq ft

|

House

6122 SAILBOAT AVE, TAVARES, FL, 32778
Community: Royal Harbor
Palm Cay 8516 SW 105TH PL, OCALA, FL, 34481, Ocala, FL 34481
$165,000

2 beds

|

2 baths

|

936 sq ft

|

House

8516 SW 105TH PL, OCALA, FL, 34481
Community: Palm Cay
Stonecrest 17799 SE 125TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$263,000

3 beds

|

2 baths

|

1,342 sq ft

|

House

17799 SE 125TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
Heritage Hills 3632 SOLANA CIR B, CLERMONT, FL, 34711, Clermont, FL 34711
$319,900

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3632 SOLANA CIR B, CLERMONT, FL, 34711
Community: Heritage Hills
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pennbrooke Fairways 32708 WESTWOOD LOOP, LEESBURG, FL, 34748, Leesburg, FL 34748
$239,000

2 beds

|

2 baths

|

1,284 sq ft

|

House

32708 WESTWOOD LOOP, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Sun City Center 2501 LONIGAN PL, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$219,000

2 beds

|

2 baths

|

1,394 sq ft

|

Condo

2501 LONIGAN PL, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Sun City Center 1306 IDLEWOOD DR # 53, SUN CITY CENTER, ..., Sun City Center, FL 33573
$229,000

2 beds

|

2 baths

|

1,642 sq ft

|

Condo

1306 IDLEWOOD DR # 53, SUN CITY CENTER, ...
Community: Sun City Center
Spruce Creek South 10185 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$274,900

2 beds

|

3 baths

|

1,982 sq ft

|

House

10185 SE 175TH LN, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Palm Cay 11237 SW 78TH CT, OCALA, FL, 34476, Ocala, FL 34476
$214,900

3 beds

|

2 baths

|

1,646 sq ft

|

House

11237 SW 78TH CT, OCALA, FL, 34476
Community: Palm Cay

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3,958 homes near Winter Garden
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