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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
Silver Lakes 6118 SILVER LAKES DR, LAKELAND, FL, 3381..., Lakeland, FL 33810
$254,000

3 beds

|

2 baths

|

1,510 sq ft

|

House

6118 SILVER LAKES DR, LAKELAND, FL, 3381...
Community: Silver Lakes
On Top of the World 8814 SW 93RD LN B, OCALA, FL, 34481, Ocala, FL 34481
$169,000

2 beds

|

2 baths

|

1,411 sq ft

|

Condo

8814 SW 93RD LN B, OCALA, FL, 34481
Community: On Top of the World
Carillon Lakes 4427 WHISTLEWOOD CIR, LAKELAND, FL, 3381..., Lakeland, FL 33811
$309,900

3 beds

|

2 baths

|

1,394 sq ft

|

House

4427 WHISTLEWOOD CIR, LAKELAND, FL, 3381...
Community: Carillon Lakes
Solivita 196 TORINO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$575,000

3 beds

|

3 baths

|

2,466 sq ft

|

House

196 TORINO LN, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 540 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$229,900

2 beds

|

2 baths

|

1,507 sq ft

|

House

540 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Palms 5137 NW 20TH PL, OCALA, FL, 34482, Ocala, FL 34482
$320,000

2 beds

|

2 baths

|

1,569 sq ft

|

House

5137 NW 20TH PL, OCALA, FL, 34482
Community: Ocala Palms
Sun City Center 1826 WOLF LAUREL DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$359,500

3 beds

|

2 baths

|

2,070 sq ft

|

House

1826 WOLF LAUREL DR, SUN CITY CENTER, FL...
Community: Sun City Center
JB Ranch 9210 SW 60TH COURT RD, OCALA, FL, 34476, Ocala, FL 34476
$450,000

4 beds

|

3 baths

|

2,280 sq ft

|

House

9210 SW 60TH COURT RD, OCALA, FL, 34476
Community: JB Ranch
On Top of the World 9491 SW 98TH CT, OCALA, FL, 34481, Ocala, FL 34481
$339,900

2 beds

|

2 baths

|

1,737 sq ft

|

House

9491 SW 98TH CT, OCALA, FL, 34481
Community: On Top of the World
Latitude Margaritaville 521 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$599,900

2 beds

|

3 baths

|

2,110 sq ft

|

House

521 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
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 1207 BLUEWATER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$319,950

2 beds

|

2 baths

|

1,756 sq ft

|

House

1207 BLUEWATER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Huntington at Hunter's Ridge 34 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$359,500

3 beds

|

2 baths

|

1,523 sq ft

|

House

34 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Spruce Creek South 17764 SE 95TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$309,000

3 beds

|

2 baths

|

1,455 sq ft

|

House

17764 SE 95TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Four Seasons at Orlando 2132 LIMESTONE TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$640,000

3 beds

|

3 baths

|

2,360 sq ft

|

House

2132 LIMESTONE TRL, KISSIMMEE, FL, 34747
Pennbrooke Fairways 705 GRAND VISTA TRL, LEESBURG, FL, 34748, Leesburg, FL 34748
$284,950

3 beds

|

2 baths

|

1,656 sq ft

|

House

705 GRAND VISTA TRL, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 501 HERITAGE TRAIL ST, KISSIMMEE, FL, 34..., Kissimmee, FL 34759
$330,000

2 beds

|

2 baths

|

1,574 sq ft

|

House

501 HERITAGE TRAIL ST, KISSIMMEE, FL, 34...
Community: Solivita
Sun City Center 702 DESERT HILLS WAY, SUN CITY CENTER, F..., Sun City Center, FL 33573
$255,000

2 beds

|

2 baths

|

1,425 sq ft

|

House

702 DESERT HILLS WAY, SUN CITY CENTER, F...
Community: Sun City Center
Solivita 153 MARABELLA LOOP, POINCIANA, FL, 34759, Poinciana, FL 34759
$260,000

2 beds

|

2 baths

|

1,467 sq ft

|

House

153 MARABELLA LOOP, POINCIANA, FL, 34759
Community: Solivita
On Top of the World 8836 SW 90TH LN B, OCALA, FL, 34481, Ocala, FL 34481
$148,900

2 beds

|

2 baths

|

1,204 sq ft

|

Villa

8836 SW 90TH LN B, OCALA, FL, 34481
Community: On Top of the World
Trilogy® Orlando 209 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$429,000

3 beds

|

2 baths

|

1,900 sq ft

|

House

209 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
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.
Carillon Lakes 4145 WHISTLEWOOD CIR, LAKELAND, FL, 3381..., Lakeland, FL 33811
$349,900

3 beds

|

2 baths

|

2,408 sq ft

|

House

4145 WHISTLEWOOD CIR, LAKELAND, FL, 3381...
Community: Carillon Lakes
Spruce Creek Country Club 11703 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$457,900

3 beds

|

2 baths

|

2,278 sq ft

|

House

11703 SE 91ST CIR, SUMMERFIELD, FL, 3449...
Ocala Palms 5916 NW 27TH PL, OCALA, FL, 34482, Ocala, FL 34482
$379,900

3 beds

|

3 baths

|

1,767 sq ft

|

House

5916 NW 27TH PL, OCALA, FL, 34482
Community: Ocala Palms
Sun City Center 1730 W DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573
$325,000

2 beds

|

2 baths

|

1,312 sq ft

|

House

1730 W DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
Sun City Center 2329 LANCASTER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$240,000

2 beds

|

2 baths

|

1,829 sq ft

|

Condo

2329 LANCASTER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8683 SW 93RD LN E, OCALA, FL, 34481, Ocala, FL 34481
$164,000

2 beds

|

2 baths

|

1,369 sq ft

|

Villa

8683 SW 93RD LN E, OCALA, FL, 34481
Community: On Top of the World
The Villages® 5754 SHEALY AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$449,000

3 beds

|

2 baths

|

1,569 sq ft

|

House

5754 SHEALY AVE, THE VILLAGES, FL, 32163
Community: The Villages®
Pelican Bay Daytona Beach 161 BLUE HERON DR C, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$228,400

2 beds

|

2 baths

|

1,192 sq ft

|

Condo

161 BLUE HERON DR C, DAYTONA BEACH, FL, ...
Summit Greens 993 EVEREST ST, CLERMONT, FL, 34711, Clermont, FL 34711
$439,999

3 beds

|

2 baths

|

2,078 sq ft

|

House

993 EVEREST ST, CLERMONT, FL, 34711
Community: Summit Greens
Traditions at Lake Ruby 2825 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$235,000

2 beds

|

2 baths

|

1,385 sq ft

|

Villa

2825 ATTWATER LOOP, WINTER HAVEN, FL, 33...
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.
Majestic Oaks Ocala 5327 SW 89TH ST, OCALA, FL, 34476, Ocala, FL 34476
$279,900

3 beds

|

2 baths

|

1,661 sq ft

|

House

5327 SW 89TH ST, OCALA, FL, 34476
Community: Majestic Oaks Ocala
JB Ranch 6444 SW 88TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$365,000

3 beds

|

2 baths

|

1,811 sq ft

|

House

6444 SW 88TH LOOP, OCALA, FL, 34476
Community: JB Ranch
On Top of the World 8218 SW 92ND CIR, OCALA, FL, 34481, Ocala, FL 34481
$558,000

3 beds

|

3 baths

|

2,311 sq ft

|

House

8218 SW 92ND CIR, OCALA, FL, 34481
Community: On Top of the World
Oak Run 11743 SW 72ND CIR, OCALA, FL, 34476, Ocala, FL 34476
$274,999

2 beds

|

2 baths

|

1,456 sq ft

|

House

11743 SW 72ND CIR, OCALA, FL, 34476
Community: Oak Run
Cresswind at Victoria Gardens 1386 RED CLOVER LN, DELAND, FL, 32724, Deland, FL 32724
$310,000

2 beds

|

2 baths

|

1,512 sq ft

|

House

1386 RED CLOVER LN, DELAND, FL, 32724
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Breakaway Trails 28 SHADOWCREEK WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$599,900

4 beds

|

3 baths

|

2,700 sq ft

|

House

28 SHADOWCREEK WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
Del Webb Oasis 11941 BRACCO ST, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787
$500,000

3 beds

|

3 baths

|

1,788 sq ft

|

House

11941 BRACCO ST, WINTER GARDEN, FL, 3478...
Community: Del Webb Oasis
Colonnades 4976 PLEASANT HOLLOW TRL, LAKELAND, FL, ..., Lakeland, FL 33811
$250,000

2 beds

|

2 baths

|

1,543 sq ft

|

House

4976 PLEASANT HOLLOW TRL, LAKELAND, FL, ...
Community: Colonnades
Pine Run Estates 10197 SW 88TH TER, OCALA, FL, 34481, Ocala, FL 34481
$140,000

2 beds

|

2 baths

|

912 sq ft

|

House

10197 SW 88TH TER, OCALA, FL, 34481
Community: Pine Run Estates
Legacy of Leesburg 27223 NOSTALGIA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$464,400

3 beds

|

3 baths

|

2,484 sq ft

|

House

27223 NOSTALGIA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg

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3,958 homes near Winter Garden
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