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

3,933 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
$100Ks - $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.
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) Trilogy® Orlando
$200Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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
$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
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
$200Ks - $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 Lakes at Harmony 3306 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$520,000

4 beds

|

3 baths

|

2,547 sq ft

|

House

3306 SAGEBRUSH ST, HARMONY, FL, 34773
Cherrywood 10557 SW 62ND CT, OCALA, FL, 34476, Ocala, FL 34476
$199,000

2 beds

|

2 baths

|

1,457 sq ft

|

House

10557 SW 62ND CT, OCALA, FL, 34476
Community: Cherrywood
SummerGlen 16292 SW 13TH TER, OCALA, FL, 34473, Ocala, FL 34473
$359,000

3 beds

|

2 baths

|

2,297 sq ft

|

House

16292 SW 13TH TER, OCALA, FL, 34473
Community: SummerGlen
Ocala Palms 5520 NW 26TH LN, OCALA, FL, 34482, Ocala, FL 34482
$265,000

3 beds

|

2 baths

|

1,526 sq ft

|

House

5520 NW 26TH LN, OCALA, FL, 34482
Community: Ocala Palms
SummerGlen 1033 SW 159TH ST, OCALA, FL, 34473, Ocala, FL 34473
$329,567

3 beds

|

2 baths

|

2,274 sq ft

|

House

1033 SW 159TH ST, OCALA, FL, 34473
Community: SummerGlen
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Huntington at Hunter's Ridge 82 WRENDALE LOOP, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$395,000

2 beds

|

2 baths

|

1,600 sq ft

|

House

82 WRENDALE LOOP, ORMOND BEACH, FL, 3217...
Vienna Square 2470 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$295,000

3 beds

|

2 baths

|

1,935 sq ft

|

House

2470 SALZBURG LOOP, WINTER HAVEN, FL, 33...
Community: Vienna Square
Breakaway Trails 8 TROPIC LAKE WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$542,000

3 beds

|

2 baths

|

2,073 sq ft

|

House

8 TROPIC LAKE WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
On Top of the World 8540 SW 91ST PL B, OCALA, FL, 34481, Ocala, FL 34481
$180,000

2 beds

|

2 baths

|

1,204 sq ft

|

Villa

8540 SW 91ST PL B, OCALA, FL, 34481
Community: On Top of the World
Majestic Oaks Ocala 5851 SW 86TH PL, OCALA, FL, 34476, Ocala, FL 34476
$433,333

3 beds

|

2 baths

|

2,196 sq ft

|

House

5851 SW 86TH PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
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.
Cherrywood 5958 SW 102ND LN, OCALA, FL, 34476, Ocala, FL 34476
$195,000

3 beds

|

2 baths

|

1,377 sq ft

|

House

5958 SW 102ND LN, OCALA, FL, 34476
Community: Cherrywood
The Villages® 1202 FERNANDO LN, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$325,000

2 beds

|

1 baths

|

1,040 sq ft

|

Villa

1202 FERNANDO LN, THE VILLAGES, FL, 3215...
Community: The Villages®
Palm Cay 8473 SW 106TH ST, OCALA, FL, 34481, Ocala, FL 34481
$139,999

2 beds

|

2 baths

|

936 sq ft

|

House

8473 SW 106TH ST, OCALA, FL, 34481
Community: Palm Cay
Plantation at Leesburg 25304 FOREST OAK CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$375,000

3 beds

|

2 baths

|

2,460 sq ft

|

House

25304 FOREST OAK CT, LEESBURG, FL, 34748
Sun City Center 2346 NANTUCKET DR # 58, SUN CITY CENTER,..., Sun City Center, FL 33573
$229,000

2 beds

|

2 baths

|

1,284 sq ft

|

Condo

2346 NANTUCKET DR # 58, SUN CITY CENTER,...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Plantation at Leesburg 25243 RIVER CREST DR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$389,900

3 beds

|

3 baths

|

2,529 sq ft

|

House

25243 RIVER CREST DR, LEESBURG, FL, 3474...
Kings Ridge 3708 FAIRFIELD DR, CLERMONT, FL, 34711, Clermont, FL 34711
$369,000

3 beds

|

2 baths

|

1,873 sq ft

|

House

3708 FAIRFIELD DR, CLERMONT, FL, 34711
Community: Kings Ridge
Sun City Center 832 KING LEON WAY, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$345,000

3 beds

|

2 baths

|

1,503 sq ft

|

House

832 KING LEON WAY, SUN CITY CENTER, FL, ...
Community: Sun City Center
Lake Ashton 1202 ASHTON PALMS DR # 6, LAKE WALES, FL..., Lake Wales, FL 33859
$229,500

2 beds

|

2 baths

|

1,436 sq ft

|

Condo

1202 ASHTON PALMS DR # 6, LAKE WALES, FL...
Community: Lake Ashton
Legacy of Leesburg 27307 PINE STRAW RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$375,000

3 beds

|

2 baths

|

2,079 sq ft

|

House

27307 PINE STRAW RD, LEESBURG, FL, 34748
Community: Legacy of Leesburg
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.
Lakes of Mount Dora 3969 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$449,990

2 beds

|

2 baths

|

1,402 sq ft

|

House

3969 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
Stonecrest 17257 SE 113TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$465,000

3 beds

|

2 baths

|

1,986 sq ft

|

House

17257 SE 113TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
Lakes of Mount Dora 3967 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$499,990

2 beds

|

2 baths

|

1,639 sq ft

|

House

3967 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
Oak Run 8239 SW 108TH ST, OCALA, FL, 34481, Ocala, FL 34481
$209,500

2 beds

|

2 baths

|

1,354 sq ft

|

House

8239 SW 108TH ST, OCALA, FL, 34481
Community: Oak Run
Oak Run 10819 SW 84TH TER, OCALA, FL, 34481, Ocala, FL 34481
$235,000

3 beds

|

2 baths

|

1,952 sq ft

|

House

10819 SW 84TH TER, 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
Highlands Ridge 3113 S PRESTWICK DR, AVON PARK, FL, 3382..., Avon Park, FL 33825
$260,000

2 beds

|

2 baths

|

2,013 sq ft

|

House

3113 S PRESTWICK DR, AVON PARK, FL, 3382...
Community: Highlands Ridge
SummerGlen 16405 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$287,870

3 beds

|

2 baths

|

1,676 sq ft

|

House

16405 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Sandpiper Golf & Country Club 6194 SANDERLING DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$299,900

3 beds

|

2 baths

|

1,928 sq ft

|

House

6194 SANDERLING DR, LAKELAND, FL, 33809
The Villages® 527 RICHBURG ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$345,000

2 beds

|

2 baths

|

1,278 sq ft

|

Villa

527 RICHBURG ST, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 2082 HARSTON TRL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$275,000

2 beds

|

2 baths

|

1,187 sq ft

|

House

2082 HARSTON TRL, THE VILLAGES, FL, 3216...
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.
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
On Top of the World 10293 SW 96TH LN, OCALA, FL, 34481, Ocala, FL 34481
$549,000

2 beds

|

3 baths

|

2,414 sq ft

|

House

10293 SW 96TH LN, OCALA, FL, 34481
Community: On Top of the World
Kings Ridge 3821 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711
$320,000

2 beds

|

2 baths

|

1,447 sq ft

|

House

3821 DOUNE WAY, CLERMONT, FL, 34711
Community: Kings Ridge
Spruce Creek South 17548 SE 96TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$243,000

2 beds

|

2 baths

|

1,398 sq ft

|

House

17548 SE 96TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Harbor Hills Country Club 6147 SPINNAKER LOOP, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$548,200

3 beds

|

2 baths

|

2,025 sq ft

|

House

6147 SPINNAKER LOOP, LADY LAKE, FL, 3215...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Mirada 10420 ECHO DOCK LOOP, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$342,500

2 beds

|

2 baths

|

1,616 sq ft

|

Villa

10420 ECHO DOCK LOOP, SAN ANTONIO, FL, 3...
Community: Mirada
Marco Polo Village 11147 SW 53RD CIR, OCALA, FL, 34476, Ocala, FL 34476
$339,900

3 beds

|

2 baths

|

2,030 sq ft

|

House

11147 SW 53RD CIR, OCALA, FL, 34476
Community: Marco Polo Village
The Villages® 488 SETH RUN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$925,750

4 beds

|

3 baths

|

2,315 sq ft

|

House

488 SETH RUN, THE VILLAGES, FL, 32163
Community: The Villages®
Majestic Oaks Ocala 8100 SW 56TH TER, OCALA, FL, 34476, Ocala, FL 34476
$299,000

3 beds

|

2 baths

|

1,843 sq ft

|

House

8100 SW 56TH TER, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Sun City Center 1609 N PEBBLE BEACH BLVD, SUN CITY CENTE..., Sun City Center, FL 33573
$250,000

2 beds

|

2 baths

|

1,662 sq ft

|

House

1609 N PEBBLE BEACH BLVD, SUN CITY CENTE...
Community: Sun City Center

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3,933 homes near Winter Garden
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