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

3,648 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 - $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 - $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 - $700Ks
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 - $700Ks
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 - $500Ks
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
<$100k - $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 - $900Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
$100Ks - $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
$100Ks - $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
$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
No reviews yet Venetian Bay
$300Ks - $2Ms
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
$300Ks - $500Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
5 rating (8 reviews) Royal Highlands
$200Ks - $500Ks
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) 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
$400Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 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
<$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 - $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 - $500Ks
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 | 1,024 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
No reviews yet Breakaway Trails
$400Ks - $1Ms
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
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
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
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet 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
No reviews yet Esplanade at Wiregrass Ra...
$400Ks - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Ridgehaven 445 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$595,370

5 beds

|

5 baths

|

3,807 sq ft

|

House

445 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
Kings Ridge 3614 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711
$344,900

2 beds

|

3 baths

|

1,722 sq ft

|

House

3614 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
Latitude Margaritaville 378 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$424,900

2 beds

|

2 baths

|

1,464 sq ft

|

House

378 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Twin Lakes 2460 PROMENADE DR, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$429,990

3 beds

|

2 baths

|

1,863 sq ft

|

House

2460 PROMENADE DR, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
Sun City Center 1103 VILLEROY DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$415,000

3 beds

|

2 baths

|

1,490 sq ft

|

House

1103 VILLEROY DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 302 ANDOVER PL S # G156, SUN CITY CENTER..., Sun City Center, FL 33573
$169,000

2 beds

|

2 baths

|

960 sq ft

|

Condo

302 ANDOVER PL S # G156, SUN CITY CENTER...
Community: Sun City Center
Spruce Creek Country Club 12771 SE 92ND TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$289,000

2 beds

|

2 baths

|

1,237 sq ft

|

House

12771 SE 92ND TER, SUMMERFIELD, FL, 3449...
Solivita 300 FALLING WATER DR, POINCIANA, FL, 347..., Poinciana, FL 34759
$199,000

2 beds

|

2 baths

|

1,171 sq ft

|

Halfplex

300 FALLING WATER DR, POINCIANA, FL, 347...
Community: Solivita
Lake Ashton 4240 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$560,000

2 beds

|

2 baths

|

1,771 sq ft

|

House

4240 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Marion Landing 8342 SW 65TH AVE, OCALA, FL, 34476, Ocala, FL 34476
$255,000

2 beds

|

2 baths

|

1,951 sq ft

|

House

8342 SW 65TH AVE, OCALA, FL, 34476
Community: Marion Landing
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 9595 SW 62ND CT, OCALA, FL, 34476, Ocala, FL 34476
$259,990

3 beds

|

2 baths

|

1,615 sq ft

|

House

9595 SW 62ND CT, OCALA, FL, 34476
Community: Cherrywood
Valencia Lakes 16005 CAPE CORAL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$649,900

3 beds

|

4 baths

|

2,725 sq ft

|

House

16005 CAPE CORAL DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
The Villages® 2291 MONTBROOK PL, THE VILLAGES, FL, 321..., The Villages, FL 32162
$358,500

3 beds

|

2 baths

|

1,392 sq ft

|

House

2291 MONTBROOK PL, THE VILLAGES, FL, 321...
Community: The Villages®
Venetian Bay 424 LUNA BELLA LN 422, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168
$339,000

3 beds

|

3 baths

|

1,953 sq ft

|

Condo

424 LUNA BELLA LN 422, NEW SMYRNA BEACH,...
Community: Venetian Bay
On Top of the World 8590 SW 95TH CT, OCALA, FL, 34481, Ocala, FL 34481
$544,900

3 beds

|

3 baths

|

2,814 sq ft

|

House

8590 SW 95TH CT, 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
Highland Lakes 5500 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$284,000

3 beds

|

2 baths

|

1,591 sq ft

|

House

5500 LAVER ST, LEESBURG, FL, 34748
Community: Highland Lakes
Stonecrest 12205 SE 173RD PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$269,000

3 beds

|

2 baths

|

1,475 sq ft

|

House

12205 SE 173RD PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Lake James 7991 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$449,500

3 beds

|

2 baths

|

1,890 sq ft

|

House

7991 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Mirada 10935 GABLE DIG LOOP, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$275,000

2 beds

|

2 baths

|

1,625 sq ft

|

Villa

10935 GABLE DIG LOOP, SAN ANTONIO, FL, 3...
Community: Mirada
Oak Run 11587 SW 72ND CIR, OCALA, FL, 34476, Ocala, FL 34476
$315,000

3 beds

|

2 baths

|

2,227 sq ft

|

House

11587 SW 72ND CIR, OCALA, FL, 34476
Community: Oak Run
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.
Valencia del Sol 15303 VALENCIA DEL SOL ST, WIMAUMA, FL, ..., Wimauma, FL 33598
$825,000

3 beds

|

4 baths

|

3,083 sq ft

|

House

15303 VALENCIA DEL SOL ST, WIMAUMA, FL, ...
Community: Valencia del Sol
Spruce Creek Preserve 11536 SW 140TH LOOP, DUNNELLON, FL, 3443..., Dunnellon, FL 34432
$262,500

2 beds

|

2 baths

|

1,830 sq ft

|

House

11536 SW 140TH LOOP, DUNNELLON, FL, 3443...
Spruce Creek Country Club 11735 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$419,900

3 beds

|

2 baths

|

2,413 sq ft

|

House

11735 SE 91ST CIR, SUMMERFIELD, FL, 3449...
On Top of the World 9481 SW 93RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$229,000

3 beds

|

2 baths

|

1,573 sq ft

|

House

9481 SW 93RD LOOP, OCALA, FL, 34481
Community: On Top of the World
Spruce Creek Preserve 11879 SW 137TH LOOP, DUNNELLON, FL, 3443..., Dunnellon, FL 34432
$209,900

2 beds

|

1 baths

|

943 sq ft

|

House

11879 SW 137TH LOOP, DUNNELLON, FL, 3443...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Preserve 11470 SW 139TH ST, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$234,950

2 beds

|

2 baths

|

1,672 sq ft

|

House

11470 SW 139TH ST, DUNNELLON, FL, 34432
SummerGlen 1044 SW 159TH ST, OCALA, FL, 34473, Ocala, FL 34473
$399,900

3 beds

|

2 baths

|

2,148 sq ft

|

House

1044 SW 159TH ST, OCALA, FL, 34473
Community: SummerGlen
Traditions at Lake Ruby 3986 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$415,000

4 beds

|

3 baths

|

2,320 sq ft

|

House

3986 BEDFORD AVE, WINTER HAVEN, FL, 3388...
Spruce Creek Preserve 15024 SW 112TH CIR, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$269,900

3 beds

|

2 baths

|

1,835 sq ft

|

House

15024 SW 112TH CIR, DUNNELLON, FL, 34432
Pine Run Estates 9055 SW 102ND PL, OCALA, FL, 34481, Ocala, FL 34481
$139,900

2 beds

|

2 baths

|

1,328 sq ft

|

House

9055 SW 102ND PL, OCALA, FL, 34481
Community: Pine Run Estates
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 3056 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$544,990

3 beds

|

4 baths

|

1,847 sq ft

|

Townhouse

3056 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Oak Run 11298 SW 73RD CIR, OCALA, FL, 34476, Ocala, FL 34476
$285,000

2 beds

|

2 baths

|

1,540 sq ft

|

House

11298 SW 73RD CIR, OCALA, FL, 34476
Community: Oak Run
Lake Jovita Golf and Country Club 12648 LAKE JOVITA BLVD, DADE CITY, FL, 3..., Dade City, FL 33525
$725,000

4 beds

|

3 baths

|

2,749 sq ft

|

House

12648 LAKE JOVITA BLVD, DADE CITY, FL, 3...
Oak Run 10966 SW 82ND TER, OCALA, FL, 34481, Ocala, FL 34481
$187,000

2 beds

|

2 baths

|

1,224 sq ft

|

House

10966 SW 82ND TER, OCALA, FL, 34481
Community: Oak Run
The Villages® 3374 CASTLEGATE CT, THE VILLAGES, FL, 32..., The Villages, FL 32163
$299,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

3374 CASTLEGATE CT, THE VILLAGES, FL, 32...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Summer Trees 128 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$299,900

3 beds

|

2 baths

|

1,268 sq ft

|

House

128 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
The Villages® 555 RANDALL RD, THE VILLAGES, FL, 32163, The Villages, FL 32163
$629,000

3 beds

|

3 baths

|

1,905 sq ft

|

House

555 RANDALL RD, THE VILLAGES, FL, 32163
Community: The Villages®
On Top of the World 8017 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$349,900

3 beds

|

2 baths

|

2,030 sq ft

|

House

8017 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
Spruce Creek Country Club 12860 SE 92ND COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$469,965

2 beds

|

2 baths

|

1,639 sq ft

|

House

12860 SE 92ND COURT RD, SUMMERFIELD, FL,...
Sun City Center 380 CLUB MANOR DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$120,000

2 beds

|

2 baths

|

1,516 sq ft

|

Villa

380 CLUB MANOR DR, SUN CITY CENTER, FL, ...
Community: Sun City Center

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3,648 homes near Winter Garden
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