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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
Sun City Center 1816 N PEBBLE BEACH BLVD, SUN CITY CENTE..., Sun City Center, FL 33573
$291,000

2 beds

|

2 baths

|

1,860 sq ft

|

Villa

1816 N PEBBLE BEACH BLVD, SUN CITY CENTE...
Community: Sun City Center
Ocala Palms 1956 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$387,000

3 beds

|

2 baths

|

1,806 sq ft

|

House

1956 NW 50TH CIR, OCALA, FL, 34482
Community: Ocala Palms
Lake Ashton 4073 SABLE LOOP DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$550,000

3 beds

|

2 baths

|

2,354 sq ft

|

House

4073 SABLE LOOP DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
Pelican Bay Daytona Beach 149 BLACK DUCK CIR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119
$229,770

2 beds

|

2 baths

|

1,075 sq ft

|

House

149 BLACK DUCK CIR, DAYTONA BEACH, FL, 3...
Sun City Center 736 MCCALLISTER AVE, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$239,900

2 beds

|

2 baths

|

1,584 sq ft

|

Condo

736 MCCALLISTER AVE, 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
The Villages® 1628 BAY MEADOWS LN, THE VILLAGES, FL, 3..., The Villages, FL 32159
$179,900

2 beds

|

2 baths

|

936 sq ft

|

Manufactured Home

1628 BAY MEADOWS LN, THE VILLAGES, FL, 3...
Community: The Villages®
On Top of the World 8796 SW 83RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$324,900

3 beds

|

2 baths

|

1,726 sq ft

|

House

8796 SW 83RD CIR, OCALA, FL, 34481
Community: On Top of the World
SummerGlen 15300 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$284,900

3 beds

|

2 baths

|

1,676 sq ft

|

House

15300 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Venetian Bay 424 LUNA BELLA LN 433, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168
$369,900

3 beds

|

3 baths

|

2,030 sq ft

|

Condo

424 LUNA BELLA LN 433, NEW SMYRNA BEACH,...
Community: Venetian Bay
Harbor Hills Country Club 5141 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$819,999

4 beds

|

3 baths

|

2,500 sq ft

|

House

5141 GREENS DR, LADY LAKE, FL, 32159
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.
On Top of the World 9085 SW 89TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$669,900

3 beds

|

3 baths

|

2,814 sq ft

|

House

9085 SW 89TH LOOP, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9286 SW 89TH COURT RD D, OCALA, FL, 3448..., Ocala, FL 34481
$159,900

2 beds

|

2 baths

|

1,113 sq ft

|

Villa

9286 SW 89TH COURT RD D, OCALA, FL, 3448...
Community: On Top of the World
Windermere 708 MORAY DR, INVERNESS, FL, 34453, Inverness, FL 34453
$285,000

3 beds

|

3 baths

|

1,915 sq ft

|

Townhouse

708 MORAY DR, INVERNESS, FL, 34453
Community: Windermere
Tarawood 10522 S DREW BRYANT CIR, FLORAL CITY, FL..., Floral City, FL 34436
$294,900

3 beds

|

2 baths

|

1,263 sq ft

|

House

10522 S DREW BRYANT CIR, FLORAL CITY, FL...
Community: Tarawood
Tarawood 10490 S DREW BRYANT CIR, FLORAL CITY, FL..., Floral City, FL 34436
$274,900

3 beds

|

2 baths

|

1,185 sq ft

|

House

10490 S DREW BRYANT CIR, FLORAL CITY, FL...
Community: Tarawood
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 663 SHOREHAVEN DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$349,900

3 beds

|

3 baths

|

2,357 sq ft

|

House

663 SHOREHAVEN DR, POINCIANA, FL, 34759
Community: Solivita
Pelican Bay Daytona Beach 240 BOB WHITE CT 2400, DAYTONA BEACH, FL..., Daytona Beach, FL 32119
$224,900

2 beds

|

2 baths

|

1,093 sq ft

|

Condo

240 BOB WHITE CT 2400, DAYTONA BEACH, FL...
The Villages® 5820 BAMBOO AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$324,900

2 beds

|

2 baths

|

1,266 sq ft

|

Villa

5820 BAMBOO AVE, THE VILLAGES, FL, 32163
Community: The Villages®
Plantation at Leesburg 5338 TIGERS TAIL, LEESBURG, FL, 34748, Leesburg, FL 34748
$269,999

2 beds

|

2 baths

|

1,050 sq ft

|

House

5338 TIGERS TAIL, LEESBURG, FL, 34748
Traditions at Lake Ruby 3457 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$238,500

2 beds

|

2 baths

|

1,118 sq ft

|

House

3457 RALEIGH DR, WINTER HAVEN, FL, 33884
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.
On Top of the World 9662 SW 95TH CT A, OCALA, FL, 34481, Ocala, FL 34481
$174,500

2 beds

|

2 baths

|

1,412 sq ft

|

Villa

9662 SW 95TH CT A, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 401 DORCHESTER PL 52, SUN CITY CENTER, F..., Sun City Center, FL 33573
$214,900

2 beds

|

2 baths

|

984 sq ft

|

Condo

401 DORCHESTER PL 52, SUN CITY CENTER, F...
Community: Sun City Center
Pelican Bay Daytona Beach 244 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$325,000

2 beds

|

2 baths

|

1,370 sq ft

|

House

244 PALM SPARROW CT, DAYTONA BEACH, FL, ...
Sun City Center 711 E BROCKTON PL, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$220,000

2 beds

|

2 baths

|

1,141 sq ft

|

House

711 E BROCKTON PL, SUN CITY CENTER, FL, ...
Community: Sun City Center
Lake Ashton 4195 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$387,000

3 beds

|

2 baths

|

2,039 sq ft

|

House

4195 MUIRFIELD LOOP, LAKE WALES, FL, 338...
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Cherrywood 5824 SW 100TH LN, OCALA, FL, 34476, Ocala, FL 34476
$359,900

4 beds

|

3 baths

|

2,433 sq ft

|

House

5824 SW 100TH LN, OCALA, FL, 34476
Community: Cherrywood
Huntington at Hunter's Ridge 103 WRENDALE LOOP, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$409,000

2 beds

|

2 baths

|

1,603 sq ft

|

House

103 WRENDALE LOOP, ORMOND BEACH, FL, 321...
Kings Ridge 2310 GRASMERE CIR, CLERMONT, FL, 34711, Clermont, FL 34711
$344,900

2 beds

|

2 baths

|

1,716 sq ft

|

House

2310 GRASMERE CIR, CLERMONT, FL, 34711
Community: Kings Ridge
Venetian Bay 2866 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$589,880

3 beds

|

3 baths

|

2,115 sq ft

|

Townhouse

2866 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Legacy of Leesburg 27437 DESERT ROSE CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$415,000

3 beds

|

2 baths

|

2,115 sq ft

|

House

27437 DESERT ROSE CT, LEESBURG, FL, 3474...
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.
Ocala Preserve 3966 NW 46TH TER, OCALA, FL, 34482, Ocala, FL 34482
$300,000

2 beds

|

2 baths

|

1,392 sq ft

|

House

3966 NW 46TH TER, OCALA, FL, 34482
Community: Ocala Preserve
Solivita 205 BELL TOWER XING W, KISSIMMEE, FL, 34..., Kissimmee, FL 34759
$289,900

2 beds

|

2 baths

|

1,405 sq ft

|

House

205 BELL TOWER XING W, KISSIMMEE, FL, 34...
Community: Solivita
On Top of the World 8626 SW 97TH LANE RD D, OCALA, FL, 34481, Ocala, FL 34481
$299,000

2 beds

|

2 baths

|

1,708 sq ft

|

Townhouse

8626 SW 97TH LANE RD D, OCALA, FL, 34481
Community: On Top of the World
Twin Lakes 2555 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$319,000

2 beds

|

2 baths

|

1,346 sq ft

|

Villa

2555 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Solivita 130 PRIMA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$435,000

3 beds

|

2 baths

|

2,141 sq ft

|

House

130 PRIMA 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
Highlands Ridge 3201 E ANGLERS STRM, AVON PARK, FL, 3382..., Avon Park, FL 33825
$299,000

2 beds

|

2 baths

|

2,034 sq ft

|

House

3201 E ANGLERS STRM, AVON PARK, FL, 3382...
Community: Highlands Ridge
Palm Cay 10881 SW 79TH TER, OCALA, FL, 34476, Ocala, FL 34476
$179,000

2 beds

|

2 baths

|

1,112 sq ft

|

House

10881 SW 79TH TER, OCALA, FL, 34476
Community: Palm Cay
Venetian Bay 3067 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$545,900

3 beds

|

4 baths

|

1,847 sq ft

|

Townhouse

3067 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Venetian Bay 3069 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$420,500

2 beds

|

2 baths

|

1,003 sq ft

|

Townhouse

3069 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Venetian Bay 3046 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$600,000

4 beds

|

4 baths

|

2,086 sq ft

|

Townhouse

3046 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay

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3,933 homes near Winter Garden
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