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

3,573 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 - $2Ms
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
$100Ks - $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 - $500Ks
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 - $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 - $500Ks
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
$200Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $500Ks
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
$300Ks - $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) 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 - $900Ks
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
$100Ks - $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 - $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 - $400Ks
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
$300Ks - $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
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $400Ks
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
On Top of the World 9251 SW 94TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$379,900

3 beds

|

3 baths

|

2,412 sq ft

|

House

9251 SW 94TH LOOP, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8833 SW 98TH STREET RD E, OCALA, FL, 344..., Ocala, FL 34481
$174,900

2 beds

|

2 baths

|

1,607 sq ft

|

Villa

8833 SW 98TH STREET RD E, OCALA, FL, 344...
Community: On Top of the World
On Top of the World 7595 SW 88TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481
$395,000

2 beds

|

2 baths

|

1,747 sq ft

|

House

7595 SW 88TH TERRACE RD, OCALA, FL, 3448...
Community: On Top of the World
The Villages® 693 CONGAREE LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163
$645,000

3 beds

|

2 baths

|

2,029 sq ft

|

House

693 CONGAREE LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
Kings Ridge 3827 WESTERHAM DR, CLERMONT, FL, 34711, Clermont, FL 34711
$299,000

2 beds

|

2 baths

|

1,465 sq ft

|

House

3827 WESTERHAM DR, CLERMONT, FL, 34711
Community: Kings Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 7577 SW 86TH CT, OCALA, FL, 34481, Ocala, FL 34481
$329,900

2 beds

|

2 baths

|

1,747 sq ft

|

House

7577 SW 86TH CT, OCALA, FL, 34481
Community: On Top of the World
Spruce Creek Country Club 9029 SE 135TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$274,900

2 beds

|

2 baths

|

1,445 sq ft

|

House

9029 SE 135TH LOOP, SUMMERFIELD, FL, 344...
Plantation at Leesburg 4514 RIVER RIDGE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,500

3 beds

|

2 baths

|

1,785 sq ft

|

House

4514 RIVER RIDGE DR, LEESBURG, FL, 34748
Spruce Creek Country Club 9049 SE 135TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$290,000

3 beds

|

2 baths

|

1,840 sq ft

|

House

9049 SE 135TH LOOP, SUMMERFIELD, FL, 344...
Twin Lakes 5081 TWIN LAKES BLVD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$489,999

3 beds

|

3 baths

|

2,208 sq ft

|

House

5081 TWIN LAKES BLVD, SAINT CLOUD, FL, 3...
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.
Kings Ridge 3684 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$339,900

3 beds

|

2 baths

|

1,552 sq ft

|

House

3684 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
New Sun City Center 2127 HAILSTONE CIR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$198,000

2 beds

|

2 baths

|

1,264 sq ft

|

Condo

2127 HAILSTONE CIR, SUN CITY CENTER, FL,...
Community: Sun City Center
Palm Cay 11153 SW 79TH AVE, OCALA, FL, 34476, Ocala, FL 34476
$214,000

3 beds

|

2 baths

|

1,646 sq ft

|

House

11153 SW 79TH AVE, OCALA, FL, 34476
Community: Palm Cay
New The Villages® 3343 SHELBY ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$314,900

3 beds

|

2 baths

|

1,240 sq ft

|

House

3343 SHELBY ST, THE VILLAGES, FL, 32162
Community: The Villages®
Quail Meadow 4886 NW 30TH PL, OCALA, FL, 34482, Ocala, FL 34482
$319,900

3 beds

|

2 baths

|

1,442 sq ft

|

House

4886 NW 30TH PL, OCALA, FL, 34482
Community: Quail Meadow
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 9541 SW 93RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$229,900

2 beds

|

2 baths

|

1,394 sq ft

|

House

9541 SW 93RD LOOP, OCALA, FL, 34481
Community: On Top of the World
Marco Polo Village 5220 SW 114TH STREET RD, OCALA, FL, 3447..., Ocala, FL 34476
$369,000

4 beds

|

2 baths

|

2,120 sq ft

|

House

5220 SW 114TH STREET RD, OCALA, FL, 3447...
Community: Marco Polo Village
New Sun City Center 615 ALLEGHENY DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$289,000

3 beds

|

2 baths

|

1,550 sq ft

|

House

615 ALLEGHENY DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
On Top of the World 9481 SW 93RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$239,900

3 beds

|

2 baths

|

1,573 sq ft

|

House

9481 SW 93RD LOOP, OCALA, FL, 34481
Community: On Top of the World
Oak Run 8440 SW 108TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$245,000

3 beds

|

2 baths

|

1,989 sq ft

|

House

8440 SW 108TH LOOP, OCALA, FL, 34481
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.
The Villages® 1469 KNUDSON RUN, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$685,000

3 beds

|

2 baths

|

2,303 sq ft

|

House

1469 KNUDSON RUN, THE VILLAGES, FL, 3216...
Community: The Villages®
Stone Creek 9090 SW 73RD LN, OCALA, FL, 34481, Ocala, FL 34481
$339,900

2 beds

|

2 baths

|

1,708 sq ft

|

House

9090 SW 73RD LN, OCALA, FL, 34481
Community: Stone Creek
Highland Lakes 26823 FOREST HILLS ST, LEESBURG, FL, 347..., Leesburg, FL 34748
$244,000

2 beds

|

2 baths

|

1,380 sq ft

|

House

26823 FOREST HILLS ST, LEESBURG, FL, 347...
Community: Highland Lakes
Cherrywood 10274 SW 61ST TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$179,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

10274 SW 61ST TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
The Villages® 8069 SE 174TH LUDLOW PL, THE VILLAGES, F..., The Villages, FL 32162
$360,000

3 beds

|

2 baths

|

1,481 sq ft

|

House

8069 SE 174TH LUDLOW PL, THE VILLAGES, F...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 2317 WHISPER ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$239,000

1 beds

|

1 baths

|

991 sq ft

|

Villa

2317 WHISPER ST, THE VILLAGES, FL, 32162
Community: The Villages®
Royal Highlands 5644 SIR CHURCHILL DR, LEESBURG, FL, 347..., Leesburg, FL 34748
$389,900

3 beds

|

2 baths

|

1,977 sq ft

|

House

5644 SIR CHURCHILL DR, LEESBURG, FL, 347...
Community: Royal Highlands
Spruce Creek Country Club 13828 SE 85TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$239,900

2 beds

|

2 baths

|

1,315 sq ft

|

House

13828 SE 85TH CIR, SUMMERFIELD, FL, 3449...
On Top of the World 6203 SW 93RD LOOP, OCALA, FL, 34476, Ocala, FL 34476
$312,999

4 beds

|

2 baths

|

2,034 sq ft

|

House

6203 SW 93RD LOOP, OCALA, FL, 34476
Community: On Top of the World
Oak Run 11598 SW 74TH CT, OCALA, FL, 34476, Ocala, FL 34476
$322,000

3 beds

|

2 baths

|

1,593 sq ft

|

House

11598 SW 74TH CT, 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.
Venetian Bay 424 LUNA BELLA LN 327, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168
$250,000

2 beds

|

2 baths

|

1,575 sq ft

|

Condo

424 LUNA BELLA LN 327, NEW SMYRNA BEACH,...
Community: Venetian Bay
The Villages® 1522 HILLCREST DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$159,000

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

1522 HILLCREST DR, LADY LAKE, FL, 32159
Community: The Villages®
Solivita 1192 VIA GALUPPI ST, POINCIANA, FL, 3475..., Poinciana, FL 34759
$365,000

3 beds

|

2 baths

|

1,723 sq ft

|

House

1192 VIA GALUPPI ST, POINCIANA, FL, 3475...
Community: Solivita
Windermere 707 PEEBLES CT, INVERNESS, FL, 34453, Inverness, FL 34453
$249,000

3 beds

|

3 baths

|

2,012 sq ft

|

Townhouse

707 PEEBLES CT, INVERNESS, FL, 34453
Community: Windermere
Spruce Creek Country Club 13944 SE 96TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$448,900

3 beds

|

2 baths

|

2,120 sq ft

|

House

13944 SE 96TH CIR, SUMMERFIELD, FL, 3449...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Royal Highlands 21242 BRAVEHEART DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$285,900

3 beds

|

2 baths

|

1,943 sq ft

|

House

21242 BRAVEHEART DR, LEESBURG, FL, 34748
Community: Royal Highlands
Southshore Bay 17249 STAR BANKS ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$410,000

3 beds

|

3 baths

|

2,128 sq ft

|

House

17249 STAR BANKS ST, WIMAUMA, FL, 33598
Community: Southshore Bay
Sun City Center 301 KINGS BLVD 130, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$93,600

1 beds

|

2 baths

|

800 sq ft

|

Condo

301 KINGS BLVD 130, SUN CITY CENTER, FL,...
Community: Sun City Center
Sun City Center 2501 SAPPHIRE GREENS LN, SUN CITY CENTER..., Sun City Center, FL 33573
$340,000

2 beds

|

2 baths

|

1,493 sq ft

|

Condo

2501 SAPPHIRE GREENS LN, SUN CITY CENTER...
Community: Sun City Center
Cherrywood 9948 SW 62ND AVE, OCALA, FL, 34476, Ocala, FL 34476
$269,900

3 beds

|

2 baths

|

1,494 sq ft

|

House

9948 SW 62ND AVE, OCALA, FL, 34476
Community: Cherrywood

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3,573 homes near Winter Garden
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