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

3,631 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 - $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 (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
$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
$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
$200Ks - $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 - $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 - $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
On Top of the World 9996 SW 88TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$279,900

2 beds

|

2 baths

|

1,495 sq ft

|

House

9996 SW 88TH LOOP, OCALA, FL, 34481
Community: On Top of the World
The Villages® 2457 UPTON ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$289,000

2 beds

|

2 baths

|

1,156 sq ft

|

House

2457 UPTON ST, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 1884 POPPY CIR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$385,000

3 beds

|

2 baths

|

1,512 sq ft

|

House

1884 POPPY CIR, THE VILLAGES, FL, 32162
Community: The Villages®
Sun City Center 1805 BUTTERFLY PL, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$315,000

2 beds

|

2 baths

|

1,516 sq ft

|

House

1805 BUTTERFLY PL, SUN CITY CENTER, FL, ...
Community: Sun City Center
Stone Creek 9178 SW 65TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$419,797

3 beds

|

2 baths

|

1,873 sq ft

|

House

9178 SW 65TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Marion Landing 8480 SW 61ST TERRACE RD, OCALA, FL, 3447..., Ocala, FL 34476
$239,900

2 beds

|

2 baths

|

1,582 sq ft

|

House

8480 SW 61ST TERRACE RD, OCALA, FL, 3447...
Community: Marion Landing
The Villages® 3031 HICKS PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$800,000

4 beds

|

3 baths

|

2,248 sq ft

|

House

3031 HICKS PL, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 1952 PALO ALTO AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159
$524,900

2 beds

|

2 baths

|

2,162 sq ft

|

House

1952 PALO ALTO AVE, THE VILLAGES, FL, 32...
Community: The Villages®
Del Webb Sunbridge 2587 CLIFF WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$429,900

2 beds

|

2 baths

|

1,401 sq ft

|

House

2587 CLIFF WAY, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
The Villages® 2557 PRIVADA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$309,000

2 beds

|

2 baths

|

1,232 sq ft

|

House

2557 PRIVADA DR, THE VILLAGES, FL, 32162
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.
The Villages® 2530 HANLON TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$344,000

3 beds

|

2 baths

|

1,724 sq ft

|

House

2530 HANLON TER, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1762 MEADOWLARK AVE, THE VILLAGES, FL, 3..., The Villages, FL 32162
$335,000

3 beds

|

2 baths

|

1,392 sq ft

|

Villa

1762 MEADOWLARK AVE, THE VILLAGES, FL, 3...
Community: The Villages®
Palm Cay 8326 SW 107TH PL, OCALA, FL, 34481, Ocala, FL 34481
$205,000

3 beds

|

2 baths

|

1,404 sq ft

|

House

8326 SW 107TH PL, OCALA, FL, 34481
Community: Palm Cay
The Villages® 301 PACOLET TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$349,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

301 PACOLET TER, THE VILLAGES, FL, 32162
Community: The Villages®
Ocala Preserve 3335 NW 52ND AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$257,585

2 beds

|

3 baths

|

1,706 sq ft

|

Halfplex

3335 NW 52ND AVENUE RD, OCALA, FL, 34482
Community: Ocala Preserve
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 3057 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$309,900

3 beds

|

3 baths

|

1,614 sq ft

|

Townhouse

3057 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Stone Creek 6094 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$330,000

3 beds

|

2 baths

|

1,587 sq ft

|

House

6094 SW 93RD CIR, OCALA, FL, 34481
Community: Stone Creek
Carillon Lakes 3102 BELLFLOWER WAY, LAKELAND, FL, 33811, Lakeland, FL 33811
$313,000

3 beds

|

2 baths

|

1,434 sq ft

|

House

3102 BELLFLOWER WAY, LAKELAND, FL, 33811
Community: Carillon Lakes
On Top of the World 9033 SW 78TH STREET RD, OCALA, FL, 34481, Ocala, FL 34481
$374,900

3 beds

|

2 baths

|

1,958 sq ft

|

House

9033 SW 78TH STREET RD, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8755 SW 79TH PL, OCALA, FL, 34481, Ocala, FL 34481
$399,900

3 beds

|

2 baths

|

2,126 sq ft

|

House

8755 SW 79TH PL, OCALA, FL, 34481
Community: On Top of the World
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.
Sandpiper Golf & Country Club 6059 CONDOR DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$375,000

3 beds

|

2 baths

|

2,195 sq ft

|

House

6059 CONDOR DR, LAKELAND, FL, 33809
On Top of the World 9662 SW 97TH LN, OCALA, FL, 34481, Ocala, FL 34481
$237,000

3 beds

|

2 baths

|

1,742 sq ft

|

House

9662 SW 97TH LN, OCALA, FL, 34481
Community: On Top of the World
Majestic Oaks Ocala 4311 SW 82ND LN, OCALA, FL, 34476, Ocala, FL 34476
$327,290

5 beds

|

3 baths

|

2,449 sq ft

|

House

4311 SW 82ND LN, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Lakeside Landings 10161 MAINSAIL DR, OXFORD, FL, 34484, Oxford, FL 34484
$319,000

3 beds

|

2 baths

|

1,550 sq ft

|

Villa

10161 MAINSAIL DR, OXFORD, FL, 34484
Community: Lakeside Landings
Legacy of Leesburg 5725 CELEBRATION WAY, LEESBURG, FL, 3474..., Leesburg, FL 34748
$335,000

3 beds

|

2 baths

|

1,732 sq ft

|

House

5725 CELEBRATION WAY, LEESBURG, FL, 3474...
Community: Legacy of Leesburg
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Del Webb Orlando 507 CADIZ DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$428,900

4 beds

|

3 baths

|

2,616 sq ft

|

House

507 CADIZ DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
SummerGlen 3970 SW 157TH PLACE RD, OCALA, FL, 34473, Ocala, FL 34473
$342,990

4 beds

|

3 baths

|

1,952 sq ft

|

House

3970 SW 157TH PLACE RD, OCALA, FL, 34473
Community: SummerGlen
Lake Ashton 4496 STRATHMORE DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$419,900

3 beds

|

2 baths

|

2,312 sq ft

|

House

4496 STRATHMORE DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
Valencia Lakes 16244 DIAMOND BAY DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$525,000

3 beds

|

3 baths

|

2,436 sq ft

|

House

16244 DIAMOND BAY DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Stonecrest 17680 SE 121ST CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$253,600

2 beds

|

2 baths

|

1,581 sq ft

|

House

17680 SE 121ST CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
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 17583 SE 96TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$214,900

2 beds

|

2 baths

|

1,008 sq ft

|

House

17583 SE 96TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Palm Cay 10141 SW 106TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$395,000

2 beds

|

2 baths

|

2,142 sq ft

|

House

10141 SW 106TH CIR, OCALA, FL, 34481
Community: Palm Cay
Stonecrest 17354 SE 112TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$430,000

3 beds

|

2 baths

|

2,114 sq ft

|

House

17354 SE 112TH COURT RD, SUMMERFIELD, FL...
Community: Stonecrest
The Villages® 1380 TALLOWTREE DR, THE VILLAGES, FL, 32..., The Villages, FL 32162
$270,000

3 beds

|

2 baths

|

1,240 sq ft

|

House

1380 TALLOWTREE DR, THE VILLAGES, FL, 32...
Community: The Villages®
Oak Run 8031 SW 108TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$229,500

2 beds

|

2 baths

|

1,433 sq ft

|

House

8031 SW 108TH LOOP, 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
Stone Creek 6832 SW 93RD AVE, OCALA, FL, 34481, Ocala, FL 34481
$374,900

3 beds

|

2 baths

|

1,714 sq ft

|

House

6832 SW 93RD AVE, OCALA, FL, 34481
Community: Stone Creek
New Ocala Palms 2199 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$325,000

3 beds

|

2 baths

|

1,822 sq ft

|

House

2199 NW 50TH CIR, OCALA, FL, 34482
Community: Ocala Palms
On Top of the World 8841 SW 79TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$369,900

2 beds

|

2 baths

|

1,767 sq ft

|

House

8841 SW 79TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Breakaway Trails 3 CROOKED BRIDGE WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174
$625,000

5 beds

|

5 baths

|

3,171 sq ft

|

House

3 CROOKED BRIDGE WAY, ORMOND BEACH, FL, ...
Community: Breakaway Trails
Windermere 820 LANARK DR, INVERNESS, FL, 34453, Inverness, FL 34453
$220,000

2 beds

|

2 baths

|

1,169 sq ft

|

House

820 LANARK DR, INVERNESS, FL, 34453
Community: Windermere

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3,631 homes near Winter Garden
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