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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!
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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
$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
The Lakes at Harmony 3156 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773
$399,990

2 beds

|

2 baths

|

1,423 sq ft

|

House

3156 SONGBIRD CIR, HARMONY, FL, 34773
Stone Creek 9584 SW 71ST LOOP, OCALA, FL, 34481, Ocala, FL 34481
$380,000

3 beds

|

2 baths

|

2,122 sq ft

|

House

9584 SW 71ST LOOP, OCALA, FL, 34481
Community: Stone Creek
Baytree 317 BAYTREE BLVD, TAVARES, FL, 32778, Tavares, FL 32778
$345,000

3 beds

|

2 baths

|

1,568 sq ft

|

House

317 BAYTREE BLVD, TAVARES, FL, 32778
Community: Baytree
The Villages® 17773 SE 90TH CLEMSON CIR, THE VILLAGES,..., The Villages, FL 32162
$369,900

3 beds

|

2 baths

|

1,662 sq ft

|

House

17773 SE 90TH CLEMSON CIR, THE VILLAGES,...
Community: The Villages®
The Villages® 5600 MCCRAY AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$289,900

2 beds

|

2 baths

|

1,203 sq ft

|

Villa

5600 MCCRAY AVE, THE VILLAGES, FL, 32163
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8895 SW 86TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$525,000

3 beds

|

3 baths

|

3,371 sq ft

|

House

8895 SW 86TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Ocala Preserve 4135 NW 55TH CT, OCALA, FL, 34482, Ocala, FL 34482
$485,000

2 beds

|

3 baths

|

2,069 sq ft

|

House

4135 NW 55TH CT, OCALA, FL, 34482
Community: Ocala Preserve
The Villages® 3223 SYLEWOOD AVE, THE VILLAGES, FL, 321..., The Villages, FL 32163
$530,000

3 beds

|

2 baths

|

1,965 sq ft

|

House

3223 SYLEWOOD AVE, THE VILLAGES, FL, 321...
Community: The Villages®
Plantation at Leesburg 25030 LAUREL VALLEY RD, LEESBURG, FL, 34..., Leesburg, FL 34748
$369,000

2 beds

|

2 baths

|

2,163 sq ft

|

House

25030 LAUREL VALLEY RD, LEESBURG, FL, 34...
Alhambra Villas Condominiums 183 N HILL AVE # 90, DELAND, FL, 32724, Deland, FL 32724
$188,000

2 beds

|

2 baths

|

979 sq ft

|

Condo

183 N HILL AVE # 90, DELAND, FL, 32724
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® 859 AMBER CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$340,000

3 beds

|

2 baths

|

1,357 sq ft

|

Villa

859 AMBER CT, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 1169 CALGARY ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$340,000

2 beds

|

2 baths

|

1,220 sq ft

|

House

1169 CALGARY ST, THE VILLAGES, FL, 32163
Community: The Villages®
New Lake Ashton 3834 LITCHFIELD LOOP, LAKE WALES, FL, 33..., Lake Wales, FL 33859
$599,900

2 beds

|

2 baths

|

1,792 sq ft

|

House

3834 LITCHFIELD LOOP, LAKE WALES, FL, 33...
Community: Lake Ashton
Venetian Bay 513 LUNA BELLA LN, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$789,000

4 beds

|

3 baths

|

2,900 sq ft

|

House

513 LUNA BELLA LN, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
The Villages® 1329 GASTON LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$485,000

3 beds

|

2 baths

|

2,000 sq ft

|

House

1329 GASTON LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 2145 ACADIA GREENS DR # AC144, SUN CITY ..., Sun City Center, FL 33573
$265,000

2 beds

|

2 baths

|

1,194 sq ft

|

Condo

2145 ACADIA GREENS DR # AC144, SUN CITY ...
Community: Sun City Center
The Villages® 1357 GREENVILLE WAY, THE VILLAGES, FL, 3..., The Villages, FL 32162
$375,000

3 beds

|

2 baths

|

1,490 sq ft

|

House

1357 GREENVILLE WAY, THE VILLAGES, FL, 3...
Community: The Villages®
Oakview 1518 OAKVIEW CIR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33880
$226,650

2 beds

|

2 baths

|

1,438 sq ft

|

House

1518 OAKVIEW CIR, WINTER HAVEN, FL, 3388...
Community: Oakview
On Top of the World 9077 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$219,900

2 beds

|

2 baths

|

1,569 sq ft

|

House

9077 SW 91ST CIR, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 1936 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$339,000

3 beds

|

2 baths

|

2,261 sq ft

|

House

1936 NEW BEDFORD DR, SUN CITY CENTER, FL...
Community: Sun City Center
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.
Marion Landing 8532 SW 65TH COURT RD, OCALA, FL, 34476, Ocala, FL 34476
$262,800

3 beds

|

2 baths

|

1,817 sq ft

|

House

8532 SW 65TH COURT RD, OCALA, FL, 34476
Community: Marion Landing
The Villages® 718 VILLITA LN, THE VILLAGES, FL, 32159, The Villages, FL 32159
$225,000

1 beds

|

1 baths

|

920 sq ft

|

House

718 VILLITA LN, THE VILLAGES, FL, 32159
Community: The Villages®
On Top of the World 10418 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$375,000

2 beds

|

2 baths

|

1,651 sq ft

|

House

10418 SW 92ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World
Stonecrest 17209 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491
$354,900

2 beds

|

2 baths

|

1,695 sq ft

|

House

17209 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
The Villages® 674 CAMINO DEL REY DR, THE VILLAGES, FL,..., The Villages, FL 32159
$310,000

2 beds

|

2 baths

|

1,148 sq ft

|

House

674 CAMINO DEL REY DR, THE VILLAGES, FL,...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Marion Landing 6897 SW 87TH ST, OCALA, FL, 34476, Ocala, FL 34476
$389,185

4 beds

|

3 baths

|

2,571 sq ft

|

House

6897 SW 87TH ST, OCALA, FL, 34476
Community: Marion Landing
On Top of the World 8620 SW 94TH ST G, OCALA, FL, 34481, Ocala, FL 34481
$229,000

2 beds

|

2 baths

|

1,409 sq ft

|

Villa

8620 SW 94TH ST G, OCALA, FL, 34481
Community: On Top of the World
Stone Creek 9125 SW 57TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$781,250

3 beds

|

4 baths

|

2,955 sq ft

|

House

9125 SW 57TH PLACE RD, OCALA, FL, 34481
Community: Stone Creek
Sun City Center 1811 BEDFORD LN APT 163, SUN CITY CENTER..., Sun City Center, FL 33573
$98,500

1 beds

|

2 baths

|

800 sq ft

|

Condo

1811 BEDFORD LN APT 163, SUN CITY CENTER...
Community: Sun City Center
The Villages® 632 DELGADO AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$409,000

2 beds

|

2 baths

|

1,139 sq ft

|

Villa

632 DELGADO AVE, LADY LAKE, FL, 32159
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.
Plantation at Leesburg 24817 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$269,900

2 beds

|

2 baths

|

1,837 sq ft

|

House

24817 CRANES ROOST CIR, LEESBURG, FL, 34...
Arlington Ridge 26925 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$239,000

2 beds

|

2 baths

|

1,254 sq ft

|

Villa

26925 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
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®
The Villages® 3473 STERLING ST, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$589,500

3 beds

|

2 baths

|

1,920 sq ft

|

House

3473 STERLING ST, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 415 LOMA PASEO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$375,000

3 beds

|

2 baths

|

1,858 sq ft

|

House

415 LOMA PASEO DR, THE VILLAGES, FL, 321...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8446 SW 86TH TER, OCALA, FL, 34481, Ocala, FL 34481
$249,000

3 beds

|

2 baths

|

1,734 sq ft

|

House

8446 SW 86TH TER, OCALA, FL, 34481
Community: On Top of the World
Royal Highlands 21524 QUEEN ANNE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$320,000

3 beds

|

2 baths

|

2,031 sq ft

|

House

21524 QUEEN ANNE CT, LEESBURG, FL, 34748
Community: Royal Highlands
Highland Fairways 2206 GOLDEN HORSESHOE CIR, LAKELAND, FL,..., Lakeland, FL 33810
$190,000

2 beds

|

2 baths

|

1,274 sq ft

|

Manufactured Home

2206 GOLDEN HORSESHOE CIR, LAKELAND, FL,...
Community: Highland Fairways
Stonecrest 17783 SE 113TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$284,500

2 beds

|

2 baths

|

1,248 sq ft

|

House

17783 SE 113TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
On Top of the World 8824 SW 104TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$349,000

2 beds

|

2 baths

|

1,983 sq ft

|

House

8824 SW 104TH CIR, OCALA, FL, 34481
Community: On Top of the World

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3,631 homes near Winter Garden
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