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

3,958 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
<$100k - $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.
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $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) 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
$300Ks - $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
$100Ks - $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
The Villages® 2005 PALO ALTO AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159
$339,500

2 beds

|

2 baths

|

1,567 sq ft

|

House

2005 PALO ALTO AVE, THE VILLAGES, FL, 32...
Community: The Villages®
Sandpiper Golf & Country Club 6235 EGRET DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$244,000

2 beds

|

2 baths

|

1,154 sq ft

|

House

6235 EGRET DR, LAKELAND, FL, 33809
Ocala Preserve 5365 NW 46TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$265,900

3 beds

|

2 baths

|

1,552 sq ft

|

Villa

5365 NW 46TH LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
Lake Ashton 4128 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$275,000

3 beds

|

2 baths

|

1,503 sq ft

|

House

4128 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Plantation at Leesburg 3923 MANOR OAKS CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$355,000

2 beds

|

2 baths

|

2,025 sq ft

|

House

3923 MANOR OAKS CT, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 17113 SE 78TH LARCHMONT CT, THE VILLAGES..., The Villages, FL 32162
$359,000

3 beds

|

2 baths

|

1,572 sq ft

|

Villa

17113 SE 78TH LARCHMONT CT, THE VILLAGES...
Community: The Villages®
Del Webb Orlando 672 CORDOBA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$399,900

2 beds

|

2 baths

|

1,956 sq ft

|

House

672 CORDOBA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
The Villages® 3248 KILLINGTON LOOP, THE VILLAGES, FL, ..., The Villages, FL 32163
$535,900

3 beds

|

2 baths

|

1,842 sq ft

|

House

3248 KILLINGTON LOOP, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 4318 ST STEPHEN ST, THE VILLAGES, FL, 32..., The Villages, FL 32163
$479,900

3 beds

|

2 baths

|

1,923 sq ft

|

House

4318 ST STEPHEN ST, THE VILLAGES, FL, 32...
Community: The Villages®
Plantation at Leesburg 3530 MULBERRY GROVE LOOP, LEESBURG, FL, ..., Leesburg, FL 34748
$389,900

3 beds

|

2 baths

|

2,429 sq ft

|

House

3530 MULBERRY GROVE LOOP, LEESBURG, FL, ...
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.
Stonecrest 12157 SE 175TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$359,900

3 beds

|

2 baths

|

1,666 sq ft

|

House

12157 SE 175TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Stonecrest 12333 SE 177TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$379,900

3 beds

|

2 baths

|

1,904 sq ft

|

House

12333 SE 177TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Oak Run 10970 SW 69TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$249,900

2 beds

|

2 baths

|

1,455 sq ft

|

House

10970 SW 69TH CIR, OCALA, FL, 34476
Community: Oak Run
Ocala Palms 5076 NW 21ST LOOP, OCALA, FL, 34482, Ocala, FL 34482
$284,700

3 beds

|

2 baths

|

1,704 sq ft

|

House

5076 NW 21ST LOOP, OCALA, FL, 34482
Community: Ocala Palms
Lake Ashton 6265 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$650,000

3 beds

|

2 baths

|

2,521 sq ft

|

House

6265 PINEHURST LOOP, WINTER HAVEN, FL, 3...
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1121 RICARDO AVE, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$365,000

2 beds

|

2 baths

|

1,674 sq ft

|

Villa

1121 RICARDO AVE, THE VILLAGES, FL, 3215...
Community: The Villages®
Palm Cay 10668 SW 85TH TER, OCALA, FL, 34481, Ocala, FL 34481
$239,900

3 beds

|

2 baths

|

1,404 sq ft

|

House

10668 SW 85TH TER, OCALA, FL, 34481
Community: Palm Cay
On Top of the World 9575 SW 92ND STREET RD, OCALA, FL, 34481, Ocala, FL 34481
$189,900

2 beds

|

2 baths

|

1,414 sq ft

|

House

9575 SW 92ND STREET RD, OCALA, FL, 34481
Community: On Top of the World
New Kings Ridge 2131 BURLEY AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$309,500

2 beds

|

2 baths

|

1,394 sq ft

|

House

2131 BURLEY AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Southshore Bay 17523 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$225,000

2 beds

|

2 baths

|

1,406 sq ft

|

Townhouse

17523 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
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 3325 PINTELLO AVE, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$395,000

4 beds

|

2 baths

|

1,662 sq ft

|

House

3325 PINTELLO AVE, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
On Top of the World 9068 SW 82ND TER A, OCALA, FL, 34481, Ocala, FL 34481
$254,900

2 beds

|

2 baths

|

1,891 sq ft

|

Villa

9068 SW 82ND TER A, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 10451 SW 98TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$485,000

3 beds

|

3 baths

|

2,288 sq ft

|

House

10451 SW 98TH PLACE RD, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 10556 SW 98TH LN, OCALA, FL, 34481, Ocala, FL 34481
$398,000

2 beds

|

2 baths

|

2,104 sq ft

|

House

10556 SW 98TH LN, OCALA, FL, 34481
Community: On Top of the World
Oak Run 7709 SW 86TH CT, OCALA, FL, 34481, Ocala, FL 34481
$349,000

2 beds

|

2 baths

|

1,747 sq ft

|

House

7709 SW 86TH CT, 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
New Palm Cay 8343 SW 105TH PL, OCALA, FL, 34481, Ocala, FL 34481
$155,000

2 beds

|

2 baths

|

936 sq ft

|

House

8343 SW 105TH PL, OCALA, FL, 34481
Community: Palm Cay
The Villages® 1417 AZTECA LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$299,900

2 beds

|

2 baths

|

1,228 sq ft

|

Villa

1417 AZTECA LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 859 PARKSVILLE PATH, THE VILLAGES, FL, 3..., The Villages, FL 32162
$485,000

3 beds

|

2 baths

|

2,086 sq ft

|

House

859 PARKSVILLE PATH, THE VILLAGES, FL, 3...
Community: The Villages®
Spruce Creek South 17421 SE 107TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$228,000

2 beds

|

2 baths

|

1,488 sq ft

|

House

17421 SE 107TH CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 3978 NOTTINGHAM LOOP, THE VILLAGES, FL, ..., The Villages, FL 32163
$500,000

3 beds

|

2 baths

|

1,854 sq ft

|

House

3978 NOTTINGHAM LOOP, THE VILLAGES, FL, ...
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.
Foxwood Lake Estates 1602 TALLY HO DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$169,500

2 beds

|

2 baths

|

1,488 sq ft

|

Manufactured Home

1602 TALLY HO DR, LAKELAND, FL, 33810
The Villages® 2712 PLAINRIDGE LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162
$434,900

3 beds

|

2 baths

|

1,572 sq ft

|

House

2712 PLAINRIDGE LOOP, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 3112 BURBANK LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$445,000

3 beds

|

2 baths

|

2,133 sq ft

|

House

3112 BURBANK LN, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 648 MISSION HILLS TRL, THE VILLAGES, FL,..., The Villages, FL 32162
$499,000

3 beds

|

2 baths

|

1,955 sq ft

|

Villa

648 MISSION HILLS TRL, THE VILLAGES, FL,...
Community: The Villages®
Latitude Margaritaville 329 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$510,000

3 beds

|

2 baths

|

1,563 sq ft

|

Villa

329 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 3396 GREENACRES TER, THE VILLAGES, FL, 3..., The Villages, FL 32163
$349,000

3 beds

|

2 baths

|

1,351 sq ft

|

House

3396 GREENACRES TER, THE VILLAGES, FL, 3...
Community: The Villages®
Spruce Creek South 17985 SE 102ND CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$269,900

3 beds

|

2 baths

|

1,498 sq ft

|

House

17985 SE 102ND CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 728 RAMIREZ AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$314,000

2 beds

|

2 baths

|

1,094 sq ft

|

Villa

728 RAMIREZ AVE, THE VILLAGES, FL, 32159
Community: The Villages®
On Top of the World 9728 SW 94TH AVE D, OCALA, FL, 34481, Ocala, FL 34481
$174,900

2 beds

|

2 baths

|

1,215 sq ft

|

Villa

9728 SW 94TH AVE D, OCALA, FL, 34481
Community: On Top of the World
Highland Fairways 1847 MASTERS LN, LAKELAND, FL, 33810, Lakeland, FL 33810
$229,900

3 beds

|

2 baths

|

1,724 sq ft

|

House

1847 MASTERS LN, LAKELAND, FL, 33810
Community: Highland Fairways

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3,958 homes near Winter Garden
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