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

3,648 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 - $500Ks
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
<$100k - $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 - $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
$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
$300Ks - $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 - $500Ks
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
<$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
Sun City Center 405 GLADSTONE PL, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$175,000

2 beds

|

2 baths

|

1,008 sq ft

|

Condo

405 GLADSTONE PL, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Sun City Center 334 NORTHWAY DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$407,800

2 beds

|

2 baths

|

1,960 sq ft

|

House

334 NORTHWAY DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
The Villages® 17718 SE 81ST WYNSTONE AVE, THE VILLAGES..., The Villages, FL 32162
$339,900

3 beds

|

2 baths

|

1,496 sq ft

|

House

17718 SE 81ST WYNSTONE AVE, THE VILLAGES...
Community: The Villages®
Esplanade at Highland Ranch 1339 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715
$630,000

3 beds

|

3 baths

|

2,449 sq ft

|

House

1339 ZEEK RIDGE ST, CLERMONT, FL, 34715
Serenity Reserve 2335 SYMPHONY CIR, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34771
$645,000

3 beds

|

4 baths

|

2,625 sq ft

|

House

2335 SYMPHONY CIR, SAINT CLOUD, FL, 3477...
Community: Serenity Reserve
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Oak Run 8297 SW 108TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$197,750

2 beds

|

2 baths

|

1,645 sq ft

|

House

8297 SW 108TH LOOP, OCALA, FL, 34481
Community: Oak Run
Cherrywood 10583 SW 62ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$234,900

2 beds

|

2 baths

|

1,444 sq ft

|

House

10583 SW 62ND TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
Latitude Margaritaville 842 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$679,900

2 beds

|

3 baths

|

2,310 sq ft

|

House

842 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
Stone Creek 9646 SW 67TH ST, OCALA, FL, 34481, Ocala, FL 34481
$535,000

2 beds

|

2 baths

|

2,039 sq ft

|

House

9646 SW 67TH ST, OCALA, FL, 34481
Community: Stone Creek
Mirada 31921 MAGNA GULF LOOP, SAN ANTONIO, FL, ..., San Antonio, FL 33576
$496,990

3 beds

|

3 baths

|

2,231 sq ft

|

House

31921 MAGNA GULF LOOP, SAN ANTONIO, FL, ...
Community: Mirada
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.
Lake Jovita Golf and Country Club 13141 PALMILLA CIR, DADE CITY, FL, 33525, Dade City, FL 33525
$449,900

2 beds

|

2 baths

|

2,019 sq ft

|

Villa

13141 PALMILLA CIR, DADE CITY, FL, 33525
The Villages® 17364 SE 74TH SEABROOK CT, THE VILLAGES,..., The Villages, FL 32162
$239,900

2 beds

|

2 baths

|

1,353 sq ft

|

House

17364 SE 74TH SEABROOK CT, THE VILLAGES,...
Community: The Villages®
The Villages® 849 YEMASSEE LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32162
$418,000

3 beds

|

2 baths

|

1,512 sq ft

|

House

849 YEMASSEE LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 9671 SE 168TH MAPLESONG LN, THE VILLAGES..., The Villages, FL 32162
$369,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

9671 SE 168TH MAPLESONG LN, THE VILLAGES...
Community: The Villages®
Oak Run 8239 SW 108TH ST, OCALA, FL, 34481, Ocala, FL 34481
$198,900

2 beds

|

2 baths

|

1,354 sq ft

|

House

8239 SW 108TH ST, 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
Summer Trees 79 CYPRESS POND RD # 79, PORT ORANGE, FL..., Port Orange, FL 32128
$227,000

2 beds

|

2 baths

|

888 sq ft

|

Condo

79 CYPRESS POND RD # 79, PORT ORANGE, FL...
Community: Summer Trees
Baytree 100 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778
$239,500

2 beds

|

2 baths

|

1,312 sq ft

|

Villa

100 JUNIPER WAY, TAVARES, FL, 32778
Community: Baytree
The Villages® 1007 ALOHA WAY, THE VILLAGES, FL, 32159, The Villages, FL 32159
$149,400

2 beds

|

2 baths

|

1,152 sq ft

|

Mobile Home

1007 ALOHA WAY, THE VILLAGES, FL, 32159
Community: The Villages®
Sullivan Ranch 22035 BELGIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$325,000

3 beds

|

2 baths

|

1,663 sq ft

|

Villa

22035 BELGIAN CT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Stonecrest 12125 SE 175TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$299,900

3 beds

|

2 baths

|

1,695 sq ft

|

House

12125 SE 175TH ST, 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 15913 SE 101ST CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$281,070

4 beds

|

2 baths

|

1,498 sq ft

|

House

15913 SE 101ST CIR, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Ocala Palms 2218 NW 50TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$244,900

2 beds

|

2 baths

|

1,544 sq ft

|

House

2218 NW 50TH AVE, OCALA, FL, 34482
Community: Ocala Palms
On Top of the World 10347 SW 99TH LN, OCALA, FL, 34481, Ocala, FL 34481
$295,000

2 beds

|

2 baths

|

1,467 sq ft

|

House

10347 SW 99TH LN, OCALA, FL, 34481
Community: On Top of the World
Lake Jovita Golf and Country Club 13922 CARRYBACK DR, DADE CITY, FL, 33525, Dade City, FL 33525
$1,450,000

3 beds

|

4 baths

|

3,174 sq ft

|

House

13922 CARRYBACK DR, DADE CITY, FL, 33525
Royal Palm 5415 SWORDFERN CT, PORT ORANGE, FL, 3212..., Port Orange, FL 32128
$429,900

3 beds

|

3 baths

|

1,942 sq ft

|

House

5415 SWORDFERN CT, PORT ORANGE, FL, 3212...
Community: Royal Palm
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Royal Highlands 21937 KING ALFRED ST, LEESBURG, FL, 3474..., Leesburg, FL 34748
$550,000

5 beds

|

3 baths

|

3,422 sq ft

|

House

21937 KING ALFRED ST, LEESBURG, FL, 3474...
Community: Royal Highlands
The Villages® 622 JENNIFER DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$169,900

2 beds

|

1 baths

|

936 sq ft

|

Manufactured Home

622 JENNIFER DR, THE VILLAGES, FL, 32159
Community: The Villages®
On Top of the World 9707 SW 79TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$492,294

3 beds

|

2 baths

|

2,659 sq ft

|

House

9707 SW 79TH LANE RD, OCALA, FL, 34481
Community: On Top of the World
Venetian Bay 426 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$356,800

3 beds

|

3 baths

|

1,779 sq ft

|

House

426 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
The Villages® 3328 DAVIS TER, THE VILLAGES, FL, 32163, The Villages, FL 32163
$310,000

2 beds

|

2 baths

|

1,240 sq ft

|

House

3328 DAVIS TER, THE VILLAGES, FL, 32163
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.
Sun City Center 1013 RICKENBACKER DR, SUN CITY CENTER, F..., Sun City Center, FL 33573
$230,000

2 beds

|

2 baths

|

1,318 sq ft

|

Villa

1013 RICKENBACKER DR, SUN CITY CENTER, F...
Community: Sun City Center
The Villages® 520 SAINT ANDREWS BLVD, THE VILLAGES, FL..., The Villages, FL 32159
$219,900

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

520 SAINT ANDREWS BLVD, THE VILLAGES, FL...
Community: The Villages®
The Villages® 3261 WISE WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163
$799,000

3 beds

|

3 baths

|

2,376 sq ft

|

House

3261 WISE WAY, THE VILLAGES, FL, 32163
Community: The Villages®
Venetian Bay 112 PORTOFINO BLVD, NEW SMYRNA BEACH, FL..., New Smyrna Beach, FL 32168
$719,000

3 beds

|

2 baths

|

2,372 sq ft

|

House

112 PORTOFINO BLVD, NEW SMYRNA BEACH, FL...
Community: Venetian Bay
Pelican Bay Daytona Beach 156 KINGBIRD CIR 2120, DAYTONA BEACH, FL..., Daytona Beach, FL 32119
$229,000

2 beds

|

2 baths

|

1,732 sq ft

|

House

156 KINGBIRD CIR 2120, DAYTONA BEACH, FL...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 316 KELSEY WAY # 316, SUN CITY CENTER, F..., Sun City Center, FL 33573
$125,000

2 beds

|

2 baths

|

1,078 sq ft

|

Condo

316 KELSEY WAY # 316, SUN CITY CENTER, F...
Community: Sun City Center
Spruce Creek North 10980 SW 62ND AVE, OCALA, FL, 34476, Ocala, FL 34476
$199,900

3 beds

|

2 baths

|

1,526 sq ft

|

House

10980 SW 62ND AVE, OCALA, FL, 34476
Community: Spruce Creek North
Spruce Creek Country Club 13828 SE 85TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$249,900

2 beds

|

2 baths

|

1,315 sq ft

|

House

13828 SE 85TH CIR, SUMMERFIELD, FL, 3449...
High Vista at Ridgewood Lakes 537 RIDGE VIEW DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$350,000

2 beds

|

2 baths

|

1,797 sq ft

|

House

537 RIDGE VIEW DR, DAVENPORT, FL, 33837
The Villages® 1507 E SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$223,900

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

1507 E SCHWARTZ BLVD, LADY LAKE, FL, 321...
Community: The Villages®

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3,648 homes near Winter Garden
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