Call us at (689) 407-5757 to learn more about active adult communities near Winter Garden

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

3,573 homes near Winter Garden

Sort by:

Relevance

Relevance

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 9880 SW 88TH TER B, OCALA, FL, 34481, Ocala, FL 34481
$255,000

2 beds

|

2 baths

|

1,748 sq ft

|

Villa

9880 SW 88TH TER B, OCALA, FL, 34481
Community: On Top of the World
Valencia Lakes 16233 AMETHYST KEY DR, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$265,000

2 beds

|

2 baths

|

1,317 sq ft

|

Villa

16233 AMETHYST KEY DR, WIMAUMA, FL, 3359...
Community: Valencia Lakes
Valencia Lakes 15731 CRYSTAL WATERS DR, WIMAUMA, FL, 33..., Wimauma, FL 33598
$400,000

3 beds

|

2 baths

|

1,986 sq ft

|

House

15731 CRYSTAL WATERS DR, WIMAUMA, FL, 33...
Community: Valencia Lakes
Valencia Lakes 16106 CEDAR KEY DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$549,000

4 beds

|

3 baths

|

2,467 sq ft

|

House

16106 CEDAR KEY DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Valencia Lakes 4821 GRAND BANKS DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$525,000

3 beds

|

3 baths

|

2,268 sq ft

|

House

4821 GRAND BANKS DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stonecrest 17652 SE 120TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$439,900

3 beds

|

2 baths

|

2,067 sq ft

|

House

17652 SE 120TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
On Top of the World 6677 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$205,000

3 beds

|

3 baths

|

1,458 sq ft

|

Townhouse

6677 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
Spruce Creek Country Club 9464 SE 132ND LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$227,500

1 beds

|

2 baths

|

1,020 sq ft

|

House

9464 SE 132ND LOOP, SUMMERFIELD, FL, 344...
On Top of the World 8457 SW 97TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$489,900

2 beds

|

2 baths

|

2,097 sq ft

|

House

8457 SW 97TH CIR, OCALA, FL, 34481
Community: On Top of the World
Spruce Creek Country Club 13729 SE 89TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$275,900

3 beds

|

2 baths

|

1,760 sq ft

|

House

13729 SE 89TH AVE, SUMMERFIELD, FL, 3449...
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 2327 PLATINUM DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$569,000

3 beds

|

2 baths

|

2,202 sq ft

|

House

2327 PLATINUM DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Venetian Bay 569 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$369,900

2 beds

|

2 baths

|

1,272 sq ft

|

House

569 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
Breakaway Trails 6 BLACK PINE WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$729,000

4 beds

|

4 baths

|

3,289 sq ft

|

House

6 BLACK PINE WAY, ORMOND BEACH, FL, 3217...
Community: Breakaway Trails
Solivita 159 OLYMPUS WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$405,000

3 beds

|

2 baths

|

1,730 sq ft

|

House

159 OLYMPUS WAY, KISSIMMEE, FL, 34759
Community: Solivita
Latitude Margaritaville 306 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$475,000

2 beds

|

2 baths

|

1,509 sq ft

|

Townhouse

306 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 182 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124
$685,699

3 beds

|

3 baths

|

2,303 sq ft

|

House

182 ISLAND BREEZE AVE, DAYTONA BEACH, FL...
Spruce Creek South 10783 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$214,500

2 beds

|

2 baths

|

1,144 sq ft

|

House

10783 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Colonnades 4846 COLONNADES CLUB BLVD, LAKELAND, FL,..., Lakeland, FL 33811
$257,000

2 beds

|

2 baths

|

1,534 sq ft

|

House

4846 COLONNADES CLUB BLVD, LAKELAND, FL,...
Community: Colonnades
The Villages® 932 MEDIRA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$419,500

2 beds

|

2 baths

|

1,732 sq ft

|

Villa

932 MEDIRA DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 3432 FAIRFIELD ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$399,900

3 beds

|

2 baths

|

1,477 sq ft

|

House

3432 FAIRFIELD ST, THE VILLAGES, FL, 321...
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® 2544 ASHVILLE AVE, THE VILLAGES, FL, 321..., The Villages, FL 32162
$661,000

3 beds

|

2 baths

|

2,725 sq ft

|

House

2544 ASHVILLE AVE, THE VILLAGES, FL, 321...
Community: The Villages®
Ocala Preserve 3231 NW 52ND AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$278,990

2 beds

|

2 baths

|

1,562 sq ft

|

Halfplex

3231 NW 52ND AVENUE RD, OCALA, FL, 34482
Community: Ocala Preserve
Carlsberg Estates on Lake Suzanne 4182 CANNES AVE, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$275,000

3 beds

|

3 baths

|

1,744 sq ft

|

House

4182 CANNES AVE, LAKE WALES, FL, 33859
Ocala Preserve 5270 NW 33RD PL, OCALA, FL, 34482, Ocala, FL 34482
$264,990

2 beds

|

2 baths

|

1,320 sq ft

|

Halfplex

5270 NW 33RD PL, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4443 NW 53RD AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$349,990

2 beds

|

2 baths

|

1,631 sq ft

|

House

4443 NW 53RD 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
On Top of the World 9285 SW 90TH ST, OCALA, FL, 34481, Ocala, FL 34481
$215,000

2 beds

|

2 baths

|

1,756 sq ft

|

House

9285 SW 90TH ST, OCALA, FL, 34481
Community: On Top of the World
Solivita 2212 PORTRAIT ST, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$290,000

3 beds

|

3 baths

|

1,373 sq ft

|

Townhouse

2212 PORTRAIT ST, KISSIMMEE, FL, 34758
Community: Solivita
Lake Jovita Golf and Country Club 13216 LEGENDS TRL, DADE CITY, FL, 33525, Dade City, FL 33525
$749,900

5 beds

|

3 baths

|

3,265 sq ft

|

House

13216 LEGENDS TRL, DADE CITY, FL, 33525
The Villages® 17037 SE 76TH CREEKSIDE CIR, THE VILLAGE..., The Villages, FL 32162
$510,000

3 beds

|

2 baths

|

2,136 sq ft

|

House

17037 SE 76TH CREEKSIDE CIR, THE VILLAGE...
Community: The Villages®
Summer Trees 111 GREY BRANCH RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$278,401

3 beds

|

2 baths

|

1,950 sq ft

|

House

111 GREY BRANCH RD, PORT ORANGE, FL, 321...
Community: Summer Trees
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 672 ALLEGHENY DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$450,000

4 beds

|

3 baths

|

1,684 sq ft

|

House

672 ALLEGHENY DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Stonecrest 11019 SE 170TH LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$304,000

3 beds

|

2 baths

|

1,324 sq ft

|

House

11019 SE 170TH LANE RD, SUMMERFIELD, FL,...
Community: Stonecrest
SummerGlen 3832 SW 157TH PLACE RD, OCALA, FL, 34473, Ocala, FL 34473
$314,900

4 beds

|

2 baths

|

1,833 sq ft

|

House

3832 SW 157TH PLACE RD, OCALA, FL, 34473
Community: SummerGlen
Tampa Bay Golf and Country Club 10534 COLLAR DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$310,000

3 beds

|

2 baths

|

1,729 sq ft

|

House

10534 COLLAR DR, SAN ANTONIO, FL, 33576
Oak Run 8321 SW 108TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$220,000

2 beds

|

2 baths

|

1,428 sq ft

|

House

8321 SW 108TH PLACE RD, 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
Breakaway Trails 9 FOREST VIEW WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$1,095,000

5 beds

|

5 baths

|

4,840 sq ft

|

House

9 FOREST VIEW WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
The Country Club of Mount Dora 1812 STAFFORD SPRINGS BLVD, MOUNT DORA, ..., Mount Dora, FL 32757
$389,000

2 beds

|

2 baths

|

1,515 sq ft

|

House

1812 STAFFORD SPRINGS BLVD, MOUNT DORA, ...
Summer Trees 127 CYPRESS POND RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$267,900

3 beds

|

2 baths

|

1,426 sq ft

|

House

127 CYPRESS POND RD, PORT ORANGE, FL, 32...
Community: Summer Trees
Latitude Margaritaville 199 CATAMARAN CV, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$915,000

2 beds

|

3 baths

|

2,339 sq ft

|

House

199 CATAMARAN CV, DAYTONA BEACH, FL, 321...
Latitude Margaritaville 557 HIGH TIDE LN, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$409,900

2 beds

|

2 baths

|

1,321 sq ft

|

House

557 HIGH TIDE LN, DAYTONA BEACH, FL, 321...

Frequently Asked Questions


Want more information about active adult communities around Winter Garden?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Winter Garden?

Call us: (689) 407-5757
3,573 homes near Winter Garden
Remove Boundaries ×
Map Satellite

Call Us Call Us
Scroll to Top