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
<$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
$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.
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) Trilogy® Orlando
$300Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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 - $900Ks
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...
$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
Highlands Ridge 4456 TOUSSANT DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$449,000

3 beds

|

2 baths

|

1,722 sq ft

|

House

4456 TOUSSANT DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Heritage Hills 3210 SONESTA CT B, CLERMONT, FL, 34711, Clermont, FL 34711
$320,000

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3210 SONESTA CT B, CLERMONT, FL, 34711
Community: Heritage Hills
Highlands Ridge 3116 OAKMONT DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$285,900

3 beds

|

2 baths

|

1,810 sq ft

|

House

3116 OAKMONT DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Spruce Creek South 10190 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$239,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

10190 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 1736 WATTS MILL WAY, THE VILLAGES, FL, 3..., The Villages, FL 32162
$295,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

1736 WATTS MILL WAY, THE VILLAGES, FL, 3...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Preserve 4687 NW 35TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$460,000

2 beds

|

2 baths

|

2,316 sq ft

|

House

4687 NW 35TH LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
Tampa Bay Golf and Country Club 29432 COHARIE LOOP, SAN ANTONIO, FL, 335..., San Antonio, FL 33576
$450,000

3 beds

|

2 baths

|

2,057 sq ft

|

House

29432 COHARIE LOOP, SAN ANTONIO, FL, 335...
The Villages® 5810 PENNEY LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$649,900

3 beds

|

2 baths

|

2,016 sq ft

|

House

5810 PENNEY LN, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 5778 HENRY LOOP, THE VILLAGES, FL, 32163, The Villages, FL 32163
$430,000

3 beds

|

2 baths

|

1,531 sq ft

|

House

5778 HENRY LOOP, THE VILLAGES, FL, 32163
Community: The Villages®
Sun City Center 2413 OXFORD DOWN CT # 58, SUN CITY CENTE..., Sun City Center, FL 33573
$240,000

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

2413 OXFORD DOWN CT # 58, SUN CITY CENTE...
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.
Sun City Center 1906 CANTERBURY LN 20, SUN CITY CENTER, ..., Sun City Center, FL 33573
$175,000

2 beds

|

2 baths

|

984 sq ft

|

Condo

1906 CANTERBURY LN 20, SUN CITY CENTER, ...
Community: Sun City Center
Sun City Center 1904 CANTERBURY LN 11, SUN CITY CENTER, ..., Sun City Center, FL 33573
$175,000

2 beds

|

2 baths

|

984 sq ft

|

Condo

1904 CANTERBURY LN 11, SUN CITY CENTER, ...
Community: Sun City Center
Carlsberg Estates on Lake Suzanne 4189 CANNES AVE, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$269,900

3 beds

|

2 baths

|

1,385 sq ft

|

House

4189 CANNES AVE, LAKE WALES, FL, 33859
Carlsberg Estates on Lake Suzanne 341 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$250,000

2 beds

|

2 baths

|

1,385 sq ft

|

House

341 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Sun City Center 717 MANCHESTER WOODS DR # 717, SUN CITY ..., Sun City Center, FL 33573
$285,000

2 beds

|

2 baths

|

1,444 sq ft

|

Condo

717 MANCHESTER WOODS DR # 717, SUN CITY ...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 10293 SW 96TH LN, OCALA, FL, 34481, Ocala, FL 34481
$539,000

2 beds

|

3 baths

|

2,414 sq ft

|

House

10293 SW 96TH LN, OCALA, FL, 34481
Community: On Top of the World
The Villages® 16950 SE 80TH BELLAVISTA CIR, THE VILLAG..., The Villages, FL 32162
$540,000

3 beds

|

2 baths

|

2,687 sq ft

|

House

16950 SE 80TH BELLAVISTA CIR, THE VILLAG...
Community: The Villages®
Valencia Lakes 4949 MARBLE SPRINGS CIR, WIMAUMA, FL, 33..., Wimauma, FL 33598
$360,000

2 beds

|

2 baths

|

1,747 sq ft

|

Villa

4949 MARBLE SPRINGS CIR, WIMAUMA, FL, 33...
Community: Valencia Lakes
Four Seasons at Orlando 7790 FOUR SEASONS BLVD, KISSIMMEE, FL, 3..., Kissimmee, FL 34747
$765,000

3 beds

|

3 baths

|

2,470 sq ft

|

House

7790 FOUR SEASONS BLVD, KISSIMMEE, FL, 3...
Spruce Creek South 9488 SE 174TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$300,000

2 beds

|

2 baths

|

1,884 sq ft

|

House

9488 SE 174TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
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 1226 LYNDHURST GREENS DR, SUN CITY CENTE..., Sun City Center, FL 33573
$255,000

3 beds

|

10 baths

|

1,429 sq ft

|

Condo

1226 LYNDHURST GREENS DR, SUN CITY CENTE...
Community: Sun City Center
Spruce Creek Country Club 9894 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$439,000

3 beds

|

2 baths

|

2,267 sq ft

|

House

9894 SE 138TH LOOP, SUMMERFIELD, FL, 344...
Highland Lakes 27141 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$239,900

2 beds

|

2 baths

|

1,564 sq ft

|

House

27141 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
Sun City Center 1015 RADISON LAKE CT # 65, SUN CITY CENT..., Sun City Center, FL 33573
$219,000

2 beds

|

2 baths

|

1,298 sq ft

|

Condo

1015 RADISON LAKE CT # 65, SUN CITY CENT...
Community: Sun City Center
The Villages® 2895 APACHE CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$479,900

3 beds

|

2 baths

|

1,865 sq ft

|

House

2895 APACHE CT, 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
Solivita 789 CIELO TRL, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$496,000

3 beds

|

3 baths

|

2,427 sq ft

|

House

789 CIELO TRL, KISSIMMEE, FL, 34759
Community: Solivita
Highlands Ridge 3115 OAKMONT DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$399,900

2 beds

|

3 baths

|

2,751 sq ft

|

House

3115 OAKMONT DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Plantation at Leesburg 3646 WESTOVER CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$390,000

2 beds

|

2 baths

|

2,400 sq ft

|

House

3646 WESTOVER CIR, LEESBURG, FL, 34748
Sun City Center 404 FULHAM CT A, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$154,900

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

404 FULHAM CT A, SUN CITY CENTER, FL, 33...
Community: Sun City Center
The Villages® 2297 MONTBROOK PL, THE VILLAGES, FL, 321..., The Villages, FL 32162
$359,900

3 beds

|

2 baths

|

1,631 sq ft

|

House

2297 MONTBROOK PL, 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.
Legacy of Leesburg 5352 TREASURE VIEW WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$299,000

3 beds

|

2 baths

|

2,241 sq ft

|

House

5352 TREASURE VIEW WAY, LEESBURG, FL, 34...
Community: Legacy of Leesburg
Venetian Bay 2816 E VENETIAN LAKE CIR, NEW SMYRNA BEA..., New Smyrna Beach, FL 32168
$855,000

3 beds

|

3 baths

|

2,536 sq ft

|

House

2816 E VENETIAN LAKE CIR, NEW SMYRNA BEA...
Community: Venetian Bay
Breakaway Trails 33 COQUINA RIDGE WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174
$699,000

4 beds

|

3 baths

|

2,602 sq ft

|

House

33 COQUINA RIDGE WAY, ORMOND BEACH, FL, ...
Community: Breakaway Trails
Sullivan Ranch 30245 CHEVAL ST, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$350,000

4 beds

|

2 baths

|

1,670 sq ft

|

House

30245 CHEVAL ST, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Sun City Center 2113 E DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573
$350,000

3 beds

|

3 baths

|

2,218 sq ft

|

House

2113 E DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Traditions at Lake Ruby 3686 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$399,900

4 beds

|

3 baths

|

2,404 sq ft

|

House

3686 PLYMOUTH DR, WINTER HAVEN, FL, 3388...
Valencia Lakes 16135 CAPE CORAL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$535,000

2 beds

|

2 baths

|

2,074 sq ft

|

House

16135 CAPE CORAL DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Lakes of Mount Dora 8456 NORWICH WAY, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$648,999

4 beds

|

3 baths

|

2,460 sq ft

|

House

8456 NORWICH WAY, MOUNT DORA, FL, 32757
Community: Lakes of Mount Dora
Twin Lakes 5014 E FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772
$479,800

3 beds

|

3 baths

|

2,208 sq ft

|

House

5014 E FOUNTAINWOOD DR, SAINT CLOUD, FL,...
Community: Twin Lakes
Ocala Palms 2051 NW 50TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$249,000

2 beds

|

2 baths

|

1,569 sq ft

|

House

2051 NW 50TH AVE, OCALA, FL, 34482
Community: Ocala Palms

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