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

3,584 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 - $600Ks
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) 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
Tampa Bay Golf and Country Club 9936 CLEGHORN DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$359,900

3 beds

|

2 baths

|

1,772 sq ft

|

House

9936 CLEGHORN DR, SAN ANTONIO, FL, 33576
Lake Ashton 1202 ASHTON PALMS DR # 6, LAKE WALES, FL..., Lake Wales, FL 33859
$219,500

2 beds

|

2 baths

|

1,436 sq ft

|

Condo

1202 ASHTON PALMS DR # 6, LAKE WALES, FL...
Community: Lake Ashton
On Top of the World 9865 SW 105TH CT, OCALA, FL, 34481, Ocala, FL 34481
$385,000

2 beds

|

2 baths

|

2,019 sq ft

|

House

9865 SW 105TH CT, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 10553 SW 98TH PL, OCALA, FL, 34481, Ocala, FL 34481
$500,000

3 beds

|

3 baths

|

2,907 sq ft

|

House

10553 SW 98TH PL, OCALA, FL, 34481
Community: On Top of the World
Kings Ridge 3706 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711
$342,000

2 beds

|

2 baths

|

1,466 sq ft

|

House

3706 DOUNE WAY, CLERMONT, FL, 34711
Community: Kings Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Preserve 5339 NW 46TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$232,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

5339 NW 46TH LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4743 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$232,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4743 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4737 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$232,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4737 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4062 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$259,990

3 beds

|

2 baths

|

1,504 sq ft

|

House

4062 NW 44TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
Stonecrest 17508 SE 119TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$317,900

2 beds

|

2 baths

|

1,539 sq ft

|

House

17508 SE 119TH CIR, SUMMERFIELD, FL, 344...
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.
Twin Lakes 2449 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$349,900

2 beds

|

2 baths

|

1,346 sq ft

|

Villa

2449 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
JB Ranch 9358 SW 60TH COURT RD, OCALA, FL, 34476, Ocala, FL 34476
$304,990

3 beds

|

2 baths

|

1,816 sq ft

|

House

9358 SW 60TH COURT RD, OCALA, FL, 34476
Community: JB Ranch
Stonecrest 11010 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$350,000

3 beds

|

2 baths

|

1,793 sq ft

|

House

11010 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Encore at Fishhawk Ranch 6230 PLOVER MEADOW ST, LITHIA, FL, 33547, Lithia, FL 33547
$505,000

2 beds

|

2 baths

|

1,768 sq ft

|

House

6230 PLOVER MEADOW ST, LITHIA, FL, 33547
Heritage Hills 3674 CALADESI RD, CLERMONT, FL, 34711, Clermont, FL 34711
$400,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

3674 CALADESI RD, CLERMONT, FL, 34711
Community: Heritage Hills
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 1423 HARBOR RIDGE DR, POINCIANA, FL, 347..., Poinciana, FL 34759
$315,000

2 beds

|

2 baths

|

1,703 sq ft

|

House

1423 HARBOR RIDGE DR, POINCIANA, FL, 347...
Community: Solivita
Pelican Bay Daytona Beach 105 MARBLED GODWIT CT, DAYTONA BEACH, FL..., Daytona Beach, FL 32119
$465,000

3 beds

|

2 baths

|

2,568 sq ft

|

House

105 MARBLED GODWIT CT, DAYTONA BEACH, FL...
The Villages® 1001 GREYFORD LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$334,900

2 beds

|

2 baths

|

1,351 sq ft

|

Villa

1001 GREYFORD LN, THE VILLAGES, FL, 3216...
Community: The Villages®
Lakeside Landings 10105 KETCH KAY LN, OXFORD, FL, 34484, Oxford, FL 34484
$319,900

3 beds

|

2 baths

|

1,856 sq ft

|

House

10105 KETCH KAY LN, OXFORD, FL, 34484
Community: Lakeside Landings
Lake Jovita Golf and Country Club 34411 SAHALEE LOOP, DADE CITY, FL, 33525, Dade City, FL 33525
$775,000

3 beds

|

3 baths

|

2,777 sq ft

|

House

34411 SAHALEE LOOP, DADE CITY, FL, 33525
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.
On Top of the World 8640 SW 83RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$305,000

3 beds

|

2 baths

|

1,906 sq ft

|

House

8640 SW 83RD LOOP, OCALA, FL, 34481
Community: On Top of the World
The Villages® 2457 UPTON ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$299,900

2 beds

|

2 baths

|

1,156 sq ft

|

House

2457 UPTON ST, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 947 COUTURE ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$459,900

3 beds

|

2 baths

|

1,484 sq ft

|

Villa

947 COUTURE ST, THE VILLAGES, FL, 32163
Community: The Villages®
Oak Run 10897 SW 80TH CT, OCALA, FL, 34481, Ocala, FL 34481
$199,000

2 beds

|

2 baths

|

1,224 sq ft

|

House

10897 SW 80TH CT, OCALA, FL, 34481
Community: Oak Run
Spruce Creek North 10980 SW 62ND AVE, OCALA, FL, 34476, Ocala, FL 34476
$204,900

3 beds

|

2 baths

|

1,526 sq ft

|

House

10980 SW 62ND AVE, OCALA, FL, 34476
Community: Spruce Creek North
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 1601 WOODMAR DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$250,000

2 beds

|

2 baths

|

1,857 sq ft

|

House

1601 WOODMAR DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Valencia Lakes 5009 SANDY BROOK CIR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$385,000

3 beds

|

2 baths

|

1,864 sq ft

|

House

5009 SANDY BROOK CIR, WIMAUMA, FL, 33598
Community: Valencia Lakes
The Villages® 3141 MANSFIELD ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$799,000

3 beds

|

2 baths

|

2,340 sq ft

|

House

3141 MANSFIELD ST, THE VILLAGES, FL, 321...
Community: The Villages®
On Top of the World 9839 SW 90TH ST, OCALA, FL, 34481, Ocala, FL 34481
$379,000

2 beds

|

2 baths

|

2,079 sq ft

|

House

9839 SW 90TH ST, OCALA, FL, 34481
Community: On Top of the World
The Villages® 415 S TIMBER TRL, WILDWOOD, FL, 34785, Wildwood, FL 34785
$119,900

2 beds

|

2 baths

|

1,144 sq ft

|

House

415 S TIMBER TRL, WILDWOOD, FL, 34785
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® 2705 LA POSADA DR, THE VILLAGES, FL, 321..., The Villages, FL 32162
$374,900

3 beds

|

2 baths

|

1,647 sq ft

|

House

2705 LA POSADA DR, THE VILLAGES, FL, 321...
Community: The Villages®
Tohoqua Reserve 1855 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$400,000

2 beds

|

2 baths

|

1,559 sq ft

|

House

1855 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
The Villages® 1885 OAKCREST PATH, THE VILLAGES, FL, 32..., The Villages, FL 32162
$640,000

3 beds

|

2 baths

|

1,937 sq ft

|

House

1885 OAKCREST PATH, THE VILLAGES, FL, 32...
Community: The Villages®
Valencia del Sol 15442 SANTA POLA DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$375,000

2 beds

|

2 baths

|

1,592 sq ft

|

House

15442 SANTA POLA DR, WIMAUMA, FL, 33598
Community: Valencia del Sol
Plantation at Leesburg 5300 TIGERS TAIL, LEESBURG, FL, 34748, Leesburg, FL 34748
$174,900

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

5300 TIGERS TAIL, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1727 HILTON HEAD BLVD, THE VILLAGES, FL,..., The Villages, FL 32159
$210,000

2 beds

|

2 baths

|

1,180 sq ft

|

Manufactured Home

1727 HILTON HEAD BLVD, THE VILLAGES, FL,...
Community: The Villages®
Vienna Square 1224 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884
$215,000

2 beds

|

2 baths

|

1,118 sq ft

|

Villa

1224 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
The Villages® 7243 SE 172ND LEGACY LN, THE VILLAGES, F..., The Villages, FL 32162
$453,900

3 beds

|

2 baths

|

1,918 sq ft

|

House

7243 SE 172ND LEGACY LN, THE VILLAGES, F...
Community: The Villages®
Highland Fairways 3618 HIGHLAND FAIRWAYS BLVD, LAKELAND, F..., Lakeland, FL 33810
$289,900

3 beds

|

2 baths

|

1,680 sq ft

|

House

3618 HIGHLAND FAIRWAYS BLVD, LAKELAND, F...
Community: Highland Fairways
SummerGlen 15692 SW 16TH TER, OCALA, FL, 34473, Ocala, FL 34473
$245,000

3 beds

|

2 baths

|

1,647 sq ft

|

House

15692 SW 16TH TER, OCALA, FL, 34473
Community: SummerGlen

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
3,584 homes near Winter Garden
Remove Boundaries ×
Map Satellite

Call Us Call Us
Scroll to Top