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

3,648 homes near Winter Garden

Sort by:

Relevance

Relevance

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!
Questions? Call us: (689) 407-5757
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) 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 - $1Ms
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
<$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 2216 W DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573
$295,000

2 beds

|

2 baths

|

2,036 sq ft

|

House

2216 W DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
Solivita 693 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759
$600,000

4 beds

|

3 baths

|

2,761 sq ft

|

House

693 SAN RAPHAEL ST, POINCIANA, FL, 34759
Community: Solivita
The Villages® 2450 MERIDA CIR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$375,000

3 beds

|

2 baths

|

1,851 sq ft

|

House

2450 MERIDA CIR, THE VILLAGES, FL, 32162
Community: The Villages®
Sun City Center 713 MANCHESTER WOODS DR, SUN CITY CENTER..., Sun City Center, FL 33573
$275,000

2 beds

|

2 baths

|

1,556 sq ft

|

Condo

713 MANCHESTER WOODS DR, SUN CITY CENTER...
Community: Sun City Center
Mirada 31510 CABANA RYE AVE, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$519,000

2 beds

|

3 baths

|

2,216 sq ft

|

House

31510 CABANA RYE AVE, SAN ANTONIO, FL, 3...
Community: Mirada
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Kings Ridge 3821 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711
$279,900

2 beds

|

2 baths

|

1,447 sq ft

|

House

3821 DOUNE WAY, CLERMONT, FL, 34711
Community: Kings Ridge
Kings Ridge 2243 ADDISON AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$320,000

3 beds

|

2 baths

|

1,892 sq ft

|

House

2243 ADDISON AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Plantation at Leesburg 4614 RIVER RIDGE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$315,000

2 beds

|

2 baths

|

2,044 sq ft

|

House

4614 RIVER RIDGE DR, LEESBURG, FL, 34748
The Villages® 1307 GALINDO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$359,000

3 beds

|

2 baths

|

1,872 sq ft

|

House

1307 GALINDO PL, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 16820 SE 74 SOULLIERE AVE, THE VILLAGES,..., The Villages, FL 32162
$384,000

3 beds

|

2 baths

|

1,635 sq ft

|

Villa

16820 SE 74 SOULLIERE AVE, THE VILLAGES,...
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.
On Top of the World 8625 SW 94TH LN A, OCALA, FL, 34481, Ocala, FL 34481
$149,900

2 beds

|

2 baths

|

1,484 sq ft

|

Villa

8625 SW 94TH LN A, OCALA, FL, 34481
Community: On Top of the World
The Villages® 428 TARRSON BLVD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$355,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

428 TARRSON BLVD, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 744 HERNANDEZ DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$279,000

2 beds

|

2 baths

|

1,102 sq ft

|

Villa

744 HERNANDEZ DR, THE VILLAGES, FL, 3215...
Community: The Villages®
Encore at Fishhawk Ranch 13890 KINGFISHER GLEN DR, LITHIA, FL, 33..., Lithia, FL 33547
$349,500

2 beds

|

2 baths

|

1,612 sq ft

|

Villa

13890 KINGFISHER GLEN DR, LITHIA, FL, 33...
Legacy of Leesburg 27121 GREENFLY ORCHID LN, LEESBURG, FL, ..., Leesburg, FL 34748
$275,000

3 beds

|

2 baths

|

1,478 sq ft

|

House

27121 GREENFLY ORCHID LN, LEESBURG, FL, ...
Community: Legacy of Leesburg
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8706 SW 88TH PL, OCALA, FL, 34481, Ocala, FL 34481
$379,900

3 beds

|

3 baths

|

1,878 sq ft

|

House

8706 SW 88TH PL, OCALA, FL, 34481
Community: On Top of the World
Twin Lakes 2672 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$625,000

3 beds

|

3 baths

|

2,935 sq ft

|

House

2672 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Huntington at Hunter's Ridge 59 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$579,000

3 beds

|

2 baths

|

1,852 sq ft

|

House

59 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Cresswind at Victoria Gardens 1069 AVERY MEADOWS WAY, DELAND, FL, 3272..., Deland, FL 32724
$380,000

2 beds

|

2 baths

|

1,651 sq ft

|

House

1069 AVERY MEADOWS WAY, DELAND, FL, 3272...
Trilogy® Orlando 228 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736
$455,000

2 beds

|

2 baths

|

2,197 sq ft

|

House

228 BAYOU BEND RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
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.
Lakes of Mount Dora 2331 WAKEFIELD WAY, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$389,900

2 beds

|

2 baths

|

1,478 sq ft

|

House

2331 WAKEFIELD WAY, MOUNT DORA, FL, 3275...
Community: Lakes of Mount Dora
The Villages® 1723 TOWNSEND TER, THE VILLAGES, FL, 321..., The Villages, FL 32162
$450,000

3 beds

|

2 baths

|

1,918 sq ft

|

House

1723 TOWNSEND TER, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 2552 MARIEL WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$287,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2552 MARIEL WAY, THE VILLAGES, FL, 32162
Community: The Villages®
Sun City Center 612 ALLEGHENY DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$299,000

2 beds

|

2 baths

|

1,696 sq ft

|

House

612 ALLEGHENY DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Trilogy® Orlando 120 CREPE MYRTLE DR, GROVELAND, FL, 3473..., Groveland, FL 34736
$329,999

3 beds

|

2 baths

|

1,671 sq ft

|

House

120 CREPE MYRTLE DR, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 3177 WILLIAMS RD, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$429,900

3 beds

|

2 baths

|

1,894 sq ft

|

House

3177 WILLIAMS RD, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 1606 TANGO ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$625,000

3 beds

|

2 baths

|

2,107 sq ft

|

House

1606 TANGO ST, THE VILLAGES, FL, 32163
Community: The Villages®
Sun City Center 2044 SIFIELD GREENS WAY, SUN CITY CENTER..., Sun City Center, FL 33573
$269,000

2 beds

|

2 baths

|

1,410 sq ft

|

Condo

2044 SIFIELD GREENS WAY, SUN CITY CENTER...
Community: Sun City Center
The Villages® 1705 KILEY CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$179,900

3 beds

|

2 baths

|

1,292 sq ft

|

Manufactured Home

1705 KILEY CT, LADY LAKE, FL, 32159
Community: The Villages®
Summit Greens 793 SUMMIT GREENS BLVD, CLERMONT, FL, 34..., Clermont, FL 34711
$370,000

2 beds

|

2 baths

|

1,731 sq ft

|

House

793 SUMMIT GREENS BLVD, CLERMONT, FL, 34...
Community: Summit Greens
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 1805 BUTTERFLY PL, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$307,000

2 beds

|

2 baths

|

1,516 sq ft

|

House

1805 BUTTERFLY PL, SUN CITY CENTER, FL, ...
Community: Sun City Center
Heritage Hills 3596 KINLEY BROOKE LN, CLERMONT, FL, 347..., Clermont, FL 34711
$399,999

3 beds

|

2 baths

|

1,677 sq ft

|

House

3596 KINLEY BROOKE LN, CLERMONT, FL, 347...
Community: Heritage Hills
The Villages® 1083 JACKSON ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$349,900

2 beds

|

2 baths

|

1,187 sq ft

|

House

1083 JACKSON ST, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 5371 WARM SPRINGS AVE, WILDWOOD, FL, 347..., Wildwood, FL 34785
$275,000

2 beds

|

1 baths

|

696 sq ft

|

House

5371 WARM SPRINGS AVE, WILDWOOD, FL, 347...
Community: The Villages®
Valencia del Sol 4922 SIENNA ISLES AVE, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$429,900

2 beds

|

2 baths

|

1,834 sq ft

|

Villa

4922 SIENNA ISLES AVE, WIMAUMA, FL, 3359...
Community: Valencia del Sol
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 3818 MIRAGALIA LN, THE VILLAGES, FL, 321..., The Villages, FL 32163
$250,000

2 beds

|

2 baths

|

1,051 sq ft

|

Villa

3818 MIRAGALIA LN, THE VILLAGES, FL, 321...
Community: The Villages®
Cypress Lakes 2165 CYPRESS CROSS DR, LAKELAND, FL, 338..., Lakeland, FL 33810
$214,900

3 beds

|

2 baths

|

1,691 sq ft

|

Manufactured Home

2165 CYPRESS CROSS DR, LAKELAND, FL, 338...
Community: Cypress Lakes
Highland Lakes 26104 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$245,000

2 beds

|

2 baths

|

1,124 sq ft

|

House

26104 NEWCOMBE CIR, LEESBURG, FL, 34748
Community: Highland Lakes
Highlands Ridge 4318 NORTH COURSE LN, AVON PARK, FL, 338..., Avon Park, FL 33825
$384,900

3 beds

|

2 baths

|

2,025 sq ft

|

House

4318 NORTH COURSE LN, AVON PARK, FL, 338...
Community: Highlands Ridge
Pine Run Estates 8973 SW 104TH PL, OCALA, FL, 34481, Ocala, FL 34481
$175,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

8973 SW 104TH PL, OCALA, FL, 34481
Community: Pine Run Estates

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
3,648 homes near Winter Garden
Remove Boundaries ×
Map Satellite

Reinmlsx

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2025 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Nov 04, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top