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

3,703 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 - $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
$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 2618 NEWCOMB CT # 12, SUN CITY CENTER, F..., Sun City Center, FL 33573
$160,000

2 beds

|

2 baths

|

963 sq ft

|

Condo

2618 NEWCOMB CT # 12, SUN CITY CENTER, F...
Community: Sun City Center
Sun City Center 1308 CRYSTAL GREENS DR, SUN CITY CENTER,..., Sun City Center, FL 33573
$515,000

3 beds

|

2 baths

|

2,117 sq ft

|

House

1308 CRYSTAL GREENS DR, SUN CITY CENTER,...
Community: Sun City Center
Lake Ashton 4168 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$359,900

3 beds

|

2 baths

|

1,756 sq ft

|

House

4168 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton
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
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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 170 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$414,500

2 beds

|

2 baths

|

1,378 sq ft

|

House

170 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Sun City Center 102 CAMBRIDGE TRL APT 230, SUN CITY CENT..., Sun City Center, FL 33573
$115,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

102 CAMBRIDGE TRL APT 230, SUN CITY CENT...
Community: Sun City Center
Venetian Bay 3606 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$769,900

3 beds

|

3 baths

|

2,460 sq ft

|

House

3606 MARIBELLA DR, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
Palms at Serenoa 17751 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$598,000

2 beds

|

2 baths

|

1,822 sq ft

|

House

17751 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
Pennbrooke Fairways 32716 WESTWOOD LOOP, LEESBURG, FL, 34748, Leesburg, FL 34748
$234,900

2 beds

|

2 baths

|

1,370 sq ft

|

House

32716 WESTWOOD LOOP, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
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.
Solivita 154 RANCHO MIRAGE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759
$625,000

3 beds

|

4 baths

|

2,616 sq ft

|

House

154 RANCHO MIRAGE DR, KISSIMMEE, FL, 347...
Community: Solivita
Plantation at Leesburg 3818 ST EMMA CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$394,900

2 beds

|

2 baths

|

2,065 sq ft

|

House

3818 ST EMMA CT, LEESBURG, FL, 34748
Solivita 726 IRVINE RANCH RD, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$484,000

3 beds

|

3 baths

|

2,427 sq ft

|

House

726 IRVINE RANCH RD, KISSIMMEE, FL, 3475...
Community: Solivita
Cherrywood 6136 SW 100TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$167,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

6136 SW 100TH LOOP, OCALA, FL, 34476
Community: Cherrywood
Sun City Center 1026 MCDANIEL ST # 1026, SUN CITY CENTER..., Sun City Center, FL 33573
$310,000

2 beds

|

2 baths

|

1,825 sq ft

|

Condo

1026 MCDANIEL ST # 1026, SUN CITY CENTER...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Valencia Lakes 5073 STONE HARBOR CIR, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$785,000

3 beds

|

4 baths

|

2,689 sq ft

|

House

5073 STONE HARBOR CIR, WIMAUMA, FL, 3359...
Community: Valencia Lakes
Sun City Center 2501 LONIGAN PL, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$199,900

2 beds

|

2 baths

|

1,394 sq ft

|

Condo

2501 LONIGAN PL, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Solivita 101 PALAZZO LN, POINCIANA, FL, 34759, Poinciana, FL 34759
$330,000

2 beds

|

2 baths

|

1,703 sq ft

|

House

101 PALAZZO LN, POINCIANA, FL, 34759
Community: Solivita
The Country Club of Mount Dora 9049 SAINT ANDREWS WAY, MOUNT DORA, FL, ..., Mount Dora, FL 32757
$368,000

2 beds

|

2 baths

|

1,978 sq ft

|

House

9049 SAINT ANDREWS WAY, MOUNT DORA, FL, ...
Ocala Preserve 5430 NW 35TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$650,000

3 beds

|

3 baths

|

2,694 sq ft

|

House

5430 NW 35TH LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
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 7732 SW 86TH CT, OCALA, FL, 34481, Ocala, FL 34481
$325,000

2 beds

|

2 baths

|

1,344 sq ft

|

House

7732 SW 86TH CT, OCALA, FL, 34481
Community: On Top of the World
Valencia Lakes 4820 GRAND BANKS DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$475,000

2 beds

|

2 baths

|

2,107 sq ft

|

House

4820 GRAND BANKS DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Twin Lakes 5172 GARDENROW DR, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$339,360

2 beds

|

2 baths

|

1,322 sq ft

|

Villa

5172 GARDENROW DR, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
Oak Run 8602 SW 116TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$239,900

3 beds

|

2 baths

|

1,927 sq ft

|

House

8602 SW 116TH PLACE RD, OCALA, FL, 34481
Community: Oak Run
Marco Polo Village 5239 SW 114TH STREET RD, OCALA, FL, 3447..., Ocala, FL 34476
$419,990

4 beds

|

3 baths

|

2,484 sq ft

|

House

5239 SW 114TH STREET RD, OCALA, FL, 3447...
Community: Marco Polo Village
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Cresswind at Victoria Gardens 145 OLD MOSS CIR, DELAND, FL, 32724, Deland, FL 32724
$658,000

3 beds

|

3 baths

|

2,222 sq ft

|

House

145 OLD MOSS CIR, DELAND, FL, 32724
Stonecrest 11041 SE 169TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$315,000

3 beds

|

2 baths

|

1,417 sq ft

|

House

11041 SE 169TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Latitude Margaritaville 374 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$549,900

2 beds

|

3 baths

|

3,011 sq ft

|

House

374 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
JB Ranch 6138 SW 89TH LANE RD, OCALA, FL, 34476, Ocala, FL 34476
$307,000

3 beds

|

2 baths

|

1,857 sq ft

|

House

6138 SW 89TH LANE RD, OCALA, FL, 34476
Community: JB Ranch
Ocala Preserve 4119 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$325,000

3 beds

|

2 baths

|

1,610 sq ft

|

House

4119 NW 44TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
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.
Royal Highlands 21120 LADY MARION WAY, LEESBURG, FL, 347..., Leesburg, FL 34748
$295,000

3 beds

|

2 baths

|

1,601 sq ft

|

House

21120 LADY MARION WAY, LEESBURG, FL, 347...
Community: Royal Highlands
Valencia Lakes 15931 GOLDEN LAKES DR, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$449,900

3 beds

|

2 baths

|

2,230 sq ft

|

House

15931 GOLDEN LAKES DR, WIMAUMA, FL, 3359...
Community: Valencia Lakes
On Top of the World 9152 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$205,000

2 beds

|

2 baths

|

1,345 sq ft

|

House

9152 SW 91ST CIR, OCALA, FL, 34481
Community: On Top of the World
High Vista at Ridgewood Lakes 725 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$290,000

3 beds

|

2 baths

|

1,594 sq ft

|

House

725 HIGH VISTA DR, DAVENPORT, FL, 33837
El Dorado 2130 SW 37TH STREET RD, OCALA, FL, 34471, Ocala, FL 34471
$798,000

5 beds

|

3 baths

|

4,333 sq ft

|

House

2130 SW 37TH STREET RD, OCALA, FL, 34471
Community: El Dorado
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pelican Bay Daytona Beach 220 SURF SCOOTER DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$279,900

2 beds

|

2 baths

|

1,760 sq ft

|

Townhouse

220 SURF SCOOTER DR, DAYTONA BEACH, FL, ...
Solivita 501 HERITAGE TRAIL ST, KISSIMMEE, FL, 34..., Kissimmee, FL 34759
$320,000

2 beds

|

2 baths

|

1,574 sq ft

|

House

501 HERITAGE TRAIL ST, KISSIMMEE, FL, 34...
Community: Solivita
On Top of the World 9925 SW 95TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$419,900

3 beds

|

3 baths

|

2,452 sq ft

|

House

9925 SW 95TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Huntington at Hunter's Ridge 14 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$424,900

3 beds

|

2 baths

|

2,001 sq ft

|

House

14 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Marion Landing 8485 SW 60TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$235,000

3 beds

|

2 baths

|

1,621 sq ft

|

House

8485 SW 60TH CIR, OCALA, FL, 34476
Community: Marion Landing

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
3,703 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 02, 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