not an image

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

Winter Garden, FL 55+ active adult communities & homes for sale - Page 46

3,654 homes near Winter Garden

Sort by:

Relevance

Relevance

4 rating (17 reviews) The Villages®
$100ks - $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
$100ks - $800ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4.2 rating (10 reviews) Stone Creek
$200ks - $500ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.7 rating (18 reviews) Solivita
$300ks - $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
4.5 rating (11 reviews) Spruce Creek Country Club
$100ks - $400ks
Spruce Creek Country Club, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
5 rating (2 reviews) Plantation at Leesburg
$100ks - $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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
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.
3.6 rating (48 reviews) Latitude Margaritaville
$300ks - $800ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes
4.6 rating (5 reviews) Ocala Preserve
$100ks - $500ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
3.8 rating (4 reviews) Spruce Creek South
$100ks - $200ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
5 rating (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 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.
4.7 rating (11 reviews) Valencia Lakes
$200ks - $700ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
5 rating (1 reviews) Del Webb Sunbridge
$400ks - $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
5 rating (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4 rating (7 reviews) Tampa Bay Golf and Countr...
$200ks - $500ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes
3.8 rating (6 reviews) Trilogy® Orlando
$200ks - $500ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
5 rating (3 reviews) Twin Lakes
$200ks - $600ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
5 rating (1 reviews) Sandpiper Golf & Coun...
$100ks - $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 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.
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4 rating (4 reviews) Lakes of Mount Dora
$300ks - $900ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes
4 rating (2 reviews) Harbor Hills Country Club
$300ks - $900ks
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
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
3.6 rating (5 reviews) Heritage Hills
$200ks - $400ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
Mirada
$300ks - $500ks
Mirada, San Antonio, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 858 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 (1 reviews) Palm Cay
$100ks - $200ks
Palm Cay, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 homes
Lake Jovita Golf and Coun...
$400ks - $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale | Age-targeted | Built 1999 - present | 875 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
12...3
Trilogy® Orlando 83 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736
$315,000

2 beds

|

2 baths

|

1,269 sq ft

|

House

83 BAYOU BEND RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Sun City Center 301 ANDOVER PL 171, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$115,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

301 ANDOVER PL 171, SUN CITY CENTER, FL,...
Community: Sun City Center
JB Ranch 6369 SW 89TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$359,900

3 beds

|

2 baths

|

2,101 sq ft

|

House

6369 SW 89TH LOOP, OCALA, FL, 34476
Community: JB Ranch
On Top of the World 10553 SW 98TH PL, OCALA, FL, 34481, Ocala, FL 34481
$650,000

3 beds

|

3 baths

|

2,907 sq ft

|

House

10553 SW 98TH PL, OCALA, FL, 34481
Community: On Top of the World
Venetian Bay 3530 TUSCANY RESERVE BLVD, NEW SMYRNA BE..., New Smyrna Beach, FL 32168
$935,000

4 beds

|

3 baths

|

3,295 sq ft

|

House

3530 TUSCANY RESERVE BLVD, NEW SMYRNA BE...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Royal Highlands 5552 KING JAMES AVE, LEESBURG, FL, 34748, Leesburg, FL 34748
$282,000

3 beds

|

2 baths

|

1,469 sq ft

|

House

5552 KING JAMES AVE, LEESBURG, FL, 34748
Community: Royal Highlands
Sun City Center 1950 ACADIA GREENS DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$289,000

2 beds

|

2 baths

|

1,618 sq ft

|

Condo

1950 ACADIA GREENS DR, SUN CITY CENTER, ...
Community: Sun City Center
Cherrywood 10447 SW 62ND CT, OCALA, FL, 34476, Ocala, FL 34476
$220,000

3 beds

|

2 baths

|

1,258 sq ft

|

House

10447 SW 62ND CT, OCALA, FL, 34476
Community: Cherrywood
Tampa Bay Golf and Country Club 29335 CADDY SHACK LN, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$310,000

3 beds

|

2 baths

|

1,355 sq ft

|

Villa

29335 CADDY SHACK LN, SAN ANTONIO, FL, 3...
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® 701 CORDOVA CIR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$469,000

3 beds

|

2 baths

|

1,927 sq ft

|

House

701 CORDOVA CIR, THE VILLAGES, FL, 32162
Community: The Villages®
Stonecrest 10957 SE 170TH LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$289,900

3 beds

|

2 baths

|

1,381 sq ft

|

House

10957 SE 170TH LANE RD, SUMMERFIELD, FL,...
Community: Stonecrest
Plantation at Leesburg 25021 BELLEVUE, LEESBURG, FL, 34748, Leesburg, FL 34748
$244,800

2 beds

|

2 baths

|

1,375 sq ft

|

Manufactured Home

25021 BELLEVUE, LEESBURG, FL, 34748
On Top of the World 7819 SW 88TH STREET RD, OCALA, FL, 34476, Ocala, FL 34476
$356,900

3 beds

|

2 baths

|

1,874 sq ft

|

House

7819 SW 88TH STREET RD, OCALA, FL, 34476
Community: On Top of the World
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lake Ashton 1166 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$445,000

3 beds

|

2 baths

|

2,045 sq ft

|

House

1166 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
Valencia Ridge 32643 NEROLI ST, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$744,900

3 beds

|

3 baths

|

2,474 sq ft

|

House

32643 NEROLI ST, WESLEY CHAPEL, FL, 3354...
Community: Valencia Ridge
Sandpiper Golf & Country Club 6380 EGRET DR 12, LAKELAND, FL, 33809, Lakeland, FL 33809
$275,000

2 beds

|

2 baths

|

1,326 sq ft

|

Villa

6380 EGRET DR 12, LAKELAND, FL, 33809
On Top of the World 9330 SW 84TH TER C, OCALA, FL, 34481, Ocala, FL 34481
$159,900

2 beds

|

2 baths

|

1,262 sq ft

|

Villa

9330 SW 84TH TER C, OCALA, FL, 34481
Community: On Top of the World
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.
Stone Creek 9284 SW 56TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$618,816

2 beds

|

3 baths

|

2,295 sq ft

|

House

9284 SW 56TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Latitude Margaritaville 410 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$515,000

2 beds

|

2 baths

|

1,848 sq ft

|

House

410 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
On Top of the World 8111 SW 95TH CT, OCALA, FL, 34481, Ocala, FL 34481
$498,000

3 beds

|

3 baths

|

2,311 sq ft

|

House

8111 SW 95TH CT, OCALA, FL, 34481
Community: On Top of the World
Spruce Creek Country Club 9050 SE 135TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$257,000

2 beds

|

2 baths

|

1,867 sq ft

|

House

9050 SE 135TH LOOP, SUMMERFIELD, FL, 344...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Foxwood Lake Estates 1811 FOX HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$189,900

2 beds

|

2 baths

|

1,296 sq ft

|

Manufactured Home

1811 FOX HILL DR, LAKELAND, FL, 33810
Latitude Margaritaville 233 SAND BAR LN, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124
$724,900

2 beds

|

3 baths

|

2,067 sq ft

|

House

233 SAND BAR LN, DAYTONA BEACH, FL, 3212...
Sun City Center 705 TILBURY CT, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$279,000

2 beds

|

2 baths

|

1,825 sq ft

|

Condo

705 TILBURY CT, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Esplanade at Wiregrass Ranch 4848 ROSATTI RD, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$1,200,000

4 beds

|

3 baths

|

3,234 sq ft

|

House

4848 ROSATTI RD, WESLEY CHAPEL, FL, 3354...
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.
Del Webb Sunbridge 2722 RIVER CREEK LN, ST CLOUD, FL, 34771, St Cloud, FL 34771
$1,049,900

3 beds

|

4 baths

|

3,778 sq ft

|

House

2722 RIVER CREEK LN, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
Sun City Center 1607 COUNCIL DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$240,000

2 beds

|

2 baths

|

1,266 sq ft

|

House

1607 COUNCIL DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Sun City Center 201 BEDFORD TRL F121, SUN CITY CENTER, F..., Sun City Center, FL 33573
$120,000

2 beds

|

2 baths

|

960 sq ft

|

Condo

201 BEDFORD TRL F121, SUN CITY CENTER, F...
Community: Sun City Center
Marco Polo Village 10795 SW 53RD CIR, OCALA, FL, 34476, Ocala, FL 34476
$321,000

3 beds

|

2 baths

|

1,691 sq ft

|

House

10795 SW 53RD CIR, OCALA, FL, 34476
Community: Marco Polo Village
Pelican Bay Daytona Beach 152 LOON CT, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119
$319,000

3 beds

|

2 baths

|

1,650 sq ft

|

House

152 LOON CT, DAYTONA BEACH, FL, 32119
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 3121 PORTOFINO BLVD, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168
$498,000

4 beds

|

4 baths

|

2,338 sq ft

|

House

3121 PORTOFINO BLVD, NEW SMYRNA BEACH, F...
Community: Venetian Bay
Stone Creek 6612 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$313,300

2 beds

|

2 baths

|

1,696 sq ft

|

Villa

6612 SW 91ST CIR, OCALA, FL, 34481
Community: Stone Creek
Spruce Creek South 10319 SE 177TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$234,900

2 beds

|

2 baths

|

1,143 sq ft

|

House

10319 SE 177TH PL, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 1319 CARVELLO DR, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$310,000

2 beds

|

2 baths

|

1,148 sq ft

|

House

1319 CARVELLO DR, THE VILLAGES, FL, 3216...
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.
Stone Creek 9823 SW 72ND LN, OCALA, FL, 34481, Ocala, FL 34481
$428,500

2 beds

|

2 baths

|

1,904 sq ft

|

House

9823 SW 72ND LN, OCALA, FL, 34481
Community: Stone Creek
Plantation at Leesburg 25233 LOST OAK CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$320,000

3 beds

|

2 baths

|

1,751 sq ft

|

House

25233 LOST OAK CIR, LEESBURG, FL, 34748
Kings Ridge 3842 AVON CT, CLERMONT, FL, 34711, Clermont, FL 34711
$474,000

3 beds

|

2 baths

|

1,786 sq ft

|

House

3842 AVON CT, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 3490 FORSYTHE TER, THE VILLAGES, FL, 321..., The Villages, FL 32162
$299,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

3490 FORSYTHE TER, THE VILLAGES, FL, 321...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lakes of Mount Dora 8293 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$649,500

3 beds

|

2 baths

|

2,559 sq ft

|

House

8293 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
The Villages® 1635 PINEHURST DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$149,900

2 beds

|

1 baths

|

940 sq ft

|

Manufactured Home

1635 PINEHURST DR, THE VILLAGES, FL, 321...
Community: The Villages®

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
3,654 homes
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.
© 2026 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: Apr 10, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top