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 72

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
Stone Creek 9566 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$282,600

2 beds

|

2 baths

|

1,556 sq ft

|

Villa

9566 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Arlington Ridge 4436 ANTIETAM CREEK TRL, LEESBURG, FL, 3..., Leesburg, FL 34748
$390,000

3 beds

|

2 baths

|

2,028 sq ft

|

House

4436 ANTIETAM CREEK TRL, LEESBURG, FL, 3...
Community: Arlington Ridge
The Villages® 17339 SE 84TH FOXGROVE AVE, THE VILLAGES..., The Villages, FL 32162
$1,299,999

3 beds

|

3 baths

|

3,693 sq ft

|

Villa

17339 SE 84TH FOXGROVE AVE, THE VILLAGES...
Community: The Villages®
Sullivan Ranch 21846 BELGIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$290,000

2 beds

|

2 baths

|

1,437 sq ft

|

House

21846 BELGIAN CT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
High Vista at Ridgewood Lakes 247 TRAVIS LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$289,900

2 beds

|

2 baths

|

1,596 sq ft

|

House

247 TRAVIS LN, DAVENPORT, FL, 33837
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 494 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$359,000

2 beds

|

2 baths

|

1,204 sq ft

|

House

494 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Spruce Creek Country Club 9385 SE 125TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$390,000

2 beds

|

2 baths

|

1,870 sq ft

|

House

9385 SE 125TH ST, SUMMERFIELD, FL, 34491
Foxwood Lake Estates 5082 FOX CLIFF DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$185,900

2 beds

|

2 baths

|

1,352 sq ft

|

Manufactured Home

5082 FOX CLIFF DR, LAKELAND, FL, 33810
Ocala Palms 1943 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$240,000

2 beds

|

2 baths

|

1,232 sq ft

|

House

1943 NW 50TH CIR, OCALA, FL, 34482
Community: Ocala Palms
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.
Traditions at Lake Ruby 3365 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$229,999

2 beds

|

2 baths

|

1,295 sq ft

|

House

3365 RALEIGH DR, WINTER HAVEN, FL, 33884
Spruce Creek South 10339 SE 179TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$194,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

10339 SE 179TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Spruce Creek Country Club 13776 SE 87TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$234,900

2 beds

|

2 baths

|

1,425 sq ft

|

House

13776 SE 87TH AVE, SUMMERFIELD, FL, 3449...
Valencia Lakes 15948 COBBLE MILL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$329,000

3 beds

|

2 baths

|

1,593 sq ft

|

House

15948 COBBLE MILL DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Plantation at Leesburg 26234 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$249,900

3 beds

|

2 baths

|

1,761 sq ft

|

House

26234 GLEN EAGLE DR, LEESBURG, FL, 34748
The Villages® 4434 SHOCKOE CIR, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$569,000

3 beds

|

2 baths

|

1,950 sq ft

|

House

4434 SHOCKOE CIR, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 1923 USEPPA OAKS LN, THE VILLAGES, FL, 3..., The Villages, FL 32163
$422,500

3 beds

|

2 baths

|

1,875 sq ft

|

House

1923 USEPPA OAKS LN, THE VILLAGES, FL, 3...
Community: The Villages®
Tampa Bay Golf and Country Club 29418 SCHINNECOCK HILLS LN, SAN ANTONIO,..., San Antonio, FL 33576
$285,000

2 beds

|

2 baths

|

1,698 sq ft

|

Villa

29418 SCHINNECOCK HILLS LN, SAN ANTONIO,...
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.
Palm Cay 10856 SW 79 AVE, OCALA, FL, 34476, Ocala, FL 34476
$228,000

3 beds

|

2 baths

|

1,080 sq ft

|

House

10856 SW 79 AVE, OCALA, FL, 34476
Community: Palm Cay
The Villages® 2167 KERWOOD LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32162
$394,500

3 beds

|

2 baths

|

1,467 sq ft

|

House

2167 KERWOOD LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
Ocala Preserve 4474 NW 53RD AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$525,000

3 beds

|

3 baths

|

2,659 sq ft

|

House

4474 NW 53RD AVENUE RD, OCALA, FL, 34482
Community: Ocala Preserve
Thunderbird Hill 3922 SUNBIRD CIR, SEBRING, FL, 33872, Sebring, FL 33872
$190,000

2 beds

|

2 baths

|

1,209 sq ft

|

Villa

3922 SUNBIRD CIR, SEBRING, FL, 33872
Community: Thunderbird Hill
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 1619 BROOKTON GREEN DR, SUN CITY CENTER,..., Sun City Center, FL 33573
$299,999

2 beds

|

2 baths

|

1,678 sq ft

|

House

1619 BROOKTON GREEN DR, SUN CITY CENTER,...
Community: Sun City Center
Spruce Creek Country Club 9033 SE 135TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$269,900

3 beds

|

2 baths

|

1,726 sq ft

|

House

9033 SE 135TH LOOP, SUMMERFIELD, FL, 344...
Royal Palm 5415 SWORDFERN CT, PORT ORANGE, FL, 3212..., Port Orange, FL 32128
$375,000

3 beds

|

3 baths

|

1,942 sq ft

|

House

5415 SWORDFERN CT, PORT ORANGE, FL, 3212...
Community: Royal Palm
On Top of the World 9335 SW 85TH TER E, OCALA, FL, 34481, Ocala, FL 34481
$239,500

2 beds

|

2 baths

|

1,748 sq ft

|

Villa

9335 SW 85TH TER E, 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.
Royal Highlands 5124 LINKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$415,000

3 beds

|

2 baths

|

1,759 sq ft

|

House

5124 LINKS LN, LEESBURG, FL, 34748
Community: Royal Highlands
Lake Jovita Golf and Country Club 13922 CARRYBACK DR, DADE CITY, FL, 33525, Dade City, FL 33525
$1,299,000

3 beds

|

4 baths

|

3,174 sq ft

|

House

13922 CARRYBACK DR, DADE CITY, FL, 33525
SummerGlen 1683 SW 156TH LN, OCALA, FL, 34473, Ocala, FL 34473
$269,999

3 beds

|

2 baths

|

2,093 sq ft

|

House

1683 SW 156TH LN, OCALA, FL, 34473
Community: SummerGlen
The Villages® 6370 DANIELSON LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163
$397,500

3 beds

|

2 baths

|

1,459 sq ft

|

House

6370 DANIELSON LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
On Top of the World 8310 SW 97TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$465,000

2 beds

|

2 baths

|

2,097 sq ft

|

House

8310 SW 97TH AVE, OCALA, FL, 34481
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
Highland Lakes 5609 ROSEWALL CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$329,900

3 beds

|

3 baths

|

2,251 sq ft

|

House

5609 ROSEWALL CIR, LEESBURG, FL, 34748
Community: Highland Lakes
Royal Highlands 5610 KING JAMES AVE, LEESBURG, FL, 34748, Leesburg, FL 34748
$229,900

3 beds

|

2 baths

|

1,606 sq ft

|

House

5610 KING JAMES AVE, LEESBURG, FL, 34748
Community: Royal Highlands
The Villages® 9671 SE 168TH MAPLESONG LN, THE VILLAGES..., The Villages, FL 32162
$327,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

9671 SE 168TH MAPLESONG LN, THE VILLAGES...
Community: The Villages®
Silver Lakes 2206 SILVER LAKES DR, LAKELAND, FL, 3381..., Lakeland, FL 33810
$309,900

3 beds

|

2 baths

|

1,597 sq ft

|

House

2206 SILVER LAKES DR, LAKELAND, FL, 3381...
Community: Silver Lakes
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.
Sullivan Ranch 22035 BELGIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$325,000

3 beds

|

2 baths

|

1,663 sq ft

|

Villa

22035 BELGIAN CT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Traditions at Lake Ruby 3686 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$369,900

4 beds

|

3 baths

|

2,404 sq ft

|

House

3686 PLYMOUTH DR, WINTER HAVEN, FL, 3388...
The Villages® 3358 BRIANNA LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$379,000

3 beds

|

2 baths

|

1,419 sq ft

|

House

3358 BRIANNA LN, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 1222 ZAPATA PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$185,000

2 beds

|

1 baths

|

936 sq ft

|

Manufactured Home

1222 ZAPATA PL, LADY LAKE, FL, 32159
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 9088 SW 95TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$235,000

3 beds

|

2 baths

|

1,745 sq ft

|

House

9088 SW 95TH AVE, OCALA, FL, 34481
Community: On Top of the World
Huntington at Hunter's Ridge 42 HUNTINGTON PL, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$389,900

4 beds

|

2 baths

|

2,003 sq ft

|

House

42 HUNTINGTON PL, ORMOND BEACH, FL, 3217...

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