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 67

3,218 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
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 rating (57 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
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
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
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
4.1 rating (29 reviews) Oak Run
$100ks - $300ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 homes
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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
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 (2 reviews) Plantation at Leesburg
$100ks - $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
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
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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
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 (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 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
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 (1 reviews) Sandpiper Golf & Coun...
$100ks - $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 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
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$200ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
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
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
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.
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
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 (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 (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 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
Mirada
$300ks - $500ks
Mirada, San Antonio, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 858 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 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
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 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.
12...3
On Top of the World 10691 SW 99TH PL, OCALA, FL, 34481, Ocala, FL 34481
$459,999

2 beds

|

2 baths

|

2,019 sq ft

|

House

10691 SW 99TH PL, OCALA, FL, 34481
Community: On Top of the World
Stone Creek 9498 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$450,000

3 beds

|

3 baths

|

2,536 sq ft

|

House

9498 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Marion Landing 8459 SW 60TH CT, OCALA, FL, 34476, Ocala, FL 34476
$263,900

3 beds

|

3 baths

|

1,778 sq ft

|

House

8459 SW 60TH CT, OCALA, FL, 34476
Community: Marion Landing
Kings Ridge 4246 NEWLAND ST, CLERMONT, FL, 34711, Clermont, FL 34711
$349,999

3 beds

|

2 baths

|

1,755 sq ft

|

House

4246 NEWLAND ST, CLERMONT, FL, 34711
Community: Kings Ridge
Venetian Bay 428 N AIRPORT RD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$300,000

3 beds

|

3 baths

|

1,794 sq ft

|

Townhouse

428 N AIRPORT RD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Palms 2318 NW 50TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$289,000

2 beds

|

2 baths

|

1,394 sq ft

|

House

2318 NW 50TH AVE, OCALA, FL, 34482
Community: Ocala Palms
Sun City Center 325 GREEN MANOR DR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$289,950

2 beds

|

2 baths

|

1,732 sq ft

|

Villa

325 GREEN MANOR DR, SUN CITY CENTER, FL,...
Community: Sun City Center
Lake Jovita Golf and Country Club 13235 PALMILLA CIR, DADE CITY, FL, 33525, Dade City, FL 33525
$354,900

3 beds

|

2 baths

|

1,683 sq ft

|

House

13235 PALMILLA CIR, DADE CITY, FL, 33525
Pine Run Estates 10182 SW 87TH TER, OCALA, FL, 34481, Ocala, FL 34481
$149,900

2 beds

|

2 baths

|

1,144 sq ft

|

House

10182 SW 87TH TER, OCALA, FL, 34481
Community: Pine Run Estates
Stone Creek 6382 SW 97TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481
$369,900

2 beds

|

2 baths

|

1,701 sq ft

|

House

6382 SW 97TH TERRACE RD, OCALA, FL, 3448...
Community: Stone Creek
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 1201 CORINTH GREENS DR 58, SUN CITY CENT..., Sun City Center, FL 33573
$260,000

2 beds

|

2 baths

|

1,450 sq ft

|

Condo

1201 CORINTH GREENS DR 58, SUN CITY CENT...
Community: Sun City Center
Solivita 795 AVIARA LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$429,000

3 beds

|

3 baths

|

2,427 sq ft

|

House

795 AVIARA LN, KISSIMMEE, FL, 34759
Community: Solivita
Venetian Bay 553 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$379,999

3 beds

|

3 baths

|

1,916 sq ft

|

House

553 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
On Top of the World 8425 SW 101ST AVE, OCALA, FL, 34481, Ocala, FL 34481
$519,005

2 beds

|

2 baths

|

2,145 sq ft

|

House

8425 SW 101ST AVE, OCALA, FL, 34481
Community: On Top of the World
Latitude Margaritaville 361 PARROT LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124
$359,900

2 beds

|

2 baths

|

1,204 sq ft

|

House

361 PARROT LN, DAYTONA BEACH, FL, 32124
Sun City Center 2243 OAKLEY GREEN DR 29, SUN CITY CENTER..., Sun City Center, FL 33573
$309,900

2 beds

|

2 baths

|

1,668 sq ft

|

Condo

2243 OAKLEY GREEN DR 29, 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
Venetian Bay 3014 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$289,000

3 beds

|

3 baths

|

1,614 sq ft

|

Townhouse

3014 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Lake Ashton 1209 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$439,000

3 beds

|

2 baths

|

2,045 sq ft

|

House

1209 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
The Villages® 2938 CHIMBORAZO WAY, THE VILLAGES, FL, 3..., The Villages, FL 32163
$400,000

3 beds

|

2 baths

|

1,459 sq ft

|

House

2938 CHIMBORAZO WAY, THE VILLAGES, FL, 3...
Community: The Villages®
Pelican Bay Daytona Beach 233 BOB WHITE CT 2330, DAYTONA BEACH, FL..., Daytona Beach, FL 32119
$172,900

2 beds

|

2 baths

|

1,189 sq ft

|

Villa

233 BOB WHITE CT 2330, DAYTONA BEACH, FL...
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® 2584 ACOSTA CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$290,000

2 beds

|

2 baths

|

1,390 sq ft

|

Villa

2584 ACOSTA CT, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1988 PALO ALTO AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159
$625,000

3 beds

|

2 baths

|

2,594 sq ft

|

House

1988 PALO ALTO AVE, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 675 KENDALL CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$299,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

675 KENDALL CT, THE VILLAGES, FL, 32162
Community: The Villages®
Spruce Creek Country Club 9495 SE 130TH PLACE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$324,900

3 beds

|

2 baths

|

2,003 sq ft

|

House

9495 SE 130TH PLACE RD, SUMMERFIELD, FL,...
Latitude Margaritaville 600 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$619,900

2 beds

|

3 baths

|

2,158 sq ft

|

House

600 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Solivita 801 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$539,000

3 beds

|

2 baths

|

2,719 sq ft

|

House

801 GLENDORA RD, KISSIMMEE, FL, 34759
Community: Solivita
Sun City Center 723 ELKHORN RD, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$355,000

2 beds

|

2 baths

|

2,188 sq ft

|

House

723 ELKHORN RD, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 5092 NE 81ST BLVD, WILDWOOD, FL, 34785, Wildwood, FL 34785
$925,000

3 beds

|

3 baths

|

3,407 sq ft

|

House

5092 NE 81ST BLVD, WILDWOOD, FL, 34785
Community: The Villages®
Del Webb Orlando 799 ASTURIAS RD, DAVENPORT, FL, 33837, Davenport, FL 33837
$279,900

2 beds

|

2 baths

|

1,281 sq ft

|

House

799 ASTURIAS RD, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Marion Landing 8783 SW 66TH TER, OCALA, FL, 34476, Ocala, FL 34476
$187,000

2 beds

|

2 baths

|

1,008 sq ft

|

Manufactured Home

8783 SW 66TH TER, OCALA, FL, 34476
Community: Marion Landing
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 8650 SW 94TH LN C, OCALA, FL, 34481, Ocala, FL 34481
$137,900

2 beds

|

2 baths

|

1,341 sq ft

|

Villa

8650 SW 94TH LN C, OCALA, FL, 34481
Community: On Top of the World
The Villages® 2454 YOUNGMANN LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163
$400,000

3 beds

|

2 baths

|

1,569 sq ft

|

House

2454 YOUNGMANN LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
On Top of the World 9526 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$252,000

2 beds

|

2 baths

|

1,896 sq ft

|

House

9526 SW 92ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World
Plantation at Leesburg 25100 PINE HL, LEESBURG, FL, 34748, Leesburg, FL 34748
$165,000

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

25100 PINE HL, LEESBURG, FL, 34748
Sun City Center 1118 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$345,000

3 beds

|

2 baths

|

1,752 sq ft

|

House

1118 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
Oak Run 8491 SW 109TH ST, OCALA, FL, 34481, Ocala, FL 34481
$169,950

2 beds

|

2 baths

|

960 sq ft

|

House

8491 SW 109TH ST, OCALA, FL, 34481
Community: Oak Run
On Top of the World 9120 SW 91ST TER, OCALA, FL, 34481, Ocala, FL 34481
$359,900

2 beds

|

2 baths

|

2,740 sq ft

|

House

9120 SW 91ST TER, OCALA, FL, 34481
Community: On Top of the World
The Villages® 1405 W SCHWARTZ BLVD, THE VILLAGES, FL, ..., The Villages, FL 32159
$289,900

2 beds

|

2 baths

|

1,192 sq ft

|

House

1405 W SCHWARTZ BLVD, THE VILLAGES, FL, ...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Heritage Hills 3464 EMBERS LN, CLERMONT, FL, 34711, Clermont, FL 34711
$435,000

3 beds

|

3 baths

|

2,032 sq ft

|

House

3464 EMBERS LN, CLERMONT, FL, 34711
Community: Heritage Hills
Colonnades 4938 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811
$225,900

2 beds

|

2 baths

|

1,188 sq ft

|

House

4938 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
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.

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
3,218 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: Jul 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