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 39

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
Legacy of Leesburg 27111 NOSTALGIA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$289,000

3 beds

|

2 baths

|

1,477 sq ft

|

House

27111 NOSTALGIA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
The Villages® 17203 SANDALWOOD DR, WILDWOOD, FL, 34785, Wildwood, FL 34785
$126,490

2 beds

|

2 baths

|

1,156 sq ft

|

House

17203 SANDALWOOD DR, WILDWOOD, FL, 34785
Community: The Villages®
The Villages® 1809 DAFFODIL LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$182,000

2 beds

|

1 baths

|

936 sq ft

|

Manufactured Home

1809 DAFFODIL LN, LADY LAKE, FL, 32159
Community: The Villages®
Trilogy® Orlando 119 FALLING ACORN AVE, GROVELAND, FL, 34..., Groveland, FL 34736
$338,000

2 beds

|

2 baths

|

1,651 sq ft

|

House

119 FALLING ACORN AVE, GROVELAND, FL, 34...
Community: Trilogy® Orlando
Sun City Center 700 RUTGERS PL, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$215,000

2 beds

|

2 baths

|

1,141 sq ft

|

Condo

700 RUTGERS PL, 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® 732 ROYAL PALM AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$219,900

3 beds

|

2 baths

|

1,100 sq ft

|

Manufactured Home

732 ROYAL PALM AVE, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 2464 NELLIE RD, THE VILLAGES, FL, 32163, The Villages, FL 32163
$365,000

3 beds

|

2 baths

|

1,425 sq ft

|

House

2464 NELLIE RD, THE VILLAGES, FL, 32163
Community: The Villages®
Esplanade at Highland Ranch 959 BRAEWOOD DR, CLERMONT, FL, 34715, Clermont, FL 34715
$450,000

2 beds

|

2 baths

|

1,788 sq ft

|

House

959 BRAEWOOD DR, CLERMONT, FL, 34715
The Villages® 3401 CARRABELLE CT, THE VILLAGES, FL, 32..., The Villages, FL 32163
$285,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

3401 CARRABELLE CT, THE VILLAGES, FL, 32...
Community: The Villages®
Carillon Lakes 4149 WINDCHIME LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$309,990

3 beds

|

2 baths

|

1,745 sq ft

|

House

4149 WINDCHIME LN, LAKELAND, FL, 33811
Community: Carillon 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.
Breakaway Trails 105 SHADOWCREEK WAY, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174
$575,000

4 beds

|

3 baths

|

2,694 sq ft

|

House

105 SHADOWCREEK WAY, ORMOND BEACH, FL, 3...
Community: Breakaway Trails
Sun City Center 1368 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$429,000

3 beds

|

2 baths

|

2,482 sq ft

|

Condo

1368 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
Sun City Center 704 OJAI AVE, SUN CITY CENTER, FL, 33573, Sun City Center, FL 33573
$224,900

2 beds

|

1 baths

|

1,149 sq ft

|

House

704 OJAI AVE, SUN CITY CENTER, FL, 33573
Community: Sun City Center
Cresswind at Victoria Gardens 1634 VICTORIA GARDENS DR, DELAND, FL, 32..., Deland, FL 32724
$425,000

2 beds

|

2 baths

|

1,928 sq ft

|

House

1634 VICTORIA GARDENS DR, DELAND, FL, 32...
The Villages® 2180 JASPER WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$339,900

3 beds

|

2 baths

|

1,240 sq ft

|

House

2180 JASPER WAY, THE VILLAGES, FL, 32162
Community: The Villages®
Oak Run 6795 SW 114TH STREET RD, OCALA, FL, 3447..., Ocala, FL 34476
$249,750

3 beds

|

2 baths

|

1,730 sq ft

|

House

6795 SW 114TH STREET RD, OCALA, FL, 3447...
Community: Oak Run
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Arlington Ridge 4258 JAMES RIVER CIR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$464,900

4 beds

|

3 baths

|

2,524 sq ft

|

House

4258 JAMES RIVER CIR, LEESBURG, FL, 3474...
Community: Arlington Ridge
Stonecrest 17789 SE 113TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$285,000

3 beds

|

3 baths

|

1,463 sq ft

|

House

17789 SE 113TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
Latitude Margaritaville 274 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$379,900

2 beds

|

2 baths

|

1,208 sq ft

|

House

274 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Stonecrest 17440 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$339,900

3 beds

|

2 baths

|

1,794 sq ft

|

House

17440 SE 112TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
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® 2859 RESMONDO RD, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$458,900

3 beds

|

2 baths

|

1,674 sq ft

|

Villa

2859 RESMONDO RD, THE VILLAGES, FL, 3216...
Community: The Villages®
Spruce Creek Country Club 9280 SE 126TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$468,000

2 beds

|

3 baths

|

2,368 sq ft

|

House

9280 SE 126TH ST, SUMMERFIELD, FL, 34491
Quail Meadow 4772 NW 30TH PL, OCALA, FL, 34482, Ocala, FL 34482
$279,998

3 beds

|

2 baths

|

1,910 sq ft

|

House

4772 NW 30TH PL, OCALA, FL, 34482
Community: Quail Meadow
Latitude Margaritaville 219 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$429,900

2 beds

|

2 baths

|

1,464 sq ft

|

House

219 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...
Sun City Center 301 ANDOVER PL 175, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$90,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

301 ANDOVER PL 175, SUN CITY CENTER, FL,...
Community: Sun City Center
Sun City Center 504 RIMINI VISTA WAY, SUN CITY CENTER, F..., Sun City Center, FL 33573
$469,950

3 beds

|

2 baths

|

2,012 sq ft

|

House

504 RIMINI VISTA WAY, SUN CITY CENTER, F...
Community: Sun City Center
Pennbrooke Fairways 32676 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$280,000

3 beds

|

2 baths

|

1,709 sq ft

|

House

32676 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 2612 MORVEN PARK WAY, THE VILLAGES, FL, ..., The Villages, FL 32162
$429,000

3 beds

|

2 baths

|

1,922 sq ft

|

House

2612 MORVEN PARK WAY, THE VILLAGES, FL, ...
Community: The Villages®
Ocala Preserve 4355 NW 53RD CT, OCALA, FL, 34482, Ocala, FL 34482
$529,900

3 beds

|

3 baths

|

2,362 sq ft

|

House

4355 NW 53RD CT, OCALA, FL, 34482
Community: Ocala Preserve
On Top of the World 8540 SW 91ST PL C, OCALA, FL, 34481, Ocala, FL 34481
$158,700

2 beds

|

2 baths

|

1,530 sq ft

|

Villa

8540 SW 91ST PL 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.
On Top of the World 8625 SW 94 LN G, OCALA, FL, 34481, Ocala, FL 34481
$169,900

2 beds

|

2 baths

|

1,715 sq ft

|

Villa

8625 SW 94 LN G, OCALA, FL, 34481
Community: On Top of the World
The Villages® 963 AVALON AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$299,900

2 beds

|

2 baths

|

1,268 sq ft

|

Villa

963 AVALON AVE, LADY LAKE, FL, 32159
Community: The Villages®
Foxwood Lake Estates 1688 FOXWAY DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$169,900

3 beds

|

2 baths

|

1,427 sq ft

|

Manufactured Home

1688 FOXWAY DR, LAKELAND, FL, 33810
Twin Lakes 2305 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772
$289,999

2 beds

|

2 baths

|

1,346 sq ft

|

Villa

2305 DATURA LOOP, ST CLOUD, FL, 34772
Community: Twin Lakes
Ocala Palms 5046 NW 21ST LOOP, OCALA, FL, 34482, Ocala, FL 34482
$229,000

2 beds

|

2 baths

|

1,378 sq ft

|

House

5046 NW 21ST LOOP, OCALA, FL, 34482
Community: Ocala Palms
Cherrywood 9832 SW 61ST CT, OCALA, FL, 34476, Ocala, FL 34476
$213,500

3 beds

|

2 baths

|

1,370 sq ft

|

House

9832 SW 61ST CT, OCALA, FL, 34476
Community: Cherrywood
Royal Highlands 21630 REGENCY PARK LN, LEESBURG, FL, 347..., Leesburg, FL 34748
$272,500

3 beds

|

2 baths

|

1,438 sq ft

|

House

21630 REGENCY PARK LN, LEESBURG, FL, 347...
Community: Royal Highlands
Oak Run 11416 SW 69TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$299,888

3 beds

|

2 baths

|

2,123 sq ft

|

House

11416 SW 69TH CIR, OCALA, FL, 34476
Community: Oak Run
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Foxwood Lake Estates 1502 LONGBOW DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$222,500

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

1502 LONGBOW DR, LAKELAND, FL, 33810
Tarawood 10494 S DREW BRYANT CIR, FLORAL CITY, FL..., Floral City, FL 34436
$238,000

3 beds

|

2 baths

|

1,311 sq ft

|

House

10494 S DREW BRYANT CIR, FLORAL CITY, FL...
Community: Tarawood
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 11, 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