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 9

3,495 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 - $2Ms
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 - $700Ks
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 - $600Ks
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 - $900Ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.1 rating (29 reviews) Oak Run
$100Ks - $500Ks
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
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 - $500Ks
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
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 - $600Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 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 - $400Ks
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
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $400Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $600Ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 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) 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
Venetian Bay
$200Ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (8 reviews) Royal Highlands
$200Ks - $400Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
4 rating (7 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) VillageWalk at Lake Nona
$300Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 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
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 (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 - $400Ks
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 - $400Ks
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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (5 reviews) SummerGlen
$100Ks - $400Ks
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
Breakaway Trails
$400Ks - $800Ks
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
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 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
4.8 rating (6 reviews) Highland Lakes
$100Ks - $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
Pine Run Estates
<$100k - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
Esplanade at Wiregrass Ra...
$400Ks - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
The Villages® 1258 WEATON CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$359,000

3 beds

|

2 baths

|

1,477 sq ft

|

House

1258 WEATON CT, THE VILLAGES, FL, 32162
Community: The Villages®
On Top of the World 8643 SW 86TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$320,000

3 beds

|

2 baths

|

1,705 sq ft

|

House

8643 SW 86TH CIR, OCALA, FL, 34481
Community: On Top of the World
The Villages® 2378 YOUNGMANN LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163
$449,000

3 beds

|

2 baths

|

1,611 sq ft

|

House

2378 YOUNGMANN LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
The Villages® 2241 HACKNEY WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$385,000

3 beds

|

2 baths

|

1,737 sq ft

|

House

2241 HACKNEY WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
New The Villages® 1803 PALO ALTO AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159
$525,000

3 beds

|

2 baths

|

2,104 sq ft

|

House

1803 PALO ALTO AVE, THE VILLAGES, FL, 32...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 928 OLEANDER ST, THE VILLAGES, FL, 32159, The Villages, FL 32159
$209,999

2 beds

|

2 baths

|

1,196 sq ft

|

Manufactured Home

928 OLEANDER ST, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 3104 BURBANK LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$385,000

3 beds

|

2 baths

|

1,932 sq ft

|

House

3104 BURBANK LN, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 9238 SE 171ST COOPER LOOP, THE VILLAGES,..., The Villages, FL 32162
$374,500

3 beds

|

2 baths

|

1,664 sq ft

|

House

9238 SE 171ST COOPER LOOP, THE VILLAGES,...
Community: The Villages®
The Villages® 512 AINSWORTH CIR, THE VILLAGES, FL, 321..., The Villages, FL 32162
$589,000

3 beds

|

2 baths

|

1,678 sq ft

|

House

512 AINSWORTH CIR, THE VILLAGES, FL, 321...
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.
The Villages® 5967 FREITAG AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$599,000

3 beds

|

2 baths

|

1,633 sq ft

|

Villa

5967 FREITAG AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 3017 HILLSIDE LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$349,900

3 beds

|

2 baths

|

1,520 sq ft

|

House

3017 HILLSIDE LN, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 17627 SE 88TH COVINGTON CIR, THE VILLAGE..., The Villages, FL 32162
$725,000

3 beds

|

2 baths

|

2,460 sq ft

|

House

17627 SE 88TH COVINGTON CIR, THE VILLAGE...
Community: The Villages®
The Villages® 7858 SE 171ST BUCHANAN PL, THE VILLAGES,..., The Villages, FL 32162
$300,000

2 beds

|

2 baths

|

1,186 sq ft

|

Villa

7858 SE 171ST BUCHANAN PL, THE VILLAGES,...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1016 PICKERING PATH, THE VILLAGES, FL, 3..., The Villages, FL 32163
$750,000

3 beds

|

2 baths

|

2,230 sq ft

|

House

1016 PICKERING PATH, THE VILLAGES, FL, 3...
Community: The Villages®
The Villages® 5617 STRICKLIN ST, THE VILLAGES, FL, 321..., The Villages, FL 32163
$499,000

3 beds

|

2 baths

|

1,696 sq ft

|

House

5617 STRICKLIN ST, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 1865 CLAVERTON ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$698,000

3 beds

|

2 baths

|

2,579 sq ft

|

House

1865 CLAVERTON ST, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 2046 DALECROFT TRL, THE VILLAGES, FL, 32..., The Villages, FL 32162
$349,900

3 beds

|

2 baths

|

1,488 sq ft

|

House

2046 DALECROFT TRL, THE VILLAGES, FL, 32...
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.
The Villages® 664 TERNBERRY FOREST DR, THE VILLAGES, F..., The Villages, FL 32162
$1,775,000

3 beds

|

3 baths

|

3,100 sq ft

|

House

664 TERNBERRY FOREST DR, THE VILLAGES, F...
Community: The Villages®
The Villages® 1221 SANTA CRUZ DR, THE VILLAGES, FL, 32..., The Villages, FL 32162
$289,900

2 beds

|

2 baths

|

1,174 sq ft

|

Villa

1221 SANTA CRUZ DR, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 6126 MULLIGAN RUN, THE VILLAGES, FL, 321..., The Villages, FL 32163
$799,900

3 beds

|

2 baths

|

2,930 sq ft

|

House

6126 MULLIGAN RUN, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 2935 CEDAR GROVE LOOP, THE VILLAGES, FL,..., The Villages, FL 32163
$895,000

3 beds

|

2 baths

|

3,466 sq ft

|

House

2935 CEDAR GROVE LOOP, 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
Trilogy® Orlando 168 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$625,000

3 beds

|

3 baths

|

2,392 sq ft

|

House

168 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Stonecrest 17842 SE 125TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$349,000

3 beds

|

2 baths

|

1,695 sq ft

|

House

17842 SE 125TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
Majestic Oaks Ocala 8284 SW 59TH TER, OCALA, FL, 34476, Ocala, FL 34476
$625,000

4 beds

|

3 baths

|

2,550 sq ft

|

House

8284 SW 59TH TER, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Sun City Center 1360 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$440,000

3 beds

|

2 baths

|

2,482 sq ft

|

Condo

1360 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
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 611 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$334,900

2 beds

|

2 baths

|

1,668 sq ft

|

Townhouse

611 CHIPPER DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Cresswind DeLand 1213 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724
$544,990

3 beds

|

3 baths

|

1,983 sq ft

|

House

1213 CRESSWIND BLVD, DELAND, FL, 32724
Community: Cresswind DeLand
Cresswind DeLand 1235 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724
$609,990

3 beds

|

4 baths

|

2,496 sq ft

|

House

1235 CRESSWIND BLVD, DELAND, FL, 32724
Community: Cresswind DeLand
Cresswind DeLand 1322 SAVOY LN, DELAND, FL, 32724, Deland, FL 32724
$493,990

3 beds

|

3 baths

|

2,289 sq ft

|

House

1322 SAVOY LN, DELAND, FL, 32724
Community: Cresswind DeLand
Cresswind DeLand 1299 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724
$586,990

3 beds

|

4 baths

|

2,776 sq ft

|

House

1299 CRESSWIND BLVD, DELAND, FL, 32724
Community: Cresswind DeLand
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Cresswind DeLand 1025 PORT BLUE WAY, DELAND, FL, 32724, Deland, FL 32724
$385,990

3 beds

|

2 baths

|

1,724 sq ft

|

House

1025 PORT BLUE WAY, DELAND, FL, 32724
Community: Cresswind DeLand
Cresswind DeLand 1304 CLUB CRESSWIND WAY, DELAND, FL, 327..., Deland, FL 32724
$473,990

3 beds

|

3 baths

|

2,129 sq ft

|

House

1304 CLUB CRESSWIND WAY, DELAND, FL, 327...
Community: Cresswind DeLand
Cresswind DeLand 1352 SAVOY LN, DELAND, FL, 32724, Deland, FL 32724
$363,990

2 beds

|

2 baths

|

1,434 sq ft

|

House

1352 SAVOY LN, DELAND, FL, 32724
Community: Cresswind DeLand
Stone Creek 9009 SW 52ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$383,470

2 beds

|

3 baths

|

2,080 sq ft

|

House

9009 SW 52ND PLACE RD, OCALA, FL, 34481
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.
The Villages® 1019 AVALON AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$280,000

2 beds

|

2 baths

|

1,623 sq ft

|

Villa

1019 AVALON AVE, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1722 BUGLE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$425,000

3 beds

|

2 baths

|

1,667 sq ft

|

House

1722 BUGLE TER, THE VILLAGES, FL, 32162
Community: The Villages®
Trilogy® Orlando 134 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$363,000

3 beds

|

2 baths

|

1,644 sq ft

|

House

134 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
New Stone Creek 5370 SW 86TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$335,360

2 beds

|

2 baths

|

1,471 sq ft

|

House

5370 SW 86TH COURT RD, OCALA, FL, 34481
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Stone Creek 5345 SW 86TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$342,780

2 beds

|

2 baths

|

1,471 sq ft

|

House

5345 SW 86TH COURT RD, OCALA, FL, 34481
Community: Stone Creek
New Stone Creek 5354 SW 86TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$344,080

2 beds

|

2 baths

|

1,655 sq ft

|

House

5354 SW 86TH COURT RD, OCALA, FL, 34481
Community: Stone Creek

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
3,495 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: Jan 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