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 85

3,769 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 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
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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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
4.1 rating (29 reviews) Oak Run
$100ks - $300ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 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
4.7 rating (18 reviews) Solivita
$300ks - $700ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
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
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.
4.6 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) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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
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 (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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
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) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 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) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 homes
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 (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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (1 reviews) Cresswind at Victoria Gar...
$300ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 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
Cresswind Lakewood Ranch
$400ks - $700ks
Cresswind Lakewood Ranch, Lakewood Ranch, FL
New and Resale | 55+ age-restricted | Built 2018 - present | 648 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.
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 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
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
The Country Club of Mount...
$200ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes
Highland Fairways
$100ks - $300ks
Highland Fairways, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes
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) Del Webb Sunbridge
$400ks - $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (1 reviews) Palm Cay
$100ks - $200ks
Palm Cay, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 homes
3.8 rating (5 reviews) Marion Landing
$100ks - $300ks
Marion Landing, Ocala, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 600 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.
123...4
Stone Creek 9601 SW 65TH PL, OCALA, FL, 34481, Ocala, FL 34481
$391,900

2 beds

|

2 baths

|

2,164 sq ft

|

House

9601 SW 65TH PL, OCALA, FL, 34481
Community: Stone Creek
On Top of the World 9698 SW 103RD TER, OCALA, FL, 34481, Ocala, FL 34481
$255,000

2 beds

|

2 baths

|

1,342 sq ft

|

House

9698 SW 103RD TER, OCALA, FL, 34481
Community: On Top of the World
Cindy Certified
2928 CANARY LN, TAVARES, FL, 32778, Tavares, FL 32778
$355,000

4 beds

|

2 baths

|

1,846 sq ft

|

House

2928 CANARY LN, TAVARES, FL, 32778
Kings Ridge 4246 NEWLAND ST, CLERMONT, FL, 34711, Clermont, FL 34711
$329,000

3 beds

|

2 baths

|

1,755 sq ft

|

House

4246 NEWLAND ST, CLERMONT, FL, 34711
Community: Kings Ridge
Cindy Certified
1078 CHELAN FALLS DR, DELAND, FL, 32724, Deland, FL 32724
$410,000

4 beds

|

2 baths

|

1,943 sq ft

|

House

1078 CHELAN FALLS DR, DELAND, FL, 32724
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
$279,950

2 beds

|

2 baths

|

1,732 sq ft

|

Villa

325 GREEN MANOR DR, SUN CITY CENTER, FL,...
Community: Sun City Center
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
Pelican Bay Daytona Beach 233 BOB WHITE CT 2330, DAYTONA BEACH, FL..., Daytona Beach, FL 32119
$168,500

2 beds

|

2 baths

|

1,189 sq ft

|

Villa

233 BOB WHITE CT 2330, DAYTONA BEACH, FL...
The Villages® 675 KENDALL CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$296,500

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

675 KENDALL CT, THE VILLAGES, FL, 32162
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.
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,...
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®
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
Cindy Certified
2713 RUNNERS CIR, CLERMONT, FL, 34714, Clermont, FL 34714
$380,000

3 beds

|

2 baths

|

1,432 sq ft

|

House

2713 RUNNERS CIR, CLERMONT, FL, 34714
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®
Plantation at Leesburg 25100 PINE HL, LEESBURG, FL, 34748, Leesburg, FL 34748
$148,000

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

25100 PINE HL, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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®
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
The Villages® 16816 SE 85TH SAPELO CT, THE VILLAGES, F..., The Villages, FL 32162
$585,000

3 beds

|

2 baths

|

1,934 sq ft

|

House

16816 SE 85TH SAPELO CT, THE VILLAGES, F...
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.
Cindy Certified
7576 BENT TREE LOOP, ST CLOUD, FL, 34773, St Cloud, FL 34773
$400,000

4 beds

|

3 baths

|

2,200 sq ft

|

House

7576 BENT TREE LOOP, ST CLOUD, FL, 34773
Scottish Highlands 1409 NEW ABBEY AVE, LEESBURG, FL, 34788, Leesburg, FL 34788
$214,999

2 beds

|

2 baths

|

1,482 sq ft

|

Condo

1409 NEW ABBEY AVE, LEESBURG, FL, 34788
Community: Scottish Highlands
Sun City Center 1520 DANBURY DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$239,900

2 beds

|

2 baths

|

1,405 sq ft

|

House

1520 DANBURY DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Summer Trees 41 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$260,000

2 beds

|

2 baths

|

1,495 sq ft

|

House

41 CROOKED PINE RD, PORT ORANGE, FL, 321...
Community: Summer Trees
On Top of the World 10555 SW 96TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$789,000

3 beds

|

3 baths

|

2,307 sq ft

|

House

10555 SW 96TH LANE RD, OCALA, FL, 34481
Community: On Top of the World
Cindy Certified
5644 ESTERO LOOP, PORT ORANGE, FL, 32128, Port Orange, FL 32128
$393,900

3 beds

|

2 baths

|

1,626 sq ft

|

House

5644 ESTERO LOOP, PORT ORANGE, FL, 32128
Trilogy® Orlando 146 CREPE MYRTLE DR, GROVELAND, FL, 3473..., Groveland, FL 34736
$325,000

3 beds

|

2 baths

|

1,728 sq ft

|

House

146 CREPE MYRTLE DR, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lakes of Mount Dora 3951 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$499,700

3 beds

|

2 baths

|

2,180 sq ft

|

House

3951 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
The Villages® 8017 SE 175TH COLUMBIA PL, THE VILLAGES,..., The Villages, FL 32162
$299,900

3 beds

|

2 baths

|

1,527 sq ft

|

House

8017 SE 175TH COLUMBIA PL, THE VILLAGES,...
Community: The Villages®
Lake Ashton 6308 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$452,000

3 beds

|

2 baths

|

2,045 sq ft

|

House

6308 PINEHURST LOOP, WINTER HAVEN, FL, 3...
Community: Lake Ashton
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.
Ocala Preserve 5504 NW 40TH LOOP, OCALA, FL, 34482, Ocala, FL 34482
$324,900

2 beds

|

2 baths

|

1,666 sq ft

|

House

5504 NW 40TH LOOP, OCALA, FL, 34482
Community: Ocala Preserve
Solivita 176 CAPE FLORIDA DR, POINCIANA, FL, 3475..., Poinciana, FL 34759
$299,000

2 beds

|

2 baths

|

1,440 sq ft

|

House

176 CAPE FLORIDA DR, POINCIANA, FL, 3475...
Community: Solivita
SummerGlen 15803 SW 11TH COURT RD, OCALA, FL, 34473, Ocala, FL 34473
$265,000

3 beds

|

2 baths

|

1,759 sq ft

|

House

15803 SW 11TH COURT RD, OCALA, FL, 34473
Community: SummerGlen
Sun City Center 202 BEDFORD ST 49, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$94,900

2 beds

|

2 baths

|

960 sq ft

|

Condo

202 BEDFORD ST 49, SUN CITY CENTER, FL, ...
Community: Sun City Center
Esplanade at Highland Ranch 1284 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715
$399,000

2 beds

|

2 baths

|

1,722 sq ft

|

House

1284 ZEEK RIDGE ST, CLERMONT, FL, 34715
The Villages® 1069 BURNETTOWN PL, THE VILLAGES, FL, 32..., The Villages, FL 32162
$359,000

2 beds

|

2 baths

|

1,300 sq ft

|

House

1069 BURNETTOWN PL, THE VILLAGES, FL, 32...
Community: The Villages®
Cindy Certified
32472 SEA LOCH LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$420,534

3 beds

|

3 baths

|

1,790 sq ft

|

House

32472 SEA LOCH LOOP, MOUNT DORA, FL, 327...
The Lakes at Harmony 3212 OXBOW CT, HARMONY, FL, 34773, Harmony, FL 34773
$370,000

3 beds

|

2 baths

|

1,580 sq ft

|

House

3212 OXBOW CT, HARMONY, FL, 34773
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Palms 5500 NW 26TH LN, OCALA, FL, 34482, Ocala, FL 34482
$210,000

3 beds

|

2 baths

|

1,499 sq ft

|

House

5500 NW 26TH LN, OCALA, FL, 34482
Community: Ocala Palms
Windermere 826 LANARK DR, INVERNESS, FL, 34453, Inverness, FL 34453
$269,900

3 beds

|

3 baths

|

1,897 sq ft

|

Townhouse

826 LANARK DR, INVERNESS, FL, 34453
Community: Windermere
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 optout@55places.com. 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
3,769 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: Aug 25, 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