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 40

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 9958 SW 97TH LN, OCALA, FL, 34481, Ocala, FL 34481
$335,000

3 beds

|

2 baths

|

1,953 sq ft

|

House

9958 SW 97TH LN, OCALA, FL, 34481
Community: On Top of the World
Ocala Preserve 4619 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$319,990

4 beds

|

2 baths

|

2,034 sq ft

|

House

4619 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Venetian Bay 424 LUNA BELLA LN 228, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168
$349,500

3 beds

|

3 baths

|

2,030 sq ft

|

Condo

424 LUNA BELLA LN 228, NEW SMYRNA BEACH,...
Community: Venetian Bay
The Villages® 1404 BRIER CREEK CIR, THE VILLAGES, FL, ..., The Villages, FL 32162
$1,299,999

4 beds

|

3 baths

|

3,537 sq ft

|

House

1404 BRIER CREEK CIR, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 2837 GRANT WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$579,000

3 beds

|

2 baths

|

1,923 sq ft

|

House

2837 GRANT WAY, THE VILLAGES, FL, 32162
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 6231 ATKINSON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$304,000

3 beds

|

2 baths

|

1,426 sq ft

|

House

6231 ATKINSON LN, THE VILLAGES, FL, 3216...
Community: The Villages®
Solivita 537 GRAND CANAL DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$215,000

2 beds

|

2 baths

|

1,071 sq ft

|

House

537 GRAND CANAL DR, POINCIANA, FL, 34759
Community: Solivita
Del Webb Orlando 436 PONTEVEDRA RD, DAVENPORT, FL, 33837, Davenport, FL 33837
$303,500

2 beds

|

2 baths

|

1,348 sq ft

|

House

436 PONTEVEDRA RD, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Plantation at Leesburg 4908 CYPRESS HEAD CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$339,900

3 beds

|

2 baths

|

2,087 sq ft

|

House

4908 CYPRESS HEAD CT, LEESBURG, FL, 3474...
The Villages® 1603 COG HILL DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$254,400

2 beds

|

2 baths

|

1,542 sq ft

|

Manufactured Home

1603 COG HILL DR, LADY LAKE, FL, 32159
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 13150 SE 93RD CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$299,900

2 beds

|

2 baths

|

2,051 sq ft

|

House

13150 SE 93RD CIR, SUMMERFIELD, FL, 3449...
The Villages® 2766 PRIVADA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$360,000

3 beds

|

2 baths

|

1,664 sq ft

|

House

2766 PRIVADA DR, THE VILLAGES, FL, 32162
Community: The Villages®
On Top of the World 8515 SW 101ST TER, OCALA, FL, 34481, Ocala, FL 34481
$565,565

3 beds

|

3 baths

|

2,373 sq ft

|

House

8515 SW 101ST TER, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 10815 SW 96TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$647,355

3 beds

|

3 baths

|

2,211 sq ft

|

House

10815 SW 96TH LANE RD, OCALA, FL, 34481
Community: On Top of the World
The Villages® 24104 SANDALWOOD DR 104, WILDWOOD, FL, 3..., Wildwood, FL 34785
$115,000

1 beds

|

1 baths

|

900 sq ft

|

Condo

24104 SANDALWOOD DR 104, WILDWOOD, FL, 3...
Community: The Villages®
Sun City Center 302 CANTON CT 59, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$119,900

2 beds

|

2 baths

|

960 sq ft

|

Condo

302 CANTON CT 59, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 101 CAMBRIDGE TRL 196, SUN CITY CENTER, ..., Sun City Center, FL 33573
$105,900

2 beds

|

2 baths

|

960 sq ft

|

Condo

101 CAMBRIDGE TRL 196, SUN CITY CENTER, ...
Community: Sun City Center
Oak Run 10972 SW 69TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$236,999

2 beds

|

2 baths

|

1,243 sq ft

|

House

10972 SW 69TH CIR, OCALA, FL, 34476
Community: Oak Run
Harbor Hills Country Club 5013 HARBOR HEIGHTS, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$340,000

3 beds

|

2 baths

|

1,954 sq ft

|

House

5013 HARBOR HEIGHTS, LADY LAKE, FL, 3215...
The Villages® 2427 SOUTHERN OAK ST, THE VILLAGES, FL, ..., The Villages, FL 32162
$299,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2427 SOUTHERN OAK ST, THE VILLAGES, FL, ...
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 13828 SE 85TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$249,900

2 beds

|

2 baths

|

1,315 sq ft

|

House

13828 SE 85TH CIR, SUMMERFIELD, FL, 3449...
Stone Creek 6276 SW 93RD TER, OCALA, FL, 34481, Ocala, FL 34481
$398,000

2 beds

|

2 baths

|

1,885 sq ft

|

House

6276 SW 93RD TER, OCALA, FL, 34481
Community: Stone Creek
On Top of the World 9511 SW 93RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$248,900

3 beds

|

2 baths

|

1,586 sq ft

|

House

9511 SW 93RD LOOP, OCALA, FL, 34481
Community: On Top of the World
Stone Creek 9021 SW 57TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$719,000

3 beds

|

4 baths

|

2,844 sq ft

|

House

9021 SW 57TH PLACE RD, OCALA, FL, 34481
Community: Stone Creek
Plantation at Leesburg 25073 RIVERWALK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$289,000

3 beds

|

2 baths

|

1,814 sq ft

|

House

25073 RIVERWALK DR, LEESBURG, FL, 34748
The Villages® 1407 FIGUEROA ST, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$300,000

3 beds

|

2 baths

|

1,687 sq ft

|

House

1407 FIGUEROA ST, THE VILLAGES, FL, 3216...
Community: The Villages®
Sullivan Ranch 22024 BELGIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$310,000

3 beds

|

2 baths

|

1,437 sq ft

|

House

22024 BELGIAN CT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 930 TARRSON BLVD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$139,800

2 beds

|

2 baths

|

960 sq ft

|

Manufactured Home

930 TARRSON BLVD, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 208 DESOTA CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$344,000

2 beds

|

2 baths

|

1,504 sq ft

|

House

208 DESOTA CT, LADY LAKE, FL, 32159
Community: The Villages®
Ocala Preserve 3584 NW 56TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$379,900

2 beds

|

3 baths

|

2,017 sq ft

|

House

3584 NW 56TH AVE, OCALA, FL, 34482
Community: Ocala Preserve
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.
Stonecrest 17552 SE 119TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$325,000

3 beds

|

3 baths

|

1,676 sq ft

|

House

17552 SE 119TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 580 GOUGH PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$569,000

3 beds

|

2 baths

|

1,918 sq ft

|

House

580 GOUGH PL, THE VILLAGES, FL, 32163
Community: The Villages®
Solivita 516 MILLIFIORA LN, POINCIANA, FL, 34759, Poinciana, FL 34759
$260,000

2 beds

|

2 baths

|

1,240 sq ft

|

House

516 MILLIFIORA LN, POINCIANA, FL, 34759
Community: Solivita
Harbor Hills Country Club 5084 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$707,150

4 beds

|

3 baths

|

2,586 sq ft

|

House

5084 GREENS DR, LADY LAKE, FL, 32159
Sun City Center 642 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$299,000

2 beds

|

2 baths

|

1,735 sq ft

|

Villa

642 CHIPPER DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Sun City Center 505 FINSBURY CIR A, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$169,000

2 beds

|

2 baths

|

1,085 sq ft

|

Condo

505 FINSBURY CIR A, SUN CITY CENTER, FL,...
Community: Sun City Center
Royal Harbor 5277 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778
$349,900

3 beds

|

2 baths

|

2,086 sq ft

|

House

5277 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
The Villages® 2975 THAYER TER, THE VILLAGES, FL, 32163, The Villages, FL 32163
$444,000

3 beds

|

2 baths

|

1,617 sq ft

|

Villa

2975 THAYER TER, THE VILLAGES, FL, 32163
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Lakes at Harmony 3415 FEATHERGRASS CT, ST CLOUD, FL, 3477..., St Cloud, FL 34773
$599,900

5 beds

|

4 baths

|

3,300 sq ft

|

House

3415 FEATHERGRASS CT, ST CLOUD, FL, 3477...
High Vista at Ridgewood Lakes 322 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$300,000

3 beds

|

2 baths

|

1,776 sq ft

|

House

322 HIGH VISTA DR, DAVENPORT, FL, 33837
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