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 64

3,776 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
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
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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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
4.1 rating (29 reviews) Oak Run
$100ks - $300ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 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 (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
5 rating (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 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
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 (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 (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
5 rating (8 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
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
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 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
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2017 - 2024 | 655 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) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 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.
The Country Club of Mount...
$200ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 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) Legacy of Leesburg
$200ks - $400ks
Legacy of Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes
5 rating (1 reviews) Palm Cay
$100ks - $200ks
Palm Cay, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 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
4.4 rating (9 reviews) Spruce Creek Preserve
$100ks - $200ks
Spruce Creek Preserve, Dunnellon, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 810 homes
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 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
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 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
Cindy Certified
5068 MOSS HAMMOCK TRL, SEBRING, FL, 3387..., Sebring, FL 33872
$549,900

3 beds

|

2 baths

|

2,273 sq ft

|

House

5068 MOSS HAMMOCK TRL, SEBRING, FL, 3387...
Sun City Center 818 MCCALLISTER AVE, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$240,000

2 beds

|

2 baths

|

1,564 sq ft

|

Condo

818 MCCALLISTER AVE, SUN CITY CENTER, FL...
Community: Sun City Center
Harbor Hills Country Club 4008 PINNACLE PLACE CT, LADY LAKE, FL, 3..., Lady Lake, FL 32159
$685,000

3 beds

|

3 baths

|

2,434 sq ft

|

House

4008 PINNACLE PLACE CT, LADY LAKE, FL, 3...
Sun City Center 1812 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$359,000

3 beds

|

2 baths

|

2,606 sq ft

|

House

1812 NEW BEDFORD DR, SUN CITY CENTER, FL...
Community: Sun City Center
Cindy Certified
31426 MANGO FADE WAY, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$300,000

3 beds

|

2 baths

|

1,587 sq ft

|

Villa

31426 MANGO FADE WAY, SAN ANTONIO, FL, 3...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 10621 SW 98TH LN, OCALA, FL, 34481, Ocala, FL 34481
$439,750

3 beds

|

3 baths

|

2,963 sq ft

|

House

10621 SW 98TH LN, OCALA, FL, 34481
Community: On Top of the World
The Villages® 1506 DELLANO WAY, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$414,000

2 beds

|

2 baths

|

1,782 sq ft

|

House

1506 DELLANO WAY, THE VILLAGES, FL, 3215...
Community: The Villages®
Cindy Certified
8846 SW 69TH TER, OCALA, FL, 34476, Ocala, FL 34476
$373,500

4 beds

|

3 baths

|

2,601 sq ft

|

House

8846 SW 69TH TER, OCALA, FL, 34476
Del Webb Minneola 2458 DEL WEBB DR, MINNEOLA, FL, 34715, Minneola, FL 34715
$725,000

3 beds

|

3 baths

|

2,260 sq ft

|

House

2458 DEL WEBB DR, MINNEOLA, FL, 34715
Community: Del Webb Minneola
Cindy Certified
7642 BENT TREE LOOP, ST CLOUD, FL, 34773, St Cloud, FL 34773
$366,900

3 beds

|

2 baths

|

1,780 sq ft

|

House

7642 BENT TREE LOOP, ST CLOUD, FL, 34773
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.
Venetian Bay 3321 MARSILI AVE, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$445,000

4 beds

|

3 baths

|

2,540 sq ft

|

House

3321 MARSILI AVE, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Pennbrooke Fairways 32222 SUMMERTREE CIR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$289,000

2 beds

|

2 baths

|

1,725 sq ft

|

House

32222 SUMMERTREE CIR, LEESBURG, FL, 3474...
Community: Pennbrooke Fairways
Valencia Lakes 5044 SANDY BROOK CIR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$610,000

4 beds

|

3 baths

|

2,799 sq ft

|

House

5044 SANDY BROOK CIR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Stone Creek 8764 SW 58TH STREET RD, OCALA, FL, 34481, Ocala, FL 34481
$298,888

2 beds

|

2 baths

|

1,406 sq ft

|

House

8764 SW 58TH STREET RD, OCALA, FL, 34481
Community: Stone Creek
Spruce Creek Country Club 9119 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$249,000

2 beds

|

2 baths

|

1,488 sq ft

|

House

9119 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Cindy Certified
4550 LIVE OAK LN, OXFORD, FL, 34484, Oxford, FL 34484
$428,990

5 beds

|

3 baths

|

2,587 sq ft

|

House

4550 LIVE OAK LN, OXFORD, FL, 34484
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Cindy Certified
545 VICEROY CT, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$315,000

3 beds

|

2 baths

|

2,035 sq ft

|

House

545 VICEROY CT, KISSIMMEE, FL, 34758
Stone Creek 9098 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$225,000

2 beds

|

2 baths

|

1,437 sq ft

|

House

9098 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek
On Top of the World 8355 SW 84TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$379,000

3 beds

|

2 baths

|

1,993 sq ft

|

House

8355 SW 84TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 1816 GRANVILLE LN, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$275,000

2 beds

|

2 baths

|

1,857 sq ft

|

House

1816 GRANVILLE LN, SUN CITY CENTER, FL, ...
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.
Venetian Bay 424 LUNA BELLA LN 231, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168
$325,000

3 beds

|

3 baths

|

1,953 sq ft

|

Condo

424 LUNA BELLA LN 231, NEW SMYRNA BEACH,...
Community: Venetian Bay
Stone Creek 8480 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$322,223

3 beds

|

2 baths

|

1,697 sq ft

|

House

8480 SW 52ND LANE RD, OCALA, FL, 34481
Community: Stone Creek
Legacy of Leesburg 27134 NOSTALGIA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,900

3 beds

|

2 baths

|

1,601 sq ft

|

House

27134 NOSTALGIA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Oak Run 6318 SW 117TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$259,255

3 beds

|

2 baths

|

1,921 sq ft

|

House

6318 SW 117TH LOOP, OCALA, FL, 34476
Community: Oak Run
SummerGlen 15771 SW 13TH CIR, OCALA, FL, 34473, Ocala, FL 34473
$231,900

2 beds

|

2 baths

|

1,558 sq ft

|

House

15771 SW 13TH CIR, OCALA, FL, 34473
Community: SummerGlen
Lake Jovita Golf and Country Club 12749 GRAND TRAVERSE DR, DADE CITY, FL, ..., Dade City, FL 33525
$924,000

3 beds

|

3 baths

|

3,109 sq ft

|

House

12749 GRAND TRAVERSE DR, DADE CITY, FL, ...
Cindy Certified
10608 OAK TREE ALY, OXFORD, FL, 34484, Oxford, FL 34484
$307,990

3 beds

|

2 baths

|

1,654 sq ft

|

House

10608 OAK TREE ALY, OXFORD, FL, 34484
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lake Jovita Golf and Country Club 12215 WOODLANDS CIR, DADE CITY, FL, 3352..., Dade City, FL 33525
$515,000

3 beds

|

2 baths

|

1,762 sq ft

|

House

12215 WOODLANDS CIR, DADE CITY, FL, 3352...
Harbor Hills Country Club 5506 CITATION CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$619,000

3 beds

|

3 baths

|

2,698 sq ft

|

House

5506 CITATION CT, LADY LAKE, FL, 32159
On Top of the World 8907 SW 84TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$289,900

3 beds

|

2 baths

|

1,705 sq ft

|

House

8907 SW 84TH CIR, 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.
Stonecrest 17719 SE 114TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$260,000

2 beds

|

2 baths

|

1,704 sq ft

|

Villa

17719 SE 114TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Cindy Certified
4558 LIVE OAK LN, OXFORD, FL, 34484, Oxford, FL 34484
$330,990

4 beds

|

3 baths

|

1,933 sq ft

|

House

4558 LIVE OAK LN, OXFORD, FL, 34484
Ocala Preserve 4530 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$299,990

2 beds

|

2 baths

|

1,816 sq ft

|

House

4530 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Heritage - The Cottages of Sanders Grove 6213 SANDERS GROVE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$327,595

4 beds

|

2 baths

|

1,625 sq ft

|

House

6213 SANDERS GROVE CIR, LEESBURG, FL, 34...
Heritage - The Cottages of Sanders Grove 6217 SANDERS GROVE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$358,389

4 beds

|

3 baths

|

1,938 sq ft

|

House

6217 SANDERS GROVE CIR, LEESBURG, FL, 34...
Heritage - The Cottages of Sanders Grove 5715 HIAWASSEE RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$344,250

4 beds

|

3 baths

|

1,938 sq ft

|

House

5715 HIAWASSEE RD, LEESBURG, FL, 34748
Heritage - The Cottages of Sanders Grove 6205 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762
$320,091

3 beds

|

2 baths

|

1,407 sq ft

|

House

6205 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
The Villages® 1516 MARTINEZ DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$479,000

2 beds

|

2 baths

|

1,546 sq ft

|

Villa

1516 MARTINEZ DR, LADY LAKE, FL, 32159
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Heritage - The Cottages of Sanders Grove 5719 HIAWASSEE RD, OKAHUMPKA, FL, 34762, Okahumpka, FL 34762
$335,990

4 beds

|

2 baths

|

1,625 sq ft

|

House

5719 HIAWASSEE RD, OKAHUMPKA, FL, 34762
Kings Ridge 3916 SCARBOROUGH CT, CLERMONT, FL, 34711, Clermont, FL 34711
$469,000

3 beds

|

2 baths

|

2,147 sq ft

|

House

3916 SCARBOROUGH CT, CLERMONT, FL, 34711
Community: Kings Ridge
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
3,776 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: Oct 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