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 64

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
Sandpiper Golf & Country Club 6087 SEAGULL LN, LAKELAND, FL, 33809, Lakeland, FL 33809
$299,000

3 beds

|

2 baths

|

1,899 sq ft

|

House

6087 SEAGULL LN, LAKELAND, FL, 33809
The Villages® 758 MOORE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$850,000

3 beds

|

2 baths

|

2,642 sq ft

|

House

758 MOORE TER, THE VILLAGES, FL, 32162
Community: The Villages®
Four Seasons at Orlando 7637 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747
$394,500

2 beds

|

2 baths

|

1,557 sq ft

|

Villa

7637 SAND PIERRE CT, KISSIMMEE, FL, 3474...
Huntington at Hunter's Ridge 33 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$489,000

4 beds

|

3 baths

|

2,156 sq ft

|

House

33 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Southshore Bay 17335 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$395,900

3 beds

|

3 baths

|

2,145 sq ft

|

House

17335 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
SummerGlen 15296 SW 15TH TERRACE RD, OCALA, FL, 344..., Ocala, FL 34473
$247,000

3 beds

|

2 baths

|

2,282 sq ft

|

House

15296 SW 15TH TERRACE RD, OCALA, FL, 344...
Community: SummerGlen
Del Webb Sunbridge 2434 N CLIFF WAY, ST CLOUD, FL, 34771, St Cloud, FL 34771
$375,000

2 beds

|

2 baths

|

1,584 sq ft

|

Villa

2434 N CLIFF WAY, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
Arlington Ridge 4622 SHENANDOAH RIVER TRL, LEESBURG, FL,..., Leesburg, FL 34748
$365,000

3 beds

|

2 baths

|

1,699 sq ft

|

House

4622 SHENANDOAH RIVER TRL, LEESBURG, FL,...
Community: Arlington Ridge
The Villages® 17760 SE 91ST FREEDOM CT, THE VILLAGES, ..., The Villages, FL 32162
$249,900

3 beds

|

2 baths

|

1,590 sq ft

|

Villa

17760 SE 91ST FREEDOM CT, THE VILLAGES, ...
Community: The Villages®
The Villages® 144 COSTA MESA DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$307,400

3 beds

|

2 baths

|

2,046 sq ft

|

House

144 COSTA MESA 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.
The Villages® 335 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$295,000

2 beds

|

2 baths

|

1,360 sq ft

|

House

335 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
Lake James 7826 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$399,900

2 beds

|

2 baths

|

1,788 sq ft

|

House

7826 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Mirada 10162 ECHO DOCK LOOP, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$277,000

2 beds

|

2 baths

|

1,614 sq ft

|

Villa

10162 ECHO DOCK LOOP, SAN ANTONIO, FL, 3...
Community: Mirada
Heritage Hills 2823 MAYPORT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$520,000

3 beds

|

3 baths

|

2,573 sq ft

|

House

2823 MAYPORT ST, CLERMONT, FL, 34711
Community: Heritage Hills
Oak Run 8695 SW 116TH STREET RD, OCALA, FL, 3448..., Ocala, FL 34481
$238,500

3 beds

|

2 baths

|

2,073 sq ft

|

House

8695 SW 116TH STREET RD, OCALA, FL, 3448...
Community: Oak Run
Quail Meadow 4634 NW 35TH ST, OCALA, FL, 34482, Ocala, FL 34482
$204,000

2 beds

|

2 baths

|

1,080 sq ft

|

House

4634 NW 35TH ST, OCALA, FL, 34482
Community: Quail Meadow
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 3074 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$575,000

4 beds

|

4 baths

|

2,092 sq ft

|

Townhouse

3074 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Solivita 786 CIELO TRL, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$375,000

2 beds

|

2 baths

|

2,170 sq ft

|

House

786 CIELO TRL, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 13811 COUNTY RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$300,000

4 beds

|

2 baths

|

2,280 sq ft

|

Manufactured Home

13811 COUNTY RD, LADY LAKE, FL, 32159
Community: The Villages®
Highland Lakes 6514 WILANDER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$349,900

3 beds

|

3 baths

|

2,546 sq ft

|

House

6514 WILANDER ST, LEESBURG, FL, 34748
Community: Highland 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.
Summit Greens 2833 FALCON RDG, CLERMONT, FL, 34711, Clermont, FL 34711
$549,000

3 beds

|

3 baths

|

2,804 sq ft

|

House

2833 FALCON RDG, CLERMONT, FL, 34711
Community: Summit Greens
The Country Club of Mount Dora 8013 PINE HOLLOW DR, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$440,000

3 beds

|

2 baths

|

2,256 sq ft

|

House

8013 PINE HOLLOW DR, MOUNT DORA, FL, 327...
Marion Landing 8594 SW 61ST CT, OCALA, FL, 34476, Ocala, FL 34476
$208,000

2 beds

|

2 baths

|

1,552 sq ft

|

House

8594 SW 61ST CT, OCALA, FL, 34476
Community: Marion Landing
Ocala Palms 5801 NW 18TH ST, OCALA, FL, 34482, Ocala, FL 34482
$450,000

3 beds

|

3 baths

|

2,614 sq ft

|

House

5801 NW 18TH ST, OCALA, FL, 34482
Community: Ocala Palms
Lake Ashton 6216 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$459,000

3 beds

|

2 baths

|

2,045 sq ft

|

House

6216 PINEHURST LOOP, WINTER HAVEN, FL, 3...
Community: Lake Ashton
Spruce Creek Country Club 13700 SE 90TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$285,000

3 beds

|

2 baths

|

2,054 sq ft

|

House

13700 SE 90TH CT, SUMMERFIELD, FL, 34491
Oak Run 10821 SW 87TH TER, OCALA, FL, 34481, Ocala, FL 34481
$245,900

2 beds

|

2 baths

|

1,415 sq ft

|

House

10821 SW 87TH TER, OCALA, FL, 34481
Community: Oak Run
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Del Webb Minneola 2750 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715
$514,900

2 beds

|

2 baths

|

1,409 sq ft

|

House

2750 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
Oak Run 8690 SW 108TH PL, OCALA, FL, 34481, Ocala, FL 34481
$168,900

2 beds

|

2 baths

|

960 sq ft

|

House

8690 SW 108TH PL, OCALA, FL, 34481
Community: Oak Run
Tampa Bay Golf and Country Club 10133 COLLAR DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$450,000

3 beds

|

2 baths

|

2,500 sq ft

|

House

10133 COLLAR DR, SAN ANTONIO, FL, 33576
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.
Plantation at Leesburg 24239 BELLE MEDE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$375,000

3 beds

|

2 baths

|

2,289 sq ft

|

House

24239 BELLE MEDE DR, LEESBURG, FL, 34748
The Villages® 8371 SE 168TH TRINITY PL, THE VILLAGES, ..., The Villages, FL 32162
$309,900

3 beds

|

2 baths

|

1,496 sq ft

|

House

8371 SE 168TH TRINITY PL, THE VILLAGES, ...
Community: The Villages®
Plantation at Leesburg 25607 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748
$251,000

2 beds

|

2 baths

|

1,345 sq ft

|

House

25607 BELLE HELENE, LEESBURG, FL, 34748
Cormorant Point 3322 WATERWOOD DR, SEBRING, FL, 33872, Sebring, FL 33872
$239,900

2 beds

|

2 baths

|

1,322 sq ft

|

House

3322 WATERWOOD DR, SEBRING, FL, 33872
Community: Cormorant Point
Royal Harbor 5685 GULF STREAM ST, TAVARES, FL, 32778, Tavares, FL 32778
$329,999

3 beds

|

2 baths

|

1,823 sq ft

|

House

5685 GULF STREAM ST, TAVARES, FL, 32778
Community: Royal Harbor
Breakaway Trails 27 LAKE VISTA WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$815,000

4 beds

|

4 baths

|

3,505 sq ft

|

House

27 LAKE VISTA WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
Solivita 884 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$264,000

2 beds

|

2 baths

|

1,507 sq ft

|

House

884 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
Quail Meadow 1795 NW 44TH COURT RD, OCALA, FL, 34482, Ocala, FL 34482
$348,990

5 beds

|

3 baths

|

2,445 sq ft

|

House

1795 NW 44TH COURT RD, OCALA, FL, 34482
Community: Quail Meadow
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 13146 SE 93RD TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$299,900

2 beds

|

2 baths

|

1,425 sq ft

|

House

13146 SE 93RD TERRACE RD, SUMMERFIELD, F...
Highland Lakes 5500 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$250,000

3 beds

|

2 baths

|

1,591 sq ft

|

House

5500 LAVER ST, LEESBURG, FL, 34748
Community: Highland 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.

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 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