Call us at (689) 407-5757 to learn more about active adult communities near Winter Garden

Winter Garden, FL 55+ active adult communities & homes for sale

3,703 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 - $1Ms
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 - $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
<$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 - $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 - $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 - $700Ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 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
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
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
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 (3 reviews) Stonecrest
<$100k - $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 - $900Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
$100Ks - $500Ks
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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $300Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $900Ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
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
No reviews yet Venetian Bay
$300Ks - $2Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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.
3.8 rating (6 reviews) Trilogy® Orlando
$300Ks - $500Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
5 rating (8 reviews) Royal Highlands
$200Ks - $500Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
3.8 rating (6 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) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$400Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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 - $300Ks
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 - $500Ks
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
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 (5 reviews) SummerGlen
$200Ks - $500Ks
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
No reviews yet Breakaway Trails
$400Ks - $1Ms
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
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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.8 rating (6 reviews) Highland Lakes
$200Ks - $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
No reviews yet Pine Run Estates
<$100k - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet 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
No reviews yet Esplanade at Wiregrass Ra...
$400Ks - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Spruce Creek Preserve 11587 SW 139TH PL, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$250,000

2 beds

|

2 baths

|

1,654 sq ft

|

House

11587 SW 139TH PL, DUNNELLON, FL, 34432
The Villages® 17370 SE 82ND ROSLYN CT, THE VILLAGES, F..., The Villages, FL 32162
$288,000

2 beds

|

2 baths

|

1,163 sq ft

|

Villa

17370 SE 82ND ROSLYN CT, THE VILLAGES, F...
Community: The Villages®
Sun City Center 2461 NANTUCKET HARBOR LOOP, SUN CITY CEN..., Sun City Center, FL 33573
$197,499

2 beds

|

2 baths

|

1,205 sq ft

|

Condo

2461 NANTUCKET HARBOR LOOP, SUN CITY CEN...
Community: Sun City Center
VillageWalk at Lake Nona 11887 DELFINA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$449,000

2 beds

|

2 baths

|

1,708 sq ft

|

House

11887 DELFINA LN, ORLANDO, FL, 32827
Huntington at Hunter's Ridge 34 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$334,900

3 beds

|

2 baths

|

1,523 sq ft

|

House

34 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Foxwood Lake Estates 1750 FOX HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$218,000

3 beds

|

2 baths

|

1,404 sq ft

|

Manufactured Home

1750 FOX HILL DR, LAKELAND, FL, 33810
Stone Creek 10134 SW 75TH STREET RD, OCALA, FL, 3448..., Ocala, FL 34481
$346,643

2 beds

|

2 baths

|

1,703 sq ft

|

House

10134 SW 75TH STREET RD, OCALA, FL, 3448...
Community: Stone Creek
Stone Creek 6678 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$298,888

2 beds

|

2 baths

|

1,696 sq ft

|

Villa

6678 SW 91ST CIR, OCALA, FL, 34481
Community: Stone Creek
Valencia del Sol 4838 SEVILLA SHORES DR, WIMAUMA, FL, 335..., Wimauma, FL 33598
$549,000

3 beds

|

3 baths

|

2,252 sq ft

|

House

4838 SEVILLA SHORES DR, WIMAUMA, FL, 335...
Community: Valencia del Sol
Spruce Creek Country Club 8806 SE 132ND LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$505,000

3 beds

|

3 baths

|

2,807 sq ft

|

House

8806 SE 132ND LOOP, SUMMERFIELD, FL, 344...
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.
Lake Ashton 4184 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$369,900

3 beds

|

2 baths

|

1,816 sq ft

|

House

4184 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton
The Villages® 1224 DUSTIN DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$239,900

2 beds

|

2 baths

|

912 sq ft

|

Manufactured Home

1224 DUSTIN DR, LADY LAKE, FL, 32159
Community: The Villages®
Stonecrest 17435 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$355,000

3 beds

|

2 baths

|

1,682 sq ft

|

House

17435 SE 112TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 670 FAYETTE CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$389,000

3 beds

|

2 baths

|

1,539 sq ft

|

House

670 FAYETTE CT, THE VILLAGES, FL, 32162
Community: The Villages®
Plantation at Leesburg 25008 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$271,900

2 beds

|

2 baths

|

1,843 sq ft

|

House

25008 CRANES ROOST CIR, LEESBURG, FL, 34...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
SummerGlen 16215 SW 15TH CT, OCALA, FL, 34473, Ocala, FL 34473
$334,900

3 beds

|

2 baths

|

1,859 sq ft

|

House

16215 SW 15TH CT, OCALA, FL, 34473
Community: SummerGlen
Tampa Bay Golf and Country Club 10118 CLEGHORN DR, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576
$420,000

3 beds

|

2 baths

|

1,799 sq ft

|

House

10118 CLEGHORN DR, SAN ANTONIO, FL, 3357...
JB Ranch 6345 SW 88TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$310,000

3 beds

|

2 baths

|

1,813 sq ft

|

House

6345 SW 88TH LOOP, OCALA, FL, 34476
Community: JB Ranch
Highland Fairways 3175 PEBBLE BEND DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$165,000

2 beds

|

2 baths

|

1,456 sq ft

|

Manufactured Home

3175 PEBBLE BEND DR, LAKELAND, FL, 33810
Community: Highland Fairways
Trilogy® Orlando 135 CREPE MYRTLE DR, GROVELAND, FL, 3473..., Groveland, FL 34736
$365,000

3 beds

|

2 baths

|

1,651 sq ft

|

House

135 CREPE MYRTLE DR, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
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.
Summer Trees 62 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$235,000

2 beds

|

2 baths

|

1,309 sq ft

|

House

62 CYPRESS POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
Latitude Margaritaville 298 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$629,900

2 beds

|

3 baths

|

2,158 sq ft

|

House

298 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 154 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$389,000

2 beds

|

2 baths

|

1,308 sq ft

|

House

154 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Lakes of Mount Dora 1977 WEYMOUTH CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$785,000

4 beds

|

3 baths

|

2,423 sq ft

|

House

1977 WEYMOUTH CT, MOUNT DORA, FL, 32757
Community: Lakes of Mount Dora
Trilogy® Orlando 243 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736
$400,000

3 beds

|

2 baths

|

1,838 sq ft

|

House

243 BAYOU BEND RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
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 12526 EASTPOINTE DR, DADE CITY, FL, 3352..., Dade City, FL 33525
$385,000

3 beds

|

2 baths

|

1,722 sq ft

|

House

12526 EASTPOINTE DR, DADE CITY, FL, 3352...
The Villages® 1496 LIME GROVE LN, THE VILLAGES, FL, 32..., The Villages, FL 32162
$375,000

2 beds

|

2 baths

|

1,132 sq ft

|

Villa

1496 LIME GROVE LN, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 5778 HENRY LOOP, THE VILLAGES, FL, 32163, The Villages, FL 32163
$430,000

3 beds

|

2 baths

|

1,531 sq ft

|

House

5778 HENRY LOOP, THE VILLAGES, FL, 32163
Community: The Villages®
Heritage Hills 3521 BELLAND CIR B, CLERMONT, FL, 34711, Clermont, FL 34711
$299,999

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3521 BELLAND CIR B, CLERMONT, FL, 34711
Community: Heritage Hills
Del Webb Sunbridge 2743 RIVER CREEK LN, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771
$679,900

4 beds

|

3 baths

|

2,321 sq ft

|

House

2743 RIVER CREEK LN, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
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.
Stone Creek 7346 SW 101ST CT, OCALA, FL, 34481, Ocala, FL 34481
$289,000

2 beds

|

2 baths

|

1,596 sq ft

|

House

7346 SW 101ST CT, OCALA, FL, 34481
Community: Stone Creek
Sun City Center 2347 GAINESBOROUGH LOOP # 2347, SUN CITY..., Sun City Center, FL 33573
$155,000

2 beds

|

2 baths

|

1,008 sq ft

|

Condo

2347 GAINESBOROUGH LOOP # 2347, SUN CITY...
Community: Sun City Center
Lake James 7953 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$514,900

2 beds

|

2 baths

|

1,990 sq ft

|

House

7953 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Solivita 448 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$346,000

3 beds

|

2 baths

|

2,141 sq ft

|

House

448 SORRENTO RD, KISSIMMEE, FL, 34759
Community: Solivita
Marion Landing 6367 SW 83RD PL, OCALA, FL, 34476, Ocala, FL 34476
$160,000

3 beds

|

2 baths

|

1,456 sq ft

|

Mobile Home

6367 SW 83RD PL, OCALA, FL, 34476
Community: Marion Landing
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 912 E DEL WEBB BLVD, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$284,900

2 beds

|

2 baths

|

1,598 sq ft

|

House

912 E DEL WEBB BLVD, SUN CITY CENTER, FL...
Community: Sun City Center
Ocala Preserve 3997 NW 48TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34482
$306,990

2 beds

|

2 baths

|

1,816 sq ft

|

House

3997 NW 48TH TERRACE RD, OCALA, FL, 3448...
Community: Ocala Preserve
Valencia del Sol 5013 SEVILLA SHORES DR, WIMAUMA, FL, 335..., Wimauma, FL 33598
$574,900

3 beds

|

2 baths

|

2,074 sq ft

|

House

5013 SEVILLA SHORES DR, WIMAUMA, FL, 335...
Community: Valencia del Sol
Esplanade at Wiregrass Ranch 29171 GINNETTO DR, WESLEY CHAPEL, FL, 33..., Wesley Chapel, FL 33543
$1,650,000

3 beds

|

3 baths

|

3,690 sq ft

|

House

29171 GINNETTO DR, WESLEY CHAPEL, FL, 33...
Sun City Center 205 WIMBLY PL, SUN CITY CENTER, FL, 3357..., Sun City Center, FL 33573
$295,000

2 beds

|

2 baths

|

2,022 sq ft

|

House

205 WIMBLY PL, SUN CITY CENTER, FL, 3357...
Community: Sun City Center

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
3,703 homes near Winter Garden
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.
© 2025 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: Nov 02, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top