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

3,573 homes near Winter Garden

Sort by:

Relevance

Relevance

No reviews yet Del Webb Oasis
$400Ks - $1Ms
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
4 rating (17 reviews) The Villages®
<$100k - $2Ms
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
<$100k - $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 - $600Ks
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 (46 reviews) Latitude Margaritaville
$300Ks - $700Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
4.2 rating (10 reviews) Stone Creek
$200Ks - $800Ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.1 rating (29 reviews) Oak Run
$100Ks - $500Ks
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 - $400Ks
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
$200Ks - $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
$200Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 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
No reviews yet Venetian Bay
$200Ks - $1Ms
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.
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 (6 reviews) Trilogy® Orlando
$300Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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) VillageWalk at Lake Nona
$400Ks - $900Ks
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 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
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
$100Ks - $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 - $400Ks
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 - $400Ks
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
$300Ks - $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
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $400Ks
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
Oak Run 11159 SW 68TH CT, OCALA, FL, 34476, Ocala, FL 34476
$235,000

2 beds

|

2 baths

|

1,380 sq ft

|

House

11159 SW 68TH CT, OCALA, FL, 34476
Community: Oak Run
Lakeside Landings 10274 JULIA ISLES AVE, OXFORD, FL, 34484, Oxford, FL 34484
$355,000

3 beds

|

2 baths

|

1,616 sq ft

|

House

10274 JULIA ISLES AVE, OXFORD, FL, 34484
Community: Lakeside Landings
Tohoqua Reserve 1875 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$355,000

3 beds

|

2 baths

|

1,559 sq ft

|

House

1875 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
The Villages® 2530 HANLON TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$374,900

2 beds

|

2 baths

|

1,724 sq ft

|

House

2530 HANLON TER, THE VILLAGES, FL, 32162
Community: The Villages®
Sun City Center 445 NOBLE FAIRE DR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$469,000

3 beds

|

3 baths

|

2,637 sq ft

|

House

445 NOBLE FAIRE DR, SUN CITY CENTER, FL,...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Royal Highlands 21815 TARTAN ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$399,000

3 beds

|

3 baths

|

2,369 sq ft

|

House

21815 TARTAN ST, LEESBURG, FL, 34748
Community: Royal Highlands
Four Seasons at Orlando 7977 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$554,900

3 beds

|

2 baths

|

2,130 sq ft

|

House

7977 HANSON BAY PL, KISSIMMEE, FL, 34747
Royal Highlands 4609 INVERNESS DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$400,000

3 beds

|

3 baths

|

2,294 sq ft

|

House

4609 INVERNESS DR, LEESBURG, FL, 34748
Community: Royal Highlands
Royal Highlands 21509 CASTLE VIEW CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$325,000

3 beds

|

3 baths

|

1,913 sq ft

|

House

21509 CASTLE VIEW CT, LEESBURG, FL, 3474...
Community: Royal Highlands
Sun City Center 1120 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$455,000

2 beds

|

2 baths

|

1,885 sq ft

|

House

1120 EMERALD DUNES DR, SUN CITY CENTER, ...
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.
Sun City Center 832 KING LEON WAY, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$345,000

3 beds

|

2 baths

|

1,503 sq ft

|

House

832 KING LEON WAY, SUN CITY CENTER, FL, ...
Community: Sun City Center
Lake Ashton 5384 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$380,000

2 beds

|

2 baths

|

1,682 sq ft

|

House

5384 HOGAN LN, WINTER HAVEN, FL, 33884
Community: Lake Ashton
The Villages® 518 SAINT ANDREWS BLVD, THE VILLAGES, FL..., The Villages, FL 32159
$240,000

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

518 SAINT ANDREWS BLVD, THE VILLAGES, FL...
Community: The Villages®
Spruce Creek South 10476 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$239,000

2 beds

|

2 baths

|

1,473 sq ft

|

House

10476 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Plantation at Leesburg 3644 PLANTATION BLVD, LEESBURG, FL, 3474..., Leesburg, FL 34748
$320,000

2 beds

|

2 baths

|

1,862 sq ft

|

House

3644 PLANTATION BLVD, LEESBURG, FL, 3474...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Encore at Fishhawk Ranch 6003 BURROWING OWL PL, LITHIA, FL, 33547, Lithia, FL 33547
$535,000

3 beds

|

3 baths

|

2,310 sq ft

|

House

6003 BURROWING OWL PL, LITHIA, FL, 33547
Stonecrest 17446 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491
$329,900

3 beds

|

2 baths

|

1,681 sq ft

|

House

17446 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
Majestic Oaks Ocala 5605 SW 89TH ST, OCALA, FL, 34476, Ocala, FL 34476
$364,000

3 beds

|

2 baths

|

2,309 sq ft

|

House

5605 SW 89TH ST, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Spruce Creek South 10492 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$260,000

2 beds

|

2 baths

|

1,066 sq ft

|

House

10492 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Spruce Creek Country Club 13195 SE 93RD CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$437,500

3 beds

|

3 baths

|

2,266 sq ft

|

House

13195 SE 93RD CIR, SUMMERFIELD, FL, 3449...
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 9120 SE 125TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$399,000

2 beds

|

2 baths

|

1,990 sq ft

|

House

9120 SE 125TH LOOP, SUMMERFIELD, FL, 344...
Venetian Bay 3048 BORASSUS DR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$600,000

3 beds

|

2 baths

|

2,214 sq ft

|

House

3048 BORASSUS DR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Del Webb Oasis 12259 BRACCO ST, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787
$555,000

4 beds

|

3 baths

|

2,082 sq ft

|

House

12259 BRACCO ST, WINTER GARDEN, FL, 3478...
Community: Del Webb Oasis
Spruce Creek Country Club 9891 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$299,900

3 beds

|

2 baths

|

1,760 sq ft

|

House

9891 SE 138TH LOOP, SUMMERFIELD, FL, 344...
Plantation at Leesburg 25057 RIVERWALK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$377,500

3 beds

|

3 baths

|

2,676 sq ft

|

House

25057 RIVERWALK DR, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Del Webb Oasis 12253 BRACCO ST, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787
$544,950

3 beds

|

3 baths

|

1,788 sq ft

|

House

12253 BRACCO ST, WINTER GARDEN, FL, 3478...
Community: Del Webb Oasis
Sun City Center 1710 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$474,900

2 beds

|

2 baths

|

2,078 sq ft

|

House

1710 NEW BEDFORD DR, SUN CITY CENTER, FL...
Community: Sun City Center
Plantation at Leesburg 25517 LAUREL VALLEY RD, LEESBURG, FL, 34..., Leesburg, FL 34748
$399,900

3 beds

|

2 baths

|

2,381 sq ft

|

House

25517 LAUREL VALLEY RD, LEESBURG, FL, 34...
Quail Meadow 1795 NW 44TH COURT RD, OCALA, FL, 34482, Ocala, FL 34482
$374,900

5 beds

|

3 baths

|

2,445 sq ft

|

House

1795 NW 44TH COURT RD, OCALA, FL, 34482
Community: Quail Meadow
Del Webb Orlando 208 ALMERIA WAY, DAVENPORT, FL, 33837, Davenport, FL 33837
$444,900

2 beds

|

2 baths

|

1,927 sq ft

|

House

208 ALMERIA WAY, DAVENPORT, FL, 33837
Community: Del Webb 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.
Plantation at Leesburg 4822 SAWGRASS LAKE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$434,900

3 beds

|

3 baths

|

2,780 sq ft

|

House

4822 SAWGRASS LAKE CIR, LEESBURG, FL, 34...
Del Webb Orlando 500 PLAYA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$335,000

2 beds

|

2 baths

|

1,728 sq ft

|

House

500 PLAYA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Royal Highlands 5430 SIR CHURCHILL DR, LEESBURG, FL, 347..., Leesburg, FL 34748
$292,000

3 beds

|

2 baths

|

1,986 sq ft

|

House

5430 SIR CHURCHILL DR, LEESBURG, FL, 347...
Community: Royal Highlands
Plantation at Leesburg 4525 EAGLEWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$249,900

2 beds

|

2 baths

|

1,214 sq ft

|

House

4525 EAGLEWOOD DR, LEESBURG, FL, 34748
Royal Highlands 21325 ROYAL TROON DR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$400,000

3 beds

|

2 baths

|

2,333 sq ft

|

House

21325 ROYAL TROON DR, LEESBURG, FL, 3474...
Community: Royal Highlands
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 508 VILLAGIO LOOP, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$339,000

3 beds

|

2 baths

|

1,817 sq ft

|

House

508 VILLAGIO LOOP, KISSIMMEE, FL, 34759
Community: Solivita
Legacy of Leesburg 27143 NOSTALGIA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$425,000

3 beds

|

2 baths

|

2,021 sq ft

|

House

27143 NOSTALGIA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Sun City Center 702 PLUMBROOK RD, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$370,000

3 beds

|

2 baths

|

2,208 sq ft

|

House

702 PLUMBROOK RD, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Sun City Center 1723 WOLF LAUREL DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$373,900

2 beds

|

2 baths

|

2,031 sq ft

|

House

1723 WOLF LAUREL DR, SUN CITY CENTER, FL...
Community: Sun City Center
Cresswind at Victoria Gardens 430 CYPRESS HILLS WAY, DELAND, FL, 32724, Deland, FL 32724
$340,000

2 beds

|

2 baths

|

1,655 sq ft

|

House

430 CYPRESS HILLS WAY, DELAND, FL, 32724

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
3,573 homes near Winter Garden
Remove Boundaries ×
Map Satellite

Call Us Call Us
Scroll to Top