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

3,648 homes near Winter Garden

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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!
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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 - $600Ks
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
Ocala Preserve 4086 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$252,990

3 beds

|

2 baths

|

1,504 sq ft

|

House

4086 NW 44TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4067 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$251,990

3 beds

|

2 baths

|

1,504 sq ft

|

House

4067 NW 44TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
Solivita 634 VIA CORSO CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$427,500

2 beds

|

2 baths

|

1,705 sq ft

|

House

634 VIA CORSO CT, KISSIMMEE, FL, 34759
Community: Solivita
Majestic Oaks Ocala 4792 SW 89TH ST, OCALA, FL, 34476, Ocala, FL 34476
$361,990

5 beds

|

3 baths

|

2,605 sq ft

|

House

4792 SW 89TH ST, OCALA, FL, 34476
Community: Majestic Oaks Ocala
On Top of the World 6561 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$227,990

3 beds

|

3 baths

|

1,458 sq ft

|

Townhouse

6561 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 6567 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$227,990

3 beds

|

3 baths

|

1,458 sq ft

|

Townhouse

6567 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
Palm Cay 11179 SW 78TH CT, OCALA, FL, 34476, Ocala, FL 34476
$179,900

2 beds

|

2 baths

|

1,086 sq ft

|

House

11179 SW 78TH CT, OCALA, FL, 34476
Community: Palm Cay
Ocala Preserve 4747 NW 35TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$330,000

2 beds

|

2 baths

|

1,666 sq ft

|

House

4747 NW 35TH LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
Sun City Center 401 DORCHESTER PL APT 69, SUN CITY CENTE..., Sun City Center, FL 33573
$125,000

1 beds

|

2 baths

|

820 sq ft

|

Condo

401 DORCHESTER PL APT 69, SUN CITY CENTE...
Community: Sun City Center
Spring Lake Towers 700 MIRROR TER 702, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$119,900

2 beds

|

2 baths

|

1,029 sq ft

|

Condo

700 MIRROR TER 702, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
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.
Oak Run 8321 SW 108TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$202,000

2 beds

|

2 baths

|

1,428 sq ft

|

House

8321 SW 108TH PLACE RD, OCALA, FL, 34481
Community: Oak Run
Marion Landing 6766 SW 88TH PL, OCALA, FL, 34476, Ocala, FL 34476
$223,000

3 beds

|

2 baths

|

1,651 sq ft

|

Manufactured Home

6766 SW 88TH PL, OCALA, FL, 34476
Community: Marion Landing
Archers Mill 3361 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$470,990

4 beds

|

4 baths

|

3,004 sq ft

|

House

3361 ARCH AVE, ORMOND BEACH, FL, 32174
Community: Archers Mill
Archers Mill 3313 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$458,990

4 beds

|

3 baths

|

2,108 sq ft

|

House

3313 ARCH AVE, ORMOND BEACH, FL, 32174
Community: Archers Mill
Ocala Preserve 5670 NW 39TH LN, OCALA, FL, 34482, Ocala, FL 34482
$407,500

3 beds

|

2 baths

|

1,854 sq ft

|

House

5670 NW 39TH LN, OCALA, FL, 34482
Community: Ocala Preserve
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek North 11215 SW 63RD TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$185,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

11215 SW 63RD TERRACE RD, OCALA, FL, 344...
Community: Spruce Creek North
Solivita 200 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$209,000

2 beds

|

2 baths

|

1,388 sq ft

|

House

200 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
Colonnades 1774 BIRCHWOOD LOOP, LAKELAND, FL, 33811, Lakeland, FL 33811
$305,000

2 beds

|

2 baths

|

1,193 sq ft

|

House

1774 BIRCHWOOD LOOP, LAKELAND, FL, 33811
Community: Colonnades
On Top of the World 8556 SW 90TH LN C, OCALA, FL, 34481, Ocala, FL 34481
$215,000

2 beds

|

2 baths

|

1,687 sq ft

|

Villa

8556 SW 90TH LN C, OCALA, FL, 34481
Community: On Top of the World
Ocala Palms 5140 NW 25TH LOOP, OCALA, FL, 34482, Ocala, FL 34482
$245,000

2 beds

|

2 baths

|

1,569 sq ft

|

House

5140 NW 25TH LOOP, OCALA, FL, 34482
Community: Ocala Palms
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® 1553 GUMWOOD DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$399,900

3 beds

|

2 baths

|

1,891 sq ft

|

House

1553 GUMWOOD DR, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 17720 SE 84TH PEYTON CT, THE VILLAGES, F..., The Villages, FL 32162
$399,900

3 beds

|

2 baths

|

1,733 sq ft

|

Villa

17720 SE 84TH PEYTON CT, THE VILLAGES, F...
Community: The Villages®
The Villages® 3567 INFINITY RUN, THE VILLAGES, FL, 321..., The Villages, FL 32163
$529,900

3 beds

|

2 baths

|

2,035 sq ft

|

House

3567 INFINITY RUN, THE VILLAGES, FL, 321...
Community: The Villages®
Ocala Palms 5247 NW 18TH ST, OCALA, FL, 34482, Ocala, FL 34482
$234,900

2 beds

|

2 baths

|

1,161 sq ft

|

House

5247 NW 18TH ST, OCALA, FL, 34482
Community: Ocala Palms
Archers Mill 3321 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$514,565

4 beds

|

4 baths

|

2,787 sq ft

|

House

3321 ARCH AVE, ORMOND BEACH, FL, 32174
Community: Archers Mill
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 1001 OTTER MILL WAY # 1001, SUN CITY CEN..., Sun City Center, FL 33573
$245,000

2 beds

|

2 baths

|

1,810 sq ft

|

Condo

1001 OTTER MILL WAY # 1001, SUN CITY CEN...
Community: Sun City Center
Palms at Serenoa 17386 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$369,900

3 beds

|

2 baths

|

1,621 sq ft

|

House

17386 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
Archers Mill 3353 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$384,990

4 beds

|

2 baths

|

2,034 sq ft

|

House

3353 ARCH AVE, ORMOND BEACH, FL, 32174
Community: Archers Mill
Harbor Hills Country Club 38800 HARBORWOODS PL, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$449,900

3 beds

|

4 baths

|

2,692 sq ft

|

House

38800 HARBORWOODS PL, LADY LAKE, FL, 321...
Archers Mill 3309 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$449,990

4 beds

|

3 baths

|

2,361 sq ft

|

House

3309 ARCH AVE, ORMOND BEACH, FL, 32174
Community: Archers Mill
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.
Traditions at Lake Ruby 3844 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$338,900

4 beds

|

3 baths

|

1,919 sq ft

|

House

3844 BEDFORD AVE, WINTER HAVEN, FL, 3388...
Cresswind at Victoria Gardens 430 CYPRESS HILLS WAY, DELAND, FL, 32724, Deland, FL 32724
$330,000

2 beds

|

2 baths

|

1,655 sq ft

|

House

430 CYPRESS HILLS WAY, DELAND, FL, 32724
Kings Ridge 4012 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$335,900

2 beds

|

2 baths

|

1,679 sq ft

|

House

4012 CAPLAND AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Oak Run 11159 SW 68TH CT, OCALA, FL, 34476, Ocala, FL 34476
$229,900

2 beds

|

2 baths

|

1,380 sq ft

|

House

11159 SW 68TH CT, OCALA, FL, 34476
Community: Oak Run
On Top of the World 10055 SW 90TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$300,000

2 beds

|

2 baths

|

1,662 sq ft

|

House

10055 SW 90TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 290 POP TOP LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124
$412,000

2 beds

|

2 baths

|

1,387 sq ft

|

House

290 POP TOP LN, DAYTONA BEACH, FL, 32124
Highlands Ridge 2881 E SPINNAKER DR, AVON PARK, FL, 3382..., Avon Park, FL 33825
$95,000

3 beds

|

2 baths

|

1,750 sq ft

|

Mobile Home

2881 E SPINNAKER DR, AVON PARK, FL, 3382...
Community: Highlands Ridge
Archers Mill 3305 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$489,990

4 beds

|

4 baths

|

2,787 sq ft

|

House

3305 ARCH AVE, ORMOND BEACH, FL, 32174
Community: Archers Mill
Colonnades 1608 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811
$259,900

2 beds

|

2 baths

|

1,305 sq ft

|

House

1608 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
Archers Mill 3299 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$439,990

4 beds

|

3 baths

|

2,361 sq ft

|

House

3299 ARCH AVE, ORMOND BEACH, FL, 32174
Community: Archers Mill

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3,648 homes near Winter Garden
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