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

3,958 homes near Winter Garden

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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 - $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
<$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
$200Ks - $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 - $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 - $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 - $600Ks
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 - $1Ms
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
<$100k - $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
$200Ks - $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 - $900Ks
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
$200Ks - $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) 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
$100Ks - $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 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
3.6 rating (5 reviews) Heritage Hills
$300Ks - $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 - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 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 - $700Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$200Ks - $800Ks
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 - $800Ks
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
$100Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $500Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
$100Ks - $400Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet 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
No reviews yet Esplanade at Wiregrass Ra...
$400Ks - $900Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Sun City Center 446 NOBLE FAIRE DR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$349,000

2 beds

|

2 baths

|

1,837 sq ft

|

House

446 NOBLE FAIRE DR, SUN CITY CENTER, FL,...
Community: Sun City Center
On Top of the World 8811 SW 77TH TER, OCALA, FL, 34476, Ocala, FL 34476
$369,900

3 beds

|

2 baths

|

1,855 sq ft

|

House

8811 SW 77TH TER, OCALA, FL, 34476
Community: On Top of the World
Lakeside Landings 10144 LAKE MIONA WAY, OXFORD, FL, 34484, Oxford, FL 34484
$599,900

3 beds

|

2 baths

|

2,319 sq ft

|

House

10144 LAKE MIONA WAY, OXFORD, FL, 34484
Community: Lakeside Landings
Sun City Center 604 MCDANIEL ST, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$299,999

3 beds

|

3 baths

|

2,105 sq ft

|

Condo

604 MCDANIEL ST, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Venetian Bay 3039 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$335,000

3 beds

|

3 baths

|

1,672 sq ft

|

House

3039 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1812 SANIBEL CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$254,900

2 beds

|

2 baths

|

1,229 sq ft

|

House

1812 SANIBEL CT, THE VILLAGES, FL, 32162
Community: The Villages®
Sun City Center 1333 MISTY GREENS DR, SUN CITY CENTER, F..., Sun City Center, FL 33573
$335,000

3 beds

|

2 baths

|

1,725 sq ft

|

House

1333 MISTY GREENS DR, SUN CITY CENTER, F...
Community: Sun City Center
The Villages® 202 ESTRADA PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$269,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

202 ESTRADA PL, THE VILLAGES, FL, 32159
Community: The Villages®
Traditions at Lake Ruby 2885 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$229,998

2 beds

|

2 baths

|

1,400 sq ft

|

Villa

2885 ATTWATER LOOP, WINTER HAVEN, FL, 33...
On Top of the World 8036 SW 78TH TERRACE RD, OCALA, FL, 3447..., Ocala, FL 34476
$268,900

3 beds

|

2 baths

|

1,576 sq ft

|

House

8036 SW 78TH TERRACE RD, OCALA, FL, 3447...
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.
Latitude Margaritaville 456 LIME AVE, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124
$397,500

2 beds

|

2 baths

|

1,308 sq ft

|

House

456 LIME AVE, DAYTONA BEACH, FL, 32124
Lakeside Landings 10105 KETCH KAY LN, OXFORD, FL, 34484, Oxford, FL 34484
$325,000

3 beds

|

2 baths

|

1,856 sq ft

|

House

10105 KETCH KAY LN, OXFORD, FL, 34484
Community: Lakeside Landings
Latitude Margaritaville 452 LIME AVE, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124
$397,500

2 beds

|

2 baths

|

1,309 sq ft

|

House

452 LIME AVE, DAYTONA BEACH, FL, 32124
Windermere 818 WINDERMERE BLVD, INVERNESS, FL, 3445..., Inverness, FL 34453
$204,900

2 beds

|

2 baths

|

1,198 sq ft

|

Townhouse

818 WINDERMERE BLVD, INVERNESS, FL, 3445...
Community: Windermere
Oak Run 7407 SW 112TH PL, OCALA, FL, 34476, Ocala, FL 34476
$250,000

2 beds

|

2 baths

|

1,657 sq ft

|

House

7407 SW 112TH PL, OCALA, FL, 34476
Community: Oak Run
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Highlands Ridge 3120 S PRESTWICK DR, AVON PARK, FL, 3382..., Avon Park, FL 33825
$299,900

3 beds

|

2 baths

|

1,901 sq ft

|

House

3120 S PRESTWICK DR, AVON PARK, FL, 3382...
Community: Highlands Ridge
Sun City Center 301 THORN HILL PL, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$565,000

3 beds

|

2 baths

|

2,402 sq ft

|

House

301 THORN HILL PL, SUN CITY CENTER, FL, ...
Community: Sun City Center
On Top of the World 8874 SW 95TH ST E, OCALA, FL, 34481, Ocala, FL 34481
$245,900

2 beds

|

2 baths

|

1,761 sq ft

|

Villa

8874 SW 95TH ST E, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8654 SW 96TH ST D, OCALA, FL, 34481, Ocala, FL 34481
$137,500

2 beds

|

2 baths

|

1,525 sq ft

|

Villa

8654 SW 96TH ST D, OCALA, FL, 34481
Community: On Top of the World
The Villages® 17606 SE 93RD BUTLER CT, THE VILLAGES, F..., The Villages, FL 32162
$299,999

3 beds

|

2 baths

|

1,392 sq ft

|

House

17606 SE 93RD BUTLER CT, THE VILLAGES, F...
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.
Plantation at Leesburg 25800 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748
$245,000

2 beds

|

2 baths

|

1,653 sq ft

|

House

25800 BELLE HELENE, LEESBURG, FL, 34748
Highland Lakes 6022 WILANDER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$250,000

3 beds

|

2 baths

|

1,460 sq ft

|

House

6022 WILANDER ST, LEESBURG, FL, 34748
Community: Highland Lakes
On Top of the World 9856 SW 100TH TERRACE RD, OCALA, FL, 344..., Ocala, FL 34481
$289,000

2 beds

|

2 baths

|

1,342 sq ft

|

House

9856 SW 100TH TERRACE RD, OCALA, FL, 344...
Community: On Top of the World
Foxwood Lake Estates 4859 FOXWOOD BLVD, LAKELAND, FL, 33810, Lakeland, FL 33810
$179,900

2 beds

|

2 baths

|

828 sq ft

|

Manufactured Home

4859 FOXWOOD BLVD, LAKELAND, FL, 33810
Sun City Center 2516 NEW HAVEN CIR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$199,000

2 beds

|

2 baths

|

1,359 sq ft

|

Condo

2516 NEW HAVEN CIR, 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
Breakaway Trails 27 WINDING CREEK WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174
$625,000

3 beds

|

3 baths

|

2,370 sq ft

|

House

27 WINDING CREEK WAY, ORMOND BEACH, FL, ...
Community: Breakaway Trails
The Villages® 2479 PORT ROYAL CT, THE VILLAGES, FL, 32..., The Villages, FL 32162
$349,999

3 beds

|

2 baths

|

1,541 sq ft

|

House

2479 PORT ROYAL CT, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 110 TIMBER WAY, WILDWOOD, FL, 34785, Wildwood, FL 34785
$139,000

2 beds

|

2 baths

|

1,352 sq ft

|

Manufactured Home

110 TIMBER WAY, WILDWOOD, FL, 34785
Community: The Villages®
Highland Lakes 6608 BORG ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$375,000

3 beds

|

2 baths

|

2,365 sq ft

|

House

6608 BORG ST, LEESBURG, FL, 34748
Community: Highland Lakes
Marion Landing 8683 SW 62ND CT, OCALA, FL, 34476, Ocala, FL 34476
$190,000

2 beds

|

2 baths

|

1,798 sq ft

|

House

8683 SW 62ND CT, OCALA, FL, 34476
Community: Marion Landing
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 2113 E DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573
$360,000

3 beds

|

3 baths

|

2,218 sq ft

|

House

2113 E DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
On Top of the World 8443 SW 82ND LOOP, OCALA, FL, 34481, Ocala, FL 34481
$379,758

2 beds

|

2 baths

|

1,709 sq ft

|

House

8443 SW 82ND LOOP, OCALA, FL, 34481
Community: On Top of the World
Ocala Preserve 4859 NW 35TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$369,000

2 beds

|

2 baths

|

1,666 sq ft

|

House

4859 NW 35TH LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
Sun City Center 1531 COUNCIL DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$239,000

2 beds

|

2 baths

|

1,266 sq ft

|

House

1531 COUNCIL DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Kings Ridge 2415 TWICKINGHAM CT, CLERMONT, FL, 34711, Clermont, FL 34711
$359,900

3 beds

|

2 baths

|

1,871 sq ft

|

House

2415 TWICKINGHAM CT, CLERMONT, FL, 34711
Community: Kings Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Oak Run 8128 SW 117TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$219,750

2 beds

|

2 baths

|

1,640 sq ft

|

House

8128 SW 117TH LOOP, OCALA, FL, 34481
Community: Oak Run
Pelican Bay Daytona Beach 100 AVOCET CT, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119
$295,000

3 beds

|

3 baths

|

1,883 sq ft

|

Townhouse

100 AVOCET CT, DAYTONA BEACH, FL, 32119
Traditions at Lake Ruby 3926 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$340,000

3 beds

|

2 baths

|

1,860 sq ft

|

House

3926 BEDFORD AVE, WINTER HAVEN, FL, 3388...
JB Ranch 4682 SW 88TH LN, OCALA, FL, 34476, Ocala, FL 34476
$327,165

4 beds

|

2 baths

|

1,828 sq ft

|

House

4682 SW 88TH LN, OCALA, FL, 34476
Community: JB Ranch
Del Webb Oasis 12898 HARVEST RAIN AVE, WINTER GARDEN, F..., Winter Garden, FL 34787
$790,052

4 beds

|

4 baths

|

2,858 sq ft

|

House

12898 HARVEST RAIN AVE, WINTER GARDEN, F...
Community: Del Webb Oasis

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3,958 homes near Winter Garden
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