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

3,573 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 - $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
$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 - $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.
3.8 rating (6 reviews) Trilogy® Orlando
$300Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
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) 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 - $900Ks
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...
$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
The Villages® 2569 ERROL TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$309,900

2 beds

|

2 baths

|

1,156 sq ft

|

House

2569 ERROL TER, THE VILLAGES, FL, 32162
Community: The Villages®
Solivita 1062 UMBRIA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$350,000

2 beds

|

2 baths

|

1,655 sq ft

|

House

1062 UMBRIA DR, KISSIMMEE, FL, 34759
Community: Solivita
Sun City Center 1813 ATRIUM DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$199,000

2 beds

|

2 baths

|

1,114 sq ft

|

House

1813 ATRIUM DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
The Villages® 2377 LONGBOW TRL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$375,000

3 beds

|

2 baths

|

1,512 sq ft

|

House

2377 LONGBOW TRL, THE VILLAGES, FL, 3216...
Community: The Villages®
Tampa Bay Golf and Country Club 9916 SEMIAHMOO LOOP, SAN ANTONIO, FL, 33..., San Antonio, FL 33576
$350,000

3 beds

|

2 baths

|

1,670 sq ft

|

House

9916 SEMIAHMOO LOOP, SAN ANTONIO, FL, 33...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Huntington at Hunter's Ridge 6 FOX LAIR CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$369,900

3 beds

|

2 baths

|

1,637 sq ft

|

House

6 FOX LAIR CT, ORMOND BEACH, FL, 32174
Oak Run 6750 SW 112TH ST, OCALA, FL, 34476, Ocala, FL 34476
$320,000

2 beds

|

2 baths

|

1,782 sq ft

|

House

6750 SW 112TH ST, OCALA, FL, 34476
Community: Oak Run
Stonecrest 17525 SE 111TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$490,000

3 beds

|

2 baths

|

2,037 sq ft

|

House

17525 SE 111TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 17917 SE 86TH AUBURN AVE, THE VILLAGES, ..., The Villages, FL 32162
$425,000

3 beds

|

2 baths

|

1,907 sq ft

|

House

17917 SE 86TH AUBURN AVE, THE VILLAGES, ...
Community: The Villages®
Spruce Creek Country Club 9825 SE 125TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$359,000

2 beds

|

2 baths

|

1,870 sq ft

|

House

9825 SE 125TH LN, SUMMERFIELD, FL, 34491
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.
Arlington Ridge 3507 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$339,900

2 beds

|

2 baths

|

1,476 sq ft

|

House

3507 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
Del Webb Sunbridge 2698 RIVER CREEK LN, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771
$625,000

3 beds

|

3 baths

|

2,080 sq ft

|

House

2698 RIVER CREEK LN, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
Oak Run 10819 SW 84TH TER, OCALA, FL, 34481, Ocala, FL 34481
$242,500

3 beds

|

2 baths

|

1,952 sq ft

|

House

10819 SW 84TH TER, OCALA, FL, 34481
Community: Oak Run
VillageWalk at Lake Nona 12286 REGAL LILY LN, ORLANDO, FL, 32827, Orlando, FL 32827
$949,000

4 beds

|

4 baths

|

4,072 sq ft

|

House

12286 REGAL LILY LN, ORLANDO, FL, 32827
Pine Run Estates 8973 SW 104TH PL, OCALA, FL, 34481, Ocala, FL 34481
$175,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

8973 SW 104TH PL, OCALA, FL, 34481
Community: Pine Run Estates
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Oak Run 8771 SW 115TH ST, OCALA, FL, 34481, Ocala, FL 34481
$249,900

3 beds

|

2 baths

|

1,685 sq ft

|

House

8771 SW 115TH ST, OCALA, FL, 34481
Community: Oak Run
The Villages® 600 OAK BLVD, WILDWOOD, FL, 34785, Wildwood, FL 34785
$155,000

2 beds

|

2 baths

|

1,288 sq ft

|

Manufactured Home

600 OAK BLVD, WILDWOOD, FL, 34785
Community: The Villages®
Oak Run 11445 SW 84TH AVENUE RD, OCALA, FL, 3448..., Ocala, FL 34481
$198,000

2 beds

|

2 baths

|

1,160 sq ft

|

House

11445 SW 84TH AVENUE RD, OCALA, FL, 3448...
Community: Oak Run
Enclave at VillageWalk 10819 SAVONA WAY, ORLANDO, FL, 32827, Orlando, FL 32827
$1,549,000

5 beds

|

6 baths

|

5,437 sq ft

|

House

10819 SAVONA WAY, ORLANDO, FL, 32827
Oak Run 11653 SW 72ND CIR, OCALA, FL, 34476, Ocala, FL 34476
$275,000

3 beds

|

2 baths

|

1,495 sq ft

|

House

11653 SW 72ND CIR, OCALA, FL, 34476
Community: Oak Run
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® 603 ROBIN LN, WILDWOOD, FL, 34785, Wildwood, FL 34785
$195,000

2 beds

|

2 baths

|

1,352 sq ft

|

Manufactured Home

603 ROBIN LN, WILDWOOD, FL, 34785
Community: The Villages®
The Villages® 104 WINTERBERRY AVE, WILDWOOD, FL, 34785, Wildwood, FL 34785
$149,900

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

104 WINTERBERRY AVE, WILDWOOD, FL, 34785
Community: The Villages®
The Villages® 106 OAK BLVD, WILDWOOD, FL, 34785, Wildwood, FL 34785
$115,000

2 beds

|

2 baths

|

828 sq ft

|

Manufactured Home

106 OAK BLVD, WILDWOOD, FL, 34785
Community: The Villages®
Oak Run 11665 SW 72ND CIR, OCALA, FL, 34476, Ocala, FL 34476
$260,000

3 beds

|

3 baths

|

1,840 sq ft

|

House

11665 SW 72ND CIR, OCALA, FL, 34476
Community: Oak Run
Arlington Ridge 3621 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$459,900

3 beds

|

2 baths

|

2,052 sq ft

|

House

3621 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 987 FREDERICK TER, THE VILLAGES, FL, 321..., The Villages, FL 32163
$824,900

3 beds

|

2 baths

|

2,060 sq ft

|

House

987 FREDERICK TER, THE VILLAGES, FL, 321...
Community: The Villages®
On Top of the World 8018 SW 83RD PL, OCALA, FL, 34476, Ocala, FL 34476
$239,900

3 beds

|

2 baths

|

1,576 sq ft

|

House

8018 SW 83RD PL, OCALA, FL, 34476
Community: On Top of the World
Sun City Center 2115 N HALCYON DR # 510, SUN CITY CENTER..., Sun City Center, FL 33573
$212,900

2 beds

|

2 baths

|

1,203 sq ft

|

Condo

2115 N HALCYON DR # 510, SUN CITY CENTER...
Community: Sun City Center
Spruce Creek North 10890 SW 63RD AVE, OCALA, FL, 34476, Ocala, FL 34476
$175,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

10890 SW 63RD AVE, OCALA, FL, 34476
Community: Spruce Creek North
Spruce Creek North 6473 SW 108TH ST, OCALA, FL, 34476, Ocala, FL 34476
$175,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

6473 SW 108TH ST, OCALA, FL, 34476
Community: Spruce Creek North
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 823 FOX HILLS DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$287,000

2 beds

|

2 baths

|

1,852 sq ft

|

House

823 FOX HILLS DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
The Villages® 3467 SIPSEY ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$310,000

3 beds

|

2 baths

|

1,240 sq ft

|

House

3467 SIPSEY ST, THE VILLAGES, FL, 32162
Community: The Villages®
Sun City Center 2005 BERRY ROBERTS DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$395,000

2 beds

|

2 baths

|

1,878 sq ft

|

House

2005 BERRY ROBERTS DR, SUN CITY CENTER, ...
Community: Sun City Center
Venetian Bay 453 VENETIAN VILLA DR, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168
$620,000

5 beds

|

4 baths

|

3,051 sq ft

|

House

453 VENETIAN VILLA DR, NEW SMYRNA BEACH,...
Community: Venetian Bay
Ocala Preserve 5651 NW 40TH PL, OCALA, FL, 34482, Ocala, FL 34482
$329,900

2 beds

|

2 baths

|

1,470 sq ft

|

House

5651 NW 40TH PL, 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
Pelican Bay Daytona Beach 169 MALLARD LN, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119
$554,900

3 beds

|

3 baths

|

2,700 sq ft

|

House

169 MALLARD LN, DAYTONA BEACH, FL, 32119
Venetian Bay 495 VENETIAN VILLA DR, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168
$670,000

5 beds

|

3 baths

|

2,909 sq ft

|

House

495 VENETIAN VILLA DR, NEW SMYRNA BEACH,...
Community: Venetian Bay
The Villages® 910 ORCHID ST, THE VILLAGES, FL, 32159, The Villages, FL 32159
$214,900

2 beds

|

2 baths

|

1,332 sq ft

|

Manufactured Home

910 ORCHID ST, THE VILLAGES, FL, 32159
Community: The Villages®
Sun City Center 2007 EAST VIEW DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$369,900

3 beds

|

2 baths

|

2,635 sq ft

|

House

2007 EAST VIEW DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Scottish Highlands 312 BRIGADOON CIR # 312, LEESBURG, FL, 3..., Leesburg, FL 34788
$209,000

2 beds

|

2 baths

|

1,310 sq ft

|

House

312 BRIGADOON CIR # 312, LEESBURG, FL, 3...
Community: Scottish Highlands

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3,573 homes near Winter Garden
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