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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.
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $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) VillageWalk at Lake Nona
$400Ks - $1Ms
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...
$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
New Plantation at Leesburg 4830 SUMMERBRIDGE CIR, LEESBURG, FL, 347..., Leesburg, FL 34748
$374,900

3 beds

|

3 baths

|

2,514 sq ft

|

House

4830 SUMMERBRIDGE CIR, LEESBURG, FL, 347...
New On Top of the World 8781 SW 82ND COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$295,000

3 beds

|

2 baths

|

1,709 sq ft

|

House

8781 SW 82ND COURT RD, OCALA, FL, 34481
Community: On Top of the World
New On Top of the World 8298 SW 79TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$339,000

3 beds

|

2 baths

|

2,026 sq ft

|

House

8298 SW 79TH CIR, OCALA, FL, 34476
Community: On Top of the World
New Heritage Hills 3281 SALOMAN LN, CLERMONT, FL, 34711, Clermont, FL 34711
$499,999

4 beds

|

3 baths

|

2,736 sq ft

|

House

3281 SALOMAN LN, CLERMONT, FL, 34711
Community: Heritage Hills
New Legacy of Leesburg 27302 STONEY BROOK DR, LEESBURG, FL, 347..., Leesburg, FL 34748
$315,000

3 beds

|

2 baths

|

1,478 sq ft

|

House

27302 STONEY BROOK DR, LEESBURG, FL, 347...
Community: Legacy of Leesburg
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Sandpiper Golf & Country Club 5857 MACAW PL, LAKELAND, FL, 33809, Lakeland, FL 33809
$279,000

2 beds

|

2 baths

|

1,352 sq ft

|

House

5857 MACAW PL, LAKELAND, FL, 33809
New Del Webb Oasis 13562 PEARL BEACH ST, WINTER GARDEN, FL,..., Winter Garden, FL 34787
$499,500

2 beds

|

2 baths

|

1,574 sq ft

|

Villa

13562 PEARL BEACH ST, WINTER GARDEN, FL,...
Community: Del Webb Oasis
New The Villages® 647 SAN PEDRO DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$320,000

2 beds

|

2 baths

|

1,383 sq ft

|

House

647 SAN PEDRO DR, LADY LAKE, FL, 32159
Community: The Villages®
New Sun City Center 205 WIMBLY PL, SUN CITY CENTER, FL, 3357..., Sun City Center, FL 33573
$300,000

2 beds

|

2 baths

|

2,022 sq ft

|

House

205 WIMBLY PL, SUN CITY CENTER, FL, 3357...
Community: Sun City Center
New Scottish Highlands 24 BRIGADOON CIR, LEESBURG, FL, 34788, Leesburg, FL 34788
$188,000

2 beds

|

2 baths

|

1,230 sq ft

|

House

24 BRIGADOON CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
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.
New Marion Landing 6190 SW 84TH PL, OCALA, FL, 34476, Ocala, FL 34476
$255,000

2 beds

|

2 baths

|

1,616 sq ft

|

House

6190 SW 84TH PL, OCALA, FL, 34476
Community: Marion Landing
New Spruce Creek Country Club 13715 SE 88TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$349,000

3 beds

|

2 baths

|

2,393 sq ft

|

House

13715 SE 88TH CT, SUMMERFIELD, FL, 34491
New Trilogy® Orlando 106 MIST FLOWER LN, GROVELAND, FL, 34736, Groveland, FL 34736
$549,000

2 beds

|

2 baths

|

2,209 sq ft

|

House

106 MIST FLOWER LN, GROVELAND, FL, 34736
Community: Trilogy® Orlando
New The Villages® 2991 SAINT THOMAS LN, THE VILLAGES, FL, ..., The Villages, FL 32162
$449,000

3 beds

|

2 baths

|

1,777 sq ft

|

House

2991 SAINT THOMAS LN, THE VILLAGES, FL, ...
Community: The Villages®
New Royal Highlands 5007 KELSO ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$279,500

2 beds

|

2 baths

|

1,469 sq ft

|

House

5007 KELSO ST, LEESBURG, FL, 34748
Community: Royal Highlands
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New On Top of the World 10562 SW 96TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$389,000

2 beds

|

2 baths

|

2,019 sq ft

|

House

10562 SW 96TH LANE RD, OCALA, FL, 34481
Community: On Top of the World
New On Top of the World 9865 SW 105TH CT, OCALA, FL, 34481, Ocala, FL 34481
$385,000

2 beds

|

2 baths

|

2,019 sq ft

|

House

9865 SW 105TH CT, OCALA, FL, 34481
Community: On Top of the World
New Sandpiper Golf & Country Club 5987 TEAL TRL, LAKELAND, FL, 33809, Lakeland, FL 33809
$370,000

3 beds

|

2 baths

|

1,478 sq ft

|

House

5987 TEAL TRL, LAKELAND, FL, 33809
New Sandpiper Golf & Country Club 5982 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$375,000

3 beds

|

2 baths

|

1,582 sq ft

|

House

5982 CORMORANT CT, LAKELAND, FL, 33809
New Cresswind at Victoria Gardens 241 OLD MOSS CIR, DELAND, FL, 32724, Deland, FL 32724
$650,000

3 beds

|

3 baths

|

2,185 sq ft

|

House

241 OLD MOSS CIR, DELAND, FL, 32724
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.
New Sandpiper Golf & Country Club 5914 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$350,000

2 beds

|

2 baths

|

1,321 sq ft

|

House

5914 CORMORANT CT, LAKELAND, FL, 33809
New Sun City Center 301 ANDOVER PL 175, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$115,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

301 ANDOVER PL 175, SUN CITY CENTER, FL,...
Community: Sun City Center
New Harbor Hills Country Club 5453 GROVE MNR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$439,000

3 beds

|

3 baths

|

2,228 sq ft

|

House

5453 GROVE MNR, LADY LAKE, FL, 32159
New Solivita 2495 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$339,000

4 beds

|

3 baths

|

2,272 sq ft

|

Villa

2495 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
Huntington at Hunter's Ridge 5 FOX LAIR CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$419,900

4 beds

|

2 baths

|

2,033 sq ft

|

House

5 FOX LAIR CT, ORMOND BEACH, FL, 32174
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Spruce Creek Country Club 8961 SE 130TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$414,000

3 beds

|

2 baths

|

2,120 sq ft

|

House

8961 SE 130TH LOOP, SUMMERFIELD, FL, 344...
Stone Creek 6780 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$274,472

2 beds

|

2 baths

|

1,706 sq ft

|

Villa

6780 SW 91ST CIR, OCALA, FL, 34481
Community: Stone Creek
JB Ranch 4763 SW 88TH LN, OCALA, FL, 34476, Ocala, FL 34476
$306,990

4 beds

|

2 baths

|

1,828 sq ft

|

House

4763 SW 88TH LN, OCALA, FL, 34476
Community: JB Ranch
Sun City Center 1623 FAXTON DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$280,000

2 beds

|

2 baths

|

1,516 sq ft

|

House

1623 FAXTON DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Stone Creek 9511 SW 71ST LOOP, OCALA, FL, 34481, Ocala, FL 34481
$470,750

3 beds

|

2 baths

|

2,122 sq ft

|

House

9511 SW 71ST LOOP, OCALA, FL, 34481
Community: Stone Creek
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 11146 SW 68TH CT, OCALA, FL, 34476, Ocala, FL 34476
$209,888

2 beds

|

2 baths

|

1,390 sq ft

|

House

11146 SW 68TH CT, OCALA, FL, 34476
Community: Oak Run
On Top of the World 9816 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$219,900

2 beds

|

2 baths

|

1,394 sq ft

|

House

9816 SW 92ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8590 SW 95TH CT, OCALA, FL, 34481, Ocala, FL 34481
$572,000

3 beds

|

3 baths

|

2,814 sq ft

|

House

8590 SW 95TH CT, OCALA, FL, 34481
Community: On Top of the World
Lakes at Laurel Highlands 2816 IVY LAKE CT, LAKELAND, FL, 33811, Lakeland, FL 33811
$390,000

5 beds

|

3 baths

|

2,696 sq ft

|

House

2816 IVY LAKE CT, LAKELAND, FL, 33811
The Villages® 1116 SAN BERNARDO RD, THE VILLAGES, FL, ..., The Villages, FL 32162
$305,000

2 beds

|

2 baths

|

1,102 sq ft

|

Villa

1116 SAN BERNARDO RD, THE VILLAGES, FL, ...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Summer Trees 67 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$258,967

2 beds

|

2 baths

|

1,313 sq ft

|

House

67 CROOKED PINE RD, PORT ORANGE, FL, 321...
Community: Summer Trees
Summer Trees 11 LAKEPOINT CIR, PORT ORANGE, FL, 32128, Port Orange, FL 32128
$269,929

2 beds

|

2 baths

|

1,415 sq ft

|

House

11 LAKEPOINT CIR, PORT ORANGE, FL, 32128
Community: Summer Trees
Summer Trees 39 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$280,000

2 beds

|

2 baths

|

1,406 sq ft

|

House

39 CROOKED PINE RD, PORT ORANGE, FL, 321...
Community: Summer Trees
Royal Highlands 6319 BERKSHIRE PASS, LEESBURG, FL, 34748, Leesburg, FL 34748
$320,000

3 beds

|

2 baths

|

1,908 sq ft

|

House

6319 BERKSHIRE PASS, LEESBURG, FL, 34748
Community: Royal Highlands
Summer Trees 109 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$273,827

2 beds

|

2 baths

|

1,106 sq ft

|

House

109 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees

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3,958 homes near Winter Garden
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