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Winter Park, FL 55+ active adult communities & homes for sale - Page 47

2,377 homes near Winter Park

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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
4.7 rating (18 reviews) Solivita
$100Ks - $600Ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
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
5 rating (1 reviews) Plantation Bay Golf &...
$200Ks - $4Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale | Age-targeted | Built 1988 - present | 3,500 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
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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
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 - $600Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 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.
Grand Haven
$300Ks - $1Ms
Grand Haven, Palm Coast, FL
New and Resale | Age-targeted | Built 1997 - present | 1,901 homes
Pelican Bay Daytona Beach
$100Ks - $400Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $400Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
5 rating (1 reviews) Cypress Lakes
$100Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
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5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
Venetian Bay
$200Ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
5 rating (2 reviews) Heritage Isle
$200Ks - $500Ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 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
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
Del Webb at Viera
$400Ks - $1Ms
Del Webb at Viera, Melbourne, FL
New Construction | 55+ age-restricted | Built 2021 - present | 1,300 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$300Ks - $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
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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 - $400Ks
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) 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.
Halifax Plantation
$200Ks - $700Ks
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 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
Breakaway Trails
$400Ks - $800Ks
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
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4.8 rating (6 reviews) Highland Lakes
$100Ks - $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
5 rating (2 reviews) Bridgewater at Viera
$300Ks - $800Ks
Bridgewater at Viera, Melbourne, FL
Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 homes
The Country Club of Mount...
$200Ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 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.
4.1 rating (9 reviews) Indian River Colony Club
$200Ks - $400Ks
Indian River Colony Club, Melbourne, FL
New and Resale | 55+ age-restricted | Built 1986 - present | 777 homes
3.9 rating (7 reviews) Summit Greens
$300Ks - $400Ks
Summit Greens, Clermont, FL
Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 homes
5 rating (1 reviews) Royal Harbor
$300Ks - $400Ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
Lakeside Landings
$200Ks - $500Ks
Lakeside Landings, Oxford, FL
New and Resale | Age-targeted | Built 2005 - present | 700 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
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1 rating (1 reviews) Sullivan Ranch
$200Ks - $700Ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
Highland Fairways
$100Ks - $300Ks
Highland Fairways, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes
Carlsberg Estates on Lake Suzanne 464 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$350,000

3 beds

|

2 baths

|

1,429 sq ft

|

House

464 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Vienna Square 1224 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884
$205,000

2 beds

|

2 baths

|

1,118 sq ft

|

Villa

1224 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
Pennbrooke Fairways 818 FOREST BREEZE PATH, LEESBURG, FL, 34..., Leesburg, FL 34748
$349,900

3 beds

|

2 baths

|

2,111 sq ft

|

House

818 FOREST BREEZE PATH, LEESBURG, FL, 34...
Community: Pennbrooke Fairways
The Lakes at Harmony 3436 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$299,900

2 beds

|

2 baths

|

1,637 sq ft

|

House

3436 SAGEBRUSH ST, HARMONY, FL, 34773
Lake Ashton 4040 BIRKDALE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$289,900

2 beds

|

2 baths

|

1,530 sq ft

|

House

4040 BIRKDALE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Traditions at Lake Ruby 3923 BALDWIN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$299,000

3 beds

|

2 baths

|

1,719 sq ft

|

House

3923 BALDWIN LN, WINTER HAVEN, FL, 33884
Highland Lakes 26320 EVERT ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$259,900

2 beds

|

2 baths

|

1,522 sq ft

|

House

26320 EVERT ST, LEESBURG, FL, 34748
Community: Highland Lakes
The Villages® 7821 SE 166TH SMALLWOOD PL, THE VILLAGES..., The Villages, FL 32162
$339,000

3 beds

|

2 baths

|

1,997 sq ft

|

House

7821 SE 166TH SMALLWOOD PL, THE VILLAGES...
Community: The Villages®
Solivita 300 FALLING WATER DR, POINCIANA, FL, 347..., Poinciana, FL 34759
$199,000

2 beds

|

2 baths

|

1,171 sq ft

|

Halfplex

300 FALLING WATER DR, POINCIANA, FL, 347...
Community: Solivita
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® 1398 BOKEELIA PL, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$249,788

2 beds

|

2 baths

|

1,156 sq ft

|

House

1398 BOKEELIA PL, THE VILLAGES, FL, 3216...
Community: The Villages®
Latitude Margaritaville 944 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$432,000

2 beds

|

2 baths

|

1,558 sq ft

|

House

944 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Lake Ashton 5337 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$369,000

3 beds

|

2 baths

|

1,833 sq ft

|

House

5337 HOGAN LN, WINTER HAVEN, FL, 33884
Community: Lake Ashton
Del Webb Sunbridge 6375 TRAILBLAZE BND, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771
$730,000

4 beds

|

4 baths

|

2,781 sq ft

|

House

6375 TRAILBLAZE BND, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Royal Highlands 20806 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748
$299,900

3 beds

|

2 baths

|

1,939 sq ft

|

House

20806 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
Plantation Bay Golf & Country Club 24 BAY POINTE DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$850,000

5 beds

|

4 baths

|

4,274 sq ft

|

House

24 BAY POINTE DR, ORMOND BEACH, FL, 3217...
Royal Highlands 5004 SAINT ANDREWS ARC, LEESBURG, FL, 34..., Leesburg, FL 34748
$259,900

2 beds

|

2 baths

|

1,483 sq ft

|

House

5004 SAINT ANDREWS ARC, LEESBURG, FL, 34...
Community: Royal Highlands
Highland Lakes 26600 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$309,900

3 beds

|

2 baths

|

2,030 sq ft

|

House

26600 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
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.
Vienna Square 1561 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884
$225,000

2 beds

|

2 baths

|

1,231 sq ft

|

Villa

1561 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
Highland Lakes 26736 CASH CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$215,000

2 beds

|

2 baths

|

1,293 sq ft

|

Villa

26736 CASH CT, LEESBURG, FL, 34748
Community: Highland Lakes
Venetian Bay 3589 GRANDE TUSCANY WAY, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$1,995,000

6 beds

|

10 baths

|

8,260 sq ft

|

House

3589 GRANDE TUSCANY WAY, NEW SMYRNA BEAC...
Community: Venetian Bay
Harbor Hills Country Club 38748 LAKEVIEW WALK, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$399,999

3 beds

|

3 baths

|

2,471 sq ft

|

House

38748 LAKEVIEW WALK, LADY LAKE, FL, 3215...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Breakaway Trails 7 LAKE VISTA WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$818,300

5 beds

|

4 baths

|

4,379 sq ft

|

House

7 LAKE VISTA WAY, ORMOND BEACH, FL, 3217...
Community: Breakaway Trails
Traditions at Lake Ruby 3667 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$350,550

3 beds

|

3 baths

|

2,562 sq ft

|

House

3667 PLYMOUTH DR, WINTER HAVEN, FL, 3388...
Stonecrest 10882 SE 170TH LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$369,000

3 beds

|

2 baths

|

1,616 sq ft

|

House

10882 SE 170TH LANE RD, SUMMERFIELD, FL,...
Community: Stonecrest
Spruce Creek South 17925 SE 100TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$230,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

17925 SE 100TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
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.
Solivita 201 LARGO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$444,000

2 beds

|

2 baths

|

2,419 sq ft

|

House

201 LARGO DR, KISSIMMEE, FL, 34759
Community: Solivita
Highland Fairways 3154 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810
$235,000

2 beds

|

2 baths

|

1,529 sq ft

|

House

3154 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
Ridgehaven 1138 CLIFFHAVEN CT, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$565,990

3 beds

|

3 baths

|

2,183 sq ft

|

House

1138 CLIFFHAVEN CT, ORMOND BEACH, FL, 32...
Community: Ridgehaven
Ridgehaven 1134 CLIFFHAVEN CT, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$545,990

4 beds

|

2 baths

|

1,945 sq ft

|

House

1134 CLIFFHAVEN CT, ORMOND BEACH, FL, 32...
Community: Ridgehaven
Ridgehaven 1130 CLIFFHAVEN CT, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$587,000

4 beds

|

3 baths

|

2,275 sq ft

|

House

1130 CLIFFHAVEN CT, ORMOND BEACH, FL, 32...
Community: Ridgehaven
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 4896 NE 123RD LN, OXFORD, FL, 34484, Oxford, FL 34484
$269,000

3 beds

|

2 baths

|

1,426 sq ft

|

House

4896 NE 123RD LN, OXFORD, FL, 34484
Community: The Villages®
Compass Pointe 839 DANVILLE CIR, MELBOURNE, FL, 32904, Melbourne, FL 32904
$335,000

3 beds

|

2 baths

|

1,976 sq ft

|

House

839 DANVILLE CIR, MELBOURNE, FL, 32904
Community: Compass Pointe
Royal Highlands 22228 OXFORD HEIGHTS DR, LEESBURG, FL, 3..., Leesburg, FL 34748
$329,999

3 beds

|

2 baths

|

1,826 sq ft

|

House

22228 OXFORD HEIGHTS DR, LEESBURG, FL, 3...
Community: Royal Highlands
Trilogy® Orlando 404 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$349,900

2 beds

|

2 baths

|

1,613 sq ft

|

House

404 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® 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.
Royal Highlands 4917 KELSO ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$289,999

3 beds

|

2 baths

|

1,601 sq ft

|

House

4917 KELSO ST, LEESBURG, FL, 34748
Community: Royal Highlands
Arlington Ridge 4411 WINCHESTER CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$414,900

3 beds

|

2 baths

|

2,428 sq ft

|

House

4411 WINCHESTER CT, LEESBURG, FL, 34748
Community: Arlington Ridge
Plantation at Leesburg 24547 BOCAGE WAY, LEESBURG, FL, 34748, Leesburg, FL 34748
$429,000

2 beds

|

3 baths

|

2,597 sq ft

|

House

24547 BOCAGE WAY, LEESBURG, FL, 34748
Royal Highlands 21122 LIONHEART DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$269,900

3 beds

|

2 baths

|

1,453 sq ft

|

House

21122 LIONHEART DR, LEESBURG, FL, 34748
Community: Royal Highlands
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Royal Highlands 4700 ST ANDREWS ARC, LEESBURG, FL, 34748, Leesburg, FL 34748
$325,000

3 beds

|

2 baths

|

2,163 sq ft

|

House

4700 ST ANDREWS ARC, LEESBURG, FL, 34748
Community: Royal Highlands
Royal Highlands 20504 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748
$339,900

2 beds

|

2 baths

|

1,722 sq ft

|

House

20504 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands

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2,377 homes
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