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Winter Park, FL 55+ active adult communities & homes for sale - Page 66

2,702 homes near Winter Park

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4 rating (17 reviews) The Villages®
$100ks - $1Ms
The Villages®, The Villages, FL
New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
4.5 rating (11 reviews) Spruce Creek Country Club
$100ks - $400ks
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 - $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes
4.7 rating (18 reviews) Solivita
$300ks - $700ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
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3.6 rating (48 reviews) Latitude Margaritaville
$300ks - $800ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
5 rating (1 reviews) Plantation Bay Golf &...
$400ks - $2Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale | Age-targeted | Built 1988 - present | 3,500 homes
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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
$200ks - $800ks
Grand Haven, Palm Coast, FL
New and Resale | Age-targeted | Built 1997 - present | 1,901 homes
5 rating (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
3.8 rating (6 reviews) Trilogy® Orlando
$200ks - $500ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 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
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
4 rating (4 reviews) Lakes of Mount Dora
$300ks - $900ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
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2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 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
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 homes
3.8 rating (4 reviews) Spruce Creek South
$100ks - $200ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 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 rating (2 reviews) Harbor Hills Country Club
$300ks - $900ks
Harbor Hills Country Club, Lady Lake, FL
New and Resale | Age-targeted | Built 1989 - present | 940 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$300ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
Highland Fairways
$100ks - $300ks
Highland Fairways, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 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
3.6 rating (5 reviews) Heritage Hills
$200ks - $400ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
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Questions? Call us: (888) 625-4885
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) Del Webb Sunbridge
$400ks - $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 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.
Heritage - The Cottages o...
$300ks
Heritage - The Cottages o..., Okahumpka, FL
New Construction | 55+ age-restricted | Built 2022 - present | 179 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
4.4 rating (16 reviews) Del Webb Orlando
$200ks - $500ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 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
The Timbers at Everlands
$200ks - $500ks
The Timbers at Everlands, Palm Bay, FL
New Construction | 55+ age-restricted | Built 2023 - present | 450 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$300ks - $700ks
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 Park? 55places can help!
Questions? Call us: (888) 625-4885
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
Colonnades
$100ks - $200ks
Colonnades, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1985 - 1994 | 360 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.
12...3
Plantation at Leesburg 25119 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$219,000

2 beds

|

2 baths

|

1,328 sq ft

|

House

25119 CRANES ROOST CIR, LEESBURG, FL, 34...
Pelican Bay Daytona Beach 236 GULL DR, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119
$249,000

2 beds

|

3 baths

|

2,137 sq ft

|

House

236 GULL DR, DAYTONA BEACH, FL, 32119
The Villages® 12406 NE 50TH VW, OXFORD, FL, 34484, Oxford, FL 34484
$269,000

4 beds

|

4 baths

|

2,096 sq ft

|

House

12406 NE 50TH VW, OXFORD, FL, 34484
Community: The Villages®
Cindy Certified
132 FAIRWAY CT, BUNNELL, FL, 32110, Bunnell, FL 32110
$271,000

4 beds

|

2 baths

|

1,857 sq ft

|

House

132 FAIRWAY CT, BUNNELL, FL, 32110
Latitude Margaritaville 154 GYPSY PALACE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$365,000

2 beds

|

2 baths

|

1,308 sq ft

|

House

154 GYPSY PALACE, DAYTONA BEACH, FL, 321...
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Cindy Certified
27 PRINCE KAAREL LN, PALM COAST, FL, 321..., Palm Coast, FL 32164
$349,900

3 beds

|

2 baths

|

1,693 sq ft

|

House

27 PRINCE KAAREL LN, PALM COAST, FL, 321...
Cindy Certified
40 PRESIDENTIAL LN, PALM COAST, FL, 3216..., Palm Coast, FL 32164
$334,900

3 beds

|

2 baths

|

1,536 sq ft

|

House

40 PRESIDENTIAL LN, PALM COAST, FL, 3216...
The Reserve at Victoria 954 MEGANO BLVD, DELAND, FL, 32724, Deland, FL 32724
$624,900

4 beds

|

3 baths

|

2,352 sq ft

|

House

954 MEGANO BLVD, DELAND, FL, 32724
Del Webb Orlando 507 CADIZ DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$380,000

4 beds

|

3 baths

|

2,616 sq ft

|

House

507 CADIZ DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
The Villages® 1497 ALEXANDRIA PL, THE VILLAGES, FL, 32..., The Villages, FL 32162
$328,900

2 beds

|

2 baths

|

1,132 sq ft

|

Villa

1497 ALEXANDRIA PL, THE VILLAGES, FL, 32...
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.
Venetian Bay 672 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$600,000

4 beds

|

4 baths

|

2,748 sq ft

|

House

672 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Traditions at Lake Ruby 3923 BALDWIN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$263,900

3 beds

|

2 baths

|

1,719 sq ft

|

House

3923 BALDWIN LN, WINTER HAVEN, FL, 33884
Del Webb Sunbridge 6376 SHIMMERING SHORES LN, ST CLOUD, FL,..., St Cloud, FL 34771
$449,900

2 beds

|

2 baths

|

1,781 sq ft

|

House

6376 SHIMMERING SHORES LN, ST CLOUD, FL,...
Community: Del Webb Sunbridge
Stonecrest 17435 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$339,500

3 beds

|

2 baths

|

1,682 sq ft

|

House

17435 SE 112TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
Latitude Margaritaville 586 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$499,000

2 beds

|

2 baths

|

1,848 sq ft

|

House

586 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
The Villages® 375 SIMPSON ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$399,900

3 beds

|

2 baths

|

1,887 sq ft

|

House

375 SIMPSON ST, THE VILLAGES, FL, 32162
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Kings Ridge 4202 HAMMERSMITH DR, CLERMONT, FL, 34711, Clermont, FL 34711
$389,900

2 beds

|

2 baths

|

1,968 sq ft

|

House

4202 HAMMERSMITH DR, CLERMONT, FL, 34711
Community: Kings Ridge
Solivita 313 SANTA BARBARA LN, KISSIMMEE, FL, 347..., Kissimmee, FL 34759
$445,000

2 beds

|

3 baths

|

2,343 sq ft

|

House

313 SANTA BARBARA LN, KISSIMMEE, FL, 347...
Community: Solivita
Highland Lakes 6033 WADE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$235,000

2 beds

|

2 baths

|

1,632 sq ft

|

House

6033 WADE ST, LEESBURG, FL, 34748
Community: Highland Lakes
Carmel Condominium 1420 HUNTINGTON LN 2105, ROCKLEDGE, FL, ..., Rockledge, FL 32955
$179,900

2 beds

|

2 baths

|

1,008 sq ft

|

Condo

1420 HUNTINGTON LN 2105, ROCKLEDGE, FL, ...
Community: Carmel Condominium
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 Timbers at Everlands 853 ANTIBES CT, PALM BAY, FL, 32907, Palm Bay, FL 32907
$370,000

3 beds

|

3 baths

|

2,182 sq ft

|

House

853 ANTIBES CT, PALM BAY, FL, 32907
The Timbers at Everlands 2223 ANTARUS DR, PALM BAY, FL, 32907, Palm Bay, FL 32907
$324,950

3 beds

|

4 baths

|

1,710 sq ft

|

House

2223 ANTARUS DR, PALM BAY, FL, 32907
Tohoqua Reserve 2015 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$412,000

3 beds

|

2 baths

|

2,054 sq ft

|

House

2015 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Spruce Creek Country Club 13944 SE 96TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$419,900

3 beds

|

2 baths

|

2,120 sq ft

|

House

13944 SE 96TH CIR, SUMMERFIELD, FL, 3449...
Royal Highlands 4738 ST ANDREWS ARC, LEESBURG, FL, 34748, Leesburg, FL 34748
$304,999

3 beds

|

2 baths

|

1,892 sq ft

|

House

4738 ST ANDREWS ARC, LEESBURG, FL, 34748
Community: Royal Highlands
Arlington Ridge 3507 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$289,900

2 beds

|

2 baths

|

1,476 sq ft

|

House

3507 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
Summer Trees 79 CYPRESS POND RD 79, PORT ORANGE, FL, ..., Port Orange, FL 32128
$220,000

2 beds

|

2 baths

|

888 sq ft

|

Condo

79 CYPRESS POND RD 79, PORT ORANGE, FL, ...
Community: Summer Trees
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Spruce Creek Country Club 12855 SE 92ND COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$329,900

2 beds

|

2 baths

|

1,995 sq ft

|

House

12855 SE 92ND COURT RD, SUMMERFIELD, FL,...
Carlsberg Estates on Lake Suzanne 464 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$310,000

3 beds

|

2 baths

|

1,429 sq ft

|

House

464 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Pelican Bay Daytona Beach 133 BLUE HERON DR D, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$183,500

2 beds

|

2 baths

|

1,242 sq ft

|

Condo

133 BLUE HERON DR D, DAYTONA BEACH, FL, ...
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.
Sullivan Ranch 30308 CHEVAL ST, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$370,000

3 beds

|

2 baths

|

1,851 sq ft

|

House

30308 CHEVAL ST, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Venetian Bay 349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$359,000

3 beds

|

2 baths

|

1,520 sq ft

|

House

349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Cresswind at Victoria Gardens 600 GARDEN CLUB DR, DELAND, FL, 32724, Deland, FL 32724
$539,900

4 beds

|

3 baths

|

2,569 sq ft

|

House

600 GARDEN CLUB DR, DELAND, FL, 32724
The Savannahs 4464 CALADIUM CIR, WEST MELBOURNE, FL, 3..., West Melbourne, FL 32904
$380,000

4 beds

|

2 baths

|

2,051 sq ft

|

House

4464 CALADIUM CIR, WEST MELBOURNE, FL, 3...
Community: The Savannahs
Highland Fairways 3154 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810
$230,000

2 beds

|

2 baths

|

1,529 sq ft

|

House

3154 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
Del Webb Minneola 2759 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715
$459,000

2 beds

|

2 baths

|

1,405 sq ft

|

House

2759 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
Lake James 7770 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$415,000

2 beds

|

2 baths

|

1,990 sq ft

|

House

7770 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Cindy Certified
336 FREE RANGE DR, GROVELAND, FL, 34736, Groveland, FL 34736
$513,990

4 beds

|

3 baths

|

2,472 sq ft

|

House

336 FREE RANGE DR, GROVELAND, FL, 34736
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Plantation Bay Golf & Country Club 829 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$375,000

3 beds

|

3 baths

|

2,101 sq ft

|

Townhouse

829 PINEWOOD DR, ORMOND BEACH, FL, 32174
Sandpiper Golf & Country Club 5976 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$370,000

3 beds

|

2 baths

|

1,478 sq ft

|

House

5976 CORMORANT CT, LAKELAND, FL, 33809
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.

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2,702 homes
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