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Winter Park, FL 55+ active adult communities & homes for sale - Page 56

2,414 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
4.7 rating (18 reviews) Solivita
$300ks - $700ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 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
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
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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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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 (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 homes
Grand Haven
$200ks - $800ks
Grand Haven, Palm Coast, FL
New and Resale | Age-targeted | Built 1997 - present | 1,901 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.
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 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) Twin Lakes
$200ks - $600ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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 (4 reviews) Spruce Creek South
$100ks - $200ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 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
4 rating (4 reviews) Lakes of Mount Dora
$300ks - $1Ms
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 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
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) Del Webb Sunbridge
$400ks - $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$200ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes
The Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 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 (2 reviews) Heritage Isle
$300ks - $500ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 homes
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 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.
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
Ridgehaven
$300ks - $600ks
Ridgehaven, Ormond Beach, FL
New Construction | 55+ age-restricted
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 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
The Country Club of Mount...
$200ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 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
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
5 rating (2 reviews) Bridgewater at Viera
$300ks - $800ks
Bridgewater at Viera, Melbourne, FL
Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 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
Royal Highlands 4802 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$425,000

2 beds

|

2 baths

|

3,034 sq ft

|

House

4802 GLEN COE ST, LEESBURG, FL, 34748
Community: Royal Highlands
Twin Lakes 2491 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$299,999

2 beds

|

2 baths

|

1,464 sq ft

|

Halfplex

2491 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Heritage Hills 3538 BELLAND CIR B, CLERMONT, FL, 34711, Clermont, FL 34711
$284,000

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3538 BELLAND CIR B, CLERMONT, FL, 34711
Community: Heritage Hills
Harbor Hills Country Club 39640 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159
$497,500

3 beds

|

3 baths

|

2,531 sq ft

|

House

39640 HARBOR HILLS BLVD, LADY LAKE, FL, ...
Lake James 7911 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$495,900

3 beds

|

2 baths

|

1,886 sq ft

|

House

7911 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Gatherings of Lake Nona 7545 LAUREATE BLVD 7208, ORLANDO, FL, 32..., Orlando, FL 32827
$417,990

2 beds

|

2 baths

|

1,368 sq ft

|

Condo

7545 LAUREATE BLVD 7208, ORLANDO, FL, 32...
Royal Highlands 4950 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$336,500

3 beds

|

2 baths

|

2,065 sq ft

|

House

4950 GLEN COE ST, LEESBURG, FL, 34748
Community: Royal Highlands
Four Seasons at Orlando 1991 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$296,901

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

1991 KEY BAY TRL, KISSIMMEE, FL, 34747
Latitude Margaritaville 663 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$429,000

2 beds

|

2 baths

|

1,464 sq ft

|

House

663 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Grand Haven 6 POINT DORAL CT, PALM COAST, FL, 32137, Palm Coast, FL 32137
$438,900

3 beds

|

2 baths

|

1,542 sq ft

|

House

6 POINT DORAL CT, PALM COAST, FL, 32137
Community: Grand Haven
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 25119 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$224,000

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
$279,900

2 beds

|

2 baths

|

2,100 sq ft

|

House

236 GULL DR, DAYTONA BEACH, FL, 32119
Sandpiper Golf & Country Club 6381 EGRET DR 28, LAKELAND, FL, 33809, Lakeland, FL 33809
$214,000

2 beds

|

2 baths

|

1,053 sq ft

|

Villa

6381 EGRET DR 28, LAKELAND, FL, 33809
Summer Trees 125 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$285,000

2 beds

|

2 baths

|

1,855 sq ft

|

House

125 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
Plantation Bay Golf & Country Club 46 LONGRIDGE LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$435,000

2 beds

|

2 baths

|

1,529 sq ft

|

Townhouse

46 LONGRIDGE LN, ORMOND BEACH, FL, 32174
Solivita 157 SAND PIPER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$314,500

3 beds

|

3 baths

|

2,267 sq ft

|

House

157 SAND PIPER DR, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Sullivan Ranch 30113 JUTLAND CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$619,900

5 beds

|

4 baths

|

3,320 sq ft

|

House

30113 JUTLAND CT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Plantation Bay Golf & Country Club 1283 ROYAL POINTE LN, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174
$535,000

3 beds

|

2 baths

|

2,029 sq ft

|

House

1283 ROYAL POINTE LN, ORMOND BEACH, FL, ...
The Villages® 12406 NE 50TH VW, OXFORD, FL, 34484, Oxford, FL 34484
$277,500

4 beds

|

4 baths

|

2,096 sq ft

|

House

12406 NE 50TH VW, OXFORD, FL, 34484
Community: The Villages®
Summer Trees 55 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$244,000

3 beds

|

2 baths

|

1,775 sq ft

|

House

55 CROOKED PINE RD, PORT ORANGE, FL, 321...
Community: Summer Trees
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.
Stonecrest 17520 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$299,000

2 beds

|

2 baths

|

1,402 sq ft

|

House

17520 SE 112TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
VillageWalk at Lake Nona 11887 DELFINA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$439,000

2 beds

|

2 baths

|

1,708 sq ft

|

House

11887 DELFINA LN, ORLANDO, FL, 32827
Stonecrest 17076 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491
$279,000

3 beds

|

2 baths

|

1,752 sq ft

|

House

17076 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
Pennbrooke Fairways 32716 WESTWOOD LOOP, LEESBURG, FL, 34748, Leesburg, FL 34748
$228,900

2 beds

|

2 baths

|

1,370 sq ft

|

House

32716 WESTWOOD LOOP, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Del Webb Orlando 507 CADIZ DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$399,900

4 beds

|

3 baths

|

2,616 sq ft

|

House

507 CADIZ DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Cresswind at Victoria Gardens 115 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724
$299,000

3 beds

|

2 baths

|

1,773 sq ft

|

House

115 HERON POINT WAY, DELAND, FL, 32724
Pelican Bay Daytona Beach 150 BLUE HERON DR B, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$230,900

3 beds

|

2 baths

|

1,365 sq ft

|

Condo

150 BLUE HERON DR B, DAYTONA BEACH, FL, ...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Lake Ashton 5225 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884
$420,000

3 beds

|

2 baths

|

2,031 sq ft

|

House

5225 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
Lake Ashton 4496 STRATHMORE DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$369,900

3 beds

|

2 baths

|

2,312 sq ft

|

House

4496 STRATHMORE DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
Pennbrooke Fairways 642 GLEN OAKS DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$209,247

2 beds

|

2 baths

|

1,632 sq ft

|

House

642 GLEN OAKS DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
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.
Tohoqua Reserve 1873 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$345,000

3 beds

|

2 baths

|

1,559 sq ft

|

Villa

1873 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Stonecrest 17409 SE 111TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$299,000

3 beds

|

2 baths

|

1,700 sq ft

|

House

17409 SE 111TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
Spruce Creek South 9667 SE 173RD LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$219,000

2 beds

|

2 baths

|

1,678 sq ft

|

House

9667 SE 173RD LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Heritage Isle 6939 MCGRADY DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$425,000

3 beds

|

2 baths

|

2,015 sq ft

|

House

6939 MCGRADY DR, MELBOURNE, FL, 32940
Community: Heritage Isle
Solivita 141 LEMON GROVE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$659,900

4 beds

|

5 baths

|

2,917 sq ft

|

House

141 LEMON GROVE DR, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 1497 ALEXANDRIA PL, THE VILLAGES, FL, 32..., The Villages, FL 32162
$331,900

2 beds

|

2 baths

|

1,132 sq ft

|

Villa

1497 ALEXANDRIA PL, THE VILLAGES, FL, 32...
Community: The Villages®
Highland Fairways 2324 SEA ISLAND CIR, LAKELAND, FL, 33810, Lakeland, FL 33810
$210,000

2 beds

|

2 baths

|

1,355 sq ft

|

House

2324 SEA ISLAND CIR, LAKELAND, FL, 33810
Community: Highland Fairways
Plantation Bay Golf & Country Club 21 JASMINE RUN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$325,000

2 beds

|

2 baths

|

1,424 sq ft

|

House

21 JASMINE RUN, ORMOND BEACH, FL, 32174
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Venetian Bay 668 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$665,138

5 beds

|

4 baths

|

3,221 sq ft

|

House

668 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Venetian Bay 672 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$625,684

4 beds

|

4 baths

|

2,748 sq ft

|

House

672 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
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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2,414 homes
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