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Winter Park, FL 55+ active adult communities & homes for sale - Page 33

2,259 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
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
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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
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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
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) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 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.
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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
3.8 rating (6 reviews) Trilogy® Orlando
$200ks - $500ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
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
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
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
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 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) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
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Questions? Call us: (888) 625-4885
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
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 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
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 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) Legacy of Leesburg
$200ks - $400ks
Legacy of Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 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
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 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
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 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
The Timbers at Everlands
$200ks - $500ks
The Timbers at Everlands, Palm Bay, FL
New Construction | 55+ age-restricted | Built 2023 - present | 450 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 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 5069 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$247,900

2 beds

|

2 baths

|

1,410 sq ft

|

House

5069 EL DESTINO DR, LEESBURG, FL, 34748
Plantation Bay Golf & Country Club 438 LONG COVE RD, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$500,000

3 beds

|

2 baths

|

1,820 sq ft

|

House

438 LONG COVE RD, ORMOND BEACH, FL, 3217...
The Villages® 1605 LYNCHBURG LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32162
$515,000

3 beds

|

3 baths

|

2,043 sq ft

|

House

1605 LYNCHBURG LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
Lakes at Laurel Highlands 2658 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$339,900

4 beds

|

2 baths

|

1,867 sq ft

|

House

2658 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Heritage Landings 2658 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$339,900

4 beds

|

2 baths

|

1,867 sq ft

|

House

2658 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Heritage Landings
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Grand Haven 32 SHINNECOCK DR, PALM COAST, FL, 32137, Palm Coast, FL 32137
$399,000

3 beds

|

2 baths

|

1,594 sq ft

|

House

32 SHINNECOCK DR, PALM COAST, FL, 32137
Community: Grand Haven
Pennbrooke Fairways 333 RANCHWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$332,500

3 beds

|

2 baths

|

1,840 sq ft

|

House

333 RANCHWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Solivita 376 INDIAN WELLS AVE, POINCIANA, FL, 347..., Poinciana, FL 34759
$347,900

3 beds

|

2 baths

|

1,902 sq ft

|

House

376 INDIAN WELLS AVE, POINCIANA, FL, 347...
Community: Solivita
Summer Trees 61 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$209,900

2 beds

|

2 baths

|

1,020 sq ft

|

House

61 CYPRESS POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
Solivita 1317 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$269,000

2 beds

|

2 baths

|

1,363 sq ft

|

House

1317 LOMBARDI CT, KISSIMMEE, FL, 34759
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.
Kings Ridge 2241 KINGSMILL WAY, CLERMONT, FL, 34711, Clermont, FL 34711
$385,000

3 beds

|

2 baths

|

2,124 sq ft

|

House

2241 KINGSMILL WAY, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 435 SANTA CLARA CIR, THE VILLAGES, FL, 3..., The Villages, FL 32159
$305,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

435 SANTA CLARA CIR, THE VILLAGES, FL, 3...
Community: The Villages®
Venetian Bay 3338 BELLINO BLVD, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$779,000

3 beds

|

2 baths

|

1,918 sq ft

|

House

3338 BELLINO BLVD, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
The Villages® 17263 SE 93RD DEMOSS CT, THE VILLAGES, F..., The Villages, FL 32162
$228,000

2 beds

|

2 baths

|

1,175 sq ft

|

Villa

17263 SE 93RD DEMOSS CT, THE VILLAGES, F...
Community: The Villages®
Latitude Margaritaville 842 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$659,900

2 beds

|

3 baths

|

2,303 sq ft

|

House

842 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
Huntington at Hunter's Ridge 23 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$399,900

3 beds

|

3 baths

|

1,853 sq ft

|

House

23 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 16596 SE 77TH NORTHRIDGE CT, THE VILLAGE..., The Villages, FL 32162
$339,999

3 beds

|

2 baths

|

1,483 sq ft

|

House

16596 SE 77TH NORTHRIDGE CT, THE VILLAGE...
Community: The Villages®
Summit Chase Villas 12418 ORANGEWOOD CIR, TAVARES, FL, 32778, Tavares, FL 32778
$180,000

2 beds

|

2 baths

|

918 sq ft

|

Villa

12418 ORANGEWOOD CIR, TAVARES, FL, 32778
Community: Summit Chase Villas
The Villages® 5450 SAMUEL ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$410,000

3 beds

|

2 baths

|

1,642 sq ft

|

Villa

5450 SAMUEL ST, THE VILLAGES, FL, 32163
Community: The Villages®
Summer Trees 18 SUMMER TREES RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$159,800

2 beds

|

2 baths

|

1,026 sq ft

|

House

18 SUMMER TREES 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.
The Villages® 4942 NE 123RD LN, OXFORD, FL, 34484, Oxford, FL 34484
$400,000

5 beds

|

4 baths

|

2,402 sq ft

|

House

4942 NE 123RD LN, OXFORD, FL, 34484
Community: The Villages®
The Villages® 481 ISLAND HOUSE PATH, THE VILLAGES, FL,..., The Villages, FL 32163
$524,900

3 beds

|

3 baths

|

1,903 sq ft

|

House

481 ISLAND HOUSE PATH, THE VILLAGES, FL,...
Community: The Villages®
Latitude Margaritaville 218 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$387,500

2 beds

|

2 baths

|

1,303 sq ft

|

Villa

218 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...
Cresswind DeLand 1293 TWIN FARMS CT, DELAND, FL, 32724, Deland, FL 32724
$569,990

2 beds

|

2 baths

|

2,029 sq ft

|

House

1293 TWIN FARMS CT, DELAND, FL, 32724
Community: Cresswind DeLand
Spruce Creek South 10622 SE 179TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$242,000

3 beds

|

2 baths

|

1,450 sq ft

|

House

10622 SE 179TH LN, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 17830 SE 88TH CASCADE CT, THE VILLAGES, ..., The Villages, FL 32162
$349,900

3 beds

|

2 baths

|

1,485 sq ft

|

House

17830 SE 88TH CASCADE CT, THE VILLAGES, ...
Community: The Villages®
The Villages® 416 CARRERA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$489,900

2 beds

|

2 baths

|

2,006 sq ft

|

House

416 CARRERA DR, THE VILLAGES, FL, 32159
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Arlington Ridge 4401 POPLAR GROVE CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$318,000

2 beds

|

2 baths

|

1,892 sq ft

|

House

4401 POPLAR GROVE CT, LEESBURG, FL, 3474...
Community: Arlington Ridge
The Villages® 1609 BLOSSOM TER, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

1609 BLOSSOM TER, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 270 MATISSE AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$729,000

3 beds

|

2 baths

|

2,075 sq ft

|

House

270 MATISSE AVE, THE VILLAGES, FL, 32162
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.
Halifax Plantation 1328 ANTRIM CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$525,000

4 beds

|

3 baths

|

2,499 sq ft

|

House

1328 ANTRIM CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
Del Webb Sunbridge 2873 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ..., St Cloud, FL 34771
$715,000

3 beds

|

3 baths

|

2,270 sq ft

|

House

2873 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ...
Community: Del Webb Sunbridge
Highland Fairways 2140 GRAND CYPRESS DR, LAKELAND, FL, 338..., Lakeland, FL 33810
$215,000

2 beds

|

2 baths

|

1,394 sq ft

|

House

2140 GRAND CYPRESS DR, LAKELAND, FL, 338...
Community: Highland Fairways
The Villages® 437 JARQUIN WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$362,000

2 beds

|

2 baths

|

1,161 sq ft

|

Villa

437 JARQUIN WAY, THE VILLAGES, FL, 32162
Community: The Villages®
Spruce Creek Country Club 13524 SE 87TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$349,000

3 beds

|

2 baths

|

1,998 sq ft

|

House

13524 SE 87TH CIR, SUMMERFIELD, FL, 3449...
Baytree 116 BAYTREE BLVD, TAVARES, FL, 32778, Tavares, FL 32778
$250,000

3 beds

|

3 baths

|

1,581 sq ft

|

Villa

116 BAYTREE BLVD, TAVARES, FL, 32778
Community: Baytree
The Villages® 16980 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162
$315,000

2 beds

|

2 baths

|

1,148 sq ft

|

House

16980 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
Cresswind at Victoria Gardens 115 AVENHAM DR, DELAND, FL, 32724, Deland, FL 32724
$289,900

3 beds

|

2 baths

|

1,687 sq ft

|

House

115 AVENHAM DR, DELAND, FL, 32724
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 1832 HARTFORD PATH, THE VILLAGES, FL, 32..., The Villages, FL 32162
$824,900

3 beds

|

2 baths

|

2,502 sq ft

|

House

1832 HARTFORD PATH, THE VILLAGES, FL, 32...
Community: The Villages®
Cresswind at Victoria Gardens 307 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724
$294,999

2 beds

|

2 baths

|

1,547 sq ft

|

House

307 HERON POINT WAY, 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.

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2,259 homes
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