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

2,513 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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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
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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 (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 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) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 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 (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) 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 (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
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Grand Haven
$200ks - $800ks
Grand Haven, Palm Coast, FL
New and Resale | Age-targeted | Built 1997 - present | 1,901 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
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 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.
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
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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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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
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
5 rating (2 reviews) Heritage Isle
$300ks - $500ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 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) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$200ks - $600ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
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Questions? Call us: (888) 625-4885
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes
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
Tohoqua Reserve
$300ks - $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2021 - present | 258 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
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 (5 reviews) Traditions at Lake Ruby
$200ks - $300ks
Traditions at Lake Ruby, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 552 homes
The Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes
12...3
Halifax Plantation 3034 ADRIAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$565,000

4 beds

|

3 baths

|

2,641 sq ft

|

House

3034 ADRIAN DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
Pelican Bay Daytona Beach 144 HERRING GULL CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$344,900

3 beds

|

2 baths

|

1,702 sq ft

|

House

144 HERRING GULL CT, DAYTONA BEACH, FL, ...
Carillon Lakes 3413 WATERLUTE WAY, LAKELAND, FL, 33811, Lakeland, FL 33811
$275,000

3 beds

|

2 baths

|

1,811 sq ft

|

House

3413 WATERLUTE WAY, LAKELAND, FL, 33811
Community: Carillon Lakes
Spruce Creek Country Club 9211 SE 130TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$309,900

2 beds

|

2 baths

|

1,708 sq ft

|

House

9211 SE 130TH LOOP, SUMMERFIELD, FL, 344...
Pennbrooke Fairways 548 GRAND VISTA TRL, LEESBURG, FL, 34748, Leesburg, FL 34748
$329,000

3 beds

|

2 baths

|

1,999 sq ft

|

House

548 GRAND VISTA TRL, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 3165 HUDSON CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$440,900

3 beds

|

2 baths

|

2,176 sq ft

|

House

3165 HUDSON CT, THE VILLAGES, FL, 32162
Community: The Villages®
Plantation Bay Golf & Country Club 645 ELK RIV, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$434,000

3 beds

|

2 baths

|

1,762 sq ft

|

House

645 ELK RIV, ORMOND BEACH, FL, 32174
Grand Isle 1690 LAGO MAR DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$410,000

3 beds

|

2 baths

|

1,997 sq ft

|

House

1690 LAGO MAR DR, MELBOURNE, FL, 32940
Community: Grand Isle
Plantation Bay Golf & Country Club 645 ELK RIVER DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$434,000

3 beds

|

2 baths

|

1,762 sq ft

|

House

645 ELK RIVER DR, ORMOND BEACH, FL, 3217...
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.
Lakeside Landings 4846 AUDREY MARIE CT, OXFORD, FL, 34484, Oxford, FL 34484
$424,700

3 beds

|

2 baths

|

2,200 sq ft

|

House

4846 AUDREY MARIE CT, OXFORD, FL, 34484
Community: Lakeside Landings
Arlington Ridge 27343 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$354,900

3 beds

|

2 baths

|

1,607 sq ft

|

House

27343 ROANOKE DR, LEESBURG, FL, 34748
Community: Arlington Ridge
Pelican Bay Daytona Beach 144 AVOCET CT, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119
$290,000

3 beds

|

3 baths

|

2,072 sq ft

|

Townhouse

144 AVOCET CT, DAYTONA BEACH, FL, 32119
Del Webb Orlando 536 ARENA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$309,900

3 beds

|

2 baths

|

1,508 sq ft

|

House

536 ARENA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Highland Lakes 6142 WADE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$264,900

3 beds

|

2 baths

|

1,841 sq ft

|

House

6142 WADE ST, LEESBURG, FL, 34748
Community: Highland Lakes
Plantation Bay Golf & Country Club 1169 KILKENNY LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$385,000

3 beds

|

2 baths

|

1,910 sq ft

|

House

1169 KILKENNY LN, ORMOND BEACH, FL, 3217...
Indian River Colony Club 1332 PILGRIM AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940
$350,000

2 beds

|

2 baths

|

1,650 sq ft

|

House

1332 PILGRIM AVE, MELBOURNE, FL, 32940
Grand Haven 15 CHINIER ST, PALM COAST, FL, 32137, Palm Coast, FL 32137
$879,990

3 beds

|

3 baths

|

2,517 sq ft

|

House

15 CHINIER ST, 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.
Esplanade at Highland Ranch 1023 TIMBERVALE TRL, CLERMONT, FL, 34715, Clermont, FL 34715
$509,900

3 beds

|

3 baths

|

2,287 sq ft

|

House

1023 TIMBERVALE TRL, CLERMONT, FL, 34715
Spruce Creek South 10599 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$214,900

2 beds

|

2 baths

|

1,008 sq ft

|

House

10599 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 870 TREVINO TER, THE VILLAGES, FL, 32159, The Villages, FL 32159
$299,000

2 beds

|

2 baths

|

1,087 sq ft

|

Villa

870 TREVINO TER, THE VILLAGES, FL, 32159
Community: The Villages®
Indian River Colony Club 1290 MAYFLOWER AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940
$355,000

2 beds

|

2 baths

|

1,616 sq ft

|

House

1290 MAYFLOWER AVE, MELBOURNE, FL, 32940
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Huntington at Hunter's Ridge 99 HUNTINGTON PL, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$474,900

3 beds

|

2 baths

|

2,238 sq ft

|

House

99 HUNTINGTON PL, ORMOND BEACH, FL, 3217...
The Villages® 2544 ASHVILLE AVE, THE VILLAGES, FL, 321..., The Villages, FL 32162
$599,000

3 beds

|

2 baths

|

2,485 sq ft

|

House

2544 ASHVILLE AVE, THE VILLAGES, FL, 321...
Community: The Villages®
Harbor Hills Country Club 39023 GRIFFIN LNDG, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$519,000

3 beds

|

3 baths

|

2,833 sq ft

|

House

39023 GRIFFIN LNDG, LADY LAKE, FL, 32159
Breakaway Trails 180 BLACK HICKORY WAY, ORMOND BEACH, FL,..., Ormond Beach, FL 32174
$505,000

3 beds

|

2 baths

|

1,983 sq ft

|

House

180 BLACK HICKORY WAY, ORMOND BEACH, FL,...
Community: Breakaway Trails
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.
Lake Ashton 4048 PHOENICIAN WAY, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$445,000

3 beds

|

2 baths

|

2,354 sq ft

|

House

4048 PHOENICIAN WAY, WINTER HAVEN, FL, 3...
Community: Lake Ashton
Trilogy® Orlando 602 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736
$589,999

2 beds

|

3 baths

|

1,900 sq ft

|

House

602 CONSERVATION BLVD, GROVELAND, FL, 34...
Community: Trilogy® Orlando
The Timbers at Everlands 1443 BLESSED ISLES DR, PALM BAY, FL, 329..., Palm Bay, FL 32907
$520,459

4 beds

|

3 baths

|

2,638 sq ft

|

House

1443 BLESSED ISLES DR, PALM BAY, FL, 329...
Venetian Bay 3367 TORRE BLVD, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$459,900

3 beds

|

2 baths

|

1,976 sq ft

|

Halfplex

3367 TORRE BLVD, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Pennbrooke Fairways 32512 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$234,000

3 beds

|

2 baths

|

1,312 sq ft

|

House

32512 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Halifax Plantation 2745 PORTADOWN ST, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$369,900

3 beds

|

2 baths

|

1,514 sq ft

|

House

2745 PORTADOWN ST, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
Cresswind DeLand 1322 SAVOY LN, DELAND, FL, 32724, Deland, FL 32724
$497,990

3 beds

|

3 baths

|

2,289 sq ft

|

House

1322 SAVOY LN, DELAND, FL, 32724
Community: Cresswind DeLand
Bridgewater at Viera 1473 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940
$420,000

3 beds

|

2 baths

|

1,598 sq ft

|

House

1473 GREAT BELT CIR, MELBOURNE, FL, 3294...
Venetian Bay 3555 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$660,000

3 beds

|

3 baths

|

2,472 sq ft

|

House

3555 MARIBELLA DR, 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.
Stonecrest 17824 SE 113TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$399,000

3 beds

|

3 baths

|

1,734 sq ft

|

House

17824 SE 113TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 17627 SE 88TH COVINGTON CIR, THE VILLAGE..., The Villages, FL 32162
$675,000

3 beds

|

2 baths

|

2,460 sq ft

|

House

17627 SE 88TH COVINGTON CIR, THE VILLAGE...
Community: The Villages®
Solivita 205 BELL TOWER XING, POINCIANA, FL, 3475..., Poinciana, FL 34759
$274,000

2 beds

|

2 baths

|

1,405 sq ft

|

House

205 BELL TOWER XING, POINCIANA, FL, 3475...
Community: Solivita
Royal Highlands 5133 LINKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$269,900

3 beds

|

2 baths

|

1,701 sq ft

|

House

5133 LINKS LN, 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
Plantation Bay Golf & Country Club 584 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$659,000

3 beds

|

2 baths

|

1,991 sq ft

|

House

584 ALDENHAM LN, ORMOND BEACH, FL, 32174
Harbor Hills Country Club 39500 HILLRISE LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$623,900

4 beds

|

3 baths

|

2,544 sq ft

|

House

39500 HILLRISE LN, LADY LAKE, FL, 32159

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2,513 homes
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