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Winter Park, FL 55+ active adult communities & homes for sale - Page 41

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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Questions? Call us: (888) 625-4885
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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Questions? Call us: (888) 625-4885
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
Kings Ridge 3814 WESTERHAM DR, CLERMONT, FL, 34711, Clermont, FL 34711
$335,000

2 beds

|

2 baths

|

1,422 sq ft

|

House

3814 WESTERHAM DR, CLERMONT, FL, 34711
Community: Kings Ridge
Lake Ashton 4081 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$399,500

3 beds

|

2 baths

|

2,027 sq ft

|

House

4081 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
The Villages® 3079 NUTWOOD AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$295,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

3079 NUTWOOD AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
Highland Lakes 26707 CASH CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$215,000

2 beds

|

2 baths

|

1,293 sq ft

|

Villa

26707 CASH CT, LEESBURG, FL, 34748
Community: Highland Lakes
Spruce Creek Country Club 13820 SE 86TH TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$259,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

13820 SE 86TH TER, SUMMERFIELD, FL, 3449...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Stonecrest 17787 SE 114TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$349,900

3 beds

|

2 baths

|

1,867 sq ft

|

House

17787 SE 114TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
Arlington Ridge 26822 BULL RUN, LEESBURG, FL, 34748, Leesburg, FL 34748
$324,000

3 beds

|

2 baths

|

1,602 sq ft

|

House

26822 BULL RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
Grand Haven 46 SHINNECOCK DR, PALM COAST, FL, 32137, Palm Coast, FL 32137
$449,999

3 beds

|

2 baths

|

1,883 sq ft

|

House

46 SHINNECOCK DR, PALM COAST, FL, 32137
Community: Grand Haven
Lake James 7991 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$410,000

2 beds

|

2 baths

|

1,890 sq ft

|

House

7991 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
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® 5885 FLINT LOOP, THE VILLAGES, FL, 32163, The Villages, FL 32163
$799,900

3 beds

|

3 baths

|

1,977 sq ft

|

House

5885 FLINT LOOP, THE VILLAGES, FL, 32163
Community: The Villages®
Del Webb Sunbridge 2575 PINE PRESERVE CT, ST CLOUD, FL, 347..., St Cloud, FL 34771
$714,000

3 beds

|

3 baths

|

2,483 sq ft

|

House

2575 PINE PRESERVE CT, ST CLOUD, FL, 347...
Community: Del Webb Sunbridge
The Villages® 5107 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484
$419,900

4 beds

|

3 baths

|

1,910 sq ft

|

House

5107 NE 122ND BLVD, OXFORD, FL, 34484
Community: The Villages®
Lake Ashton 4577 BACK NINE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33884
$359,900

3 beds

|

2 baths

|

1,918 sq ft

|

House

4577 BACK NINE DR, WINTER HAVEN, FL, 338...
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Plantation at Leesburg 25040 BETTON HL, LEESBURG, FL, 34748, Leesburg, FL 34748
$179,900

2 beds

|

2 baths

|

1,428 sq ft

|

Manufactured Home

25040 BETTON HL, LEESBURG, FL, 34748
Summer Trees 49 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$235,000

2 beds

|

2 baths

|

1,048 sq ft

|

House

49 CYPRESS POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
Venetian Bay 3595 ROMEA CIR, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$335,000

3 beds

|

3 baths

|

2,036 sq ft

|

Townhouse

3595 ROMEA CIR, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
The Timbers at Everlands 1273 BLESSED ISLES DR, PALM BAY, FL, 329..., Palm Bay, FL 32907
$475,990

3 beds

|

3 baths

|

2,601 sq ft

|

House

1273 BLESSED ISLES DR, PALM BAY, FL, 329...
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 Isle 3670 FUNSTON CIR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$279,000

2 beds

|

2 baths

|

1,407 sq ft

|

Townhouse

3670 FUNSTON CIR, MELBOURNE, FL, 32940
Community: Heritage Isle
Solivita 251 ROCK SPRINGS DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$325,000

2 beds

|

2 baths

|

2,050 sq ft

|

House

251 ROCK SPRINGS DR, KISSIMMEE, FL, 3475...
Community: Solivita
Plantation at Leesburg 25300 HIBISCUS ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$259,000

2 beds

|

2 baths

|

1,908 sq ft

|

House

25300 HIBISCUS ST, LEESBURG, FL, 34748
Latitude Margaritaville 272 LAST MANGO DR, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$422,900

2 beds

|

2 baths

|

1,464 sq ft

|

House

272 LAST MANGO DR, DAYTONA BEACH, FL, 32...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Trilogy® Orlando 168 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$580,000

3 beds

|

3 baths

|

2,392 sq ft

|

House

168 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Solivita 1689 TRABUCO CANYON CT, KISSIMMEE, FL, 3..., Kissimmee, FL 34759
$324,900

2 beds

|

2 baths

|

1,719 sq ft

|

House

1689 TRABUCO CANYON CT, KISSIMMEE, FL, 3...
Community: Solivita
Del Webb at Viera 3040 REEF ROCK PL, MELBOURNE, FL, 32940, Melbourne, FL 32940
$1,000,000

2 beds

|

4 baths

|

2,359 sq ft

|

House

3040 REEF ROCK PL, MELBOURNE, FL, 32940
Community: Del Webb at Viera
Royal Harbor 3370 SAINT LUCIA CT, TAVARES, FL, 32778, Tavares, FL 32778
$359,900

3 beds

|

2 baths

|

1,893 sq ft

|

House

3370 SAINT LUCIA CT, TAVARES, FL, 32778
Community: Royal Harbor
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 Bay Golf & Country Club 655 SOUTHLAKE DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$674,900

3 beds

|

2 baths

|

1,987 sq ft

|

House

655 SOUTHLAKE DR, ORMOND BEACH, FL, 3217...
Solivita 699 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$449,000

3 beds

|

3 baths

|

2,450 sq ft

|

House

699 GLENDORA RD, KISSIMMEE, FL, 34759
Community: Solivita
Latitude Margaritaville 562 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$345,000

2 beds

|

2 baths

|

1,160 sq ft

|

Villa

562 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Stonecrest 17842 SE 125TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$315,000

3 beds

|

2 baths

|

1,695 sq ft

|

House

17842 SE 125TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 8089 SE 174TH BELHAVEN LOOP, THE VILLAGE..., The Villages, FL 32162
$375,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

8089 SE 174TH BELHAVEN LOOP, THE VILLAGE...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Solivita 513 VINEYARD WAY, POINCIANA, FL, 34759, Poinciana, FL 34759
$265,000

2 beds

|

2 baths

|

1,240 sq ft

|

House

513 VINEYARD WAY, POINCIANA, FL, 34759
Community: Solivita
Solivita 2376 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$294,500

2 beds

|

2 baths

|

1,539 sq ft

|

Halfplex

2376 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 9239 SE 171ST COOPER LOOP, THE VILLAGES,..., The Villages, FL 32162
$349,000

3 beds

|

2 baths

|

1,993 sq ft

|

House

9239 SE 171ST COOPER LOOP, THE VILLAGES,...
Community: The Villages®
The Villages® 17101 SE 94TH BERRIEN CT, THE VILLAGES, ..., The Villages, FL 32162
$389,000

3 beds

|

2 baths

|

1,922 sq ft

|

House

17101 SE 94TH BERRIEN CT, THE VILLAGES, ...
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.
VillageWalk at Lake Nona 11863 FIORE DR, ORLANDO, FL, 32827, Orlando, FL 32827
$449,900

2 beds

|

2 baths

|

1,582 sq ft

|

Halfplex

11863 FIORE DR, ORLANDO, FL, 32827
Del Webb Minneola 1517 EVENING SUMMIT CIR, MINNEOLA, FL, 3..., Minneola, FL 34715
$1,200,000

4 beds

|

4 baths

|

2,808 sq ft

|

House

1517 EVENING SUMMIT CIR, MINNEOLA, FL, 3...
Community: Del Webb Minneola
Lake Ashton 4576 BACK NINE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33884
$344,500

2 beds

|

2 baths

|

1,514 sq ft

|

House

4576 BACK NINE DR, WINTER HAVEN, FL, 338...
Community: Lake Ashton
Del Webb Sunbridge 2575 PINE PRESERVE CT, ST. CLOUD, FL, 34..., St. Cloud, FL 34771
$714,000

3 beds

|

3 baths

|

2,483 sq ft

|

House

2575 PINE PRESERVE CT, ST. 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
VillageWalk at Lake Nona 8681 LOWER VILLAGEWALK CIR, ORLANDO, FL,..., Orlando, FL 32827
$475,000

3 beds

|

3 baths

|

1,830 sq ft

|

Townhouse

8681 LOWER VILLAGEWALK CIR, ORLANDO, FL,...
The Villages® 1028 COTTAGE DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$1,099,900

2 beds

|

2 baths

|

2,525 sq ft

|

House

1028 COTTAGE DR, THE VILLAGES, FL, 32162
Community: The Villages®

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2,513 homes
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