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Winter Park, FL 55+ active adult communities & homes for sale - Page 4

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
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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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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
Latitude Margaritaville 601 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$385,000

2 beds

|

2 baths

|

1,308 sq ft

|

House

601 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Plantation at Leesburg 24345 AMBERLEAF CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$349,900

3 beds

|

2 baths

|

1,898 sq ft

|

House

24345 AMBERLEAF CT, LEESBURG, FL, 34748
Plantation at Leesburg 5044 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$254,900

3 beds

|

2 baths

|

1,610 sq ft

|

House

5044 EL DESTINO DR, LEESBURG, FL, 34748
Solivita 454 COLONY ORCHARD CT, KISSIMMEE, FL, 34..., Kissimmee, FL 34759
$525,000

4 beds

|

3 baths

|

2,506 sq ft

|

House

454 COLONY ORCHARD CT, KISSIMMEE, FL, 34...
Community: Solivita
The Villages® 17350 SE 77TH SYCAMORE AVE, THE VILLAGES..., The Villages, FL 32162
$249,900

2 beds

|

1 baths

|

1,071 sq ft

|

Villa

17350 SE 77TH SYCAMORE AVE, THE VILLAGES...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 17300 SE 93RD HEYWARD AVE, THE VILLAGES,..., The Villages, FL 32162
$265,000

2 beds

|

2 baths

|

1,160 sq ft

|

Villa

17300 SE 93RD HEYWARD AVE, THE VILLAGES,...
Community: The Villages®
The Villages® 1672 GUMWOOD DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$424,000

3 beds

|

2 baths

|

1,621 sq ft

|

House

1672 GUMWOOD DR, THE VILLAGES, FL, 32162
Community: The Villages®
Kings Ridge 3811 WESTERHAM DR, CLERMONT, FL, 34711, Clermont, FL 34711
$335,000

2 beds

|

2 baths

|

1,679 sq ft

|

House

3811 WESTERHAM DR, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 1616 BAYHILL DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$249,000

2 beds

|

2 baths

|

1,300 sq ft

|

Manufactured Home

1616 BAYHILL DR, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 1979 REMBERT RD, THE VILLAGES, FL, 32162, The Villages, FL 32162
$465,000

3 beds

|

2 baths

|

2,179 sq ft

|

House

1979 REMBERT RD, 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.
The Villages® 1507 E SCHWARTZ BLVD, THE VILLAGES, FL, ..., The Villages, FL 32159
$199,900

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

1507 E SCHWARTZ BLVD, THE VILLAGES, FL, ...
Community: The Villages®
VillageWalk at Lake Nona 11943 XENIA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$600,000

3 beds

|

2 baths

|

1,958 sq ft

|

House

11943 XENIA LN, ORLANDO, FL, 32827
The Villages® 7372 SE 168TH MITZI ST, THE VILLAGES, FL..., The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,442 sq ft

|

Villa

7372 SE 168TH MITZI ST, THE VILLAGES, FL...
Community: The Villages®
Cresswind at Hammock Oaks 948 CLUB CRESSWIND DR, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$645,110

3 beds

|

3 baths

|

2,289 sq ft

|

House

948 CLUB CRESSWIND DR, LADY LAKE, FL, 32...
Del Webb Orlando 500 ARENA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$360,000

3 beds

|

2 baths

|

2,249 sq ft

|

House

500 ARENA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
The Villages® 2885 INTERLOCHEN RD, THE VILLAGES, FL, 3..., The Villages, FL 32163
$582,500

3 beds

|

2 baths

|

1,851 sq ft

|

Villa

2885 INTERLOCHEN RD, THE VILLAGES, FL, 3...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Cresswind at Lake Harris 1613 BELLAGIO LOOP, TAVARES, FL, 32778, Tavares, FL 32778
$674,990

3 beds

|

3 baths

|

2,490 sq ft

|

House

1613 BELLAGIO LOOP, TAVARES, FL, 32778
Sullivan Ranch 21345 SULLIVAN RANCH BLVD, MOUNT DORA, F..., Mount Dora, FL 32757
$625,000

4 beds

|

4 baths

|

3,544 sq ft

|

House

21345 SULLIVAN RANCH BLVD, MOUNT DORA, F...
Community: Sullivan Ranch
Lake Henry Estates 494 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844
$279,000

3 beds

|

2 baths

|

1,727 sq ft

|

House

494 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
Arlington Ridge 27103 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$316,000

2 beds

|

2 baths

|

1,589 sq ft

|

House

27103 ROANOKE DR, LEESBURG, FL, 34748
Community: Arlington Ridge
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.
Del Webb Orlando 423 ARMADA LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$359,900

2 beds

|

2 baths

|

1,970 sq ft

|

House

423 ARMADA LN, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Plantation at Leesburg 4750 SAWGRASS LAKE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$424,900

2 beds

|

2 baths

|

1,880 sq ft

|

House

4750 SAWGRASS LAKE CIR, LEESBURG, FL, 34...
Lake Ashton 4436 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$229,900

2 beds

|

2 baths

|

1,083 sq ft

|

House

4436 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
The Villages® 1606 SNELLING AVE, THE VILLAGES, FL, 321..., The Villages, FL 32162
$620,000

3 beds

|

2 baths

|

1,684 sq ft

|

House

1606 SNELLING AVE, THE VILLAGES, FL, 321...
Community: The Villages®
Pelican Bay Daytona Beach 520 BROWN PELICAN DR, DAYTONA BEACH, FL,..., Daytona Beach, FL 32119
$249,900

3 beds

|

2 baths

|

1,630 sq ft

|

House

520 BROWN PELICAN DR, DAYTONA BEACH, FL,...
The Villages® 1033 ALOHA WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$385,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

1033 ALOHA WAY, LADY LAKE, FL, 32159
Community: The Villages®
Plantation at Leesburg 25335 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$244,900

2 beds

|

2 baths

|

1,386 sq ft

|

House

25335 CRANES ROOST CIR, LEESBURG, FL, 34...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 871 AMBER CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$350,000

3 beds

|

2 baths

|

1,357 sq ft

|

Villa

871 AMBER CT, THE VILLAGES, FL, 32163
Community: The Villages®
Solivita 453 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$499,900

3 beds

|

4 baths

|

2,580 sq ft

|

House

453 SORRENTO RD, KISSIMMEE, FL, 34759
Community: Solivita
Grand Haven 102 LAGARE ST, PALM COAST, FL, 32137, Palm Coast, FL 32137
$929,000

3 beds

|

4 baths

|

2,760 sq ft

|

House

102 LAGARE 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.
Lake James 7783 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$414,000

2 beds

|

2 baths

|

1,925 sq ft

|

House

7783 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Vienna Square 1590 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884
$210,000

2 beds

|

2 baths

|

1,231 sq ft

|

Villa

1590 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
Plantation at Leesburg 5106 CHANTICLEER DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$535,000

3 beds

|

3 baths

|

3,112 sq ft

|

House

5106 CHANTICLEER DR, LEESBURG, FL, 34748
The Villages® 1428 CARRILLO ST, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$334,900

3 beds

|

2 baths

|

1,520 sq ft

|

House

1428 CARRILLO ST, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 403 MCLEOD LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$375,000

3 beds

|

2 baths

|

1,512 sq ft

|

House

403 MCLEOD LN, THE VILLAGES, FL, 32162
Community: The Villages®
Heritage - The Cottages of Sanders Grove 6201 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762
$341,535

4 beds

|

2 baths

|

1,625 sq ft

|

House

6201 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
Lake Ashton 4572 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$289,900

2 beds

|

2 baths

|

1,530 sq ft

|

House

4572 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Twin Lakes 5019 DANCY LN, ST CLOUD, FL, 34772, St Cloud, FL 34772
$589,000

3 beds

|

3 baths

|

2,305 sq ft

|

House

5019 DANCY LN, ST CLOUD, FL, 34772
Community: Twin Lakes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Harbor Hills Country Club 5009 HARBOR HEIGHTS, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$339,900

3 beds

|

2 baths

|

2,018 sq ft

|

House

5009 HARBOR HEIGHTS, LADY LAKE, FL, 3215...
Heritage - The Cottages of Sanders Grove 6205 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762
$325,091

3 beds

|

2 baths

|

1,407 sq ft

|

House

6205 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
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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