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Winter Park, FL 55+ active adult communities & homes for sale - Page 35

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
Scottish Highlands 55 ABERDEEN CIR, LEESBURG, FL, 34788, Leesburg, FL 34788
$165,000

2 beds

|

2 baths

|

1,056 sq ft

|

House

55 ABERDEEN CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
Grand Haven 16 VILLAGE VIEW WAY, PALM COAST, FL, 321..., Palm Coast, FL 32137
$499,000

3 beds

|

3 baths

|

1,980 sq ft

|

House

16 VILLAGE VIEW WAY, PALM COAST, FL, 321...
Community: Grand Haven
Trilogy® Orlando 115 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736
$330,000

3 beds

|

2 baths

|

1,856 sq ft

|

House

115 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
Stonecrest 17424 SE 111TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$260,000

3 beds

|

2 baths

|

1,446 sq ft

|

House

17424 SE 111TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
Indian River Colony Club 1680 OLD GLORY BLVD, MELBOURNE, FL, 3294..., Melbourne, FL 32940
$269,000

2 beds

|

2 baths

|

1,033 sq ft

|

House

1680 OLD GLORY BLVD, MELBOURNE, FL, 3294...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Spruce Creek South 9980 SE 176TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$289,900

3 beds

|

2 baths

|

1,826 sq ft

|

House

9980 SE 176TH ST, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Summit Greens 3008 PINNACLE CT, CLERMONT, FL, 34711, Clermont, FL 34711
$359,000

2 beds

|

2 baths

|

1,543 sq ft

|

House

3008 PINNACLE CT, CLERMONT, FL, 34711
Community: Summit Greens
Spruce Creek South 17929 SE 104TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$229,000

2 beds

|

2 baths

|

1,295 sq ft

|

House

17929 SE 104TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Lakes of Mount Dora 8045 WATERBURY WAY, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$459,000

3 beds

|

2 baths

|

2,152 sq ft

|

House

8045 WATERBURY WAY, MOUNT DORA, FL, 3275...
Community: Lakes of Mount Dora
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.
Spruce Creek Country Club 9153 SE 137TH STREET RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$429,000

3 beds

|

2 baths

|

2,120 sq ft

|

House

9153 SE 137TH STREET RD, SUMMERFIELD, FL...
Stonecrest 11078 SE 175TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$310,000

3 beds

|

2 baths

|

1,972 sq ft

|

House

11078 SE 175TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Bridgewater at Viera 2529 MILLENNIUM CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940
$699,000

3 beds

|

3 baths

|

2,468 sq ft

|

House

2529 MILLENNIUM CIR, MELBOURNE, FL, 3294...
Royal Harbor 5588 GULF STREAM ST, TAVARES, FL, 32778, Tavares, FL 32778
$335,000

3 beds

|

2 baths

|

1,634 sq ft

|

House

5588 GULF STREAM ST, TAVARES, FL, 32778
Community: Royal Harbor
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Venetian Bay 505 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$347,500

3 beds

|

3 baths

|

1,758 sq ft

|

House

505 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
Venetian Bay 2912 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$360,000

3 beds

|

3 baths

|

1,779 sq ft

|

House

2912 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
The Villages® 3245 RIVERTON RD, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$254,000

2 beds

|

2 baths

|

1,143 sq ft

|

Villa

3245 RIVERTON RD, THE VILLAGES, FL, 3216...
Community: The Villages®
Solivita 684 SAN AUGUSTO DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$519,000

3 beds

|

3 baths

|

2,363 sq ft

|

House

684 SAN AUGUSTO DR, POINCIANA, 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.
Spruce Creek South 17576 SE 96TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$289,000

3 beds

|

2 baths

|

1,726 sq ft

|

House

17576 SE 96TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Spruce Creek Country Club 13907 DEL WEBB BLVD, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$289,900

2 beds

|

2 baths

|

1,869 sq ft

|

House

13907 DEL WEBB BLVD, SUMMERFIELD, FL, 34...
Latitude Margaritaville 198 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$399,900

2 beds

|

2 baths

|

1,464 sq ft

|

House

198 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Venetian Bay 527 LUNA BELLA LN, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$755,000

3 beds

|

2 baths

|

2,416 sq ft

|

House

527 LUNA BELLA LN, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 1033 OAK FOREST DR, THE VILLAGES, FL, 32..., The Villages, FL 32162
$362,500

3 beds

|

2 baths

|

1,840 sq ft

|

House

1033 OAK FOREST DR, THE VILLAGES, FL, 32...
Community: The Villages®
Spruce Creek Country Club 13160 SE 93RD CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$335,000

2 beds

|

2 baths

|

1,875 sq ft

|

House

13160 SE 93RD CIR, SUMMERFIELD, FL, 3449...
The Villages® 2346 ARBORDALE AVE, THE VILLAGES, FL, 32..., The Villages, FL 32162
$299,000

2 beds

|

2 baths

|

1,161 sq ft

|

Villa

2346 ARBORDALE AVE, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 3001 EGERTON PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$354,900

3 beds

|

2 baths

|

1,527 sq ft

|

House

3001 EGERTON PL, 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.
Kings Ridge 4246 NEWLAND ST, CLERMONT, FL, 34711, Clermont, FL 34711
$369,900

3 beds

|

2 baths

|

1,755 sq ft

|

House

4246 NEWLAND ST, CLERMONT, FL, 34711
Community: Kings Ridge
Venetian Bay 428 N AIRPORT RD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$318,000

3 beds

|

3 baths

|

1,794 sq ft

|

Townhouse

428 N AIRPORT RD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
The Villages® 1289 ADDISON AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$315,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

1289 ADDISON AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
Venetian Bay 367 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$380,000

3 beds

|

2 baths

|

1,653 sq ft

|

House

367 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Lake James 7903 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$499,000

2 beds

|

2 baths

|

1,966 sq ft

|

House

7903 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
The Villages® 952 TALAPIA LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$379,000

3 beds

|

2 baths

|

1,711 sq ft

|

House

952 TALAPIA LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Venetian Bay 3371 MEDICI BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$369,900

3 beds

|

2 baths

|

1,466 sq ft

|

House

3371 MEDICI BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Kings Ridge 3914 ALLAMANDA CT, CLERMONT, FL, 34711, Clermont, FL 34711
$375,000

3 beds

|

2 baths

|

1,893 sq ft

|

House

3914 ALLAMANDA CT, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 717 ROYAL PALM AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$240,000

2 beds

|

2 baths

|

1,248 sq ft

|

Modular

717 ROYAL PALM AVE, LADY LAKE, FL, 32159
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.
Spruce Creek Country Club 11703 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$399,500

3 beds

|

2 baths

|

1,958 sq ft

|

House

11703 SE 91ST CIR, SUMMERFIELD, FL, 3449...
Cresswind DeLand 1274 BRUSH CREEK DR, DELAND, FL, 32724, Deland, FL 32724
$789,990

3 beds

|

4 baths

|

2,776 sq ft

|

House

1274 BRUSH CREEK DR, DELAND, FL, 32724
Community: Cresswind DeLand
Cresswind DeLand 1292 JACKSON HOLE CT, DELAND, FL, 32724, Deland, FL 32724
$449,990

3 beds

|

2 baths

|

1,724 sq ft

|

House

1292 JACKSON HOLE CT, DELAND, FL, 32724
Community: Cresswind DeLand
The Villages® 5705 CRAFT CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$289,900

3 beds

|

2 baths

|

1,426 sq ft

|

Villa

5705 CRAFT CT, THE VILLAGES, FL, 32163
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Solivita 795 AVIARA LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$459,000

3 beds

|

3 baths

|

2,427 sq ft

|

House

795 AVIARA LN, KISSIMMEE, FL, 34759
Community: Solivita
Indian River Colony Club 1444 PATRIOT DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$298,000

3 beds

|

2 baths

|

1,874 sq ft

|

House

1444 PATRIOT DR, MELBOURNE, FL, 32940

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2,513 homes
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