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

2,298 homes near Winter Park

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4 rating (17 reviews) The Villages®
<$100k - $2Ms
The Villages®, The Villages, FL
New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes
4.7 rating (18 reviews) Solivita
$100Ks - $600Ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
3.6 rating (48 reviews) Latitude Margaritaville
$300Ks - $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
5 rating (1 reviews) Plantation Bay Golf &...
$200Ks - $4Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale | Age-targeted | Built 1988 - present | 3,500 homes
4.5 rating (11 reviews) Spruce Creek Country Club
$200Ks - $500Ks
Spruce Creek Country Club, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes
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5 rating (2 reviews) Plantation at Leesburg
$100Ks - $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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 (7 reviews) Kings Ridge
$200Ks - $400Ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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
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.
Grand Haven
$300Ks - $1Ms
Grand Haven, Palm Coast, FL
New and Resale | Age-targeted | Built 1997 - present | 1,901 homes
Pelican Bay Daytona Beach
$100Ks - $400Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $400Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
5 rating (1 reviews) Cypress Lakes
$100Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
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5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
Venetian Bay
$200Ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
5 rating (2 reviews) Heritage Isle
$200Ks - $500Ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 homes
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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) Royal Highlands
$200Ks - $500Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
Del Webb at Viera
$400Ks - $1Ms
Del Webb at Viera, Melbourne, FL
New Construction | 55+ age-restricted | Built 2021 - present | 1,300 homes
5 rating (1 reviews) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$300Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
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5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
5 rating (1 reviews) Sandpiper Golf & Coun...
$200Ks - $400Ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
3.6 rating (5 reviews) Heritage Hills
$200Ks - $500Ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$300Ks - $600Ks
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.
Halifax Plantation
$200Ks - $700Ks
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 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
Breakaway Trails
$400Ks - $800Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$400Ks - $900Ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
4 rating (2 reviews) Harbor Hills Country Club
$200Ks - $1Ms
Harbor Hills Country Club, Lady Lake, FL
New and Resale | Age-targeted | Built 1989 - present | 940 homes
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4.8 rating (6 reviews) Highland Lakes
$100Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
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
The Country Club of Mount...
$200Ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 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.
4.1 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
3.9 rating (7 reviews) Summit Greens
$300Ks - $400Ks
Summit Greens, Clermont, FL
Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 homes
5 rating (1 reviews) Royal Harbor
$300Ks - $700Ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
Lakeside Landings
$200Ks - $500Ks
Lakeside Landings, Oxford, FL
New and Resale | Age-targeted | Built 2005 - present | 700 homes
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1 rating (1 reviews) Sullivan Ranch
$200Ks - $700Ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
Highland Fairways
$100Ks - $300Ks
Highland Fairways, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes
The Villages® 1822 ATHENS LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$309,900

2 beds

|

2 baths

|

1,322 sq ft

|

Villa

1822 ATHENS LN, THE VILLAGES, FL, 32162
Community: The Villages®
Legacy of Leesburg 5135 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$344,900

3 beds

|

2 baths

|

2,055 sq ft

|

House

5135 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
The Villages® 913 SOLEDAD WAY, THE VILLAGES, FL, 32159, The Villages, FL 32159
$469,000

3 beds

|

2 baths

|

1,982 sq ft

|

House

913 SOLEDAD WAY, THE VILLAGES, FL, 32159
Community: The Villages®
Pelican Bay Daytona Beach 5 SKIMMER CIR, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119
$337,900

3 beds

|

3 baths

|

2,086 sq ft

|

House

5 SKIMMER CIR, DAYTONA BEACH, FL, 32119
Venetian Bay 3362 MARSILI AVE, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$399,000

3 beds

|

2 baths

|

1,952 sq ft

|

House

3362 MARSILI AVE, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
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The Villages® 611 ALLENWOOD LOOP, THE VILLAGES, FL, 32..., The Villages, FL 32162
$429,999

3 beds

|

2 baths

|

1,927 sq ft

|

House

611 ALLENWOOD LOOP, THE VILLAGES, FL, 32...
Community: The Villages®
Venetian Bay 3566 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$725,000

5 beds

|

3 baths

|

2,405 sq ft

|

House

3566 MARIBELLA DR, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
Pelican Bay Daytona Beach 157 WOODCOCK CT, DAYTONA BEACH, FL, 3211..., Daytona Beach, FL 32119
$354,499

3 beds

|

3 baths

|

2,137 sq ft

|

House

157 WOODCOCK CT, DAYTONA BEACH, FL, 3211...
Pelican Bay Daytona Beach 102 BLUE HERON DR A, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$198,000

2 beds

|

2 baths

|

1,237 sq ft

|

Condo

102 BLUE HERON DR A, DAYTONA BEACH, FL, ...
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.
New Latitude Margaritaville 121 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$424,900

2 beds

|

2 baths

|

1,466 sq ft

|

Townhouse

121 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...
Del Webb at Viera 3132 TIDEPOOL PL, MELBOURNE, FL, 32940, Melbourne, FL 32940
$724,982

3 beds

|

2 baths

|

1,902 sq ft

|

House

3132 TIDEPOOL PL, MELBOURNE, FL, 32940
Community: Del Webb at Viera
New Venetian Bay 3617 ROMEA CIR, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$328,000

3 beds

|

3 baths

|

1,824 sq ft

|

Townhouse

3617 ROMEA CIR, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
The Villages® 2117 ZARAGOZA PL, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$310,000

2 beds

|

2 baths

|

1,344 sq ft

|

House

2117 ZARAGOZA PL, THE VILLAGES, FL, 3215...
Community: The Villages®
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Carillon Lakes 4048 WINDCHIME LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$399,000

5 beds

|

3 baths

|

2,788 sq ft

|

House

4048 WINDCHIME LN, LAKELAND, FL, 33811
Community: Carillon Lakes
VillageWalk at Lake Nona 11846 NAUTICA DR, ORLANDO, FL, 32827, Orlando, FL 32827
$425,000

3 beds

|

3 baths

|

1,810 sq ft

|

Townhouse

11846 NAUTICA DR, ORLANDO, FL, 32827
Spruce Creek Country Club 13485 SE 93RD COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$349,900

2 beds

|

2 baths

|

1,826 sq ft

|

House

13485 SE 93RD COURT RD, SUMMERFIELD, FL,...
Stonecrest 12135 SE 172ND LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$450,000

3 beds

|

2 baths

|

2,031 sq ft

|

House

12135 SE 172ND LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
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® 16938 SE 94TH SUNNYBROOK CIR, THE VILLAG..., The Villages, FL 32162
$271,900

2 beds

|

2 baths

|

1,163 sq ft

|

House

16938 SE 94TH SUNNYBROOK CIR, THE VILLAG...
Community: The Villages®
The Villages® 219 CARRERA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$685,900

3 beds

|

2 baths

|

1,831 sq ft

|

House

219 CARRERA DR, THE VILLAGES, FL, 32159
Community: The Villages®
Latitude Margaritaville 1082 CASTAWAY CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$535,000

2 beds

|

2 baths

|

1,684 sq ft

|

House

1082 CASTAWAY CT, DAYTONA BEACH, FL, 321...
The Villages® 5609 HANCOCK DR, WILDWOOD, FL, 34785, Wildwood, FL 34785
$135,000

2 beds

|

1 baths

|

660 sq ft

|

Mobile Home

5609 HANCOCK DR, WILDWOOD, FL, 34785
Community: The Villages®
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The Villages® 1865 CLAVERTON ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$698,000

3 beds

|

2 baths

|

2,579 sq ft

|

House

1865 CLAVERTON ST, THE VILLAGES, FL, 321...
Community: The Villages®
Venetian Bay 354 N AIRPORT RD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$329,999

2 beds

|

3 baths

|

1,837 sq ft

|

Townhouse

354 N AIRPORT RD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
New Halifax Plantation 1324 TULLAMORE BLVD, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174
$695,000

4 beds

|

3 baths

|

2,598 sq ft

|

House

1324 TULLAMORE BLVD, ORMOND BEACH, FL, 3...
Community: Halifax Plantation
Venetian Bay 360 N AIRPORT RD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$299,000

2 beds

|

3 baths

|

1,837 sq ft

|

Townhouse

360 N AIRPORT RD, 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.
The Villages® 17211 SE 85TH WILLOWICK CIR, THE VILLAGE..., The Villages, FL 32162
$575,000

3 beds

|

2 baths

|

2,350 sq ft

|

House

17211 SE 85TH WILLOWICK CIR, THE VILLAGE...
Community: The Villages®
The Villages® 1001 MATTHEW AVE, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$224,900

2 beds

|

2 baths

|

1,149 sq ft

|

Manufactured Home

1001 MATTHEW AVE, THE VILLAGES, FL, 3215...
Community: The Villages®
The Villages® 2063 THORNTON TER, THE VILLAGES, FL, 321..., The Villages, FL 32162
$280,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2063 THORNTON TER, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 926 LONG LEAF LN, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$449,999

3 beds

|

2 baths

|

1,541 sq ft

|

House

926 LONG LEAF LN, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 879 CHAPMAN LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$439,900

3 beds

|

2 baths

|

1,621 sq ft

|

House

879 CHAPMAN LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
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The Villages® 7177 SE 172ND HAZELWOOD LOOP, THE VILLAG..., The Villages, FL 32162
$448,500

3 beds

|

2 baths

|

1,918 sq ft

|

House

7177 SE 172ND HAZELWOOD LOOP, THE VILLAG...
Community: The Villages®
The Villages® 1999 KELMSCOTT ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$299,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

1999 KELMSCOTT ST, THE VILLAGES, FL, 321...
Community: The Villages®
New Latitude Margaritaville 488 HIGH TIDE LN, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$375,000

2 beds

|

2 baths

|

1,308 sq ft

|

House

488 HIGH TIDE LN, DAYTONA BEACH, FL, 321...
Kings Ridge 3412 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$365,000

3 beds

|

2 baths

|

1,728 sq ft

|

House

3412 CAPLAND AVE, CLERMONT, FL, 34711
Community: Kings 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.
Royal Palm 5415 SWORDFERN CT, PORT ORANGE, FL, 3212..., Port Orange, FL 32128
$414,900

3 beds

|

3 baths

|

1,942 sq ft

|

House

5415 SWORDFERN CT, PORT ORANGE, FL, 3212...
Community: Royal Palm
Colonnades 1635 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811
$290,000

2 beds

|

2 baths

|

1,751 sq ft

|

House

1635 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
Summit Greens 793 HAWKS BLF, CLERMONT, FL, 34711, Clermont, FL 34711
$480,000

2 beds

|

3 baths

|

2,209 sq ft

|

House

793 HAWKS BLF, CLERMONT, FL, 34711
Community: Summit Greens
The Villages® 1001 GREYFORD LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$304,900

2 beds

|

2 baths

|

1,351 sq ft

|

Villa

1001 GREYFORD LN, THE VILLAGES, FL, 3216...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
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New Halifax Plantation 3639 MALLOW DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$525,000

3 beds

|

2 baths

|

2,176 sq ft

|

House

3639 MALLOW DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
The Villages® 1221 SANTA CRUZ DR, THE VILLAGES, FL, 32..., The Villages, FL 32162
$289,900

2 beds

|

2 baths

|

1,174 sq ft

|

Villa

1221 SANTA CRUZ DR, THE VILLAGES, FL, 32...
Community: The Villages®

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