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

2,487 homes near Winter Park

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4 rating (17 reviews) The Villages®
<$100k - $1Ms
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
Grand Haven
$300Ks - $1Ms
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.
Pelican Bay Daytona Beach
$100Ks - $500Ks
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 - $300Ks
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
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
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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 - $500Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
5 rating (8 reviews) Royal Highlands
$200Ks - $500Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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
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 at Viera
$300Ks - $800Ks
Del Webb at Viera, Melbourne, FL
New Construction | 55+ age-restricted | Built 2021 - present | 1,300 homes
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
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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 - $700Ks
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
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.
4.8 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 - $600Ks
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
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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
$200Ks - $400Ks
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
1 rating (1 reviews) Sullivan Ranch
$300Ks - $600Ks
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® 2046 DALECROFT TRL, THE VILLAGES, FL, 32..., The Villages, FL 32162
$359,900

3 beds

|

2 baths

|

1,488 sq ft

|

House

2046 DALECROFT TRL, THE VILLAGES, FL, 32...
Community: The Villages®
Pennbrooke Fairways 32819 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$210,000

2 beds

|

2 baths

|

1,162 sq ft

|

House

32819 TIMBERWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Del Webb Oasis 15843 GEM VIEW ST, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$451,090

2 beds

|

2 baths

|

1,579 sq ft

|

House

15843 GEM VIEW ST, WINTER GARDEN, FL, 34...
Community: Del Webb Oasis
Del Webb Oasis 15837 GEM VIEW ST, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$455,410

2 beds

|

2 baths

|

1,579 sq ft

|

House

15837 GEM VIEW ST, WINTER GARDEN, FL, 34...
Community: Del Webb Oasis
Del Webb Oasis 15831 GEM VIEW ST, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$442,090

3 beds

|

2 baths

|

1,579 sq ft

|

House

15831 GEM VIEW ST, WINTER GARDEN, FL, 34...
Community: Del Webb Oasis
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Questions? Call us: (888) 625-4885
Del Webb Oasis 15825 GEM VIEW ST, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$440,080

2 beds

|

2 baths

|

1,579 sq ft

|

House

15825 GEM VIEW ST, WINTER GARDEN, FL, 34...
Community: Del Webb Oasis
Halifax Plantation 1422 CARLOW CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$314,900

3 beds

|

2 baths

|

1,684 sq ft

|

Townhouse

1422 CARLOW CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
Solivita 313 SANTA BARBARA LN, KISSIMMEE, FL, 347..., Kissimmee, FL 34759
$449,900

2 beds

|

3 baths

|

2,343 sq ft

|

House

313 SANTA BARBARA LN, KISSIMMEE, FL, 347...
Community: Solivita
Sandpiper Golf & Country Club 6381 EGRET DR APT 25, LAKELAND, FL, 3380..., Lakeland, FL 33809
$270,000

2 beds

|

2 baths

|

1,383 sq ft

|

Villa

6381 EGRET DR APT 25, LAKELAND, FL, 3380...
Heritage Isle 3029 VALLEJO WAY, MELBOURNE, FL, 32940, Melbourne, FL 32940
$328,700

2 beds

|

2 baths

|

1,532 sq ft

|

Townhouse

3029 VALLEJO WAY, MELBOURNE, FL, 32940
Community: Heritage Isle
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.
Venetian Bay 3211 MODENA WAY, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$949,132

3 beds

|

3 baths

|

2,542 sq ft

|

House

3211 MODENA WAY, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
High Vista at Ridgewood Lakes 537 RIDGE VIEW DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$350,000

2 beds

|

2 baths

|

1,797 sq ft

|

House

537 RIDGE VIEW DR, DAVENPORT, FL, 33837
Breakaway Trails 3 CROOKED BRIDGE WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174
$585,000

5 beds

|

5 baths

|

3,171 sq ft

|

House

3 CROOKED BRIDGE WAY, ORMOND BEACH, FL, ...
Community: Breakaway Trails
The Villages® 4216 BALCHARAN TER, THE VILLAGES, FL, 32..., The Villages, FL 32163
$539,900

3 beds

|

2 baths

|

1,924 sq ft

|

House

4216 BALCHARAN TER, THE VILLAGES, FL, 32...
Community: The Villages®
Heritage Isle 6488 VAN NESS DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$430,000

3 beds

|

2 baths

|

1,861 sq ft

|

House

6488 VAN NESS DR, MELBOURNE, FL, 32940
Community: Heritage Isle
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Legacy of Leesburg 5422 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$315,000

3 beds

|

2 baths

|

1,745 sq ft

|

House

5422 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Twin Lakes 2712 SOUTHLAND ST, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$419,000

3 beds

|

2 baths

|

1,863 sq ft

|

House

2712 SOUTHLAND ST, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
Plantation at Leesburg 25633 LAUREL VALLEY RD, LEESBURG, FL, 34..., Leesburg, FL 34748
$429,900

3 beds

|

2 baths

|

2,410 sq ft

|

House

25633 LAUREL VALLEY RD, LEESBURG, FL, 34...
Lakeside Landings 5336 EDGEWATER WAY, OXFORD, FL, 34484, Oxford, FL 34484
$225,000

3 beds

|

2 baths

|

1,291 sq ft

|

Condo

5336 EDGEWATER WAY, OXFORD, FL, 34484
Community: Lakeside Landings
Bridgewater at Viera 963 GREAT BELT CIR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$645,000

3 beds

|

3 baths

|

2,532 sq ft

|

House

963 GREAT BELT CIR, MELBOURNE, FL, 32940
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 2883 GALINDO CIR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$550,000

4 beds

|

3 baths

|

2,271 sq ft

|

House

2883 GALINDO CIR, MELBOURNE, FL, 32940
Community: Heritage Isle
Heritage Isle 3710 FUNSTON CIR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$299,000

2 beds

|

2 baths

|

1,407 sq ft

|

Townhouse

3710 FUNSTON CIR, MELBOURNE, FL, 32940
Community: Heritage Isle
Heritage Isle 7105 MENDELL WAY, MELBOURNE, FL, 32940, Melbourne, FL 32940
$450,000

3 beds

|

2 baths

|

2,023 sq ft

|

House

7105 MENDELL WAY, MELBOURNE, FL, 32940
Community: Heritage Isle
Venetian Bay 3583 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$789,900

3 beds

|

2 baths

|

2,273 sq ft

|

House

3583 MARIBELLA DR, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
Huntington at Hunter's Ridge 24 SHEAR WATER TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$369,000

3 beds

|

2 baths

|

2,031 sq ft

|

House

24 SHEAR WATER TRL, ORMOND BEACH, FL, 32...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Venetian Bay 3362 GALLIA ST, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$360,000

3 beds

|

2 baths

|

1,476 sq ft

|

House

3362 GALLIA ST, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Latitude Margaritaville 710 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$559,900

2 beds

|

3 baths

|

1,743 sq ft

|

House

710 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Pelican Bay Daytona Beach 108 MARSH WREN CT, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32119
$249,900

3 beds

|

2 baths

|

1,384 sq ft

|

House

108 MARSH WREN CT, DAYTONA BEACH, FL, 32...
Plantation Bay Golf & Country Club 626 ELK RIVER DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$575,000

3 beds

|

3 baths

|

2,251 sq ft

|

House

626 ELK RIVER DR, ORMOND BEACH, FL, 3217...
Halifax Plantation 3203 GALTY CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$497,000

3 beds

|

2 baths

|

2,412 sq ft

|

House

3203 GALTY CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
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 1157 KILKENNY LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$409,000

3 beds

|

2 baths

|

1,910 sq ft

|

House

1157 KILKENNY LN, ORMOND BEACH, FL, 3217...
Huntington at Hunter's Ridge 13 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$418,900

4 beds

|

3 baths

|

2,156 sq ft

|

House

13 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Huntington at Hunter's Ridge 59 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$559,000

3 beds

|

2 baths

|

1,852 sq ft

|

House

59 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Plantation Bay Golf & Country Club 38 TREETOP CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$479,000

3 beds

|

3 baths

|

3,026 sq ft

|

House

38 TREETOP CIR, ORMOND BEACH, FL, 32174
Latitude Margaritaville 664 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$609,900

2 beds

|

2 baths

|

1,922 sq ft

|

House

664 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Hills 3542 FAIRWATERS CT D, CLERMONT, FL, 3471..., Clermont, FL 34711
$295,000

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3542 FAIRWATERS CT D, CLERMONT, FL, 3471...
Community: Heritage Hills
The Villages® 2377 LONGBOW TRL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$360,000

3 beds

|

2 baths

|

1,512 sq ft

|

House

2377 LONGBOW TRL, THE VILLAGES, FL, 3216...
Community: The Villages®
Spruce Creek Country Club 9450 SE 130TH PLACE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$399,000

3 beds

|

3 baths

|

2,252 sq ft

|

House

9450 SE 130TH PLACE RD, SUMMERFIELD, FL,...
Summit Greens 748 SUMMIT GREENS BLVD, CLERMONT, FL, 34..., Clermont, FL 34711
$419,000

3 beds

|

2 baths

|

1,777 sq ft

|

House

748 SUMMIT GREENS BLVD, CLERMONT, FL, 34...
Community: Summit Greens
Four Seasons at Orlando 2074 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$645,000

3 beds

|

2 baths

|

2,130 sq ft

|

House

2074 FLORA PASS PL, KISSIMMEE, FL, 34747

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2,487 homes near Winter Park
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