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Winter Park, FL 55+ active adult communities & homes for sale - Page 14

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 (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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 (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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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
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 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 (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.
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
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 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
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
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
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
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.
Tohoqua Reserve
$300ks - $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2021 - present | 258 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
Four Seasons at Orlando 2185 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747
$575,000

3 beds

|

2 baths

|

1,904 sq ft

|

House

2185 ANTILLES CLUB DR, KISSIMMEE, FL, 34...
The Villages® 2679 LANTANA AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$559,000

3 beds

|

2 baths

|

1,966 sq ft

|

House

2679 LANTANA AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 258 ARBELLA LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$310,000

2 beds

|

2 baths

|

1,130 sq ft

|

House

258 ARBELLA LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Latitude Margaritaville 227 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$489,900

2 beds

|

2 baths

|

1,778 sq ft

|

House

227 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Harbor Hills Country Club 39634 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159
$449,900

3 beds

|

2 baths

|

2,579 sq ft

|

House

39634 HARBOR HILLS BLVD, LADY LAKE, FL, ...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Venetian Bay 656 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$779,576

5 beds

|

4 baths

|

3,221 sq ft

|

House

656 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
The Villages® 281 KATHERINE PL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$329,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

281 KATHERINE PL, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 1607 MOUNT CROGHAN TRL, THE VILLAGES, FL..., The Villages, FL 32162
$549,900

3 beds

|

3 baths

|

2,075 sq ft

|

House

1607 MOUNT CROGHAN TRL, THE VILLAGES, FL...
Community: The Villages®
The Villages® 2454 SOUTHERN OAK ST, THE VILLAGES, FL, ..., The Villages, FL 32162
$235,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2454 SOUTHERN OAK ST, THE VILLAGES, FL, ...
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.
Plantation at Leesburg 4908 CYPRESS HEAD CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$350,000

2 beds

|

2 baths

|

2,087 sq ft

|

House

4908 CYPRESS HEAD CT, LEESBURG, FL, 3474...
The Villages® 2311 CRESTVIEW ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$435,000

3 beds

|

2 baths

|

1,602 sq ft

|

Villa

2311 CRESTVIEW ST, THE VILLAGES, FL, 321...
Community: The Villages®
Plantation Bay Golf & Country Club 410 WINGSPAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$1,495,000

4 beds

|

4 baths

|

3,055 sq ft

|

House

410 WINGSPAN DR, ORMOND BEACH, FL, 32174
Twin Lakes 4918 DRAWDY CT, ST CLOUD, FL, 34772, St Cloud, FL 34772
$479,900

3 beds

|

3 baths

|

2,365 sq ft

|

House

4918 DRAWDY CT, 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
Stonecrest 11890 SE 172ND LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$349,900

2 beds

|

2 baths

|

1,494 sq ft

|

House

11890 SE 172ND LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Villages® 111 WINTERBERRY AVE, WILDWOOD, FL, 34785, Wildwood, FL 34785
$149,500

2 beds

|

2 baths

|

960 sq ft

|

Manufactured Home

111 WINTERBERRY AVE, WILDWOOD, FL, 34785
Community: The Villages®
Arlington Ridge 26922 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$195,000

2 beds

|

2 baths

|

964 sq ft

|

House

26922 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
The Villages® 8108 SE 169TH TWEEDSIDE LOOP, THE VILLAG..., The Villages, FL 32162
$319,900

3 beds

|

3 baths

|

1,352 sq ft

|

Villa

8108 SE 169TH TWEEDSIDE LOOP, THE VILLAG...
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.
Legacy of Leesburg 27106 GREENFLY ORCHID LN, LEESBURG, FL, ..., Leesburg, FL 34748
$289,900

3 beds

|

2 baths

|

1,541 sq ft

|

House

27106 GREENFLY ORCHID LN, LEESBURG, FL, ...
Community: Legacy of Leesburg
The Villages® 1259 ADDISON AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$399,900

3 beds

|

2 baths

|

1,880 sq ft

|

House

1259 ADDISON AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 2420 RICHARDSON RD, THE VILLAGES, FL, 32..., The Villages, FL 32162
$324,900

3 beds

|

2 baths

|

1,240 sq ft

|

House

2420 RICHARDSON RD, THE VILLAGES, FL, 32...
Community: The Villages®
Stonecrest 17776 SE 114TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$316,900

3 beds

|

3 baths

|

1,646 sq ft

|

Villa

17776 SE 114TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 2977 STEPPING STONE PATH, THE VILLAGES, ..., The Villages, FL 32163
$724,900

3 beds

|

2 baths

|

1,958 sq ft

|

House

2977 STEPPING STONE PATH, THE VILLAGES, ...
Community: The Villages®
The Villages® 5596 MATANZAS LOOP, THE VILLAGES, FL, 32..., The Villages, FL 32163
$529,900

3 beds

|

3 baths

|

1,919 sq ft

|

House

5596 MATANZAS LOOP, THE VILLAGES, FL, 32...
Community: The Villages®
Latitude Margaritaville 538 DAIQUIRI PL, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124
$379,500

2 beds

|

2 baths

|

1,308 sq ft

|

House

538 DAIQUIRI PL, DAYTONA BEACH, FL, 3212...
Archers Mill 3295 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$589,900

4 beds

|

4 baths

|

2,787 sq ft

|

House

3295 ARCH AVE, ORMOND BEACH, FL, 32174
Community: Archers Mill
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 352 STIRLING BRIDGE DR, ORMOND BEACH, FL..., Ormond Beach, FL 32174
$849,900

3 beds

|

3 baths

|

2,560 sq ft

|

House

352 STIRLING BRIDGE DR, ORMOND BEACH, FL...
Indian River Colony Club 1071 CONTINENTAL AVE, MELBOURNE, FL, 329..., Melbourne, FL 32940
$360,000

4 beds

|

3 baths

|

1,919 sq ft

|

House

1071 CONTINENTAL AVE, MELBOURNE, FL, 329...
Plantation Bay Golf & Country Club 1404 SUNNINGDALE LN, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174
$524,900

3 beds

|

2 baths

|

2,172 sq ft

|

House

1404 SUNNINGDALE LN, ORMOND BEACH, FL, 3...
Latitude Margaritaville 1068 SEA SHELL CT, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$609,000

2 beds

|

2 baths

|

1,922 sq ft

|

House

1068 SEA SHELL CT, DAYTONA BEACH, FL, 32...
Legacy of Leesburg 5154 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$350,000

3 beds

|

2 baths

|

2,045 sq ft

|

House

5154 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Royal Harbor 5481 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778
$338,500

3 beds

|

2 baths

|

1,513 sq ft

|

House

5481 BOUNTY CIR, TAVARES, FL, 32778
Community: Royal Harbor
Spruce Creek Country Club 9435 SE 124TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$329,900

2 beds

|

2 baths

|

1,720 sq ft

|

House

9435 SE 124TH PL, SUMMERFIELD, FL, 34491
Spruce Creek Country Club 12507 SE 90TH TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$354,500

2 beds

|

2 baths

|

1,870 sq ft

|

House

12507 SE 90TH TER, SUMMERFIELD, FL, 3449...
Venetian Bay 365 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$380,000

3 beds

|

2 baths

|

1,614 sq ft

|

House

365 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
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.
Del Webb Orlando 715 ASTURIAS RD, DAVENPORT, FL, 33837, Davenport, FL 33837
$434,900

2 beds

|

2 baths

|

2,056 sq ft

|

House

715 ASTURIAS RD, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Lakes of Mount Dora 2489 PAWTUCKET PASS, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$489,500

2 beds

|

2 baths

|

2,090 sq ft

|

House

2489 PAWTUCKET PASS, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
Royal Highlands 21325 ROYAL TROON DR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$379,900

2 beds

|

2 baths

|

2,333 sq ft

|

House

21325 ROYAL TROON DR, LEESBURG, FL, 3474...
Community: Royal Highlands
Venetian Bay 3446 MEDICI BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$420,000

4 beds

|

4 baths

|

2,379 sq ft

|

Townhouse

3446 MEDICI BLVD, 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
Cresswind at Victoria Gardens 215 AVENHAM DR, DELAND, FL, 32724, Deland, FL 32724
$585,000

3 beds

|

3 baths

|

2,792 sq ft

|

House

215 AVENHAM DR, DELAND, FL, 32724
Heritage Isle 3684 GURRERO DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$400,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

3684 GURRERO DR, MELBOURNE, FL, 32940
Community: Heritage Isle

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2,513 homes
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