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Winter Park, FL 55+ active adult communities & homes for sale - Page 31

2,259 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
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
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
Want to learn more about 55+ communities in Winter Park? 55places can help!
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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
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) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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
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.
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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
3.8 rating (6 reviews) Trilogy® Orlando
$200ks - $500ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
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
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
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
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 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) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
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Questions? Call us: (888) 625-4885
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
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 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
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 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) Legacy of Leesburg
$200ks - $400ks
Legacy of Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 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
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 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
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 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
The Timbers at Everlands
$200ks - $500ks
The Timbers at Everlands, Palm Bay, FL
New Construction | 55+ age-restricted | Built 2023 - present | 450 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 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
The Villages® 2343 PINE RIDGE ST, THE VILLAGES, FL, 32..., The Villages, FL 32162
$265,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2343 PINE RIDGE ST, THE VILLAGES, FL, 32...
Community: The Villages®
Legacy of Leesburg 27545 DISCOVER CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$269,900

2 beds

|

2 baths

|

1,600 sq ft

|

House

27545 DISCOVER CT, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Pennbrooke Fairways 32744 WESTWOOD LOOP, LEESBURG, FL, 34748, Leesburg, FL 34748
$198,247

2 beds

|

2 baths

|

1,232 sq ft

|

House

32744 WESTWOOD LOOP, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Cresswind at Lake Harris 1736 POINT GRACE RD, TAVARES, FL, 32778, Tavares, FL 32778
$489,990

2 beds

|

2 baths

|

1,968 sq ft

|

House

1736 POINT GRACE RD, TAVARES, FL, 32778
The Villages® 8690 SE 173RD WISTERIA ST, THE VILLAGES,..., The Villages, FL 32162
$625,000

3 beds

|

3 baths

|

2,478 sq ft

|

House

8690 SE 173RD WISTERIA ST, THE VILLAGES,...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Gatherings of Lake Nona 7573 LAUREATE BLVD 1-307, ORLANDO, FL, 3..., Orlando, FL 32827
$460,000

3 beds

|

2 baths

|

1,805 sq ft

|

Condo

7573 LAUREATE BLVD 1-307, ORLANDO, FL, 3...
Plantation Bay Golf & Country Club 641 WOODBRIDGE DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$3,159,000

4 beds

|

6 baths

|

4,642 sq ft

|

House

641 WOODBRIDGE DR, ORMOND BEACH, FL, 321...
The Villages® 17107 SE 93RD EXETER CT, THE VILLAGES, F..., The Villages, FL 32162
$365,000

3 beds

|

2 baths

|

1,512 sq ft

|

House

17107 SE 93RD EXETER CT, THE VILLAGES, F...
Community: The Villages®
Arlington Ridge 4334 BENT CREEK LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$565,000

3 beds

|

3 baths

|

2,565 sq ft

|

House

4334 BENT CREEK LN, LEESBURG, FL, 34748
Community: Arlington Ridge
Grand Haven 12 NATIVE OAK CT, PALM COAST, FL, 32137, Palm Coast, FL 32137
$1,300,000

4 beds

|

4 baths

|

3,817 sq ft

|

House

12 NATIVE OAK CT, 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.
The Villages® 1514 HILLCREST DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$205,000

2 beds

|

2 baths

|

1,513 sq ft

|

Manufactured Home

1514 HILLCREST DR, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 511 ALAMEDA AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$299,000

2 beds

|

2 baths

|

1,122 sq ft

|

Villa

511 ALAMEDA AVE, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1166 BLOUNT AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$769,000

3 beds

|

2 baths

|

2,103 sq ft

|

House

1166 BLOUNT AVE, THE VILLAGES, FL, 32163
Community: The Villages®
Cresswind at Victoria Gardens 1169 AVERY MEADOWS WAY, DELAND, FL, 3272..., Deland, FL 32724
$554,000

3 beds

|

3 baths

|

2,185 sq ft

|

House

1169 AVERY MEADOWS WAY, DELAND, FL, 3272...
Legacy of Leesburg 27210 STONEY BROOK DR, LEESBURG, FL, 347..., Leesburg, FL 34748
$299,000

3 beds

|

2 baths

|

1,601 sq ft

|

House

27210 STONEY BROOK DR, LEESBURG, FL, 347...
Community: Legacy of Leesburg
Solivita 477 VILLA PARK RD, POINCIANA, FL, 34759, Poinciana, FL 34759
$450,000

3 beds

|

3 baths

|

2,345 sq ft

|

House

477 VILLA PARK RD, POINCIANA, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Latitude Margaritaville 484 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$389,500

2 beds

|

2 baths

|

1,464 sq ft

|

House

484 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Solivita 244 LARGO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$339,500

2 beds

|

2 baths

|

2,057 sq ft

|

House

244 LARGO DR, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 17325 SE 73RD PARK GLEN CT, THE VILLAGES..., The Villages, FL 32162
$425,000

3 beds

|

2 baths

|

1,986 sq ft

|

House

17325 SE 73RD PARK GLEN CT, THE VILLAGES...
Community: The Villages®
Plantation at Leesburg 5712 SUMMERBROOKE CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$525,000

3 beds

|

3 baths

|

2,961 sq ft

|

House

5712 SUMMERBROOKE CT, LEESBURG, FL, 3474...
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.
Lakes of Mount Dora 2472 PAWTUCKET PASS, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$599,900

3 beds

|

2 baths

|

2,437 sq ft

|

House

2472 PAWTUCKET PASS, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
The Villages® 8354 SE 177TH BARTRAM LOOP, THE VILLAGES..., The Villages, FL 32162
$365,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

8354 SE 177TH BARTRAM LOOP, THE VILLAGES...
Community: The Villages®
Plantation at Leesburg 24618 STILLRIDGE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$295,000

3 beds

|

2 baths

|

1,790 sq ft

|

House

24618 STILLRIDGE CT, LEESBURG, FL, 34748
The Country Club of Mount Dora 1741 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$1,280,000

5 beds

|

5 baths

|

5,573 sq ft

|

House

1741 EDGEWATER DR, MOUNT DORA, FL, 32757
The Reserve at Victoria 819 LILIANA DR, DELAND, FL, 32724, Deland, FL 32724
$479,000

3 beds

|

2 baths

|

1,724 sq ft

|

House

819 LILIANA DR, DELAND, FL, 32724
Arlington Ridge 26921 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$229,000

2 beds

|

2 baths

|

1,254 sq ft

|

Villa

26921 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
Latitude Margaritaville 132 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$414,900

3 beds

|

2 baths

|

1,464 sq ft

|

House

132 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Royal Highlands 5607 SIR CHURCHILL DR, LEESBURG, FL, 347..., Leesburg, FL 34748
$414,999

3 beds

|

2 baths

|

2,312 sq ft

|

House

5607 SIR CHURCHILL DR, LEESBURG, FL, 347...
Community: Royal Highlands
Harbor Hills Country Club 6120 LANDINGS BLVD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$699,000

3 beds

|

2 baths

|

2,598 sq ft

|

House

6120 LANDINGS BLVD, LADY LAKE, FL, 32159
Cresswind at Victoria Gardens 103 OLD MOSS CIR, DELAND, FL, 32724, Deland, FL 32724
$499,600

3 beds

|

2 baths

|

2,001 sq ft

|

House

103 OLD MOSS CIR, DELAND, FL, 32724
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® 5556 COLUMBUS CIR, WILDWOOD, FL, 34785, Wildwood, FL 34785
$185,000

3 beds

|

3 baths

|

1,680 sq ft

|

Manufactured Home

5556 COLUMBUS CIR, WILDWOOD, FL, 34785
Community: The Villages®
Solivita 779 VIA COMO ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$365,000

2 beds

|

2 baths

|

1,653 sq ft

|

House

779 VIA COMO ST, KISSIMMEE, FL, 34759
Community: Solivita
Alamanda Key 4050 ALAMANDA KEY DR DRIVE, MELBOURNE, F..., Melbourne, FL 32901
$285,000

3 beds

|

2 baths

|

1,550 sq ft

|

House

4050 ALAMANDA KEY DR DRIVE, MELBOURNE, F...
Community: Alamanda Key
The Villages® 17009 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162
$339,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

17009 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
Plantation Bay Golf & Country Club 715 COBBLESTONE DR, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$369,000

2 beds

|

3 baths

|

1,875 sq ft

|

House

715 COBBLESTONE DR, ORMOND BEACH, FL, 32...
Lakes of Mount Dora 2359 WAKEFIELD WAY, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$439,000

3 beds

|

2 baths

|

1,615 sq ft

|

House

2359 WAKEFIELD WAY, MOUNT DORA, FL, 3275...
Community: Lakes of Mount Dora
The Villages® 324 EMMALEE PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$289,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

324 EMMALEE PL, THE VILLAGES, FL, 32162
Community: The Villages®
Breakaway Trails 59 SHADOWCREEK WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$638,000

4 beds

|

3 baths

|

3,227 sq ft

|

House

59 SHADOWCREEK WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Spruce Creek Country Club 8475 SE 137TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$259,000

2 beds

|

2 baths

|

1,652 sq ft

|

House

8475 SE 137TH LOOP, SUMMERFIELD, FL, 344...
Plantation Bay Golf & Country Club 708 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$299,900

2 beds

|

2 baths

|

1,510 sq ft

|

Townhouse

708 ALDENHAM LN, ORMOND BEACH, FL, 32174
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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2,259 homes
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