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Winter Park, FL 55+ active adult communities & homes for sale - Page 60

2,377 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 - $400Ks
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) VillageWalk at Lake Nona
$300Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 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
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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 - $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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
Gatherings of Lake Nona 7565 LAUREATE BLVD UNIT 3308, ORLANDO, F..., Orlando, FL 32827
$379,000

2 beds

|

2 baths

|

1,368 sq ft

|

Condo

7565 LAUREATE BLVD UNIT 3308, ORLANDO, F...
Lake Ashton 4276 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$625,000

2 beds

|

2 baths

|

2,328 sq ft

|

House

4276 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Stonecrest 17520 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$329,000

2 beds

|

2 baths

|

1,402 sq ft

|

House

17520 SE 112TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
Solivita 105 PALAZZO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$326,000

2 beds

|

2 baths

|

1,590 sq ft

|

House

105 PALAZZO LN, KISSIMMEE, FL, 34759
Community: Solivita
Pelican Bay Daytona Beach 176 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$325,000

2 beds

|

2 baths

|

1,335 sq ft

|

House

176 PALM SPARROW CT, DAYTONA BEACH, FL, ...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Solivita 188 OLYMPUS WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$299,999

2 beds

|

2 baths

|

1,250 sq ft

|

House

188 OLYMPUS WAY, KISSIMMEE, FL, 34759
Community: Solivita
Stonecrest 11799 SE 173RD LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$470,000

3 beds

|

2 baths

|

2,008 sq ft

|

House

11799 SE 173RD LANE RD, SUMMERFIELD, FL,...
Community: Stonecrest
Spruce Creek Country Club 13340 SE 86TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$329,000

3 beds

|

2 baths

|

1,723 sq ft

|

House

13340 SE 86TH CIR, SUMMERFIELD, FL, 3449...
Stonecrest 11839 SE 173RD LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$550,000

3 beds

|

3 baths

|

2,502 sq ft

|

House

11839 SE 173RD LANE RD, SUMMERFIELD, FL,...
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.
Plantation Bay Golf & Country Club 21 SOUTHAMPTON ST, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$474,900

2 beds

|

2 baths

|

1,642 sq ft

|

Townhouse

21 SOUTHAMPTON ST, ORMOND BEACH, FL, 321...
Lakes of Mount Dora 2046 WALLINGFORD LOOP, MOUNT DORA, FL, 3..., Mount Dora, FL 32757
$559,990

3 beds

|

2 baths

|

2,180 sq ft

|

House

2046 WALLINGFORD LOOP, MOUNT DORA, FL, 3...
Community: Lakes of Mount Dora
Lakes of Mount Dora 8592 HEMPSTEAD WAY, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$450,000

3 beds

|

2 baths

|

1,524 sq ft

|

House

8592 HEMPSTEAD WAY, MOUNT DORA, FL, 3275...
Community: Lakes of Mount Dora
Pennbrooke Fairways 32525 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$285,000

2 beds

|

3 baths

|

1,643 sq ft

|

House

32525 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Kings Ridge 2096 BRAXTON ST, CLERMONT, FL, 34711, Clermont, FL 34711
$294,500

2 beds

|

2 baths

|

1,170 sq ft

|

House

2096 BRAXTON ST, CLERMONT, FL, 34711
Community: Kings Ridge
Pelican Bay Daytona Beach 244 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$325,000

2 beds

|

2 baths

|

1,370 sq ft

|

House

244 PALM SPARROW CT, DAYTONA BEACH, FL, ...
Arlington Ridge 4546 SHENANDOAH RIVER TRL, LEESBURG, FL,..., Leesburg, FL 34748
$410,000

3 beds

|

2 baths

|

1,948 sq ft

|

House

4546 SHENANDOAH RIVER TRL, LEESBURG, FL,...
Community: Arlington Ridge
Breakaway Trails 4 CREEK BLUFF WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$500,000

3 beds

|

2 baths

|

2,575 sq ft

|

House

4 CREEK BLUFF WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
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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2,377 homes
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