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Winter Park, FL 55+ active adult communities & homes for sale - Page 52

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
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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
Pennbrooke Fairways 32712 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$284,900

3 beds

|

2 baths

|

1,909 sq ft

|

House

32712 TIMBERWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Kings Ridge 4217 CHAMBERLAIN WAY, CLERMONT, FL, 3471..., Clermont, FL 34711
$265,000

2 beds

|

2 baths

|

1,200 sq ft

|

House

4217 CHAMBERLAIN WAY, CLERMONT, FL, 3471...
Community: Kings Ridge
Enclave at VillageWalk 11675 SAVONA WAY, ORLANDO, FL, 32827, Orlando, FL 32827
$1,435,000

4 beds

|

5 baths

|

4,622 sq ft

|

House

11675 SAVONA WAY, ORLANDO, FL, 32827
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
Royal Harbor 5138 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778
$368,000

3 beds

|

2 baths

|

1,889 sq ft

|

House

5138 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
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Summer Trees 55 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$291,000

3 beds

|

2 baths

|

1,775 sq ft

|

House

55 CROOKED PINE RD, PORT ORANGE, FL, 321...
Community: Summer Trees
Plantation at Leesburg 24725 BRIGHTWATER CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$346,400

3 beds

|

3 baths

|

2,132 sq ft

|

House

24725 BRIGHTWATER CT, LEESBURG, FL, 3474...
Spruce Creek Country Club 13184 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$544,900

2 beds

|

3 baths

|

2,423 sq ft

|

House

13184 SE 97TH TERRACE RD, SUMMERFIELD, F...
Royal Palm 1419 ARECA PALM DR, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$400,000

3 beds

|

2 baths

|

2,038 sq ft

|

House

1419 ARECA PALM DR, PORT ORANGE, FL, 321...
Community: Royal Palm
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® 5647 KEY DEER PATH, THE VILLAGES, FL, 32..., The Villages, FL 32163
$799,900

3 beds

|

2 baths

|

1,971 sq ft

|

House

5647 KEY DEER PATH, THE VILLAGES, FL, 32...
Community: The Villages®
Sullivan Ranch 22011 BELGIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$335,000

3 beds

|

2 baths

|

1,762 sq ft

|

Villa

22011 BELGIAN CT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Sandpiper Golf & Country Club 6380 EGRET DR 22, LAKELAND, FL, 33809, Lakeland, FL 33809
$229,900

2 beds

|

2 baths

|

893 sq ft

|

Villa

6380 EGRET DR 22, LAKELAND, FL, 33809
Halifax Plantation 3034 ADRIAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$565,000

4 beds

|

3 baths

|

2,641 sq ft

|

House

3034 ADRIAN DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Four Seasons at Orlando 2160 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747
$379,990

2 beds

|

2 baths

|

1,778 sq ft

|

House

2160 ANTILLES CLUB DR, KISSIMMEE, FL, 34...
The Villages® 2732 PRIVADA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$289,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

2732 PRIVADA DR, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1003 PARKER PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$218,000

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

1003 PARKER PL, THE VILLAGES, FL, 32159
Community: The Villages®
Solivita 972 LADERA RANCH RD, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$475,000

3 beds

|

3 baths

|

2,318 sq ft

|

House

972 LADERA RANCH RD, KISSIMMEE, FL, 3475...
Community: Solivita
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.
Stonecrest 11280 SE 170TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$259,900

2 beds

|

2 baths

|

1,251 sq ft

|

House

11280 SE 170TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Palms at Serenoa 3903 WINGED ELM CT, CLERMONT, FL, 34714, Clermont, FL 34714
$430,000

2 beds

|

2 baths

|

1,822 sq ft

|

House

3903 WINGED ELM CT, CLERMONT, FL, 34714
Community: Palms at Serenoa
Pelican Bay Daytona Beach 240 BOB WHITE CT 2400, DAYTONA BEACH, FL..., Daytona Beach, FL 32119
$205,000

2 beds

|

2 baths

|

1,093 sq ft

|

Condo

240 BOB WHITE CT 2400, DAYTONA BEACH, FL...
Foxwood Lake Estates 5038 FOXWOOD BLVD, LAKELAND, FL, 33810, Lakeland, FL 33810
$229,900

2 beds

|

2 baths

|

1,404 sq ft

|

Manufactured Home

5038 FOXWOOD BLVD, LAKELAND, FL, 33810
Want to learn more about 55+ communities in Winter Park? 55places can help!
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Sandpiper Golf & Country Club 6096 KITTIWAKE DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$315,000

3 beds

|

2 baths

|

1,489 sq ft

|

House

6096 KITTIWAKE DR, LAKELAND, FL, 33809
Palms at Serenoa 3435 YELLOWTOP LOOP, CLERMONT, FL, 34714, Clermont, FL 34714
$384,500

3 beds

|

2 baths

|

1,621 sq ft

|

House

3435 YELLOWTOP LOOP, CLERMONT, FL, 34714
Community: Palms at Serenoa
The Lakes at Harmony 3144 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773
$405,990

3 beds

|

2 baths

|

1,852 sq ft

|

House

3144 SONGBIRD CIR, HARMONY, FL, 34773
Twin Lakes 2337 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$340,000

2 beds

|

2 baths

|

1,351 sq ft

|

Villa

2337 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
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.
Twin Lakes 2323 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$355,000

2 beds

|

2 baths

|

1,449 sq ft

|

Villa

2323 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Twin Lakes 2335 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$340,000

2 beds

|

2 baths

|

1,351 sq ft

|

Villa

2335 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
The Lakes at Harmony 7520 CASTLEWOOD CT, HARMONY, FL, 34773, Harmony, FL 34773
$401,990

2 beds

|

2 baths

|

1,455 sq ft

|

House

7520 CASTLEWOOD CT, HARMONY, FL, 34773
The Lakes at Harmony 3156 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773
$399,990

2 beds

|

2 baths

|

1,423 sq ft

|

House

3156 SONGBIRD CIR, HARMONY, FL, 34773
Twin Lakes 5031 DANCY LN, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$400,000

2 beds

|

2 baths

|

1,423 sq ft

|

House

5031 DANCY LN, SAINT 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
Solivita 560 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$274,900

2 beds

|

2 baths

|

1,543 sq ft

|

House

560 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 536 PORTOFINO DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$289,500

2 beds

|

2 baths

|

1,491 sq ft

|

House

536 PORTOFINO DR, POINCIANA, FL, 34759
Community: Solivita
Solivita 350 BALBOA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$399,990

3 beds

|

3 baths

|

2,334 sq ft

|

House

350 BALBOA DR, KISSIMMEE, FL, 34759
Community: Solivita
Highland Lakes 5616 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$288,900

2 beds

|

2 baths

|

2,003 sq ft

|

House

5616 LAVER ST, LEESBURG, FL, 34748
Community: Highland Lakes
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.
Colonnades 4849 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$185,000

2 beds

|

2 baths

|

1,220 sq ft

|

Modular

4849 GOLDENVIEW LN, LAKELAND, FL, 33811
Community: Colonnades
The Villages® 2149 SANDALWOOD PL, THE VILLAGES, FL, 32..., The Villages, FL 32163
$364,900

3 beds

|

2 baths

|

1,357 sq ft

|

Villa

2149 SANDALWOOD PL, THE VILLAGES, FL, 32...
Community: The Villages®
Venetian Bay 2916 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$350,000

3 beds

|

3 baths

|

1,754 sq ft

|

House

2916 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Carlsberg Estates on Lake Suzanne 400 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$280,000

3 beds

|

3 baths

|

1,718 sq ft

|

House

400 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Tohoqua Reserve 1875 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$355,000

2 beds

|

2 baths

|

1,559 sq ft

|

House

1875 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Kings Ridge 3713 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711
$345,000

2 beds

|

2 baths

|

1,705 sq ft

|

House

3713 DOUNE WAY, CLERMONT, FL, 34711
Community: Kings Ridge

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2,377 homes
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