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

2,569 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 (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
4.7 rating (3 reviews) Spruce Creek South
$100ks - $200ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 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) Plantation Bay Golf &...
$400ks - $2Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale | Age-targeted | Built 1988 - present | 3,500 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 (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
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Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 homes
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 (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
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.
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 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
5 rating (2 reviews) Heritage Isle
$300ks - $500ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 homes
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
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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
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
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 (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.
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 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
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
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
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4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
Colonnades
$100ks - $200ks
Colonnades, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1985 - 1994 | 360 homes
Ridgehaven
$300ks - $600ks
Ridgehaven, Ormond Beach, FL
New Construction | 55+ age-restricted
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
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 Country Club of Mount...
$200ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
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
12...3
New Four Seasons at Orlando 7956 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$550,000

3 beds

|

3 baths

|

2,360 sq ft

|

House

7956 HANSON BAY PL, KISSIMMEE, FL, 34747
New The Villages® 1228 MARIA CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$249,900

2 beds

|

2 baths

|

1,432 sq ft

|

Manufactured Home

1228 MARIA CT, LADY LAKE, FL, 32159
Community: The Villages®
New Solivita 819 SAN RAPHAEL ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$494,900

3 beds

|

3 baths

|

2,427 sq ft

|

House

819 SAN RAPHAEL ST, KISSIMMEE, FL, 34759
Community: Solivita
New Latitude Margaritaville 345 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$399,900

2 beds

|

2 baths

|

1,308 sq ft

|

House

345 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
New Cresswind at Victoria Gardens 1375 HAZELDENE MNR, DELAND, FL, 32724, Deland, FL 32724
$349,900

3 beds

|

2 baths

|

1,670 sq ft

|

House

1375 HAZELDENE MNR, DELAND, FL, 32724
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
New Kings Ridge 3673 ROLLINGBROOK ST, CLERMONT, FL, 3471..., Clermont, FL 34711
$322,000

2 beds

|

2 baths

|

1,334 sq ft

|

House

3673 ROLLINGBROOK ST, CLERMONT, FL, 3471...
Community: Kings Ridge
New Kings Ridge 3513 ROLLINGBROOK ST, CLERMONT, FL, 3471..., Clermont, FL 34711
$324,900

2 beds

|

2 baths

|

1,460 sq ft

|

House

3513 ROLLINGBROOK ST, CLERMONT, FL, 3471...
Community: Kings Ridge
New Venetian Bay 112 PORTOFINO BLVD, NEW SMYRNA BEACH, FL..., New Smyrna Beach, FL 32168
$729,000

3 beds

|

2 baths

|

2,372 sq ft

|

House

112 PORTOFINO BLVD, NEW SMYRNA BEACH, FL...
Community: Venetian Bay
New Solivita 214 PRIMA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$309,900

3 beds

|

2 baths

|

1,939 sq ft

|

House

214 PRIMA DR, POINCIANA, FL, 34759
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.
New The Villages® 724 ROYAL PALM AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$179,900

2 beds

|

2 baths

|

1,152 sq ft

|

Manufactured Home

724 ROYAL PALM AVE, LADY LAKE, FL, 32159
Community: The Villages®
New Solivita 537 VILLA PARK RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$489,000

3 beds

|

3 baths

|

2,394 sq ft

|

House

537 VILLA PARK RD, KISSIMMEE, FL, 34759
Community: Solivita
New The Villages® 1305 LEONE LN, THE VILLAGES, FL, 32159, The Villages, FL 32159
$345,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

1305 LEONE LN, THE VILLAGES, FL, 32159
Community: The Villages®
New Summit Greens 2390 CALEDONIAN ST, CLERMONT, FL, 34711, Clermont, FL 34711
$450,000

3 beds

|

2 baths

|

1,961 sq ft

|

House

2390 CALEDONIAN ST, CLERMONT, FL, 34711
Community: Summit Greens
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Questions? Call us: (888) 625-4885
New Kings Ridge 3617 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711
$329,900

2 beds

|

2 baths

|

1,681 sq ft

|

House

3617 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
New Kings Ridge 2190 CAXTON AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$425,000

3 beds

|

2 baths

|

1,892 sq ft

|

House

2190 CAXTON AVE, CLERMONT, FL, 34711
Community: Kings Ridge
New The Villages® 8761 SE 168TH KITTREDGE LOOP, THE VILLAG..., The Villages, FL 32162
$481,000

3 beds

|

2 baths

|

1,916 sq ft

|

House

8761 SE 168TH KITTREDGE LOOP, THE VILLAG...
Community: The Villages®
New Alamanda Key 475 LORELEI AVE, MELBOURNE, FL, 32901, Melbourne, FL 32901
$450,000

3 beds

|

2 baths

|

1,731 sq ft

|

House

475 LORELEI AVE, MELBOURNE, FL, 32901
Community: Alamanda Key
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.
New Royal Harbor 5732 FREEPORT DR, TAVARES, FL, 32778, Tavares, FL 32778
$359,000

3 beds

|

2 baths

|

1,756 sq ft

|

House

5732 FREEPORT DR, TAVARES, FL, 32778
Community: Royal Harbor
New The Villages® 17360 SE 78TH DRAUGHTON CT, THE VILLAGES..., The Villages, FL 32162
$242,000

2 beds

|

2 baths

|

1,160 sq ft

|

Villa

17360 SE 78TH DRAUGHTON CT, THE VILLAGES...
Community: The Villages®
New The Villages® 3449 KEITH LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$459,000

3 beds

|

2 baths

|

1,492 sq ft

|

Villa

3449 KEITH LN, THE VILLAGES, FL, 32163
Community: The Villages®
New Colonnades 1768 BIRCHWOOD LOOP, LAKELAND, FL, 33811, Lakeland, FL 33811
$325,000

2 beds

|

2 baths

|

1,849 sq ft

|

House

1768 BIRCHWOOD LOOP, LAKELAND, FL, 33811
Community: Colonnades
Want to learn more about 55+ communities in Winter Park? 55places can help!
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New Plantation at Leesburg 25323 CASA DEL LAGO LN, LEESBURG, FL, 34..., Leesburg, FL 34748
$137,000

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

25323 CASA DEL LAGO LN, LEESBURG, FL, 34...
New The Villages® 2436 HILL ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$350,000

2 beds

|

2 baths

|

1,314 sq ft

|

Villa

2436 HILL ST, THE VILLAGES, FL, 32163
Community: The Villages®
New The Villages® 2251 OPAL CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$600,000

3 beds

|

2 baths

|

1,978 sq ft

|

House

2251 OPAL CT, THE VILLAGES, FL, 32162
Community: The Villages®
New The Villages® 741 ROYAL PALM AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159
$169,900

2 beds

|

2 baths

|

1,056 sq ft

|

Manufactured Home

741 ROYAL PALM AVE, THE VILLAGES, FL, 32...
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.
New Scottish Highlands 1625 NEW ABBEY AVE, LEESBURG, FL, 34788, Leesburg, FL 34788
$225,000

2 beds

|

2 baths

|

1,040 sq ft

|

House

1625 NEW ABBEY AVE, LEESBURG, FL, 34788
Community: Scottish Highlands
New The Villages® 2569 ERROL TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$307,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2569 ERROL TER, THE VILLAGES, FL, 32162
Community: The Villages®
New Heritage Isle 3811 FUNSTON CIR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$545,900

4 beds

|

3 baths

|

2,425 sq ft

|

House

3811 FUNSTON CIR, MELBOURNE, FL, 32940
Community: Heritage Isle
New Lakeside Landings 5427 COMPASS PT # 1, OXFORD, FL, 34484, Oxford, FL 34484
$224,900

2 beds

|

2 baths

|

1,281 sq ft

|

Condo

5427 COMPASS PT # 1, OXFORD, FL, 34484
Community: Lakeside Landings
New Cresswind at Victoria Gardens 526 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724
$449,000

3 beds

|

2 baths

|

2,119 sq ft

|

House

526 HERON POINT WAY, DELAND, FL, 32724
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
New The Villages® 1003 MATTHEW AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$228,000

2 beds

|

2 baths

|

1,191 sq ft

|

Manufactured Home

1003 MATTHEW AVE, LADY LAKE, FL, 32159
Community: The Villages®
New Sullivan Ranch 20913 SULLIVAN RANCH BLVD, MOUNT DORA, F..., Mount Dora, FL 32757
$409,000

3 beds

|

2 baths

|

1,990 sq ft

|

House

20913 SULLIVAN RANCH BLVD, MOUNT DORA, F...
Community: Sullivan Ranch
New Venetian Bay 3004 BORASSUS DR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$589,000

4 beds

|

3 baths

|

2,115 sq ft

|

House

3004 BORASSUS DR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
New The Villages® 3448 INVERARY AVE, THE VILLAGES, FL, 321..., The Villages, FL 32163
$350,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

3448 INVERARY AVE, THE VILLAGES, FL, 321...
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.
New Plantation at Leesburg 3715 MULBERRY GROVE LOOP, LEESBURG, FL, ..., Leesburg, FL 34748
$349,999

3 beds

|

3 baths

|

2,173 sq ft

|

House

3715 MULBERRY GROVE LOOP, LEESBURG, FL, ...
New Arlington Ridge 3519 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$419,900

2 beds

|

2 baths

|

2,270 sq ft

|

House

3519 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
New The Villages® 8338 SE 178TH DEVEAUX LN, THE VILLAGES, ..., The Villages, FL 32162
$350,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

8338 SE 178TH DEVEAUX LN, THE VILLAGES, ...
Community: The Villages®
New Gatherings of Lake Nona 7545 LAUREATE BLVD UNIT 7305, ORLANDO, F..., Orlando, FL 32827
$459,990

2 beds

|

2 baths

|

1,486 sq ft

|

Condo

7545 LAUREATE BLVD UNIT 7305, ORLANDO, F...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
New Harbor Hills Country Club 39644 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159
$425,000

3 beds

|

2 baths

|

2,009 sq ft

|

House

39644 HARBOR HILLS BLVD, LADY LAKE, FL, ...
New The Villages® 210 PALERMO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$450,000

3 beds

|

3 baths

|

2,118 sq ft

|

House

210 PALERMO PL, THE VILLAGES, FL, 32159
Community: The Villages®

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2,569 homes
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