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

2,703 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
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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
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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 (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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) Twin Lakes
$200ks - $600ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
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.
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) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 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
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) Cresswind at Victoria Gar...
$300ks - $500ks
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
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 homes
5 rating (8 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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
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
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) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 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
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 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
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 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
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Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 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.
Heritage - The Cottages o...
$300ks
Heritage - The Cottages o..., Okahumpka, FL
New Construction | 55+ age-restricted | Built 2022 - present | 179 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
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 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
Highland Fairways
$100ks - $300ks
Highland Fairways, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes
Del Webb at Viera
$400ks - $1Ms
Del Webb at Viera, Melbourne, FL
New Construction | 55+ age-restricted | Built 2021 - present | 1,300 homes
Lakeside Landings
$100ks - $300ks
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
The Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 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® 1126 MIONA SHORES DR, THE VILLAGES, FL, ..., The Villages, FL 32162
$949,900

3 beds

|

2 baths

|

2,680 sq ft

|

House

1126 MIONA SHORES DR, THE VILLAGES, FL, ...
Community: The Villages®
Spruce Creek South 10701 SE 179TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$279,900

3 beds

|

2 baths

|

1,668 sq ft

|

House

10701 SE 179TH LN, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Latitude Margaritaville 294 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$358,888

2 beds

|

2 baths

|

1,308 sq ft

|

House

294 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
The Villages® 1075 BURNETTOWN PL, THE VILLAGES, FL, 32..., The Villages, FL 32162
$349,900

2 beds

|

2 baths

|

1,258 sq ft

|

Villa

1075 BURNETTOWN PL, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 2289 SWANSEA TER, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$429,900

3 beds

|

2 baths

|

1,612 sq ft

|

Villa

2289 SWANSEA TER, THE VILLAGES, FL, 3216...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Trilogy® Orlando 306 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736
$350,000

3 beds

|

2 baths

|

1,925 sq ft

|

House

306 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
The Villages® 1507 BARRERA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$329,900

3 beds

|

2 baths

|

1,553 sq ft

|

House

1507 BARRERA CT, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1339 LAJOLLA CIR, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$319,900

2 beds

|

2 baths

|

1,094 sq ft

|

Villa

1339 LAJOLLA CIR, THE VILLAGES, FL, 3215...
Community: The Villages®
Solivita 513 BARCELONA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$295,000

2 beds

|

2 baths

|

1,574 sq ft

|

House

513 BARCELONA DR, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 1068 BURNETTOWN PL, THE VILLAGES, FL, 32..., The Villages, FL 32162
$598,700

3 beds

|

2 baths

|

1,837 sq ft

|

Villa

1068 BURNETTOWN PL, 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.
The Villages® 1606 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$260,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

1606 CAMPOS DR, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1930 RHETT RD, THE VILLAGES, FL, 32163, The Villages, FL 32163
$319,900

2 beds

|

2 baths

|

1,434 sq ft

|

Villa

1930 RHETT RD, THE VILLAGES, FL, 32163
Community: The Villages®
Baytree 615 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778
$285,000

3 beds

|

2 baths

|

1,440 sq ft

|

House

615 JUNIPER WAY, TAVARES, FL, 32778
Community: Baytree
The Villages® 17648 SE 93RD BUTLER CT, THE VILLAGES, F..., The Villages, FL 32162
$299,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

17648 SE 93RD BUTLER CT, THE VILLAGES, F...
Community: The Villages®
The Villages® 1707 GOMEZ PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$269,900

2 beds

|

2 baths

|

1,344 sq ft

|

House

1707 GOMEZ PL, THE VILLAGES, FL, 32162
Community: The Villages®
Twin Lakes 2777 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772
$550,000

3 beds

|

3 baths

|

2,365 sq ft

|

House

2777 SOUTHLAND ST, 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
The Villages® 1214 SAN BERNARDO RD, THE VILLAGES, FL, ..., The Villages, FL 32162
$349,900

2 beds

|

2 baths

|

1,146 sq ft

|

Villa

1214 SAN BERNARDO RD, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 4946 NE 124TH RD, OXFORD, FL, 34484, Oxford, FL 34484
$380,000

3 beds

|

3 baths

|

2,547 sq ft

|

House

4946 NE 124TH RD, OXFORD, FL, 34484
Community: The Villages®
Breakaway Trails 1 CROOKED BRIDGE WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174
$725,000

5 beds

|

3 baths

|

3,193 sq ft

|

House

1 CROOKED BRIDGE WAY, ORMOND BEACH, FL, ...
Community: Breakaway Trails
The Villages® 1806 QUEENSBURY TER, THE VILLAGES, FL, 3..., The Villages, FL 32162
$269,900

2 beds

|

2 baths

|

1,188 sq ft

|

Villa

1806 QUEENSBURY TER, THE VILLAGES, FL, 3...
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.
Stonecrest 12271 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$389,000

4 beds

|

3 baths

|

2,246 sq ft

|

House

12271 SE 175TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Latitude Margaritaville 224 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$357,900

2 beds

|

2 baths

|

1,308 sq ft

|

House

224 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Cresswind at Victoria Gardens 1157 AVERY MEADOWS WAY, DELAND, FL, 3272..., Deland, FL 32724
$449,700

2 beds

|

2 baths

|

1,928 sq ft

|

House

1157 AVERY MEADOWS WAY, DELAND, FL, 3272...
Lake Ashton 4193 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859
$535,000

3 beds

|

2 baths

|

2,058 sq ft

|

House

4193 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
Latitude Margaritaville 444 LIME AVE, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124
$359,900

2 beds

|

2 baths

|

1,308 sq ft

|

House

444 LIME AVE, DAYTONA BEACH, FL, 32124
Spruce Creek Country Club 9512 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$399,900

2 beds

|

3 baths

|

2,475 sq ft

|

House

9512 SE 124TH LOOP, SUMMERFIELD, FL, 344...
Latitude Margaritaville 373 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$399,900

2 beds

|

2 baths

|

1,466 sq ft

|

House

373 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Latitude Margaritaville 198 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$386,495

2 beds

|

2 baths

|

1,464 sq ft

|

House

198 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Carlsberg Estates on Lake Suzanne 364 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$284,900

2 beds

|

2 baths

|

1,387 sq ft

|

House

364 LAKE SUZANNE DR, LAKE WALES, FL, 338...
New Halifax Plantation 3250 BAILEY ANN DR, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$335,000

2 beds

|

2 baths

|

1,687 sq ft

|

House

3250 BAILEY ANN DR, ORMOND BEACH, FL, 32...
Community: Halifax Plantation
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® 1863 DALTON DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$300,000

2 beds

|

2 baths

|

1,152 sq ft

|

Villa

1863 DALTON DR, THE VILLAGES, FL, 32162
Community: The Villages®
New Venetian Bay 2942 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$315,000

3 beds

|

3 baths

|

1,754 sq ft

|

House

2942 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
New Lake Ashton 4029 SABLE LOOP DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$599,000

3 beds

|

2 baths

|

2,330 sq ft

|

House

4029 SABLE LOOP DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
New Halifax Plantation 1303 BANGOR DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$350,000

2 beds

|

2 baths

|

1,687 sq ft

|

Townhouse

1303 BANGOR DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
New The Villages® 1700 JADESTONE TER, THE VILLAGES, FL, 32..., The Villages, FL 32162
$359,000

2 beds

|

2 baths

|

1,138 sq ft

|

Villa

1700 JADESTONE TER, THE VILLAGES, FL, 32...
Community: The Villages®
New The Villages® 798 MILLHORN LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163
$359,000

3 beds

|

2 baths

|

1,500 sq ft

|

House

798 MILLHORN LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
New Royal Palm 1671 ARECA PALM DR, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$355,000

2 beds

|

2 baths

|

1,451 sq ft

|

Townhouse

1671 ARECA PALM DR, PORT ORANGE, FL, 321...
Community: Royal Palm
New Twin Lakes 4918 DRAWDY CT, ST CLOUD, FL, 34772, St Cloud, FL 34772
$439,000

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
New Plantation at Leesburg 24907 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$375,000

3 beds

|

2 baths

|

1,848 sq ft

|

House

24907 CRANES ROOST CIR, LEESBURG, FL, 34...
New Plantation Bay Golf & Country Club 1025 HAMPSTEAD LN, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$1,375,000

4 beds

|

4 baths

|

4,342 sq ft

|

House

1025 HAMPSTEAD LN, ORMOND BEACH, FL, 321...
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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2,703 homes
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