Winter Park, FL 55+ active adult communities & homes for sale - Page 27

2,702 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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

New and Resale | Age-targeted | Built 2004 - present | 1,561 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

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

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

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Questions? Call us: (888) 625-4885

4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 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)

Twin Lakes

$200ks - $600ks

Twin Lakes, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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

$200ks - $800ks

Grand Haven, Palm Coast, FL

New and Resale | Age-targeted | Built 1997 - present | 1,901 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 (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 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 (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

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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

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

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

New and Resale | Age-targeted | Built 1980 - present | 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

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

The Country Club of Mount...

$200ks - $1Ms

The Country Club of Mount..., Mount Dora, FL

Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 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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Questions? Call us: (888) 625-4885

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)

Del Webb Sunbridge

$400ks - $800ks

Del Webb Sunbridge, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes

Heritage - The Cottages o...

$300ks

Heritage - The Cottages o..., Okahumpka, FL

New Construction | 55+ age-restricted | Built 2022 - present | 179 homes

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes

4.4 rating (16 reviews)

Del Webb Orlando

$200ks - $500ks

Del Webb Orlando, Davenport, FL

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 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

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

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

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes

Colonnades

$100ks - $200ks

Colonnades, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1985 - 1994 | 360 homes

354 HIGH TIDE LN, DAYTONA BEACH, FL, 321...

Community: Latitude Margaritaville

Highland Fairways

$273,500

2 beds

2 baths

1,675 sq ft

House

3537 HIGHLAND FAIRWAYS BLVD, LAKELAND, F...

2 baths

1,148 sq ft

House

712 ARTESIA AVE, THE VILLAGES, FL, 32162

Community: The Villages®

Carmel Condominium

1420 HUNTINGTON LN 2202, ROCKLEDGE, FL, ..., Rockledge, FL 32955

$110,000

2 beds

2 baths

1,008 sq ft

Condo

1420 HUNTINGTON LN 2202, ROCKLEDGE, FL, ...

Community: Carmel Condominium

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Twin Lakes

2632 MEADOWEDGE LOOP, ST CLOUD, FL, 3477..., St Cloud, FL 34772

$488,500

3 beds

3 baths

2,335 sq ft

House

2632 MEADOWEDGE LOOP, ST CLOUD, FL, 3477...

Community: Twin Lakes

Solivita

176 CAPE FLORIDA DR, ,, FL, 34759, ,, FL 34759

$299,000

2 beds

2 baths

1,440 sq ft

House

176 CAPE FLORIDA DR, ,, FL, 34759

Community: Solivita

The Villages®

1259 AVENIDA DE LAS CASAS, LADY LAKE, FL..., Lady Lake, FL 32159

$795,000

3 beds

3 baths

2,088 sq ft

Townhouse

1259 AVENIDA DE LAS CASAS, LADY LAKE, FL...

Community: The Villages®

Archers Mill

345 E MERIMONT LN, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$560,000

4 beds

4 baths

2,862 sq ft

House

345 E MERIMONT LN, ORMOND BEACH, FL, 321...

Community: Archers Mill

The Villages®

$189,900

2 beds

2 baths

1,196 sq ft

Manufactured Home

1550 HILLCREST DR, THE VILLAGES, FL, 321...

Community: The Villages®

Stonecrest

11363 SE 177TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$360,000

3 beds

3 baths

2,637 sq ft

House

11363 SE 177TH LN, SUMMERFIELD, FL, 3449...

Community: Stonecrest

Spruce Creek Country Club

8588 SE 134TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$314,000

2 beds

2 baths

1,575 sq ft

House

8588 SE 134TH ST, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

Solivita

1155 N GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$529,000

3 beds

2 baths

2,719 sq ft

House

1155 N GLENDORA RD, KISSIMMEE, FL, 34759

Community: Solivita

Solivita

204 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$254,000

2 beds

2 baths

1,548 sq ft

House

204 GRAND CANAL DR, KISSIMMEE, FL, 34759

Community: Solivita

Plantation Bay Golf & Country Club

18 MAGNOLIA DR B, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$289,900

2 beds

2 baths

1,300 sq ft

Condo

18 MAGNOLIA DR B, ORMOND BEACH, FL, 3217...

Community: Plantation Bay Golf & Country Club

Arlington Ridge

$369,000

3 beds

2 baths

1,857 sq ft

House

4110 ARLINGTON RIDGE BLVD, LEESBURG, FL,...

Community: Arlington Ridge

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Venetian Bay

367 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$375,000

3 beds

2 baths

1,653 sq ft

House

367 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

The Villages®

$379,000

3 beds

2 baths

1,512 sq ft

House

2530 SAFFRON LN, THE VILLAGES, FL, 32162

Community: The Villages®

Halifax Plantation

1105 GLENGAD RUN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$300,000

2 beds

2 baths

1,532 sq ft

House

1105 GLENGAD RUN, ORMOND BEACH, FL, 3217...

Community: Halifax Plantation

Venetian Bay

123 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168

$399,990

3 beds

2 baths

1,900 sq ft

House

123 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...

Community: Venetian Bay

Pelican Bay Daytona Beach

228 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119

$264,000

3 beds

2 baths

1,648 sq ft

House

228 PALM SPARROW CT, DAYTONA BEACH, FL, ...

Community: Pelican Bay Daytona Beach

Summer Trees

114 HICKORY LN, PORT ORANGE, FL, 32128, Port Orange, FL 32128

$277,000

2 beds

2 baths

1,403 sq ft

House

114 HICKORY LN, PORT ORANGE, FL, 32128

Community: Summer Trees

Venetian Bay

3255 TIGER PALM WAY, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168

$439,990

4 beds

3 baths

2,081 sq ft

House

3255 TIGER PALM WAY, NEW SMYRNA BEACH, F...

Community: Venetian Bay

Plantation Bay Golf & Country Club

18 MAGNOLIA DR S, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$289,900

2 beds

2 baths

1,300 sq ft

Condo

18 MAGNOLIA DR S, ORMOND BEACH, FL, 3217...

Community: Plantation Bay Golf & Country Club

Pennbrooke Fairways

830 OLD OAKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748

$379,247

3 beds

2 baths

1,976 sq ft

House

830 OLD OAKS LN, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

The Villages®

$569,900

3 beds

2 baths

1,957 sq ft

House

632 CORONACA CT, THE VILLAGES, FL, 32163

Community: The Villages®

The Lakes at Harmony

3485 MIDDLEBROOK PL, HARMONY, FL, 34773, Harmony, FL 34773

$419,999

4 beds

2 baths

2,064 sq ft

House

3485 MIDDLEBROOK PL, HARMONY, FL, 34773

Community: The Lakes at Harmony

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Plantation Bay Golf & Country Club

1274 ROYAL POINTE LN, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174

$529,900

3 beds

2 baths

2,032 sq ft

House

1274 ROYAL POINTE LN, ORMOND BEACH, FL, ...

Community: Plantation Bay Golf & Country Club

Grand Haven

45 SAINT ANDREWS CT, PALM COAST, FL, 321..., Palm Coast, FL 32137

$559,000

4 beds

3 baths

2,514 sq ft

House

45 SAINT ANDREWS CT, PALM COAST, FL, 321...

Community: Grand Haven

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Frequently Asked Questions

What size 55+ communities are there in Winter Park?

In Winter Park, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winter Park?

The smallest 55+ community in Winter Park has 178 homes, the largest has 178 homes, and the average community consists of 178 homes.

Are there new 55+ homes available in Winter Park?

Yes, there is new 55+ home available in Winter Park. The most recent community started in Winter Park include Rosalia Winter Park. There is also 1 community in Winter Park that offers new construction homes, including Rosalia Winter Park.

Are there gated 55+ communities in Winter Park?

Yes, there is gated 55+ community in Winter Park. The only 55+ community in Winter Park is gated. For instance, Rosalia Winter Park is a gated community with 178 homes.

Want more information about active adult communities around Winter Park?

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2,702 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 27

98 communities near Winter Park

2,702 homes near Winter Park

2 beds

2 baths

1,464 sq ft

House

3 beds

2 baths

1,922 sq ft

House

2 beds

2 baths

1,466 sq ft

Townhouse

2 beds

2 baths

1,771 sq ft

House

2 beds

2 baths

1,675 sq ft

House

3 beds

2 baths

1,512 sq ft

House

3 beds

3 baths

2,087 sq ft

House

3 beds

2 baths

1,534 sq ft

House

3 beds

2 baths

1,392 sq ft

House

3 beds

2 baths

2,381 sq ft

House

3 beds

2 baths

1,860 sq ft

House

2 beds

2 baths

1,248 sq ft

House

2 beds

2 baths

1,437 sq ft

House

3 beds

2 baths

1,832 sq ft

House

2 beds

2 baths

1,148 sq ft

House

2 beds

2 baths

1,008 sq ft

Condo

3 beds

3 baths

2,335 sq ft

House

2 beds

2 baths

1,440 sq ft

House

3 beds

3 baths

2,088 sq ft

Townhouse

4 beds