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

3,933 homes near Winter Garden

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Del Webb Oasis

$400Ks - $1Ms

Del Webb Oasis, Winter Garden, FL

New Construction | 55+ age-restricted | Built 2020 - present | 422 homes

4 rating (17 reviews)

The Villages®

<$100k - $1Ms

The Villages®, The Villages, FL

New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes

4.1 rating (55 reviews)

On Top of the World

$100Ks - $600Ks

On Top of the World, Ocala, FL

New and Resale | 55+ age-restricted | Built 1981 - present | 10,000 homes

3.8 rating (14 reviews)

Sun City Center

<$100k - $600Ks

Sun City Center, Sun City Center, FL

Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes

4.7 rating (18 reviews)

Solivita

$200Ks - $700Ks

Solivita, Kissimmee, FL

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

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3.6 rating (46 reviews)

Latitude Margaritaville

$300Ks - $700Ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes

4.2 rating (10 reviews)

Stone Creek

$200Ks - $800Ks

Stone Creek, Ocala, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes

4.1 rating (29 reviews)

Oak Run

$100Ks - $300Ks

Oak Run, Ocala, FL

Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 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

5 rating (2 reviews)

Plantation at Leesburg

$100Ks - $400Ks

Plantation at Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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 (3 reviews)

Stonecrest

$200Ks - $600Ks

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 - $1Ms

Twin Lakes, St. Cloud, FL

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

No reviews yet

Pelican Bay Daytona Beach

<$100k - $600Ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

4.6 rating (5 reviews)

Ocala Preserve

$200Ks - $600Ks

Ocala Preserve, Ocala, FL

New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 homes

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

Questions? Call us: (689) 407-5757

4.7 rating (3 reviews)

Spruce Creek South

$200Ks - $300Ks

Spruce Creek South, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes

4.7 rating (11 reviews)

Valencia Lakes

$200Ks - $900Ks

Valencia Lakes, Wimauma, FL

Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes

5 rating (1 reviews)

Cypress Lakes

$200Ks - $200Ks

Cypress Lakes, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes

5 rating (3 reviews)

Lake Ashton

$200Ks - $900Ks

Lake Ashton, Lake Wales, FL

Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes

No reviews yet

Venetian Bay

$200Ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

5 rating (8 reviews)

Royal Highlands

$200Ks - $400Ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 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

3.8 rating (6 reviews)

Tampa Bay Golf and Countr...

$200Ks - $400Ks

Tampa Bay Golf and Countr..., San Antonio, FL

Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes

5 rating (1 reviews)

VillageWalk at Lake Nona

$400Ks - $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

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

Questions? Call us: (689) 407-5757

5 rating (8 reviews)

Pennbrooke Fairways

$100Ks - $300Ks

Pennbrooke Fairways, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 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

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)

Ocala Palms

$100Ks - $400Ks

Ocala Palms, Ocala, FL

Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 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

5 rating (5 reviews)

SummerGlen

$200Ks - $500Ks

SummerGlen, Ocala, FL

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 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

No reviews yet

Breakaway Trails

$400Ks - $700Ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 homes

4 rating (4 reviews)

Lakes of Mount Dora

$200Ks - $800Ks

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 - $800Ks

Harbor Hills Country Club, Lady Lake, FL

New and Resale | Age-targeted | Built 1989 - present | 940 homes

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

Questions? Call us: (689) 407-5757

4.8 rating (6 reviews)

Highland Lakes

$200Ks - $300Ks

Highland Lakes, Leesburg, FL

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

4.3 rating (15 reviews)

Del Webb Orlando

$200Ks - $500Ks

Del Webb Orlando, Davenport, FL

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

No reviews yet

Pine Run Estates

$100Ks - $400Ks

Pine Run Estates, Ocala, FL

Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes

No reviews yet

Lake Jovita Golf and Coun...

$400Ks - $1Ms

Lake Jovita Golf and Coun..., Dade City, FL

New and Resale | Age-targeted | Built 1999 - present | 875 homes

No reviews yet

Esplanade at Wiregrass Ra...

$400Ks - $900Ks

Esplanade at Wiregrass Ra..., Wesley Chapel, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes

1 2 3

Sun City Center

$291,000

2 beds

2 baths

1,860 sq ft

Villa

1816 N PEBBLE BEACH BLVD, SUN CITY CENTE...

Community: Sun City Center

Ocala Palms

1956 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482

$387,000

3 beds

2 baths

1,806 sq ft

House

1956 NW 50TH CIR, OCALA, FL, 34482

Community: Ocala Palms

Lake Ashton

4073 SABLE LOOP DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859

$550,000

3 beds

2 baths

2,354 sq ft

House

4073 SABLE LOOP DR, LAKE WALES, FL, 3385...

Community: Lake Ashton

Pelican Bay Daytona Beach

149 BLACK DUCK CIR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119

$229,770

2 beds

2 baths

1,075 sq ft

House

149 BLACK DUCK CIR, DAYTONA BEACH, FL, 3...

Community: Pelican Bay Daytona Beach

Sun City Center

$239,900

2 beds

2 baths

1,584 sq ft

Condo

736 MCCALLISTER AVE, SUN CITY CENTER, FL...

Community: Sun City Center

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

Questions? Call us: (689) 407-5757

The Villages®

$179,900

2 beds

2 baths

936 sq ft

Manufactured Home

1628 BAY MEADOWS LN, THE VILLAGES, FL, 3...

Community: The Villages®

On Top of the World

8796 SW 83RD CIR, OCALA, FL, 34481, Ocala, FL 34481

$324,900

3 beds

2 baths

1,726 sq ft

House

8796 SW 83RD CIR, OCALA, FL, 34481

Community: On Top of the World

SummerGlen

15300 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473

$284,900

3 beds

2 baths

1,676 sq ft

House

15300 SW 14TH AVENUE RD, OCALA, FL, 3447...

Community: SummerGlen

Venetian Bay

424 LUNA BELLA LN 433, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168

$369,900

3 beds

3 baths

2,030 sq ft

Condo

424 LUNA BELLA LN 433, NEW SMYRNA BEACH,...

Community: Venetian Bay

Harbor Hills Country Club

5141 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$819,999

4 beds

3 baths

2,500 sq ft

House

5141 GREENS DR, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

On Top of the World

9085 SW 89TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$669,900

3 beds

3 baths

2,814 sq ft

House

9085 SW 89TH LOOP, OCALA, FL, 34481

Community: On Top of the World

On Top of the World

9286 SW 89TH COURT RD D, OCALA, FL, 3448..., Ocala, FL 34481

$159,900

2 beds

2 baths

1,113 sq ft

Villa

9286 SW 89TH COURT RD D, OCALA, FL, 3448...

Community: On Top of the World

Windermere

708 MORAY DR, INVERNESS, FL, 34453, Inverness, FL 34453

$285,000

3 beds

3 baths

1,915 sq ft

Townhouse

708 MORAY DR, INVERNESS, FL, 34453

Community: Windermere

Tarawood

10522 S DREW BRYANT CIR, FLORAL CITY, FL..., Floral City, FL 34436

$294,900

3 beds

2 baths

1,263 sq ft

House

10522 S DREW BRYANT CIR, FLORAL CITY, FL...

Community: Tarawood

Tarawood

10490 S DREW BRYANT CIR, FLORAL CITY, FL..., Floral City, FL 34436

$274,900

3 beds

2 baths

1,185 sq ft

House

10490 S DREW BRYANT CIR, FLORAL CITY, FL...

Community: Tarawood

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

Questions? Call us: (689) 407-5757

Solivita

663 SHOREHAVEN DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$349,900

3 beds

3 baths

2,357 sq ft

House

663 SHOREHAVEN DR, POINCIANA, FL, 34759

Community: Solivita

Pelican Bay Daytona Beach

240 BOB WHITE CT 2400, DAYTONA BEACH, FL..., Daytona Beach, FL 32119

$224,900

2 beds

2 baths

1,093 sq ft

Condo

240 BOB WHITE CT 2400, DAYTONA BEACH, FL...

Community: Pelican Bay Daytona Beach

The Villages®

$324,900

2 beds

2 baths

1,266 sq ft

Villa

5820 BAMBOO AVE, THE VILLAGES, FL, 32163

Community: The Villages®

Plantation at Leesburg

5338 TIGERS TAIL, LEESBURG, FL, 34748, Leesburg, FL 34748

$269,999

2 beds

2 baths

1,050 sq ft

House

5338 TIGERS TAIL, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Traditions at Lake Ruby

3457 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$238,500

2 beds

2 baths

1,118 sq ft

House

3457 RALEIGH DR, WINTER HAVEN, FL, 33884

Community: Traditions at Lake Ruby

On Top of the World

9662 SW 95TH CT A, OCALA, FL, 34481, Ocala, FL 34481

$174,500

2 beds

2 baths

1,412 sq ft

Villa

9662 SW 95TH CT A, OCALA, FL, 34481

Community: On Top of the World

Sun City Center

$214,900

2 beds

2 baths

984 sq ft

Condo

401 DORCHESTER PL 52, SUN CITY CENTER, F...

Community: Sun City Center

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, ...

Community: Pelican Bay Daytona Beach

Sun City Center

$220,000

2 beds

2 baths

1,141 sq ft

House

711 E BROCKTON PL, SUN CITY CENTER, FL, ...

Community: Sun City Center

Lake Ashton

4195 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859

$387,000

3 beds

2 baths

2,039 sq ft

House

4195 MUIRFIELD LOOP, LAKE WALES, FL, 338...

Community: Lake Ashton

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

Questions? Call us: (689) 407-5757

Cherrywood

5824 SW 100TH LN, OCALA, FL, 34476, Ocala, FL 34476

$359,900

4 beds

3 baths

2,433 sq ft

House

5824 SW 100TH LN, OCALA, FL, 34476

Community: Cherrywood

Huntington at Hunter's Ridge

103 WRENDALE LOOP, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$409,000

2 beds

2 baths

1,603 sq ft

House

103 WRENDALE LOOP, ORMOND BEACH, FL, 321...

Community: Huntington at Hunter's Ridge

Kings Ridge

2310 GRASMERE CIR, CLERMONT, FL, 34711, Clermont, FL 34711

$344,900

2 beds

2 baths

1,716 sq ft

House

2310 GRASMERE CIR, CLERMONT, FL, 34711

Community: Kings Ridge

Venetian Bay

2866 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$589,880

3 beds

3 baths

2,115 sq ft

Townhouse

2866 ISLES WAY, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

Legacy of Leesburg

27437 DESERT ROSE CT, LEESBURG, FL, 3474..., Leesburg, FL 34748

$415,000

3 beds

2 baths

2,115 sq ft

House

27437 DESERT ROSE CT, LEESBURG, FL, 3474...

Community: Legacy of Leesburg

Ocala Preserve

3966 NW 46TH TER, OCALA, FL, 34482, Ocala, FL 34482

$300,000

2 beds

2 baths

1,392 sq ft

House

3966 NW 46TH TER, OCALA, FL, 34482

Community: Ocala Preserve

Solivita

205 BELL TOWER XING W, KISSIMMEE, FL, 34..., Kissimmee, FL 34759

$289,900

2 beds

2 baths

1,405 sq ft

House

205 BELL TOWER XING W, KISSIMMEE, FL, 34...

Community: Solivita

On Top of the World

8626 SW 97TH LANE RD D, OCALA, FL, 34481, Ocala, FL 34481

$299,000

2 beds

2 baths

1,708 sq ft

Townhouse

8626 SW 97TH LANE RD D, OCALA, FL, 34481

Community: On Top of the World

Twin Lakes

2555 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772

$319,000

2 beds

2 baths

1,346 sq ft

Villa

2555 YELLOW BRICK RD, SAINT CLOUD, FL, 3...

Community: Twin Lakes

Solivita

130 PRIMA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$435,000

3 beds

2 baths

2,141 sq ft

House

130 PRIMA DR, KISSIMMEE, FL, 34759

Community: Solivita

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

Questions? Call us: (689) 407-5757

Highlands Ridge

3201 E ANGLERS STRM, AVON PARK, FL, 3382..., Avon Park, FL 33825

$299,000

2 beds

2 baths

2,034 sq ft

House

3201 E ANGLERS STRM, AVON PARK, FL, 3382...

Community: Highlands Ridge

Palm Cay

10881 SW 79TH TER, OCALA, FL, 34476, Ocala, FL 34476

$179,000

2 beds

2 baths

1,112 sq ft

House

10881 SW 79TH TER, OCALA, FL, 34476

Community: Palm Cay

Venetian Bay

3067 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$545,900

3 beds

4 baths

1,847 sq ft

Townhouse

3067 ISLES WAY, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

Venetian Bay

3069 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$420,500

2 beds

2 baths

1,003 sq ft

Townhouse

3069 ISLES WAY, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

Venetian Bay

3046 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$600,000

4 beds

4 baths

2,086 sq ft

Townhouse

3046 ISLES WAY, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

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Frequently Asked Questions

What size 55+ communities are there in Winter Garden?

In Winter Garden, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.

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

The smallest 55+ communities in Winter Garden has 163 homes, the largest has 422 homes, and the average communities consists of 292 homes.

Are there new 55+ homes available in Winter Garden?

Yes, there are new 55+ homes available in Winter Garden. The most recent communities started in Winter Garden include Overture Hamlin, Del Webb Oasis. There are also 2 communities in Winter Garden that offer new construction homes, including Overture Hamlin, Del Webb Oasis.

Are there gated 55+ communities in Winter Garden?

Yes, there is gated 55+ communities in Winter Garden. Approximately 50.0% of 55+ communities in the area are gated. For instance, Del Webb Oasis is a gated communities with 422 homes.

How long do listings in 55+ communities in Winter Garden typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in Winter Garden stay on the market for around 143 days. The average price of homes for sale in these communities is approximately $502,460, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Del Webb Oasis average around $502,460.

Want more information about active adult communities around Winter Garden?

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3,933 homes near Winter Garden

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

106 communities near Winter Garden

3,933 homes near Winter Garden

2 beds

2 baths

1,860 sq ft

Villa

3 beds

2 baths

1,806 sq ft

House

3 beds

2 baths

2,354 sq ft

House

2 beds

2 baths

1,075 sq ft

House

2 beds

2 baths

1,584 sq ft

Condo

2 beds

2 baths

936 sq ft

Manufactured Home

3 beds

2 baths

1,726 sq ft

House

3 beds

2 baths

1,676 sq ft

House

3 beds

3 baths

2,030 sq ft

Condo

4 beds

3 baths

2,500 sq ft

House

3 beds

3 baths

2,814 sq ft

House

2 beds

2 baths

1,113 sq ft

Villa

3 beds

3 baths

1,915 sq ft

Townhouse

3 beds

2 baths

1,263 sq ft

House

3 beds

2 baths

1,185 sq ft

House

3 beds

3 baths

2,357 sq ft

House

2 beds

2 baths

1,093 sq ft

Condo

2 beds

2 baths

1,266 sq ft

Villa

2 beds

2 baths

1,050 sq ft

House

2 beds