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

2,487 homes near Winter Park

Sort by:

Relevance

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

4.7 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

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

Questions? Call us: (888) 625-4885

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

Grand Haven

$300Ks - $1Ms

Grand Haven, Palm Coast, FL

New and Resale | Age-targeted | Built 1997 - present | 1,901 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 - $500Ks

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 - $300Ks

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

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

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

Questions? Call us: (888) 625-4885

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 - $500Ks

Trilogy® Orlando, Groveland, FL

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

5 rating (8 reviews)

Royal Highlands

$200Ks - $500Ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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

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

Del Webb at Viera

$300Ks - $800Ks

Del Webb at Viera, Melbourne, FL

New Construction | 55+ age-restricted | Built 2021 - present | 1,300 homes

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

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

Questions? Call us: (888) 625-4885

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 - $700Ks

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

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 - $600Ks

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

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

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

Questions? Call us: (888) 625-4885

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

$200Ks - $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

1 rating (1 reviews)

Sullivan Ranch

$300Ks - $600Ks

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

1 2...3

The Country Club of Mount Dora

1861 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$1,099,999

4 beds

5 baths

4,733 sq ft

House

1861 EDGEWATER DR, MOUNT DORA, FL, 32757

Community: The Country Club of Mount Dora

Alhambra Villas Condominiums

201 N HILL AVE 150, DELAND, FL, 32724, Deland, FL 32724

$199,900

2 beds

2 baths

1,090 sq ft

Condo

201 N HILL AVE 150, DELAND, FL, 32724

Community: Alhambra Villas Condominiums

Alhambra Villas Condominiums

217 N HILL AVE 20, DELAND, FL, 32724, Deland, FL 32724

$234,900

2 beds

2 baths

1,066 sq ft

Condo

217 N HILL AVE 20, DELAND, FL, 32724

Community: Alhambra Villas Condominiums

Heritage - The Cottages of Sanders Grove

6342 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762

$314,900

3 beds

2 baths

1,788 sq ft

House

6342 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...

Community: Heritage - The Cottages of Sanders Grove

Spruce Creek Country Club

13822 SE 85TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$267,500

2 beds

2 baths

1,540 sq ft

House

13822 SE 85TH CIR, SUMMERFIELD, FL, 3449...

House

4496 STRATHMORE DR, LAKE WALES, FL, 3385...

Community: Lake Ashton

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

Questions? Call us: (888) 625-4885

Spruce Creek South

17583 SE 96TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$214,900

2 beds

2 baths

1,008 sq ft

House

Community: Latitude Margaritaville

Spruce Creek Country Club

9343 SE 124TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$469,000

3 beds

3 baths

2,324 sq ft

House

9343 SE 124TH PL, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

The Villages®

4908 NE 123RD LN, OXFORD, FL, 34484, Oxford, FL 34484

$299,900

4 beds

4 baths

1,912 sq ft

House

4908 NE 123RD LN, OXFORD, FL, 34484

Community: The Villages®

Legacy of Leesburg

5839 WOODLAND MOSS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748

$327,000

3 beds

2 baths

1,993 sq ft

House

5839 WOODLAND MOSS WAY, LEESBURG, FL, 34...

Community: Legacy of Leesburg

VillageWalk at Lake Nona

11794 BARLETTA DR, ORLANDO, FL, 32827, Orlando, FL 32827

$699,987

3 beds

2 baths

1,949 sq ft

House

11794 BARLETTA DR, ORLANDO, FL, 32827

Community: VillageWalk at Lake Nona

Legacy of Leesburg

27536 STONEY BROOK DR, LEESBURG, FL, 347..., Leesburg, FL 34748

$299,000

3 beds

2 baths

1,478 sq ft

House

27536 STONEY BROOK DR, LEESBURG, FL, 347...

Community: Legacy of Leesburg

VillageWalk at Lake Nona

11753 FAN TAIL LN, ORLANDO, FL, 32827, Orlando, FL 32827

$470,000

2 beds

2 baths

1,680 sq ft

Halfplex

11753 FAN TAIL LN, ORLANDO, FL, 32827

Manufactured Home

4859 FOXWOOD BLVD, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

Heritage Isle

6858 TOLAND DR APT 304, MELBOURNE, FL, 3..., Melbourne, FL 32940

$299,000

2 beds

2 baths

1,194 sq ft

Condo

6858 TOLAND DR APT 304, MELBOURNE, FL, 3...

Community: Heritage Isle

Lake Ashton

4489 STRATHMORE DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859

$319,000

2 beds

2 baths

1,530 sq ft

House

4489 STRATHMORE DR, LAKE WALES, FL, 3385...

Community: Lake Ashton

Del Webb Sunbridge

3122 VANGUARD CT, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771

$1,275,000

5 beds

4 baths

3,460 sq ft

House

3122 VANGUARD CT, SAINT CLOUD, FL, 34771

Community: Del Webb Sunbridge

Silver Lakes

$250,000

2 beds

2 baths

1,545 sq ft

House

2244 SILVER LAKES DR, LAKELAND, FL, 3381...

House

17739 SE 121ST TERRACE RD, SUMMERFIELD, ...

Community: Stonecrest

1…50 51 52 53 54 55 56 57 58 59 60 61 62…63

Want more information about active adult communities around Winter Park?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Winter Park?

Call us: (888) 625-4885

2,487 homes near Winter Park

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2025 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Nov 30, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

90 communities near Winter Park

2,487 homes near Winter Park

4 beds

5 baths

4,733 sq ft

House

2 beds

2 baths

1,090 sq ft

Condo

2 beds

2 baths

1,066 sq ft

Condo

3 beds

2 baths

1,788 sq ft

House

2 beds

2 baths

1,540 sq ft

House

3 beds

2 baths

1,615 sq ft

House

3 beds

2 baths

1,813 sq ft

House

3 beds

2 baths

1,559 sq ft

House

2 beds

2 baths

2,271 sq ft

House

3 beds

2 baths

1,409 sq ft

House

3 beds

2 baths

2,002 sq ft

House

2 beds

2 baths

1,792 sq ft

House

2 beds

2 baths

1,695 sq ft

House

2 beds

2 baths

1,460 sq ft

House

3 beds

2 baths

2,312 sq ft

House

2 beds

2 baths

1,008 sq ft

House

3 beds

2 baths

2,114 sq ft

House

2 beds

2 baths

1,800 sq ft

House

2 beds

2 baths

1,563 sq ft

House

3 beds