Winter Park, FL 55+ active adult communities & homes for sale - Page 2

90 communities near Winter Park

Sort by:

Relevance

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

The Country Club of Mount...

$200ks - $1Ms

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

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

Lakeside Landings

$100ks - $300ks

Lakeside Landings, Oxford, FL

New and Resale | Age-targeted | Built 2005 - present | 700 homes

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

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

Tohoqua Reserve

$300ks - $600ks

Tohoqua Reserve, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2021 - present | 258 homes

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

Questions? Call us: (888) 625-4885

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

Questions? Call us: (888) 625-4885

The Timbers at Everlands

$200ks - $500ks

The Timbers at Everlands, Palm Bay, FL

New Construction | 55+ age-restricted | Built 2023 - present | 450 homes

5 rating (1 reviews)

Del Webb Oasis

$400ks - $700ks

Del Webb Oasis, Winter Garden, FL

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

Lake James

$300ks

Lake James, Lakeland, FL

New and Resale | 55+ age-restricted | Built 2004 - present | 216 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.

Huntington at Hunter's Ri...

$300ks

Huntington at Hunter's Ri..., Ormond Beach, FL

New Construction | 55+ age-restricted | Built 2015 - present | 326 homes

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

Cresswind DeLand

$300ks - $500ks

Cresswind DeLand, DeLand, FL

New Construction | 55+ age-restricted | Built 2023 - present | 600 homes

5 rating (2 reviews)

Bridgewater at Viera

$300ks - $800ks

Bridgewater at Viera, Melbourne, FL

Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 homes

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

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

Vienna Square

$100ks - $200ks

Vienna Square, Winter Haven, FL

New and Resale | 55+ age-restricted | Built 2007 - present | 181 homes

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

Questions? Call us: (888) 625-4885

5 rating (1 reviews)

Esplanade at Highland Ran...

$300ks - $600ks

Esplanade at Highland Ran..., Clermont, FL

Resale Only | 55+ age-restricted | Built 2014 - 2022 | 475 homes

5 rating (2 reviews)

Palms at Serenoa

$200ks - $400ks

Palms at Serenoa, Clermont, FL

New Construction | 55+ age-restricted | Built 2018 - present | 570 homes

Del Webb Minneola

$400ks - $700ks

Del Webb Minneola, Minneola, FL

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

5 rating (4 reviews)

Grand Isle

$400ks

Grand Isle, Melbourne, FL

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 336 homes

Carmel Condominium

$100ks

Carmel Condominium, Rockledge, FL

Resale Only | 55+ age-restricted | Built 1996 - 1996 | 60 homes

Del Webb at Viera

$400ks - $1Ms

Del Webb at Viera, Melbourne, FL

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

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

Questions? Call us: (888) 625-4885

Lakes at Laurel Highlands

$200ks - $300ks

Lakes at Laurel Highlands, Lakeland, FL

New Construction | Age-targeted | Built 2017 - present | 65 homes

5 rating (4 reviews)

Carillon Lakes

$200ks - $400ks

Carillon Lakes, Lakeland, FL

Resale Only | Age-targeted | Built 2000 - 2006 | 650 homes

5 rating (2 reviews)

American Village

$300ks

American Village, Palm Coast, FL

New Construction | 55+ age-restricted | Built 2018 - present | 141 homes

4 rating (4 reviews)

High Vista at Ridgewood L...

$200ks - $300ks

High Vista at Ridgewood L..., Davenport, FL

Resale Only | 55+ age-restricted | Built 1995 - 2005 | 623 homes

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

Questions? Call us: (888) 625-4885

Lake Henry Estates

$100ks - $300ks

Lake Henry Estates, Haines City, FL

Resale Only | 55+ age-restricted | Built 1992 - 2004 | 280 homes

2 rating (1 reviews)

Heritage Landings

$200ks - $300ks

Heritage Landings, Lakeland, FL

New Construction | 55+ age-restricted | Built 2017 - 2020 | 65 homes

Alhambra Villas Condomini...

$100ks - $200ks

Alhambra Villas Condomini..., DeLand, FL

Resale Only | 55+ age-restricted | Built 1970 - 1972 | 60 homes

Carlsberg Estates on Lake...

$200ks

Carlsberg Estates on Lake..., Lake Wales, FL

Resale Only | 55+ age-restricted | Built 1998 - 2006 | 162 homes

Royal Palm

$200ks - $300ks

Royal Palm, Port Orange, FL

Resale Only | 55+ age-restricted | Built 2002 - 2016 | 458 homes

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

Questions? Call us: (888) 625-4885

5 rating (1 reviews)

Park Place

$200ks - $400ks

Park Place, Palm Coast, FL

Resale Only | 55+ age-restricted | Built 2015 - present | 123 homes

Alamanda Key

$300ks - $500ks

Alamanda Key, Melbourne, FL

Resale Only | 55+ age-restricted | Built 2005 - 2021 | 300 homes

Compass Pointe

$200ks - $300ks

Compass Pointe, West Melbourne, FL

Resale Only | 55+ age-restricted | Built 1999 - 2004 | 155 homes

Archers Mill

$300ks - $500ks

Archers Mill, Ormond Beach, FL

New Construction | Age-targeted | 94 homes

Enclave at VillageWalk

$700ks - $1Ms

Enclave at VillageWalk, Orlando, FL

Resale Only | Age-targeted | Built 2015 - 2021 | 144 homes

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

Questions? Call us: (888) 625-4885

Oakview

$100ks - $200ks

Oakview, Winter Haven, FL

Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 homes

Spring Lake Towers

$100ks

Spring Lake Towers, Winter Haven, FL

Resale Only | 55+ age-restricted | Built 1970 - 1970 | 79 homes

5 rating (1 reviews)

Silver Lakes

$100ks - $300ks

Silver Lakes, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1996 - 2001 | 148 homes

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

Questions? Call us: (888) 625-4885

Baytree

$100ks - $300ks

Baytree, Tavares, FL

Resale Only | 55+ age-restricted | Built 1990 - 2003 | 221 homes

The Savannahs

$400ks - $500ks

The Savannahs, West Melbourne, FL

Resale Only | 55+ age-restricted | Built 2017 - 2020 | 125 homes

1 2...3

New Lakes at Laurel Highlands

2788 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811

$314,000

3 beds

2 baths

1,711 sq ft

House

Community: Highland Fairways

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

Questions? Call us: (888) 625-4885

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

Questions? Call us: (888) 625-4885

New Solivita

531 VILLA PARK RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$399,000

3 beds

3 baths

2,307 sq ft

House

531 VILLA PARK RD, KISSIMMEE, FL, 34759

Community: Solivita

New Venetian Bay

452 VENETIAN VILLA DR, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168

$519,900

2 beds

2 baths

2,267 sq ft

House

452 VENETIAN VILLA DR, NEW SMYRNA BEACH,...

Community: Venetian Bay

New Royal Harbor

6210 SAILBOAT AVE, TAVARES, FL, 32778, Tavares, FL 32778

$315,000

3 beds

2 baths

1,594 sq ft

House

6210 SAILBOAT AVE, TAVARES, FL, 32778

Community: Royal Harbor

New The Villages®

2074 BILLER CIR, THE VILLAGES, FL, 32163, The Villages, FL 32163

$929,000

3 beds

3 baths

2,013 sq ft

House

2074 BILLER CIR, THE VILLAGES, FL, 32163

Community: The Villages®

New Trilogy® Orlando

163 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736

$450,000

2 beds

2 baths

2,197 sq ft

House

163 BAYOU BEND RD, GROVELAND, FL, 34736

Community: Trilogy® Orlando

New Trilogy® Orlando

95 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736

$319,000

2 beds

2 baths

1,568 sq ft

House

95 BAYOU BEND RD, GROVELAND, FL, 34736

Community: Trilogy® Orlando

New The Villages®

2083 JASPER WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162

$339,900

3 beds

2 baths

1,397 sq ft

Villa

2083 JASPER WAY, THE VILLAGES, FL, 32162

Community: The Villages®

New Solivita

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

$249,000

2 beds

2 baths

1,258 sq ft

House

521 GRAND CANAL DR, KISSIMMEE, FL, 34759

Community: Solivita

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

Questions? Call us: (888) 625-4885

New The Villages®

2405 KINGSTREE PL, THE VILLAGES, FL, 321..., The Villages, FL 32162

$278,000

2 beds

2 baths

1,188 sq ft

House

2405 KINGSTREE PL, THE VILLAGES, FL, 321...

Community: The Villages®

New Grand Isle

1575 BOCA RIO DR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$439,999

3 beds

2 baths

1,764 sq ft

House

1575 BOCA RIO DR, MELBOURNE, FL, 32940

House

3976 IRONWOOD LN, THE VILLAGES, FL, 3216...

Community: The Villages®

New Summer Trees

102 UNDERBRUSH TRL, PORT ORANGE, FL, 321..., Port Orange, FL 32128

$275,000

2 beds

2 baths

1,370 sq ft

House

102 UNDERBRUSH TRL, PORT ORANGE, FL, 321...

Community: Summer Trees

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

Questions? Call us: (888) 625-4885

New Del Webb Sunbridge

6362 SHIMMERING SHORES LN, ST CLOUD, FL,..., St Cloud, FL 34771

$724,900

3 beds

3 baths

2,249 sq ft

House

6362 SHIMMERING SHORES LN, ST CLOUD, FL,...

Community: Del Webb Sunbridge

New Latitude Margaritaville

672 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$775,000

3 beds

4 baths

2,542 sq ft

House

672 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

New Harbor Hills Country Club

39545 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159

$639,000

4 beds

3 baths

2,954 sq ft

House

39545 HARBOR HILLS BLVD, LADY LAKE, FL, ...

Community: Harbor Hills Country Club

New The Villages®

5186 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484

$280,000

3 beds

4 baths

1,929 sq ft

House

5186 NE 122ND BLVD, OXFORD, FL, 34484

House

47 CROOKED PINE RD, PORT ORANGE, FL, 321...

Community: Summer Trees

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

Questions? Call us: (888) 625-4885

New The Villages®

9041 SE 166TH KATHY LOOP, THE VILLAGES, ..., The Villages, FL 32162

$520,000

3 beds

2 baths

1,808 sq ft

Villa

9041 SE 166TH KATHY LOOP, THE VILLAGES, ...

Community: The Villages®

New Highland Fairways

3202 OTTER CREEK CT, LAKELAND, FL, 33810, Lakeland, FL 33810

$169,900

2 beds

2 baths

1,274 sq ft

Manufactured Home

3202 OTTER CREEK CT, LAKELAND, FL, 33810

Community: Highland Fairways

New Lakeside Landings

5076 NEPTUNE CIR, OXFORD, FL, 34484, Oxford, FL 34484

$262,500

3 beds

2 baths

1,404 sq ft

House

5076 NEPTUNE CIR, OXFORD, FL, 34484

Community: Lakeside Landings

New Sullivan Ranch

30337 GIDRAN TER, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$544,000

4 beds

3 baths

2,307 sq ft

House

30337 GIDRAN TER, MOUNT DORA, FL, 32757

Community: Sullivan Ranch

New Bridgewater at Viera

1765 VELKY LN, MELBOURNE, FL, 32940, Melbourne, FL 32940

$425,000

2 beds

2 baths

1,565 sq ft

House

1765 VELKY LN, MELBOURNE, FL, 32940

Condo

134 BLUE HERON DR C, DAYTONA BEACH, FL, ...

Community: Pelican Bay Daytona Beach

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

Questions? Call us: (888) 625-4885

New The Villages®

2004 FLOWERSVILLE PL, THE VILLAGES, FL, ..., The Villages, FL 32163

$429,850

3 beds

2 baths

1,589 sq ft

House

2004 FLOWERSVILLE PL, THE VILLAGES, FL, ...

Community: The Villages®

New The Villages®

5837 STORMS AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163

$710,000

3 beds

2 baths

1,933 sq ft

House

5837 STORMS AVE, THE VILLAGES, FL, 32163

Community: The Villages®

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

90 communities

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.
© 2026 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: Mar 01, 2026.
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 - Page 2

90 communities near Winter Park

2,540 homes near Winter Park

3 beds

2 baths

1,711 sq ft

House

3 beds

2 baths

1,711 sq ft

House

3 beds

2 baths

1,827 sq ft

House

3 beds

2 baths

1,887 sq ft

House

3 beds

2 baths

2,213 sq ft

House

3 beds

3 baths

2,307 sq ft

House

2 beds

2 baths

2,267 sq ft

House

3 beds

2 baths

1,594 sq ft

House

3 beds

3 baths

2,013 sq ft

House

2 beds

2 baths

2,197 sq ft

House

2 beds

2 baths

1,568 sq ft

House

3 beds

2 baths

1,397 sq ft

Villa

2 beds

2 baths

1,258 sq ft

House

2 beds

2 baths

1,188 sq ft

House

3 beds

2 baths

1,764 sq ft

House

3 beds

2 baths

1,842 sq ft

House

4 beds

2 baths

2,204 sq ft

House

3 beds

2 baths

1,526 sq ft

House

3 beds

2 baths

1,925 sq ft

House

3 beds