Winter Park, FL 55+ active adult communities & homes for sale - Page 18

2,414 homes near Winter Park

Sort by:

Relevance

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

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

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

Questions? Call us: (888) 625-4885

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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 homes

Grand Haven

$200ks - $800ks

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.

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

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

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 (4 reviews)

Spruce Creek South

$100ks - $200ks

Spruce Creek South, Summerfield, FL

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

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

Questions? Call us: (888) 625-4885

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

New and Resale | Age-targeted | Built 1980 - present | 1,000 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 - $1Ms

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

$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)

Del Webb Sunbridge

$400ks - $800ks

Del Webb Sunbridge, St. Cloud, FL

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

5 rating (1 reviews)

Cresswind at Victoria Gar...

$200ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

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

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 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

$300ks - $500ks

Heritage Isle, Viera, FL

Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 homes

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

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

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2017 - present | 557 homes

Ridgehaven

$300ks - $600ks

Ridgehaven, Ormond Beach, FL

New Construction | 55+ age-restricted

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 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

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)

VillageWalk at Lake Nona

$300ks - $700ks

VillageWalk at Lake Nona, Orlando, FL

Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

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

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

Questions? Call us: (888) 625-4885

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

5 rating (2 reviews)

Bridgewater at Viera

$300ks - $800ks

Bridgewater at Viera, Melbourne, FL

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

1 2...3

The Country Club of Mount Dora

1741 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$1,290,000

5 beds

5 baths

5,573 sq ft

House

1741 EDGEWATER DR, MOUNT DORA, FL, 32757

Community: The Country Club of Mount Dora

Arlington Ridge

$328,000

2 beds

2 baths

1,518 sq ft

House

4313 ARLINGTON RIDGE BLVD, LEESBURG, FL,...

Community: Arlington Ridge

Arlington Ridge

26921 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748

$229,000

2 beds

2 baths

1,254 sq ft

Villa

26921 WHITE PLAINS WAY, LEESBURG, FL, 34...

Community: Arlington Ridge

Latitude Margaritaville

132 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124

$424,900

3 beds

2 baths

1,464 sq ft

House

132 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...

Community: Latitude Margaritaville

Royal Highlands

5607 SIR CHURCHILL DR, LEESBURG, FL, 347..., Leesburg, FL 34748

$425,000

3 beds

2 baths

2,312 sq ft

House

5607 SIR CHURCHILL DR, LEESBURG, FL, 347...

Manufactured Home

5556 COLUMBUS CIR, WILDWOOD, FL, 34785

4050 ALAMANDA KEY DR DRIVE, MELBOURNE, F...

Community: Alamanda Key

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

Questions? Call us: (888) 625-4885

The Villages®

$349,900

3 beds

2 baths

1,392 sq ft

House

17009 SE 96TH CHAPELWOOD CIR, THE VILLAG...

Community: The Villages®

Plantation Bay Golf & Country Club

715 COBBLESTONE DR, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$369,000

2 beds

3 baths

1,875 sq ft

House

715 COBBLESTONE DR, ORMOND BEACH, FL, 32...

Community: Plantation Bay Golf & Country Club

Lakes of Mount Dora

2359 WAKEFIELD WAY, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757

$449,000

3 beds

2 baths

1,615 sq ft

House

2359 WAKEFIELD WAY, MOUNT DORA, FL, 3275...

Community: Lakes of Mount Dora

Cresswind at Victoria Gardens

1157 AVERY MEADOWS WAY, DELAND, FL, 3272..., Deland, FL 32724

$479,900

2 beds

2 baths

1,928 sq ft

House

1157 AVERY MEADOWS WAY, DELAND, FL, 3272...

Community: Cresswind at Victoria Gardens

The Villages®

$300,000

2 beds

2 baths

1,156 sq ft

Villa

324 EMMALEE PL, THE VILLAGES, FL, 32162

Community: The Villages®

Breakaway Trails

59 SHADOWCREEK WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$650,000

4 beds

3 baths

3,227 sq ft

House

59 SHADOWCREEK WAY, ORMOND BEACH, FL, 32...

Community: Breakaway Trails

Spruce Creek Country Club

8475 SE 137TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$259,000

2 beds

2 baths

1,652 sq ft

House

8475 SE 137TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

The Villages®

$349,900

3 beds

2 baths

1,556 sq ft

House

603 EVESBOROUGH PATH, THE VILLAGES, FL, ...

Community: The Villages®

Plantation Bay Golf & Country Club

708 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$314,900

2 beds

2 baths

1,510 sq ft

Townhouse

708 ALDENHAM LN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Breakaway Trails

120 BLACK HICKORY WAY, ORMOND BEACH, FL,..., Ormond Beach, FL 32174

$450,000

3 beds

2 baths

1,931 sq ft

House

120 BLACK HICKORY WAY, ORMOND BEACH, FL,...

Community: Breakaway Trails

Grand Haven

82 LAGARE ST, PALM COAST, FL, 32137, Palm Coast, FL 32137

$750,000

3 beds

4 baths

2,792 sq ft

House

82 LAGARE ST, PALM COAST, FL, 32137

Community: Grand Haven

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

Questions? Call us: (888) 625-4885

Latitude Margaritaville

228 CHEESEBURGER DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$839,900

2 beds

3 baths

2,339 sq ft

House

228 CHEESEBURGER DR, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

Solivita

152 GLENDALE CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$284,900

2 beds

2 baths

1,548 sq ft

House

152 GLENDALE CT, KISSIMMEE, FL, 34759

Community: Solivita

The Savannahs

4156 CATGRASS LN, WEST MELBOURNE, FL, 32..., West Melbourne, FL 32904

$390,000

3 beds

2 baths

1,812 sq ft

House

4156 CATGRASS LN, WEST MELBOURNE, FL, 32...

Community: The Savannahs

Arlington Ridge

27102 CAMERONS RUN, LEESBURG, FL, 34748, Leesburg, FL 34748

$360,000

3 beds

2 baths

2,000 sq ft

House

27102 CAMERONS RUN, LEESBURG, FL, 34748

Community: Arlington Ridge

The Country Club of Mount Dora

1760 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$749,500

4 beds

3 baths

3,141 sq ft

House

1760 EDGEWATER DR, MOUNT DORA, FL, 32757

Community: The Country Club of Mount Dora

Pelican Bay Daytona Beach

770 PELICAN BAY DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119

$795,000

5 beds

4 baths

3,165 sq ft

House

770 PELICAN BAY DR, DAYTONA BEACH, FL, 3...

Community: Pelican Bay Daytona Beach

The Villages®

5090 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484

$275,000

4 beds

4 baths

1,929 sq ft

House

5090 NE 122ND BLVD, OXFORD, FL, 34484

Community: The Villages®

Arlington Ridge

4307 BENT CREEK LN, LEESBURG, FL, 34748, Leesburg, FL 34748

$379,900

3 beds

2 baths

1,683 sq ft

House

4307 BENT CREEK LN, LEESBURG, FL, 34748

Community: Arlington Ridge

The Villages®

$545,000

3 beds

2 baths

1,958 sq ft

House

491 HARLOW LN, THE VILLAGES, FL, 32163

Community: The Villages®

Kings Ridge

3871 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711

$289,900

2 beds

2 baths

1,327 sq ft

House

3871 EVERSHOLT ST, CLERMONT, FL, 34711

Community: Kings Ridge

Baytree

220 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778

$207,000

2 beds

2 baths

1,104 sq ft

Villa

220 JUNIPER WAY, TAVARES, FL, 32778

Community: Baytree

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

Questions? Call us: (888) 625-4885

Traditions at Lake Ruby

3890 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$395,000

4 beds

3 baths

2,322 sq ft

House

3890 BEDFORD AVE, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

Stonecrest

11750 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$497,000

3 beds

2 baths

2,069 sq ft

House

11750 SE 178TH ST, SUMMERFIELD, FL, 3449...

Community: Stonecrest

1…12 13 14 15 16 17 18 19 20 21 22 23 24…61

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?

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

2,414 homes

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: May 25, 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 18

93 communities near Winter Park

2,414 homes near Winter Park

5 beds

5 baths

5,573 sq ft

House

2 beds

2 baths

1,518 sq ft

House

2 beds

2 baths

1,254 sq ft

Villa

3 beds

2 baths

1,464 sq ft

House

3 beds

2 baths

2,312 sq ft

House

3 beds

2 baths

1,715 sq ft

House

3 beds

2 baths

2,598 sq ft

House

3 beds

2 baths

2,581 sq ft

House

3 beds

2 baths

2,001 sq ft

House

3 beds

3 baths

1,680 sq ft

Manufactured Home

3 beds

2 baths

2,113 sq ft

House

2 beds

2 baths

1,973 sq ft

Halfplex

2 beds

2 baths

1,653 sq ft

House

3 beds

2 baths

2,018 sq ft

House

3 beds

2 baths

2,519 sq ft

House

3 beds

2 baths

1,550 sq ft

House

3 beds

2 baths

1,392 sq ft

House

2 beds

3 baths

1,875 sq ft

House

3 beds

2 baths

1,615 sq ft

House

2 beds