Call us at (888) 625-4885 to learn more about active adult communities in Winter Park

Winter Park, FL 55+ active adult communities & homes for sale - Page 7

2,377 homes near Winter Park

Sort by:

Relevance

Relevance

4 rating (17 reviews) The Villages®
<$100k - $2Ms
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
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
$300Ks - $1Ms
Grand Haven, Palm Coast, FL
New and Resale | Age-targeted | Built 1997 - present | 1,901 homes
Pelican Bay Daytona Beach
$100Ks - $400Ks
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 - $400Ks
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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
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 - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 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 (8 reviews) Royal Highlands
$200Ks - $400Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
Del Webb at Viera
$400Ks - $1Ms
Del Webb at Viera, Melbourne, FL
New Construction | 55+ age-restricted | Built 2021 - 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
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 Park? 55places can help!
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) 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
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.
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 - $800Ks
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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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 - $800Ks
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
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.
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
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
$300Ks - $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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
1 rating (1 reviews) Sullivan Ranch
$200Ks - $700Ks
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
The Villages® 2046 DALECROFT TRL, THE VILLAGES, FL, 32..., The Villages, FL 32162
$349,900

3 beds

|

2 baths

|

1,488 sq ft

|

House

2046 DALECROFT TRL, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 664 TERNBERRY FOREST DR, THE VILLAGES, F..., The Villages, FL 32162
$1,775,000

3 beds

|

3 baths

|

3,100 sq ft

|

House

664 TERNBERRY FOREST DR, THE VILLAGES, F...
Community: The Villages®
The Villages® 1221 SANTA CRUZ DR, THE VILLAGES, FL, 32..., The Villages, FL 32162
$289,900

2 beds

|

2 baths

|

1,174 sq ft

|

Villa

1221 SANTA CRUZ DR, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 6126 MULLIGAN RUN, THE VILLAGES, FL, 321..., The Villages, FL 32163
$799,900

3 beds

|

2 baths

|

2,930 sq ft

|

House

6126 MULLIGAN RUN, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 2935 CEDAR GROVE LOOP, THE VILLAGES, FL,..., The Villages, FL 32163
$895,000

3 beds

|

2 baths

|

3,466 sq ft

|

House

2935 CEDAR GROVE LOOP, THE VILLAGES, FL,...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Trilogy® Orlando 168 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$625,000

3 beds

|

3 baths

|

2,392 sq ft

|

House

168 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Stonecrest 17842 SE 125TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$349,000

3 beds

|

2 baths

|

1,695 sq ft

|

House

17842 SE 125TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
Cresswind DeLand 1213 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724
$544,990

3 beds

|

3 baths

|

1,983 sq ft

|

House

1213 CRESSWIND BLVD, DELAND, FL, 32724
Community: Cresswind DeLand
Cresswind DeLand 1235 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724
$609,990

3 beds

|

4 baths

|

2,496 sq ft

|

House

1235 CRESSWIND BLVD, DELAND, FL, 32724
Community: Cresswind DeLand
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.
Cresswind DeLand 1322 SAVOY LN, DELAND, FL, 32724, Deland, FL 32724
$493,990

3 beds

|

3 baths

|

2,289 sq ft

|

House

1322 SAVOY LN, DELAND, FL, 32724
Community: Cresswind DeLand
Cresswind DeLand 1299 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724
$586,990

3 beds

|

4 baths

|

2,776 sq ft

|

House

1299 CRESSWIND BLVD, DELAND, FL, 32724
Community: Cresswind DeLand
Cresswind DeLand 1025 PORT BLUE WAY, DELAND, FL, 32724, Deland, FL 32724
$385,990

3 beds

|

2 baths

|

1,724 sq ft

|

House

1025 PORT BLUE WAY, DELAND, FL, 32724
Community: Cresswind DeLand
Cresswind DeLand 1304 CLUB CRESSWIND WAY, DELAND, FL, 327..., Deland, FL 32724
$473,990

3 beds

|

3 baths

|

2,129 sq ft

|

House

1304 CLUB CRESSWIND WAY, DELAND, FL, 327...
Community: Cresswind DeLand
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Cresswind DeLand 1352 SAVOY LN, DELAND, FL, 32724, Deland, FL 32724
$363,990

2 beds

|

2 baths

|

1,434 sq ft

|

House

1352 SAVOY LN, DELAND, FL, 32724
Community: Cresswind DeLand
The Villages® 1019 AVALON AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$280,000

2 beds

|

2 baths

|

1,623 sq ft

|

Villa

1019 AVALON AVE, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1722 BUGLE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$425,000

3 beds

|

2 baths

|

1,667 sq ft

|

House

1722 BUGLE TER, THE VILLAGES, FL, 32162
Community: The Villages®
Trilogy® Orlando 134 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$363,000

3 beds

|

2 baths

|

1,644 sq ft

|

House

134 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
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.
The Villages® 1130 AVENIDA DE LAS CASAS, LADY LAKE, FL..., Lady Lake, FL 32159
$445,000

2 beds

|

3 baths

|

1,780 sq ft

|

Condo

1130 AVENIDA DE LAS CASAS, LADY LAKE, FL...
Community: The Villages®
New Lake Ashton 4105 LIMERICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$535,000

3 beds

|

3 baths

|

2,371 sq ft

|

House

4105 LIMERICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
New Carlsberg Estates on Lake Suzanne 235 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$289,900

3 beds

|

3 baths

|

1,744 sq ft

|

House

235 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Sandpiper Golf & Country Club 6381 EGRET DR 28, LAKELAND, FL, 33809, Lakeland, FL 33809
$232,000

2 beds

|

2 baths

|

941 sq ft

|

Villa

6381 EGRET DR 28, LAKELAND, FL, 33809
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
New The Villages® 3065 GLENWOOD PL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$345,900

3 beds

|

2 baths

|

1,490 sq ft

|

House

3065 GLENWOOD PL, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 109 LYONIA LN, WILDWOOD, FL, 34785, Wildwood, FL 34785
$110,000

2 beds

|

2 baths

|

1,152 sq ft

|

Manufactured Home

109 LYONIA LN, WILDWOOD, FL, 34785
Community: The Villages®
The Villages® 421 ALDAMA AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$349,247

3 beds

|

2 baths

|

1,392 sq ft

|

House

421 ALDAMA AVE, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 3258 IIAMS CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$349,900

3 beds

|

2 baths

|

1,476 sq ft

|

House

3258 IIAMS CT, THE VILLAGES, FL, 32163
Community: The Villages®
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.
New The Villages® 17883 SE 87TH MELROSE CT, THE VILLAGES, ..., The Villages, FL 32162
$369,900

3 beds

|

2 baths

|

1,855 sq ft

|

House

17883 SE 87TH MELROSE CT, THE VILLAGES, ...
Community: The Villages®
The Villages® 3468 ROANOKE ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$265,000

2 beds

|

2 baths

|

1,182 sq ft

|

Villa

3468 ROANOKE ST, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1850 KYRLE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$1,050,000

3 beds

|

2 baths

|

2,227 sq ft

|

House

1850 KYRLE TER, THE VILLAGES, FL, 32162
Community: The Villages®
Solivita 601 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$239,239

2 beds

|

2 baths

|

1,258 sq ft

|

House

601 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
Venetian Bay 2967 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$358,500

3 beds

|

3 baths

|

1,672 sq ft

|

House

2967 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 2864 MANOR DOWNS, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$485,000

3 beds

|

2 baths

|

1,927 sq ft

|

House

2864 MANOR DOWNS, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 703 MELENDEZ WAY, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$339,000

3 beds

|

2 baths

|

1,509 sq ft

|

House

703 MELENDEZ WAY, THE VILLAGES, FL, 3215...
Community: The Villages®
The Villages® 651 D ANGELO LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$435,000

3 beds

|

2 baths

|

1,357 sq ft

|

Villa

651 D ANGELO LN, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 3604 CAMBRIA CIR, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$265,000

2 beds

|

2 baths

|

1,188 sq ft

|

Villa

3604 CAMBRIA CIR, THE VILLAGES, FL, 3216...
Community: The Villages®
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.
The Villages® 733 PALMA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$340,000

3 beds

|

2 baths

|

1,936 sq ft

|

House

733 PALMA DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1850 LAKE RIDGE DR, THE VILLAGES, FL, 32..., The Villages, FL 32162
$1,150,000

3 beds

|

3 baths

|

2,964 sq ft

|

House

1850 LAKE RIDGE DR, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 290 JEFFERSON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$340,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

290 JEFFERSON LN, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 1717 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$280,000

2 beds

|

2 baths

|

1,143 sq ft

|

Villa

1717 CAMPOS DR, THE VILLAGES, FL, 32162
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 3377 CLARA CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$299,900

2 beds

|

2 baths

|

1,240 sq ft

|

Villa

3377 CLARA CT, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 9231 SE 171ST COOPER LOOP, THE VILLAGES,..., The Villages, FL 32162
$375,900

3 beds

|

2 baths

|

1,850 sq ft

|

House

9231 SE 171ST COOPER LOOP, THE VILLAGES,...
Community: The Villages®

Want more information about active adult communities around Winter Park?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
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
2,377 homes
Remove Boundaries ×
Map Satellite

Reinmlsx

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: Jan 10, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top