not an image

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 30

2,513 homes near Winter Park

Sort by:

Relevance

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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes
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
5 rating (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 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.
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
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 (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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Grand Haven
$200ks - $800ks
Grand Haven, Palm Coast, FL
New and Resale | Age-targeted | Built 1997 - present | 1,901 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
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 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.
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
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4 rating (4 reviews) Lakes of Mount Dora
$300ks - $900ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
5 rating (2 reviews) Heritage Isle
$300ks - $500ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 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) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$200ks - $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
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 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
Tohoqua Reserve
$300ks - $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2021 - present | 258 homes
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
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.
3.8 rating (5 reviews) Traditions at Lake Ruby
$200ks - $300ks
Traditions at Lake Ruby, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 552 homes
The Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes
12...3
The Villages® 7821 SE 166TH SMALLWOOD PL, THE VILLAGES..., The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,997 sq ft

|

House

7821 SE 166TH SMALLWOOD PL, THE VILLAGES...
Community: The Villages®
Royal Harbor 5928 BRITTANIA BLVD, TAVARES, FL, 32778, Tavares, FL 32778
$309,000

3 beds

|

2 baths

|

1,754 sq ft

|

House

5928 BRITTANIA BLVD, TAVARES, FL, 32778
Community: Royal Harbor
Plantation Bay Golf & Country Club 831 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$389,999

3 beds

|

3 baths

|

2,101 sq ft

|

Townhouse

831 PINEWOOD DR, ORMOND BEACH, FL, 32174
The Villages® 650 BRADFORD LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163
$400,000

3 beds

|

2 baths

|

1,875 sq ft

|

House

650 BRADFORD LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
Del Webb at Viera 3032 TIDEPOOL PL, MELBOURNE, FL, 32940, Melbourne, FL 32940
$644,900

3 beds

|

2 baths

|

1,991 sq ft

|

House

3032 TIDEPOOL PL, MELBOURNE, FL, 32940
Community: Del Webb at Viera
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Grand Isle 1635 TIMACUAN DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$485,000

3 beds

|

2 baths

|

2,010 sq ft

|

House

1635 TIMACUAN DR, MELBOURNE, FL, 32940
Community: Grand Isle
The Villages® 1920 TRANQUILITY LN, THE VILLAGES, FL, 3..., The Villages, FL 32162
$399,900

3 beds

|

2 baths

|

1,608 sq ft

|

Villa

1920 TRANQUILITY LN, THE VILLAGES, FL, 3...
Community: The Villages®
Solivita 632 PORTOFINO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$279,999

2 beds

|

2 baths

|

1,456 sq ft

|

House

632 PORTOFINO DR, KISSIMMEE, FL, 34759
Community: Solivita
American Village 33 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164
$364,990

3 beds

|

3 baths

|

2,033 sq ft

|

House

33 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
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.
Del Webb Sunbridge 6237 CITRUS GROVE CT, ST CLOUD, FL, 3477..., St Cloud, FL 34771
$560,000

3 beds

|

2 baths

|

2,084 sq ft

|

House

6237 CITRUS GROVE CT, ST CLOUD, FL, 3477...
Community: Del Webb Sunbridge
The Villages® 2144 BILLER CIR, THE VILLAGES, FL, 32163, The Villages, FL 32163
$889,900

3 beds

|

3 baths

|

1,975 sq ft

|

House

2144 BILLER CIR, THE VILLAGES, FL, 32163
Community: The Villages®
Latitude Margaritaville 584 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$462,500

2 beds

|

2 baths

|

1,563 sq ft

|

House

584 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
The Timbers at Everlands 821 ANTIBES CT, PALM BAY, FL, 32907, Palm Bay, FL 32907
$399,000

3 beds

|

3 baths

|

2,132 sq ft

|

House

821 ANTIBES CT, PALM BAY, FL, 32907
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Park Place 21 PARK PLACE CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164
$360,000

3 beds

|

2 baths

|

1,878 sq ft

|

House

21 PARK PLACE CIR, PALM COAST, FL, 32164
Community: Park Place
The Villages® 2001 CIPRIANO PL, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$344,900

3 beds

|

2 baths

|

1,527 sq ft

|

House

2001 CIPRIANO PL, THE VILLAGES, FL, 3215...
Community: The Villages®
Cresswind at Victoria Gardens 1539 LAMBROOK DR, DELAND, FL, 32724, Deland, FL 32724
$495,000

3 beds

|

3 baths

|

2,206 sq ft

|

House

1539 LAMBROOK DR, DELAND, FL, 32724
The Villages® 805 OAK BLVD, WILDWOOD, FL, 34785, Wildwood, FL 34785
$186,000

2 beds

|

2 baths

|

1,560 sq ft

|

Manufactured Home

805 OAK BLVD, WILDWOOD, FL, 34785
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® 605 RAINBOW BLVD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$213,000

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

605 RAINBOW BLVD, LADY LAKE, FL, 32159
Community: The Villages®
Sandpiper Golf & Country Club 6087 SEAGULL LN, LAKELAND, FL, 33809, Lakeland, FL 33809
$324,900

3 beds

|

2 baths

|

1,899 sq ft

|

House

6087 SEAGULL LN, LAKELAND, FL, 33809
Del Webb Oasis 13343 SUNNY RETREAT LN, WINTER GARDEN, F..., Winter Garden, FL 34787
$899,900

3 beds

|

2 baths

|

2,214 sq ft

|

House

13343 SUNNY RETREAT LN, WINTER GARDEN, F...
Community: Del Webb Oasis
The Villages® 758 MOORE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$895,000

3 beds

|

2 baths

|

2,642 sq ft

|

House

758 MOORE TER, 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
Stonecrest 12104 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$375,000

3 beds

|

2 baths

|

1,609 sq ft

|

House

12104 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Spruce Creek South 10525 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$190,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

10525 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Colonnades 4861 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811
$199,900

2 beds

|

2 baths

|

1,014 sq ft

|

House

4861 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
Four Seasons at Orlando 7637 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747
$425,000

2 beds

|

2 baths

|

1,557 sq ft

|

Villa

7637 SAND PIERRE CT, KISSIMMEE, FL, 3474...
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 Ridge 33 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$489,000

4 beds

|

3 baths

|

2,156 sq ft

|

House

33 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Del Webb Sunbridge 2434 N CLIFF WAY, ST CLOUD, FL, 34771, St Cloud, FL 34771
$419,900

2 beds

|

2 baths

|

1,584 sq ft

|

Villa

2434 N CLIFF WAY, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
Stonecrest 11702 SE 173RD LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$459,900

3 beds

|

2 baths

|

2,009 sq ft

|

House

11702 SE 173RD LANE RD, SUMMERFIELD, FL,...
Community: Stonecrest
Plantation at Leesburg 25003 CYPRESS POND CT, LEESBURG, FL, 347..., Leesburg, FL 34748
$309,000

2 beds

|

2 baths

|

1,868 sq ft

|

House

25003 CYPRESS POND CT, LEESBURG, FL, 347...
The Villages® 8620 SE 166TH BIRCHBROOK LOOP, THE VILLA..., The Villages, FL 32162
$349,900

2 beds

|

2 baths

|

1,245 sq ft

|

Villa

8620 SE 166TH BIRCHBROOK LOOP, THE VILLA...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Spruce Creek South 17866 SE 108TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$224,900

2 beds

|

2 baths

|

1,450 sq ft

|

House

17866 SE 108TH CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Arlington Ridge 4622 SHENANDOAH RIVER TRL, LEESBURG, FL,..., Leesburg, FL 34748
$365,000

3 beds

|

2 baths

|

1,699 sq ft

|

House

4622 SHENANDOAH RIVER TRL, LEESBURG, FL,...
Community: Arlington Ridge
The Villages® 17760 SE 91ST FREEDOM CT, THE VILLAGES, ..., The Villages, FL 32162
$279,900

3 beds

|

2 baths

|

1,590 sq ft

|

Villa

17760 SE 91ST FREEDOM CT, THE VILLAGES, ...
Community: The Villages®
The Villages® 920 SAINT ANDREWS BLVD, THE VILLAGES, FL..., The Villages, FL 32159
$249,000

2 beds

|

2 baths

|

1,340 sq ft

|

Manufactured Home

920 SAINT ANDREWS BLVD, THE VILLAGES, FL...
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® 144 COSTA MESA DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$329,900

3 beds

|

2 baths

|

2,046 sq ft

|

House

144 COSTA MESA DR, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 8275 SE 177TH WINTERTHUR LOOP, THE VILLA..., The Villages, FL 32162
$365,500

3 beds

|

2 baths

|

1,581 sq ft

|

House

8275 SE 177TH WINTERTHUR LOOP, THE VILLA...
Community: The Villages®
The Villages® 335 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$300,000

2 beds

|

2 baths

|

1,360 sq ft

|

House

335 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
Lake James 7826 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$399,900

2 beds

|

2 baths

|

1,788 sq ft

|

House

7826 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 737 DOWDING WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$925,000

4 beds

|

3 baths

|

2,518 sq ft

|

House

737 DOWDING WAY, THE VILLAGES, FL, 32162
Community: The Villages®
Tohoqua Reserve 1911 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$370,000

2 beds

|

2 baths

|

1,579 sq ft

|

Villa

1911 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve

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
2,513 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: Apr 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