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 40

2,259 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
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
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
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 - $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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
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.
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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
3.8 rating (6 reviews) Trilogy® Orlando
$200ks - $500ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
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
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
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 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
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 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) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 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
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 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) Legacy of Leesburg
$200ks - $400ks
Legacy of Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 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
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 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
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 Timbers at Everlands
$200ks - $500ks
The Timbers at Everlands, Palm Bay, FL
New Construction | 55+ age-restricted | Built 2023 - present | 450 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 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.
12...3
Indian River Colony Club 1071 CONTINENTAL AVE, MELBOURNE, FL, 329..., Melbourne, FL 32940
$330,000

4 beds

|

3 baths

|

1,919 sq ft

|

House

1071 CONTINENTAL AVE, MELBOURNE, FL, 329...
Spruce Creek Country Club 9435 SE 124TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$309,900

2 beds

|

2 baths

|

1,720 sq ft

|

House

9435 SE 124TH PL, SUMMERFIELD, FL, 34491
Venetian Bay 365 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$375,000

3 beds

|

2 baths

|

1,614 sq ft

|

House

365 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Del Webb Orlando 715 ASTURIAS RD, DAVENPORT, FL, 33837, Davenport, FL 33837
$414,900

2 beds

|

2 baths

|

2,056 sq ft

|

House

715 ASTURIAS RD, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Venetian Bay 3446 MEDICI BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$420,000

4 beds

|

4 baths

|

2,379 sq ft

|

Townhouse

3446 MEDICI 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
Cresswind at Victoria Gardens 215 AVENHAM DR, DELAND, FL, 32724, Deland, FL 32724
$575,000

3 beds

|

3 baths

|

2,792 sq ft

|

House

215 AVENHAM DR, DELAND, FL, 32724
Latitude Margaritaville 281 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$629,000

2 beds

|

2 baths

|

1,922 sq ft

|

House

281 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Trilogy® Orlando 125 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$370,000

3 beds

|

2 baths

|

1,680 sq ft

|

House

125 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Del Webb Sunbridge 2555 PINE PRESERVE CT, ST CLOUD, FL, 347..., St Cloud, FL 34771
$875,000

3 beds

|

4 baths

|

2,866 sq ft

|

House

2555 PINE PRESERVE CT, ST CLOUD, FL, 347...
Community: Del Webb Sunbridge
Latitude Margaritaville 338 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$635,000

3 beds

|

3 baths

|

2,393 sq ft

|

House

338 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
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.
Lakeside Landings 10144 LAKE MIONA WAY, OXFORD, FL, 34484, Oxford, FL 34484
$529,000

4 beds

|

2 baths

|

2,319 sq ft

|

House

10144 LAKE MIONA WAY, OXFORD, FL, 34484
Community: Lakeside Landings
The Villages® 17559 SE 81ST PARNASSUS CT, THE VILLAGES..., The Villages, FL 32162
$384,900

3 beds

|

2 baths

|

1,597 sq ft

|

House

17559 SE 81ST PARNASSUS CT, THE VILLAGES...
Community: The Villages®
Traditions at Lake Ruby 4019 CARTERET DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$262,500

2 beds

|

2 baths

|

1,719 sq ft

|

House

4019 CARTERET DR, WINTER HAVEN, FL, 3388...
Halifax Plantation 1437 CARLOW CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$330,000

3 beds

|

2 baths

|

1,684 sq ft

|

House

1437 CARLOW CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
Latitude Margaritaville 673 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$379,000

2 beds

|

2 baths

|

1,308 sq ft

|

House

673 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Kings Ridge 3622 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$369,900

2 beds

|

2 baths

|

1,792 sq ft

|

House

3622 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Royal Harbor 6105 DORY WAY, TAVARES, FL, 32778, Tavares, FL 32778
$300,000

3 beds

|

2 baths

|

1,556 sq ft

|

House

6105 DORY WAY, TAVARES, FL, 32778
Community: Royal Harbor
The Villages® 17369 SE 75TH COACHMAN CT, THE VILLAGES,..., The Villages, FL 32162
$249,900

2 beds

|

2 baths

|

1,213 sq ft

|

House

17369 SE 75TH COACHMAN CT, THE VILLAGES,...
Community: The Villages®
The Villages® 2303 NAUTILUS LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$324,900

2 beds

|

2 baths

|

1,196 sq ft

|

Villa

2303 NAUTILUS LN, THE VILLAGES, FL, 3216...
Community: The Villages®
Solivita 162 TALL PINES PASS, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$315,000

2 beds

|

2 baths

|

2,038 sq ft

|

House

162 TALL PINES PASS, KISSIMMEE, FL, 3475...
Community: Solivita
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.
Solivita 813 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$499,000

3 beds

|

3 baths

|

2,454 sq ft

|

House

813 GLENDORA RD, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 17470 SE 93RD VINE AVE, THE VILLAGES, FL..., The Villages, FL 32162
$250,000

2 beds

|

2 baths

|

1,172 sq ft

|

Villa

17470 SE 93RD VINE AVE, THE VILLAGES, FL...
Community: The Villages®
The Villages® 624 FAYETTE CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$405,999

3 beds

|

2 baths

|

1,502 sq ft

|

House

624 FAYETTE CT, THE VILLAGES, FL, 32162
Community: The Villages®
Venetian Bay 3049 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$315,000

3 beds

|

3 baths

|

1,614 sq ft

|

House

3049 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
The Villages® 1988 DOVE HOLLOW RUN, THE VILLAGES, FL, ..., The Villages, FL 32162
$814,900

4 beds

|

2 baths

|

2,544 sq ft

|

House

1988 DOVE HOLLOW RUN, THE VILLAGES, FL, ...
Community: The Villages®
Venetian Bay 3057 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$545,000

4 beds

|

4 baths

|

2,086 sq ft

|

Townhouse

3057 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Trilogy® Orlando 334 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$445,000

2 beds

|

2 baths

|

1,967 sq ft

|

House

334 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Harbor Hills Country Club 39125 TACOMA DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$499,000

3 beds

|

3 baths

|

2,584 sq ft

|

House

39125 TACOMA DR, LADY LAKE, FL, 32159
Kings Ridge 3734 HASTING LN, CLERMONT, FL, 34711, Clermont, FL 34711
$369,900

2 beds

|

2 baths

|

1,985 sq ft

|

House

3734 HASTING LN, CLERMONT, FL, 34711
Community: Kings Ridge
Trilogy® Orlando 371 SALT MARSH LN, GROVELAND, FL, 34736, Groveland, FL 34736
$379,000

2 beds

|

2 baths

|

1,624 sq ft

|

House

371 SALT MARSH LN, GROVELAND, FL, 34736
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® 5716 MELVIN DR, THE VILLAGES, FL, 32163, The Villages, FL 32163
$524,550

3 beds

|

3 baths

|

1,901 sq ft

|

House

5716 MELVIN DR, THE VILLAGES, FL, 32163
Community: The Villages®
Plantation Bay Golf & Country Club 1290 ROYAL POINTE LN, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174
$545,000

4 beds

|

2 baths

|

2,141 sq ft

|

House

1290 ROYAL POINTE LN, ORMOND BEACH, FL, ...
The Villages® 2261 WELCOME WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$375,000

3 beds

|

2 baths

|

1,488 sq ft

|

House

2261 WELCOME WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
Bridgewater at Viera 2718 MILLENNIUM CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940
$615,000

4 beds

|

4 baths

|

2,390 sq ft

|

House

2718 MILLENNIUM CIR, MELBOURNE, FL, 3294...
Trilogy® Orlando 651 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736
$425,000

3 beds

|

2 baths

|

1,862 sq ft

|

House

651 CONSERVATION BLVD, GROVELAND, FL, 34...
Community: Trilogy® Orlando
Solivita 113 TIVOLI TRACE CT, POINCIANA, FL, 3475..., Poinciana, FL 34759
$489,900

3 beds

|

3 baths

|

2,450 sq ft

|

House

113 TIVOLI TRACE CT, POINCIANA, FL, 3475...
Community: Solivita
Grand Haven 3 RIVER PARK DR, PALM COAST, FL, 32137, Palm Coast, FL 32137
$450,000

2 beds

|

2 baths

|

1,828 sq ft

|

Townhouse

3 RIVER PARK DR, PALM COAST, FL, 32137
Community: Grand Haven
Trilogy® Orlando 389 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$460,000

2 beds

|

2 baths

|

1,932 sq ft

|

House

389 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Venetian Bay 2910 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$329,990

3 beds

|

3 baths

|

1,758 sq ft

|

House

2910 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Summer Trees 111 CYPRESS POND RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$229,900

2 beds

|

2 baths

|

1,160 sq ft

|

House

111 CYPRESS POND RD, PORT ORANGE, FL, 32...
Community: Summer Trees
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.

Frequently Asked Questions


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
2,259 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: Jul 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