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 43

2,414 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
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
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
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
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.
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
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
The Villages® 3073 RIVERDALE RD, THE VILLAGES, FL, 321..., The Villages, FL 32162
$411,000

3 beds

|

2 baths

|

1,700 sq ft

|

House

3073 RIVERDALE RD, THE VILLAGES, FL, 321...
Community: The Villages®
Alamanda Key 543 HEMING WAY, MELBOURNE, FL, 32901, Melbourne, FL 32901
$399,500

3 beds

|

2 baths

|

1,937 sq ft

|

House

543 HEMING WAY, MELBOURNE, FL, 32901
Community: Alamanda Key
Venetian Bay 3470 TESORO CIR, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$890,000

3 beds

|

3 baths

|

2,852 sq ft

|

House

3470 TESORO CIR, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Solivita 790 CARMEL LN, POINCIANA, FL, 34759, Poinciana, FL 34759
$417,500

4 beds

|

3 baths

|

2,430 sq ft

|

House

790 CARMEL LN, POINCIANA, FL, 34759
Community: Solivita
The Villages® 12392 NE 48TH LOOP, OXFORD, FL, 34484, Oxford, FL 34484
$295,000

4 beds

|

4 baths

|

2,002 sq ft

|

House

12392 NE 48TH LOOP, OXFORD, FL, 34484
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 4913 NE 122ND AVE, OXFORD, FL, 34484, Oxford, FL 34484
$390,000

4 beds

|

3 baths

|

2,629 sq ft

|

House

4913 NE 122ND AVE, OXFORD, FL, 34484
Community: The Villages®
Del Webb Orlando 516 PAMPLONA PL, DAVENPORT, FL, 33837, Davenport, FL 33837
$305,000

2 beds

|

2 baths

|

1,445 sq ft

|

House

516 PAMPLONA PL, DAVENPORT, FL, 33837
Community: Del Webb Orlando
The Villages® 8241 SE 176TH LAWSON LOOP, THE VILLAGES,..., The Villages, FL 32162
$249,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

8241 SE 176TH LAWSON LOOP, THE VILLAGES,...
Community: The Villages®
Kings Ridge 3656 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$349,900

3 beds

|

2 baths

|

1,498 sq ft

|

House

3656 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
Legacy of Leesburg 27601 COUNTRY STONE CT, LEESBURG, FL, 34..., Leesburg, FL 34748
$369,000

3 beds

|

2 baths

|

2,066 sq ft

|

House

27601 COUNTRY STONE CT, LEESBURG, FL, 34...
Community: Legacy of Leesburg
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 305 ROCK SPRINGS DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$499,000

3 beds

|

3 baths

|

2,454 sq ft

|

House

305 ROCK SPRINGS DR, KISSIMMEE, FL, 3475...
Community: Solivita
The Villages® 3435 INVERARY AVE, THE VILLAGES, FL, 321..., The Villages, FL 32163
$364,900

3 beds

|

2 baths

|

1,635 sq ft

|

House

3435 INVERARY AVE, THE VILLAGES, FL, 321...
Community: The Villages®
Breakaway Trails 71 CARRIAGE CREEK WAY, ORMOND BEACH, FL,..., Ormond Beach, FL 32174
$450,000

4 beds

|

3 baths

|

2,295 sq ft

|

House

71 CARRIAGE CREEK WAY, ORMOND BEACH, FL,...
Community: Breakaway Trails
The Villages® 1967 FLOWERSVILLE PL, THE VILLAGES, FL, ..., The Villages, FL 32163
$577,500

3 beds

|

3 baths

|

2,016 sq ft

|

House

1967 FLOWERSVILLE PL, THE VILLAGES, FL, ...
Community: The Villages®
Scottish Highlands 1 DURNESS CT 1, LEESBURG, FL, 34788, Leesburg, FL 34788
$183,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

1 DURNESS CT 1, LEESBURG, FL, 34788
Community: Scottish Highlands
Scottish Highlands 510 GALLOWAY CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$185,000

2 beds

|

2 baths

|

1,171 sq ft

|

House

510 GALLOWAY CT, LEESBURG, FL, 34788
Community: Scottish Highlands
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Kings Ridge 4207 KINGSLEY ST, CLERMONT, FL, 34711, Clermont, FL 34711
$355,000

3 beds

|

2 baths

|

1,722 sq ft

|

House

4207 KINGSLEY ST, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 1115 SALIDO AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$365,000

3 beds

|

2 baths

|

1,728 sq ft

|

House

1115 SALIDO AVE, THE VILLAGES, FL, 32159
Community: The Villages®
Pennbrooke Fairways 32747 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$229,247

2 beds

|

2 baths

|

1,504 sq ft

|

House

32747 TIMBERWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Lake Ashton 4632 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$399,900

3 beds

|

2 baths

|

2,354 sq ft

|

House

4632 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
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 2892 MONAGHAN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$474,900

3 beds

|

3 baths

|

2,040 sq ft

|

House

2892 MONAGHAN DR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
Solivita 308 BEACON AVE, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$310,000

2 beds

|

2 baths

|

2,038 sq ft

|

House

308 BEACON AVE, KISSIMMEE, FL, 34759
Community: Solivita
Spruce Creek Country Club 13667 SE 91ST AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$459,000

3 beds

|

2 baths

|

2,270 sq ft

|

House

13667 SE 91ST AVE, SUMMERFIELD, FL, 3449...
Lake Ashton 4189 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859
$695,000

3 beds

|

2 baths

|

2,478 sq ft

|

House

4189 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
Royal Harbor 5008 ADRIATIC AVE, TAVARES, FL, 32778, Tavares, FL 32778
$359,000

3 beds

|

2 baths

|

2,101 sq ft

|

House

5008 ADRIATIC AVE, TAVARES, FL, 32778
Community: Royal Harbor
Lake Ashton 4360 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$375,000

3 beds

|

2 baths

|

2,265 sq ft

|

House

4360 ASHTON CLUB DR, LAKE WALES, FL, 338...
Community: Lake Ashton
The Timbers at Everlands 2322 ANTARUS DR, PALM BAY, FL, 32907, Palm Bay, FL 32907
$384,900

3 beds

|

3 baths

|

2,070 sq ft

|

House

2322 ANTARUS DR, PALM BAY, FL, 32907
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Venetian Bay 3621 CASELLO DR, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$349,900

3 beds

|

3 baths

|

1,827 sq ft

|

Townhouse

3621 CASELLO DR, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
The Villages® 1653 HOMER AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$394,000

3 beds

|

2 baths

|

1,887 sq ft

|

House

1653 HOMER AVE, THE VILLAGES, FL, 32162
Community: The Villages®
Solivita 3810 VIA MAZZINI CT, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$725,000

3 beds

|

3 baths

|

3,064 sq ft

|

House

3810 VIA MAZZINI CT, 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.
Lake Henry Estates 422 HARBOURVIEW DR, HAINES CITY, FL, 338..., Haines City, FL 33844
$284,900

3 beds

|

2 baths

|

1,793 sq ft

|

House

422 HARBOURVIEW DR, HAINES CITY, FL, 338...
Community: Lake Henry Estates
Fountain View 1477 FOUNTAIN VIEW ST, ORMOND BEACH, FL,..., Ormond Beach, FL 32174
$367,000

4 beds

|

2 baths

|

1,836 sq ft

|

House

1477 FOUNTAIN VIEW ST, ORMOND BEACH, FL,...
Community: Fountain View
The Villages® 1819 CAPTIVA CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$317,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

1819 CAPTIVA CT, THE VILLAGES, FL, 32162
Community: The Villages®
Spruce Creek Country Club 13589 SE 87TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$299,900

3 beds

|

2 baths

|

1,719 sq ft

|

House

13589 SE 87TH CIR, SUMMERFIELD, FL, 3449...
Indian River Colony Club 1372 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940
$319,000

2 beds

|

2 baths

|

1,616 sq ft

|

House

1372 INDEPENDENCE AVE, MELBOURNE, FL, 32...
The Timbers at Everlands 845 ANTIBES CT, PALM BAY, FL, 32907, Palm Bay, FL 32907
$429,950

3 beds

|

3 baths

|

2,006 sq ft

|

House

845 ANTIBES CT, PALM BAY, FL, 32907
The Timbers at Everlands 2213 ANTARUS DR, PALM BAY, FL, 32907, Palm Bay, FL 32907
$419,950

2 beds

|

3 baths

|

1,670 sq ft

|

House

2213 ANTARUS DR, PALM BAY, FL, 32907
Scottish Highlands 55 ABERDEEN CIR, LEESBURG, FL, 34788, Leesburg, FL 34788
$165,000

2 beds

|

2 baths

|

1,056 sq ft

|

House

55 ABERDEEN CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Stonecrest 17424 SE 111TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$257,000

3 beds

|

2 baths

|

1,446 sq ft

|

House

17424 SE 111TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
Indian River Colony Club 1680 OLD GLORY BLVD, MELBOURNE, FL, 3294..., Melbourne, FL 32940
$259,999

2 beds

|

2 baths

|

1,033 sq ft

|

House

1680 OLD GLORY BLVD, MELBOURNE, FL, 3294...
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
2,414 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: May 25, 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