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 61
98 communities near Winter Park
2,698 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
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
$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 (3 reviews)
![Stonecrest]()
$200ks
- $500ks
Stonecrest, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 2024
|
2,224 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)
![Twin Lakes]()
$200ks
- $600ks
Twin Lakes, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
2,000 homes
$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 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
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 (3 reviews)
![Lake Ashton]()
$200ks
- $500ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
$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 (8 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
5 rating (1 reviews)
![Cresswind at Victoria Gar...]()
$300ks
- $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 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
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
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
5 rating (1 reviews)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
$200ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 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
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
$100ks
- $200ks
Scottish Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1992
|
653 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
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
$300ks
- $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
557 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.
$300ks
Heritage - The Cottages o..., Okahumpka, FL
New Construction
|
55+ age-restricted
|
Built 2022 - present
|
179 homes
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 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
$300ks
- $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
216 homes
$400ks
- $1Ms
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
1,300 homes
$100ks
- $300ks
Highland Fairways, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1998
|
660 homes
$100ks
- $300ks
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
$200ks
- $400ks
The Lakes at Harmony, Harmony, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
400 homes
1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 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.
Venetian Bay
![2910 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,758 sq ft
|House
2910 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS A4685766 • REALTY ONE GROUP MVP, Loukas Masou... • REALTY ONE GROUP MVP
Indian River Colony Club
![1161 CONTINENTAL AVE, MELBOURNE, FL, 329..., Melbourne, FL 32940]()
2 beds
|2 baths
|1,880 sq ft
|House
1161 CONTINENTAL AVE, MELBOURNE, FL, 329...
Community: Indian River Colony Club
MLS 1071561 • Four Star Real Estate LLC, Shellie ... • Four Star Real Estate LLC
Traditions at Lake Ruby
![4020 CARTERET DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884]()
4 beds
|3 baths
|2,282 sq ft
|House
4020 CARTERET DR, WINTER HAVEN, FL, 3388...
Community: Traditions at Lake Ruby
MLS O6389154 • KELLER WILLIAMS ADVANTAGE III, Sof... • KELLER WILLIAMS ADVANTAGE III
Royal Harbor
![5245 CHINA SEA DR, TAVARES, FL, 32778, Tavares, FL 32778]()
3 beds
|2 baths
|1,862 sq ft
|House
5245 CHINA SEA DR, TAVARES, FL, 32778
Community: Royal Harbor
MLS G5109305 • BHHS FLORIDA REALTY, Catherine Lan... • BHHS FLORIDA REALTY
Tohoqua Reserve
![1823 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
3 beds
|2 baths
|1,579 sq ft
|Halfplex
1823 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS O6389198 • REALTY ONE GROUP ESTATES, Kelly Te... • REALTY ONE GROUP ESTATES
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
Trilogy® Orlando
![374 SALT MARSH LN, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|1,624 sq ft
|House
374 SALT MARSH LN, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS O6389203 • CENTURY 21 ALTON CLARK, Ginny Pete... • CENTURY 21 ALTON CLARK
Stonecrest
![11900 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,613 sq ft
|House
11900 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5108970 • RE/MAX PREMIER REALTY LADY LK, Cin... • RE/MAX PREMIER REALTY LADY LK
Trilogy® Orlando
![115 SALT MARSH LN, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|1,940 sq ft
|House
115 SALT MARSH LN, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS G5109207 • KELLER WILLIAMS ELITE PARTNERS III... • KELLER WILLIAMS ELITE PARTNERS III REALTY
Venetian Bay
![3038 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
2 beds
|2 baths
|1,096 sq ft
|Townhouse
3038 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS NS1087572 • EXIT REAL ESTATE PROPERTY SOL, Ca... • EXIT REAL ESTATE PROPERTY SOL
Cindy Certified
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.
Cindy Certified
Pelican Bay Daytona Beach
![240 BOB WHITE CT 240, DAYTONA BEACH, FL,..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,093 sq ft
|Condo
240 BOB WHITE CT 240, DAYTONA BEACH, FL,...
Community: Pelican Bay Daytona Beach
MLS NS1087527 • COLLADO REAL ESTATE, Chad Erickso... • COLLADO REAL ESTATE
Plantation at Leesburg
![3810 ST EMMA CT, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|4 baths
|2,473 sq ft
|House
3810 ST EMMA CT, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6386925 • BURNHAM REALTY LLC, Clinton Burnha... • BURNHAM REALTY LLC
Cindy Certified
Solivita
![524 MURANO DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS G5108775 • FLORIDA PLUS REALTY, LLC, Christin... • FLORIDA PLUS REALTY, LLC
Foxwood Lake Estates
![4969 DEERWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,040 sq ft
|Manufactured Home
4969 DEERWOOD DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS P4938047 • FLORIDA REALTY MARKETPLACE, Debra ... • FLORIDA REALTY MARKETPLACE
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
Lakes of Mount Dora
![3942 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
3 beds
|2 baths
|2,034 sq ft
|House
3942 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
MLS O6388176 • DR HORTON REALTY OF CENTRAL FLORID... • DR HORTON REALTY OF CENTRAL FLORIDA LLC
Cindy Certified
Cindy Certified
The Villages®
![16938 SE 94TH SUNNYBROOK CIR, THE VILLAG..., The Villages, FL 32162]()
2 beds
|2 baths
|1,163 sq ft
|Villa
16938 SE 94TH SUNNYBROOK CIR, THE VILLAG...
Community: The Villages®
MLS G5108710 • RE/MAX PREMIER REALTY LADY LK, Nao... • RE/MAX PREMIER REALTY LADY LK
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.
Sandpiper Golf & Country Club
![669 EAGLE RUN, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,134 sq ft
|House
669 EAGLE RUN, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4959718 • COLDWELL BANKER REALTY, Ginger Qui... • COLDWELL BANKER REALTY
Cindy Certified
Cindy Certified
Esplanade at Highland Ranch
![1282 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715]()
2 beds
|2 baths
|1,710 sq ft
|House
1282 ZEEK RIDGE ST, CLERMONT, FL, 34715
Community: Esplanade at Highland Ranch
MLS G5108850 • WATSON REALTY CORP., REALTORS, Ron... • WATSON REALTY CORP., REALTORS
Cresswind at Victoria Gardens
![109 AVENHAM DR, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,508 sq ft
|House
109 AVENHAM DR, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS O6385448 • NONA LEGACY POWERED BY LA ROSA, Pe... • NONA LEGACY POWERED BY LA ROSA
Alamanda Key
![3720 ALAMANDA KEY DR DRIVE, MELBOURNE, F..., Melbourne, FL 32901]()
3 beds
|2 baths
|1,729 sq ft
|House
3720 ALAMANDA KEY DR DRIVE, MELBOURNE, F...
Community: Alamanda Key
MLS 1070767 • Ellingson Properties, Jack C Jeffco... • Ellingson Properties
Heritage Hills
![2876 SANDY CAY ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|2,123 sq ft
|House
2876 SANDY CAY ST, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6386650 • BHHS FLORIDA REALTY, Patti Kincaid • BHHS FLORIDA REALTY
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
Cindy Certified
Cindy Certified
The Villages®
![5186 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484]()
3 beds
|4 baths
|1,929 sq ft
|House
5186 NE 122ND BLVD, OXFORD, FL, 34484
Community: The Villages®
MLS OM719308 • KELLER WILLIAMS CORNERSTONE RE, Ci... • KELLER WILLIAMS CORNERSTONE RE
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.
Stonecrest
![17584 SE 119TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,482 sq ft
|House
17584 SE 119TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS OM719422 • KELLER WILLIAMS CORNERSTONE RE, Ka... • KELLER WILLIAMS CORNERSTONE RE
Cindy Certified
Cindy Certified
Cindy Certified
Royal Harbor
![5732 FREEPORT DR, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS G5108407 • BHHS FLORIDA REALTY, Doug Piazza • BHHS FLORIDA REALTY
Lakeside Landings
![5427 COMPASS PT 1, OXFORD, FL, 34484, Oxford, FL 34484]()
2 beds
|2 baths
|1,281 sq ft
|Condo
5427 COMPASS PT 1, OXFORD, FL, 34484
Community: Lakeside Landings
MLS G5108257 • EXP REALTY LLC, Brenda Bell • EXP REALTY LLC
The Country Club of Mount Dora
![1500 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|3 baths
|2,544 sq ft
|House
1500 EDGEWATER DR, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS O6383176 • COLDWELL BANKER VANGUARD EDGE, Kay... • COLDWELL BANKER VANGUARD EDGE
Cindy Certified
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
The Villages®
![648 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159]()
3 beds
|2 baths
|1,774 sq ft
|House
648 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5108179 • CENTURY 21 ALTON CLARK, Kwynn Nich... • CENTURY 21 ALTON CLARK
Oakview
![1581 OAKVIEW CIR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33880]()
2 beds
|2 baths
|1,220 sq ft
|House
1581 OAKVIEW CIR, WINTER HAVEN, FL, 3388...
Community: Oakview
MLS G5108372 • LPT REALTY, LLC, Vanessa Aybar Bad... • LPT REALTY, LLC
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
In Winter Park, there is 1 small community with less than 500 homes.
The smallest 55+ community in Winter Park has 178 homes, the largest has 178 homes, and the average community consists of 178 homes.
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.
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?
Want to learn more about 55+ communities in Winter Park?
2,698
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: Oct 10, 2026.
This application does not include information on all of the properties available for sale at this time.
