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Winter Park, FL 55+ active adult communities & homes for sale - Page 56
98 communities near Winter Park
2,702 homes near Winter Park
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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
$300ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 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
4.7 rating (18 reviews)
![Solivita]()
$300ks
- $700ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 homes
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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 (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)
![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.
$200ks
- $800ks
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 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 (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)
![Lake Ashton]()
$200ks
- $500ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
5 rating (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 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
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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)
![Sandpiper Golf & Coun...]()
$100ks
- $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale
|
55+ age-restricted
|
Built 1985 - present
|
1,193 homes
$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 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
Download the Ultimate 55+ Homebuying Guide
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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)
![Cresswind at Victoria Gar...]()
$300ks
- $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
$100ks
- $300ks
Highland Fairways, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1998
|
660 homes
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
$200ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 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)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
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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)
![Del Webb Sunbridge]()
$400ks
- $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
1,300 homes
$300ks
- $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
216 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
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
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
$100ks
- $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
|
545 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
$200ks
- $500ks
The Timbers at Everlands, Palm Bay, FL
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
450 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
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
$300ks
- $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
557 homes
$100ks
- $200ks
Colonnades, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1985 - 1994
|
360 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.
Trilogy® Orlando
![389 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736]()
2 beds
|2 baths
|1,932 sq ft
|House
389 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
MLS S5145090 • WATSON REALTY CORP., William Sirig... • WATSON REALTY CORP.
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
The Villages®
![889 JAY ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,986 sq ft
|Villa
889 JAY ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5109340 • SELLSTATE SUPERIOR REALTY, Susan B... • SELLSTATE SUPERIOR REALTY
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
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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
Summer Trees
![111 CYPRESS POND RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,160 sq ft
|House
111 CYPRESS POND RD, PORT ORANGE, FL, 32...
Community: Summer Trees
MLS 1223959 • Collado Real Estate, Bryan Disbrow • Collado Real Estate
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
Carillon Lakes
![3818 SERENADE LN 3818, LAKELAND, FL, 338..., Lakeland, FL 33811]()
3 beds
|2 baths
|1,908 sq ft
|Condo
3818 SERENADE LN 3818, LAKELAND, FL, 338...
Community: Carillon Lakes
MLS L4960111 • KELLER WILLIAMS REALTY SMART 1, Je... • KELLER WILLIAMS REALTY SMART 1
Latitude Margaritaville
![544 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,608 sq ft
|House
544 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS 1223929 • Keller Williams Realty Florida Part... • Keller Williams Realty Florida Partners
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.
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
Arlington Ridge
![27040 CAMERONS RUN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,007 sq ft
|House
27040 CAMERONS RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS G5106477 • COLDWELL BANKER VANGUARD EDGE, Lyn... • COLDWELL BANKER VANGUARD EDGE
Lake Ashton
![6261 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884]()
3 beds
|2 baths
|2,512 sq ft
|House
6261 PINEHURST LOOP, WINTER HAVEN, FL, 3...
Community: Lake Ashton
MLS L4959857 • LOCKHART & ASSOCIATES INC, Anita L... • LOCKHART & ASSOCIATES INC
Huntington at Hunter's Ridge
![82 WRENDALE LOOP, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,600 sq ft
|House
82 WRENDALE LOOP, ORMOND BEACH, FL, 3217...
Community: Huntington at Hunter's Ridge
MLS 1223905 • Collado Real Estate, Melissa Rechic... • Collado Real Estate
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
Want to learn more about 55+ communities in Winter Park?
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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
Lake Ashton
![4432 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
2 beds
|2 baths
|1,083 sq ft
|House
4432 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS L4960054 • ROOST REALTY GROUP LLC, Barb Wiech... • ROOST REALTY GROUP LLC
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
Cindy Certified
Arlington Ridge
![3749 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,031 sq ft
|House
3749 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
MLS G5109269 • FLORIDA PLUS REALTY, LLC, Simon Am... • FLORIDA PLUS REALTY, LLC
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
The Villages®
![4193 SILVANA WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,492 sq ft
|Villa
4193 SILVANA WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5109267 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Del Webb Sunbridge
![6354 SHIMMERING SHORES LN, ST CLOUD, FL,..., St Cloud, FL 34771]()
2 beds
|2 baths
|1,670 sq ft
|House
6354 SHIMMERING SHORES LN, ST CLOUD, FL,...
Community: Del Webb Sunbridge
MLS O6388693 • REALTY ONE GROUP MAGIC CITY, Jory ... • REALTY ONE GROUP MAGIC CITY
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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
Spruce Creek Country Club
![9845 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,638 sq ft
|House
9845 SE 138TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS GC538263 • MOMENTUM REALTY - GAINESVILLE, Che... • MOMENTUM REALTY - GAINESVILLE
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®
![16865 SE 93RD CUTHBERT CIR, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,855 sq ft
|House
16865 SE 93RD CUTHBERT CIR, THE VILLAGES...
Community: The Villages®
MLS G5109136 • SALLY LOVE REAL ESTATE, Julie Nay ... • SALLY LOVE REAL ESTATE
Solivita
![524 MURANO DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS G5108775 • FLORIDA PLUS REALTY, LLC, Christin... • FLORIDA PLUS REALTY, LLC
Cindy Certified
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
Esplanade at Highland Ranch
![2330 HAMILTON RIDGE RD, CLERMONT, FL, 34..., Clermont, FL 34715]()
2 beds
|2 baths
|1,778 sq ft
|House
2330 HAMILTON RIDGE RD, CLERMONT, FL, 34...
Community: Esplanade at Highland Ranch
MLS O6387965 • PREFERRED REAL ESTATE BROKERS, Lis... • PREFERRED REAL ESTATE BROKERS
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
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
The Villages®
![646 STRATFORD LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|3 baths
|2,245 sq ft
|House
646 STRATFORD LN, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS OM719997 • RE/MAX PREMIER REALTY LADY LK, Jay... • RE/MAX PREMIER REALTY LADY LK
Plantation at Leesburg
![5024 LONG MEADOW DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,847 sq ft
|House
5024 LONG MEADOW DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5109100 • CARLINO REAL ESTATE GROUP INC, Mar... • CARLINO REAL ESTATE GROUP INC
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?
2,702
homes
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REIN updates its listings on a daily basis. Data last updated: Aug 25, 2026.
This application does not include information on all of the properties available for sale at this time.
