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Winter Park, FL 55+ active adult communities & homes for sale - Page 52
98 communities near Winter Park
2,698 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
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
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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
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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
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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)
![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?
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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.
Plantation at Leesburg
![3538 MULBERRY GROVE LOOP, LEESBURG, FL, ..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,407 sq ft
|House
3538 MULBERRY GROVE LOOP, LEESBURG, FL, ...
Community: Plantation at Leesburg
MLS G5112827 • COLDWELL BANKER VANGUARD EDGE, Deb... • COLDWELL BANKER VANGUARD EDGE
Cindy Certified
Traditions at Lake Ruby
![4130 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,819 sq ft
|House
4130 BEDFORD AVE, WINTER HAVEN, FL, 3388...
Community: Traditions at Lake Ruby
MLS L4962090 • COLDWELL BANKER REALTY, Bryan Dick... • COLDWELL BANKER REALTY
The Villages®
![2047 DUNSTER CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,851 sq ft
|House
2047 DUNSTER CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS OM725287 • EXP REALTY LLC, Cristine Kelty • EXP REALTY LLC
Cindy Certified
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Questions? Call us:
(888) 625-4885
Royal Harbor
![3257 BALTIC SEA BLVD, TAVARES, FL, 32778, Tavares, FL 32778]()
3 beds
|3 baths
|2,012 sq ft
|House
3257 BALTIC SEA BLVD, TAVARES, FL, 32778
Community: Royal Harbor
MLS G5112738 • BHHS FLORIDA REALTY, Catherine Lan... • BHHS FLORIDA REALTY
The Villages®
![418 FLOSSMOOR CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,685 sq ft
|Villa
418 FLOSSMOOR CT, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5112799 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Plantation at Leesburg
![5030 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,308 sq ft
|House
5030 EL DESTINO DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5112760 • CENTURY 21 CARIOTI, Bonnie Valenti... • CENTURY 21 CARIOTI
Highland Lakes
![26912 BECKER CT, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,498 sq ft
|House
26912 BECKER CT, LEESBURG, FL, 34748
Community: Highland Lakes
MLS S5150365 • PARTNERSHIP REALTY INC., Yudit Her... • PARTNERSHIP REALTY INC.
Latitude Margaritaville
![328 TIKI TER, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,563 sq ft
|House
328 TIKI TER, DAYTONA BEACH, FL, 32124
Community: Latitude Margaritaville
MLS 1226768 • Bob Hodges and Sons Realty, Kelley ... • Bob Hodges and Sons Realty
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.
Spruce Creek South
![9532 SE 173RD LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,678 sq ft
|House
9532 SE 173RD LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS OM725266 • COLDWELL REALTY SOLD GUARANTEE, Sc... • COLDWELL REALTY SOLD GUARANTEE
Pennbrooke Fairways
![412 WESTWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,140 sq ft
|House
412 WESTWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5112777 • RIGHT REALTY CONNECTION, INC., Joh... • RIGHT REALTY CONNECTION, INC.
Harbor Hills Country Club
![5066 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
4 beds
|3 baths
|2,544 sq ft
|House
5066 GREENS DR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS NS1088297 • COLLADO REAL ESTATE, Michelle Alb... • COLLADO REAL ESTATE
Palms at Serenoa
![17386 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714]()
3 beds
|2 baths
|1,621 sq ft
|House
17386 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
MLS G5112773 • LIST NOW REALTY, LLC, Matt Buttner • LIST NOW REALTY, LLC
Lakes of Mount Dora
![8237 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
4 beds
|3 baths
|3,159 sq ft
|House
8237 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS G5112496 • COAST TO COAST REAL ESTATE PRO, Al... • COAST TO COAST REAL ESTATE PRO
Highland Lakes
![5503 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS G5112726 • COLDWELL BANKER REALTY, Sara Suthe... • COLDWELL BANKER REALTY
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
The Villages®
![23202 SANDALWOOD DR 202, WILDWOOD, FL, 3..., Wildwood, FL 34785]()
3 beds
|3 baths
|1,474 sq ft
|Condo
23202 SANDALWOOD DR 202, WILDWOOD, FL, 3...
Community: The Villages®
MLS G5112607 • MORRIS REALTY AND INVESTMENTS, The... • MORRIS REALTY AND INVESTMENTS
Highland Lakes
![6419 BORG ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS G5112734 • COLDWELL BANKER REALTY, Sara Suthe... • COLDWELL BANKER REALTY
Solivita
![184 VENTANA DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5150079 • PELLEGO, LLC, Stan Wilson • PELLEGO, LLC
Royal Highlands
![21101 BRAVEHEART DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|3 baths
|2,221 sq ft
|House
21101 BRAVEHEART DR, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5112516 • FLORIDA PLUS REALTY, LLC, Tonya Ti... • FLORIDA PLUS 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.
The Villages®
![2382 OTHELLO CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,196 sq ft
|Villa
2382 OTHELLO CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS OM725096 • RE/MAX PREMIER REALTY, Cory Freili... • RE/MAX PREMIER REALTY
Carmel Condominium
![1420 HUNTINGTON LN 2402, ROCKLEDGE, FL, ..., Rockledge, FL 32955]()
2 beds
|2 baths
|1,008 sq ft
|Condo
1420 HUNTINGTON LN 2402, ROCKLEDGE, FL, ...
Community: Carmel Condominium
MLS 1077994 • Jason Mitchell Real Estate FL, Coll... • Jason Mitchell Real Estate FL
The Villages®
![170 PALERMO PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,979 sq ft
|House
170 PALERMO PL, LADY LAKE, FL, 32159
Community: The Villages®
MLS O6400750 • KEY LIME REALTY LLC, Paul Cates • KEY LIME REALTY LLC
The Villages®
![3746 NEW MOON AVE, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|2 baths
|1,905 sq ft
|House
3746 NEW MOON AVE, THE VILLAGES, FL, 321...
Community: The Villages®
MLS B26031567 • Balistreri Real Estate Inc, Natal... • Balistreri Real Estate Inc
Twin Lakes
![2764 GREENLANDS ST, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
3 beds
|3 baths
|2,208 sq ft
|House
2764 GREENLANDS ST, ST CLOUD, FL, 34772
Community: Twin Lakes
MLS O6409694 • EXP REALTY LLC, Brittany Pride • EXP REALTY LLC
Latitude Margaritaville
![408 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,509 sq ft
|House
408 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS FC318712 • SIMPLY REAL ESTATE, Emily Schans • SIMPLY REAL ESTATE
Kings Ridge
![4215 GREENWICH CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|2,000 sq ft
|House
4215 GREENWICH CT, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5112455 • ERA GRIZZARD REAL ESTATE, Kodee Na... • ERA GRIZZARD REAL ESTATE
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
Cindy Certified
Royal Harbor
![4962 RAINBOW TROUT RD, TAVARES, FL, 3277..., Tavares, FL 32778]()
3 beds
|2 baths
|1,489 sq ft
|House
4962 RAINBOW TROUT RD, TAVARES, FL, 3277...
Community: Royal Harbor
MLS G5112324 • EXIT REALTY TRI-COUNTY, Chelsey Da... • EXIT REALTY TRI-COUNTY
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.
Latitude Margaritaville
![768 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124]()
2 beds
|3 baths
|2,160 sq ft
|House
768 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Community: Latitude Margaritaville
MLS FC318677 • RE/MAX SELECT PROFESSIONALS, Morga... • RE/MAX SELECT PROFESSIONALS
Cindy Certified
The Villages®
![1678 GOVAN PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,978 sq ft
|Villa
1678 GOVAN PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5112111 • RE/MAX PREMIER REALTY, Gina Johnso... • RE/MAX PREMIER REALTY
Venetian Bay
![424 LUNA BELLA LN 415, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168]()
2 beds
|2 baths
|1,492 sq ft
|Condo
424 LUNA BELLA LN 415, NEW SMYRNA BEACH,...
Community: Venetian Bay
MLS NS1088267 • EXIT REAL ESTATE PROPERTY SOL, Ca... • EXIT REAL ESTATE PROPERTY SOL
Pelican Bay Daytona Beach
![100 BLACK CROW CIR 4000, DAYTONA BEACH, ..., Daytona Beach, FL 32119]()
3 beds
|3 baths
|1,869 sq ft
|Condo
100 BLACK CROW CIR 4000, DAYTONA BEACH, ...
Community: Pelican Bay Daytona Beach
MLS 1226635 • Century 21 Sundance Realty, Susan S... • Century 21 Sundance Realty
Cindy Certified
Cindy Certified
Cindy Certified
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
Latitude Margaritaville
![616 BEACH BUM BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
3 beds
|3 baths
|2,083 sq ft
|House
616 BEACH BUM BLVD, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1226630 • Bob Hodges and Sons Realty, Didi Wo... • Bob Hodges and Sons Realty
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.
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
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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.
