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Winter Park, FL 55+ active adult communities & homes for sale - Page 63
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
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$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
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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.
Twin Lakes
![4909 W FOUNTAINWOOD DR, ST CLOUD, FL, 34..., St Cloud, FL 34772]()
3 beds
|3 baths
|2,365 sq ft
|House
4909 W FOUNTAINWOOD DR, ST CLOUD, FL, 34...
Community: Twin Lakes
MLS O6367771 • DIAMOND REAL ESTATE GROUP, George ... • DIAMOND REAL ESTATE GROUP
Spruce Creek Country Club
![9685 SE 136TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,873 sq ft
|House
9685 SE 136TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM715214 • RE/MAX FOXFIRE - SUMMERFIELD, Ed D... • RE/MAX FOXFIRE - SUMMERFIELD
Cindy Certified
Cindy Certified
Cindy Certified
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Cindy Certified
Lake Ashton
![5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,677 sq ft
|House
5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
MLS P4937220 • LAKE ASHTON REALTY INC., Lori Raat... • LAKE ASHTON REALTY INC.
VillageWalk at Lake Nona
![11932 LORENZA LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
3 beds
|3 baths
|1,830 sq ft
|Townhouse
11932 LORENZA LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS S5140170 • KELLER WILLIAMS LEGACY REALTY, Gir... • KELLER WILLIAMS LEGACY REALTY
Sullivan Ranch
![20930 SULLIVAN RANCH BLVD, MOUNT DORA, F..., Mount Dora, FL 32757]()
6 beds
|4 baths
|3,499 sq ft
|House
20930 SULLIVAN RANCH BLVD, MOUNT DORA, F...
Community: Sullivan Ranch
MLS O6362834 • HOME WISE REALTY GROUP, INC., Cher... • HOME WISE REALTY GROUP, INC.
Spruce Creek Country Club
![13766 SE 89TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,025 sq ft
|House
13766 SE 89TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM714790 • KELLER WILLIAMS CORNERSTONE RE, Do... • 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.
Plantation at Leesburg
![3605 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,868 sq ft
|House
3605 MOUNT HOPE LOOP, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS G5105434 • RE/MAX PREMIER REALTY, Adriana Sko... • RE/MAX PREMIER REALTY
The Villages®
![3229 KILLINGTON LOOP, THE VILLAGES, FL, ..., The Villages, FL 32163]()
3 beds
|3 baths
|2,072 sq ft
|House
3229 KILLINGTON LOOP, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5105368 • RE/MAX PREMIER REALTY, Debbie Mart... • RE/MAX PREMIER REALTY
Venetian Bay
![664 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
4 beds
|4 baths
|3,221 sq ft
|House
664 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS O6365891 • TAYLOR MORRISON REALTY OF FLORIDA ... • TAYLOR MORRISON REALTY OF FLORIDA INC
Ridgehaven
![1138 CLIFFHAVEN CT, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,183 sq ft
|House
1138 CLIFFHAVEN CT, ORMOND BEACH, FL, 32...
Community: Ridgehaven
MLS O6365949 • LPT REALTY, LLC, James Bessinger • LPT REALTY, LLC
Ridgehaven
![1134 CLIFFHAVEN CT, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
4 beds
|2 baths
|1,945 sq ft
|House
1134 CLIFFHAVEN CT, ORMOND BEACH, FL, 32...
Community: Ridgehaven
MLS O6365935 • LPT REALTY, LLC, James Bessinger • LPT REALTY, LLC
Solivita
![1192 VIA GALUPPI ST, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
3 beds
|2 baths
|1,723 sq ft
|House
1192 VIA GALUPPI ST, KISSIMMEE, FL, 3475...
Community: Solivita
MLS G5105188 • EXP REALTY LLC, Edalys Ramos • EXP REALTY LLC
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Questions? Call us:
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Spruce Creek Country Club
![8789 SE 136TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
3 beds
|2 baths
|2,029 sq ft
|House
8789 SE 136TH LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS G5105202 • RE/MAX PREMIER REALTY LADY LK, Rob... • RE/MAX PREMIER REALTY LADY LK
VillageWalk at Lake Nona
![7991 ESTA LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
4 beds
|5 baths
|3,454 sq ft
|House
7991 ESTA LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6365393 • ENGEL & VOLKERS NEW SMYRNA, Chris ... • ENGEL & VOLKERS NEW SMYRNA
Scottish Highlands
![2105 GREENLAW CT 2105, LEESBURG, FL, 347..., Leesburg, FL 34788]()
2 beds
|2 baths
|932 sq ft
|Condo
2105 GREENLAW CT 2105, LEESBURG, FL, 347...
Community: Scottish Highlands
MLS S5139750 • RIVA REALTY GROUP LLC, Vildan Nigr... • RIVA REALTY GROUP LLC
Cresswind at Victoria Gardens
![322 BELLINGRATH TER, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|3 baths
|2,708 sq ft
|House
322 BELLINGRATH TER, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS O6364136 • BETTER HOMES AND GARDENS REAL ESTA... • BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P
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
![806 EBB TIDE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5139382 • PELLEGO, LLC, Paul Maiatico • PELLEGO, LLC
Summer Trees
![127 CYPRESS POND RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128]()
3 beds
|2 baths
|1,426 sq ft
|House
127 CYPRESS POND RD, PORT ORANGE, FL, 32...
Community: Summer Trees
MLS O6363893 • CHARLES RUTENBERG REALTY ORLANDO, ... • CHARLES RUTENBERG REALTY ORLANDO
Foxwood Lake Estates
![4969 FOXWOOD LAKE DR, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,456 sq ft
|Manufactured Home
4969 FOXWOOD LAKE DR, LAKELAND, FL, 3381...
Community: Foxwood Lake Estates
MLS P4937150 • KELLER WILLIAMS REALTY SMART 1, Ma... • KELLER WILLIAMS REALTY SMART 1
Cindy Certified
Lake James
![7914 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,925 sq ft
|House
7914 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
MLS L4957618 • KELLER WILLIAMS REALTY, Kim McKeel • KELLER WILLIAMS REALTY
Plantation at Leesburg
![4704 RIVER RIDGE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,155 sq ft
|House
4704 RIVER RIDGE DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5105014 • FLORIDA REALTY INVESTMENTS, Michel... • FLORIDA REALTY INVESTMENTS
Sullivan Ranch
![21632 HIDDEN CRK, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|4 baths
|3,853 sq ft
|House
21632 HIDDEN CRK, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS A4673135 • SAVVY AVENUE, LLC, Moe Mossa • SAVVY AVENUE, LLC
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
Spruce Creek South
![10767 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,690 sq ft
|House
10767 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Spruce Creek South
MLS OM714323 • KELLER WILLIAMS CORNERSTONE RE, Ri... • KELLER WILLIAMS CORNERSTONE RE
Cindy Certified
Grand Haven
![150 W WATERSIDE PKWY, PALM COAST, FL, 32..., Palm Coast, FL 32137]()
2 beds
|2 baths
|1,619 sq ft
|House
150 W WATERSIDE PKWY, PALM COAST, FL, 32...
Community: Grand Haven
MLS FC314375 • GRAND LIVING REALTY, Joan Paulus • GRAND LIVING 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.
Twin Lakes
![2557 YELLOW BRICK RD, ST CLOUD, FL, 3477..., St Cloud, FL 34772]()
2 beds
|2 baths
|1,464 sq ft
|Villa
2557 YELLOW BRICK RD, ST CLOUD, FL, 3477...
Community: Twin Lakes
MLS S5139225 • WEICHERT REALTORS HALLMARK PRO, Sh... • WEICHERT REALTORS HALLMARK PRO
Lakes of Mount Dora
![8852 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
3 beds
|2 baths
|2,081 sq ft
|House
8852 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS G5102771 • ERA GRIZZARD REAL ESTATE, Scott Mc... • ERA GRIZZARD REAL ESTATE
Cindy Certified
Venetian Bay
![3009 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,614 sq ft
|Townhouse
3009 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS O6362128 • KELLER WILLIAMS WINTER PARK, Jill ... • KELLER WILLIAMS WINTER PARK
Halifax Plantation
![3034 ADRIAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,641 sq ft
|House
3034 ADRIAN DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS O6361712 • REDFIN CORPORATION, Tammy Shaver • REDFIN CORPORATION
Lakeside Landings
![4846 AUDREY MARIE CT, OXFORD, FL, 34484, Oxford, FL 34484]()
3 beds
|2 baths
|2,200 sq ft
|House
4846 AUDREY MARIE CT, OXFORD, FL, 34484
Community: Lakeside Landings
MLS G5104749 • LPT REALTY, LLC, Carlos Fuentes • LPT REALTY, LLC
Arlington Ridge
![27343 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,607 sq ft
|House
27343 ROANOKE DR, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS R4910273 • ARROW STAR REALTY LLC, Eric Fiori • ARROW STAR REALTY LLC
Del Webb Orlando
![536 ARENA DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|2 baths
|1,508 sq ft
|House
536 ARENA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS S5138798 • RIDGE REALTY GROUP LLC, Linda Spen... • RIDGE REALTY GROUP LLC
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(888) 625-4885
Spruce Creek South
![10599 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,008 sq ft
|House
10599 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS G5104689 • RE/MAX PREMIER REALTY LADY LK, Ger... • RE/MAX PREMIER REALTY LADY LK
Indian River Colony Club
![1290 MAYFLOWER AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
2 beds
|2 baths
|1,616 sq ft
|House
1290 MAYFLOWER AVE, MELBOURNE, FL, 32940
Community: Indian River Colony Club
MLS 1062414 • Four Star Real Estate LLC, Shellie ... • Four Star Real Estate 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?
2,702
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.
