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Winter Park, FL 55+ active adult communities & homes for sale - Page 51
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
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
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4.7 rating (18 reviews)
![Solivita]()
$300ks
- $700ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 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 (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
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
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
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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
2.8 rating (6 reviews)
![Arlington Ridge]()
$200ks
- $500ks
Arlington Ridge, Leesburg, FL
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
629 homes
$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 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)
![Cresswind at Victoria Gar...]()
$300ks
- $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
$200ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 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
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
Heritage - The Cottages o..., Okahumpka, FL
New Construction
|
55+ age-restricted
|
Built 2022 - present
|
179 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
- $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
216 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
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
$200ks
- $500ks
The Timbers at Everlands, Palm Bay, FL
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
450 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
$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.
Cindy Certified
The Villages®
![1411 FRANKLIN CT, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,969 sq ft
|Villa
1411 FRANKLIN CT, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5110409 • IM REALTY, Ira Miller • IM REALTY
The Villages®
![9108 SE 177TH BELMONT PL, THE VILLAGES, ..., The Villages, FL 32162]()
2 beds
|2 baths
|1,284 sq ft
|Villa
9108 SE 177TH BELMONT PL, THE VILLAGES, ...
Community: The Villages®
MLS G5110858 • RE/MAX TITANIUM GROUP, Lisa Lugo M... • RE/MAX TITANIUM GROUP
Spruce Creek South
![17990 SE 100TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,870 sq ft
|House
17990 SE 100TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS OM722484 • KELLER WILLIAMS CORNERSTONE RE, Ri... • KELLER WILLIAMS CORNERSTONE RE
Colonnades
![1690 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,317 sq ft
|House
1690 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
MLS L4960471 • COLDWELL BANKER REALTY, Lisa Broch... • COLDWELL BANKER REALTY
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Questions? Call us:
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Cindy Certified
Kings Ridge
![2308 TWICKINGHAM CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,892 sq ft
|House
2308 TWICKINGHAM CT, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5110559 • REAL BROKER, LLC, Diane Rogers • REAL BROKER, LLC
Cresswind at Victoria Gardens
![412 TISBURY CT, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,512 sq ft
|House
412 TISBURY CT, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS V4948420 • KEMP REALTY GROUP, Maureen Kemp • KEMP REALTY GROUP
The Villages®
![8015 SE 174TH BELHAVEN LOOP, THE VILLAGE..., The Villages, FL 32162]()
2 beds
|2 baths
|1,148 sq ft
|House
8015 SE 174TH BELHAVEN LOOP, THE VILLAGE...
Community: The Villages®
MLS G5110762 • RE/MAX FOXFIRE - SUMMERFIELD, Kell... • RE/MAX FOXFIRE - SUMMERFIELD
Scottish Highlands
![27 GORDON CT, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,252 sq ft
|House
27 GORDON CT, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5110540 • RE/MAX PREMIER REALTY, James Donov... • RE/MAX PREMIER 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.
The Country Club of Mount Dora
![1901 PARK FOREST BLVD, MOUNT DORA, FL, 3..., Mount Dora, FL 32757]()
3 beds
|2 baths
|2,286 sq ft
|House
1901 PARK FOREST BLVD, MOUNT DORA, FL, 3...
Community: The Country Club of Mount Dora
MLS G5109489 • MOUNT DORA GOLF AND LAKE RLTY, Joh... • MOUNT DORA GOLF AND LAKE RLTY
Twin Lakes
![4902 W FOUNTAINWOOD DR, ST CLOUD, FL, 34..., St Cloud, FL 34772]()
2 beds
|2 baths
|1,624 sq ft
|House
4902 W FOUNTAINWOOD DR, ST CLOUD, FL, 34...
Community: Twin Lakes
MLS O6396943 • KEY CLASSIC REALTY LLC, Laisa Sant... • KEY CLASSIC REALTY LLC
Foxwood Lake Estates
![1798 FOX HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
3 beds
|2 baths
|1,176 sq ft
|Manufactured Home
1798 FOX HILL DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS L4960510 • LA ROSA REALTY PRESTIGE, Liliana G... • LA ROSA REALTY PRESTIGE
Four Seasons at Orlando
![1999 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
2 beds
|2 baths
|1,557 sq ft
|Villa
1999 KEY BAY TRL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS O6396388 • CHARLES RUTENBERG REALTY ORLANDO, ... • CHARLES RUTENBERG REALTY ORLANDO
High Vista at Ridgewood Lakes
![116 FLEMING LN, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|2 baths
|1,776 sq ft
|House
116 FLEMING LN, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS O6395393 • EXP REALTY LLC, Corinne Defilippis • EXP REALTY LLC
The Villages®
![603 ROBIN LN, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
2 beds
|2 baths
|1,352 sq ft
|Manufactured Home
603 ROBIN LN, WILDWOOD, FL, 34785
Community: The Villages®
MLS G5110683 • FOUR STAR HOME BROKERS, INC., Darl... • FOUR STAR HOME BROKERS, INC.
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(888) 625-4885
The Villages®
![2254 ISLEWORTH CIR, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|2 baths
|3,082 sq ft
|House
2254 ISLEWORTH CIR, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5110744 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Harbor Hills Country Club
![5204 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|3 baths
|2,248 sq ft
|House
5204 GREENS DR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5110432 • WORTH CLARK REALTY, Michael Simpso... • WORTH CLARK REALTY
Lake Ashton
![5268 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884]()
3 beds
|2 baths
|2,354 sq ft
|House
5268 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
MLS L4960893 • ROOST REALTY GROUP LLC, Barb Wiech... • ROOST REALTY GROUP LLC
The Villages®
![7809 SE 171ST HARLESTON ST, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|2,048 sq ft
|Villa
7809 SE 171ST HARLESTON ST, THE VILLAGES...
Community: The Villages®
MLS G5110522 • EXP REALTY LLC, Deborah Smith • EXP 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.
Plantation at Leesburg
![4960 HERON RUN CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,289 sq ft
|House
4960 HERON RUN CIR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6396736 • RE/MAX 200 REALTY, Abby Nelson • RE/MAX 200 REALTY
The Villages®
![1639 ALLENDALE PL, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
1639 ALLENDALE PL, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5110758 • ERA GRIZZARD REAL ESTATE, Ann Van ... • ERA GRIZZARD REAL ESTATE
Cindy Certified
The Villages®
![2604 ALCADE PL, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,654 sq ft
|House
2604 ALCADE PL, THE VILLAGES, FL, 32163
Community: The Villages®
MLS O6397201 • LIVE MVRK LLC, Jared Dunn • LIVE MVRK LLC
Lake Ashton
![4120 LIMERICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|4 baths
|2,968 sq ft
|House
4120 LIMERICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS L4960891 • CENTURY 21 MYERS REALTY, Chelsey P... • CENTURY 21 MYERS REALTY
Plantation Bay Golf & Country Club
![822 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,056 sq ft
|Townhouse
822 ALDENHAM LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS 1224999 • Coldwell Banker Coast Realty, Sheri... • Coldwell Banker Coast Realty
Breakaway Trails
![5 LAKE ISLE WAY, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,204 sq ft
|House
5 LAKE ISLE WAY, ORMOND BEACH, FL, 32174
Community: Breakaway Trails
MLS 1224991 • Florida Realty Plus LLC, Suzana Pet... • Florida Realty Plus LLC
Want to learn more about 55+ communities in Winter Park?
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The Villages®
![2623 ASCOT LOOP, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
2623 ASCOT LOOP, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5110340 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Cindy Certified
Enclave at VillageWalk
![8591 ADALINA PL, ORLANDO, FL, 32827, Orlando, FL 32827]()
5 beds
|5 baths
|4,924 sq ft
|House
8591 ADALINA PL, ORLANDO, FL, 32827
Community: Enclave at VillageWalk
MLS O6393523 • REAL BROKER, LLC, Peter Luu • REAL BROKER, 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.
Cindy Certified
Venetian Bay
![633 MARISOL DR, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|2,335 sq ft
|House
633 MARISOL DR, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS 1224970 • Beycome of Florida LLC, Steven Kole... • Beycome of Florida LLC
Kings Ridge
![3739 HASTING LN, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5110269 • WATSON REALTY CORP., REALTORS, Chr... • WATSON REALTY CORP., REALTORS
Bridgewater at Viera
![8904 ALISTER DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|3 baths
|2,132 sq ft
|House
8904 ALISTER DR, MELBOURNE, FL, 32940
Community: Bridgewater at Viera
MLS 1073739 • LPT Realty LLC, Kate Flack • LPT Realty LLC
Spruce Creek Country Club
![9210 SE 118TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,575 sq ft
|House
9210 SE 118TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM722246 • KELLER WILLIAMS CORNERSTONE RE, Cr... • KELLER WILLIAMS CORNERSTONE RE
Grand Haven
![455 RIVERFRONT DR A303, PALM COAST, FL, ..., Palm Coast, FL 32137]()
3 beds
|2 baths
|1,762 sq ft
|Condo
455 RIVERFRONT DR A303, PALM COAST, FL, ...
Community: Grand Haven
MLS FC317191 • COASTAL GATEWAY REAL ESTATE GR, La... • COASTAL GATEWAY REAL ESTATE GR
The Villages®
![1411 JUAREZ PL, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,388 sq ft
|House
1411 JUAREZ PL, THE VILLAGES, FL, 32159
Community: The Villages®
MLS R4911000 • BLACK TIE REAL ESTATE PROFESSIONAL... • BLACK TIE REAL ESTATE PROFESSIONALS, INC.
The Villages®
![1147 ELIZABETH CT, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,602 sq ft
|Villa
1147 ELIZABETH CT, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5110344 • VISIONARY PROPERTIES INC, Judy Blu... • VISIONARY PROPERTIES INC
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Plantation Bay Golf & Country Club
![1029 STONE LAKE DR, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
4 beds
|2 baths
|2,575 sq ft
|House
1029 STONE LAKE DR, ORMOND BEACH, FL, 32...
Community: Plantation Bay Golf & Country Club
MLS FC317448 • KELLER WILLIAMS RLTY FL. PARTN, Wi... • KELLER WILLIAMS RLTY FL. PARTN
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?
2,702
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.
