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Winter Park, FL 55+ active adult communities & homes for sale - Page 62
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
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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
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3,250 homes
5 rating (2 reviews)
![Plantation at Leesburg]()
$100ks
- $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only
|
55+ age-restricted
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Built 1987 - 2008
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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
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Built 2017 - 2025
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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
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3,500 homes
5 rating (3 reviews)
![Stonecrest]()
$200ks
- $500ks
Stonecrest, Summerfield, FL
Resale Only
|
55+ age-restricted
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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
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Built 2016 - present
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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
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Built 1995 - 2000
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2,088 homes
3.8 rating (6 reviews)
![Trilogy® Orlando]()
$200ks
- $500ks
Trilogy® Orlando, Groveland, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2022
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1,500 homes
5 rating (3 reviews)
![Lake Ashton]()
$200ks
- $500ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
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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
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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
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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
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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
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Built 2005 - 2020
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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
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937 homes
$100ks
- $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
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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?
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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.
Solivita
![176 CAPE FLORIDA DR, POINCIANA, FL, 3475..., Poinciana, FL 34759]()
2 beds
|2 baths
|1,440 sq ft
|House
176 CAPE FLORIDA DR, POINCIANA, FL, 3475...
Community: Solivita
MLS R11110545 • Coral Cove Realty Inc, Helen May ... • Coral Cove Realty Inc
Esplanade at Highland Ranch
![1284 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715]()
2 beds
|2 baths
|1,722 sq ft
|House
1284 ZEEK RIDGE ST, CLERMONT, FL, 34715
Community: Esplanade at Highland Ranch
MLS G5106537 • WATSON REALTY CORP., REALTORS, Chr... • WATSON REALTY CORP., REALTORS
The Villages®
![1069 BURNETTOWN PL, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
2 beds
|2 baths
|1,300 sq ft
|House
1069 BURNETTOWN PL, THE VILLAGES, FL, 32...
Community: The Villages®
MLS O6373355 • BEYCOME OF FLORIDA LLC, Steven Kol... • BEYCOME OF FLORIDA LLC
Cindy Certified
The Lakes at Harmony
![3212 OXBOW CT, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|2 baths
|1,580 sq ft
|House
3212 OXBOW CT, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS S5141393 • FIERCE REALTY, Rachel Coolidge • FIERCE REALTY
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Cindy Certified
Enclave at VillageWalk
![10938 SAVONA WAY, ORLANDO, FL, 32827, Orlando, FL 32827]()
6 beds
|6 baths
|5,334 sq ft
|House
10938 SAVONA WAY, ORLANDO, FL, 32827
Community: Enclave at VillageWalk
MLS O6373094 • REAL ESTATE PROFESSIONALS SE, Vale... • REAL ESTATE PROFESSIONALS SE
Del Webb Sunbridge
![2745 NATURE VIEW RD, ST CLOUD, FL, 34771, St Cloud, FL 34771]()
3 beds
|4 baths
|2,806 sq ft
|House
2745 NATURE VIEW RD, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS O6372481 • ROYALTY R E BOUTIQUE INC, Domeniqu... • ROYALTY R E BOUTIQUE INC
Cindy Certified
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.
Plantation Bay Golf & Country Club
![21 SOUTHAMPTON ST, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,643 sq ft
|Townhouse
21 SOUTHAMPTON ST, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS FC315221 • VENTURE DEVELOPMENT REALTY,INC, De... • VENTURE DEVELOPMENT REALTY,INC
Cindy Certified
Cindy Certified
Plantation at Leesburg
![4900 HERON RUN CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,289 sq ft
|House
4900 HERON RUN CIR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5106484 • CENTURY 21 MYERS ROSE REALTY, Cary... • CENTURY 21 MYERS ROSE REALTY
The Villages®
![518 SAINT ANDREWS BLVD, LADY LAKE, FL, 3..., Lady Lake, FL 32159]()
2 beds
|2 baths
|1,248 sq ft
|Manufactured Home
518 SAINT ANDREWS BLVD, LADY LAKE, FL, 3...
Community: The Villages®
MLS G5106347 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Lake Ashton
![4081 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|2,027 sq ft
|House
4081 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS S5141060 • MAZELG REALTY, Mary Sorrell • MAZELG REALTY
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Questions? Call us:
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The Villages®
![5107 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484]()
4 beds
|3 baths
|1,910 sq ft
|House
5107 NE 122ND BLVD, OXFORD, FL, 34484
Community: The Villages®
MLS O6370099 • COLDWELL BANKER REALTY, James Gips... • COLDWELL BANKER REALTY
Lake Ashton
![4577 BACK NINE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33884]()
3 beds
|2 baths
|1,918 sq ft
|House
4577 BACK NINE DR, WINTER HAVEN, FL, 338...
Community: Lake Ashton
MLS P4937386 • LAKE ASHTON REALTY INC., Lori Raat... • LAKE ASHTON REALTY INC.
Summer Trees
![49 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,048 sq ft
|House
49 CYPRESS POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
MLS 2123962 • PLANTANA REALTY, INC., SANDRA FISHE... • PLANTANA REALTY, INC.
Plantation at Leesburg
![25300 HIBISCUS ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,908 sq ft
|House
25300 HIBISCUS ST, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS TB8460495 • HOMECOIN.COM, Jonathan Minerick • HOMECOIN.COM
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
![699 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS TB8452905 • FLORIDA EXECUTIVE REALTY, Jason L... • FLORIDA EXECUTIVE REALTY
VillageWalk at Lake Nona
![8681 LOWER VILLAGEWALK CIR, ORLANDO, FL,..., Orlando, FL 32827]()
3 beds
|3 baths
|1,830 sq ft
|Townhouse
8681 LOWER VILLAGEWALK CIR, ORLANDO, FL,...
Community: VillageWalk at Lake Nona
MLS O6369740 • RE/MAX VANTAGE, AnnMarie Vachala • RE/MAX VANTAGE
Cindy Certified
Heritage Landings
![2651 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811]()
5 beds
|3 baths
|2,696 sq ft
|House
2651 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Heritage Landings
MLS L4958127 • KELLER WILLIAMS REALTY SMART 1, He... • KELLER WILLIAMS REALTY SMART 1
Lakes at Laurel Highlands
![2651 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811]()
5 beds
|3 baths
|2,696 sq ft
|House
2651 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Lakes at Laurel Highlands
MLS L4958127 • KELLER WILLIAMS REALTY SMART 1, He... • KELLER WILLIAMS REALTY SMART 1
Solivita
![677 VIA CORSO CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5140636 • JASON MITCHELL REAL ESTATE FLO, Da... • JASON MITCHELL REAL ESTATE FLO
Harbor Hills Country Club
![39819 GROVE HEIGHTS, LADY LAKE, FL, 3215..., Lady Lake, FL 32159]()
3 beds
|2 baths
|2,504 sq ft
|House
39819 GROVE HEIGHTS, LADY LAKE, FL, 3215...
Community: Harbor Hills Country Club
MLS O6369259 • COLDWELL BANKER REALTY, Ken Dalton • COLDWELL BANKER REALTY
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The Villages®
![1568 BLACK LAKE DR, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
4 beds
|5 baths
|4,654 sq ft
|House
1568 BLACK LAKE DR, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5105802 • FLORIDA FINE HOMES REALTY, LLC, Ca... • FLORIDA FINE HOMES REALTY, LLC
Cindy Certified
Heritage Hills
![3550 FAIRWATERS CT C, CLERMONT, FL, 3471..., Clermont, FL 34711]()
2 beds
|2 baths
|1,374 sq ft
|Villa
3550 FAIRWATERS CT C, CLERMONT, FL, 3471...
Community: Heritage Hills
MLS O6368915 • LIFESTYLE INTERNATIONAL REALTY, Jo... • LIFESTYLE INTERNATIONAL 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.
Stonecrest
![11351 SE 175TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,717 sq ft
|House
11351 SE 175TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5105707 • CHARLES RUTENBERG REALTY ORLANDO, ... • CHARLES RUTENBERG REALTY ORLANDO
Spruce Creek Country Club
![13324 SE 91ST COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,870 sq ft
|House
13324 SE 91ST COURT RD, SUMMERFIELD, FL,...
Community: Spruce Creek Country Club
MLS G5105785 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Alhambra Villas Condominiums
![249 N HILL AVE 30, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,043 sq ft
|Condo
249 N HILL AVE 30, DELAND, FL, 32724
Community: Alhambra Villas Condominiums
MLS V4946364 • CHARLES RUTENBERG REALTY ORLANDO, ... • CHARLES RUTENBERG REALTY ORLANDO
Traditions at Lake Ruby
![2925 DAYTON DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
3 beds
|2 baths
|2,109 sq ft
|House
2925 DAYTON DR, WINTER HAVEN, FL, 33884
Community: Traditions at Lake Ruby
MLS P4937324 • CENTURY 21 MYERS REALTY LAKE WALES... • CENTURY 21 MYERS REALTY LAKE WALES
Plantation Bay Golf & Country Club
![503 WINGSPAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
5 beds
|4 baths
|3,067 sq ft
|House
503 WINGSPAN DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS 1221014 • Florida Homes Realty & Mortgage, Tr... • Florida Homes Realty & Mortgage
Cindy Certified
Cindy Certified
Cindy Certified
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
Pelican Bay Daytona Beach
![196 GRAY DOVE CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32119]()
3 beds
|3 baths
|1,833 sq ft
|Townhouse
196 GRAY DOVE CT, DAYTONA BEACH, FL, 321...
Community: Pelican Bay Daytona Beach
MLS 1221002 • Best Way Realty of Volusia LLC, Jim... • Best Way Realty of Volusia LLC
Heritage Isle
![6531 INGALLS ST, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,806 sq ft
|House
6531 INGALLS ST, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1064566 • Coastal Life Properties LLC, Kane S... • Coastal Life Properties 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.
