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Winter Park, FL 55+ active adult communities & homes for sale - Page 50
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.
Stonecrest
![12066 SE 176 LOOP, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,911 sq ft
|House
12066 SE 176 LOOP, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5111107 • MRE REALTY SERVICES, Janice Hart • MRE REALTY SERVICES
The Villages®
![2403 BATON PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
2403 BATON PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5110656 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
The Villages®
![23104 SANDALWOOD DR 104, WILDWOOD, FL, 3..., Wildwood, FL 34785]()
2 beds
|2 baths
|1,110 sq ft
|Condo
23104 SANDALWOOD DR 104, WILDWOOD, FL, 3...
Community: The Villages®
MLS OM722811 • SINGH REAL ESTATE SERVICES, Navin ... • SINGH REAL ESTATE SERVICES
Ridgehaven
![172 PARKHAVEN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,454 sq ft
|House
172 PARKHAVEN DR, ORMOND BEACH, FL, 3217...
Community: Ridgehaven
MLS TB8491173 • MERITAGE HOMES OF FL REALTY, Brya... • MERITAGE HOMES OF FL REALTY
Plantation Bay Golf & Country Club
![438 LONG COVE RD, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,820 sq ft
|House
438 LONG COVE RD, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS 1225319 • LPT Realty, LLC, Will Ferro • LPT Realty, LLC
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Cindy Certified
Heritage Landings
![2658 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811]()
4 beds
|2 baths
|1,867 sq ft
|House
2658 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Heritage Landings
MLS L4961112 • COLDWELL BANKER REALTY, Nicole Ell... • COLDWELL BANKER REALTY
Lakes at Laurel Highlands
![2658 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811]()
4 beds
|2 baths
|1,867 sq ft
|House
2658 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Lakes at Laurel Highlands
MLS L4961112 • COLDWELL BANKER REALTY, Nicole Ell... • COLDWELL BANKER REALTY
The Villages®
![2873 CHARLEVOIX ST, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|2 baths
|1,938 sq ft
|Villa
2873 CHARLEVOIX ST, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5110573 • RE/MAX PREMIER REALTY, Matthew Rob... • RE/MAX PREMIER REALTY
Grand Haven
![32 SHINNECOCK DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
3 beds
|2 baths
|1,594 sq ft
|House
32 SHINNECOCK DR, PALM COAST, FL, 32137
Community: Grand Haven
MLS FC317792 • EXP REALTY LLC, Laura Morrison • 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.
Pennbrooke Fairways
![333 RANCHWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,840 sq ft
|House
333 RANCHWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5110691 • CENTURY 21 ALTON CLARK, Regina Rod... • CENTURY 21 ALTON CLARK
Summer Trees
![61 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,020 sq ft
|House
61 CYPRESS POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
MLS 1225303 • Beach Towne Realtors, Mark Valerien • Beach Towne Realtors
Cindy Certified
Cindy Certified
Solivita
![1317 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6399378 • SOGO REAL ESTATE SERVICES LLC, Chr... • SOGO REAL ESTATE SERVICES LLC
Kings Ridge
![2241 KINGSMILL WAY, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|2,124 sq ft
|House
2241 KINGSMILL WAY, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5110676 • COLDWELL BANKER HUBBARD HANSEN, Je... • COLDWELL BANKER HUBBARD HANSEN
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
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Venetian Bay
![3338 BELLINO BLVD, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|1,918 sq ft
|House
3338 BELLINO BLVD, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
MLS NS1087962 • BARSOTTELLI PRIME REAL ESTATE, Ig... • BARSOTTELLI PRIME REAL ESTATE
Huntington at Hunter's Ridge
![23 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|1,853 sq ft
|House
23 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Community: Huntington at Hunter's Ridge
MLS 1225277 • Coldwell Banker Premier Properties,... • Coldwell Banker Premier Properties
The Villages®
![16596 SE 77TH NORTHRIDGE CT, THE VILLAGE..., The Villages, FL 32162]()
3 beds
|2 baths
|1,483 sq ft
|House
16596 SE 77TH NORTHRIDGE CT, THE VILLAGE...
Community: The Villages®
MLS G5111003 • COLDWELL BANKER VANGUARD LIFESTYLE... • COLDWELL BANKER VANGUARD LIFESTYLE REALTY
Summit Chase Villas
![12418 ORANGEWOOD CIR, TAVARES, FL, 32778, Tavares, FL 32778]()
2 beds
|2 baths
|918 sq ft
|Villa
12418 ORANGEWOOD CIR, TAVARES, FL, 32778
Community: Summit Chase Villas
MLS G5111062 • DENIZ REALTY PARTNERS LLC, Tommy M... • DENIZ REALTY PARTNERS 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®
![5450 SAMUEL ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,642 sq ft
|Villa
5450 SAMUEL ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5110801 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Summer Trees
![18 SUMMER TREES RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,026 sq ft
|House
18 SUMMER TREES RD, PORT ORANGE, FL, 321...
Community: Summer Trees
MLS 1225259 • Florida Homes Realty & Mortgage, La... • Florida Homes Realty & Mortgage
Cindy Certified
The Villages®
![481 ISLAND HOUSE PATH, THE VILLAGES, FL,..., The Villages, FL 32163]()
3 beds
|3 baths
|1,903 sq ft
|House
481 ISLAND HOUSE PATH, THE VILLAGES, FL,...
Community: The Villages®
MLS G5111007 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Latitude Margaritaville
![218 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,303 sq ft
|Villa
218 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...
Community: Latitude Margaritaville
MLS FC317687 • COASTAL GATEWAY REAL ESTATE GR, Ki... • COASTAL GATEWAY REAL ESTATE GR
The Villages®
![416 CARRERA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|2,006 sq ft
|House
416 CARRERA DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5110213 • RE/MAX PREMIER REALTY, Guy William... • RE/MAX PREMIER REALTY
The Villages®
![1609 BLOSSOM TER, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
1609 BLOSSOM TER, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5110982 • LPT REALTY, LLC, Lena Morgan • LPT REALTY, LLC
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
The Villages®
![270 MATISSE AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|2,075 sq ft
|House
270 MATISSE AVE, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5110907 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Halifax Plantation
![1328 ANTRIM CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,499 sq ft
|House
1328 ANTRIM CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS 1225203 • RE/MAX Signature, David Lieb • RE/MAX Signature
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.
Del Webb Sunbridge
![2873 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ..., St Cloud, FL 34771]()
3 beds
|3 baths
|2,270 sq ft
|House
2873 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ...
Community: Del Webb Sunbridge
MLS O6398185 • INTERNATIONAL TEAM INC, Jo Costa • INTERNATIONAL TEAM INC
The Villages®
![16980 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162]()
2 beds
|2 baths
|1,148 sq ft
|House
16980 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
MLS OM722622 • RE/MAX ALLSTARS REALTY, Christie C... • RE/MAX ALLSTARS REALTY
Spruce Creek Country Club
![9570 SE 136TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,528 sq ft
|House
9570 SE 136TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM722590 • REALTY ONE GROUP DAVALLS, David St... • REALTY ONE GROUP DAVALLS
The Lakes at Harmony
![3113 SONGBIRD CIR, ST CLOUD, FL, 34773, St Cloud, FL 34773]()
3 beds
|2 baths
|1,876 sq ft
|House
3113 SONGBIRD CIR, ST CLOUD, FL, 34773
Community: The Lakes at Harmony
MLS S5146996 • CORCORAN CONNECT LLC, Jeanine Corc... • CORCORAN CONNECT LLC
Cindy Certified
The Villages®
![1982 SOMERSET AVE, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,404 sq ft
|House
1982 SOMERSET AVE, THE VILLAGES, FL, 321...
Community: The Villages®
MLS OM722473 • KELLER WILLIAMS CORNERSTONE RE, Ci... • KELLER WILLIAMS CORNERSTONE RE
Solivita
![130 PRIMA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5146916 • CENTURY 21 ALL HOMES & PROPERT, Na... • CENTURY 21 ALL HOMES & PROPERT
The Villages®
![1521 HOLLYBERRY PL, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|1,527 sq ft
|House
1521 HOLLYBERRY PL, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5110807 • SALLY LOVE REAL ESTATE, Kim Coffer • SALLY LOVE REAL ESTATE
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
The Villages®
![8331 COUNTY RD 109, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
4 beds
|2 baths
|2,240 sq ft
|Manufactured Home
8331 COUNTY RD 109, LADY LAKE, FL, 32159
Community: The Villages®
MLS S5147176 • TOWN CENTER REALTY LLC, John Kovac... • TOWN CENTER REALTY LLC
The Villages®
![3135 BURNS DR, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,527 sq ft
|House
3135 BURNS DR, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5110838 • DOWN HOME REALTY, LLLP, Colleen A.... • DOWN HOME REALTY, LLLP
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.
