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Winter Park, FL 55+ active adult communities & homes for sale - Page 49
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
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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
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.
Royal Highlands
![5607 SIR CHURCHILL DR, LEESBURG, FL, 347..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,312 sq ft
|House
5607 SIR CHURCHILL DR, LEESBURG, FL, 347...
Community: Royal Highlands
MLS G5111130 • FLORIDA PLUS REALTY, LLC, Tonya Ti... • FLORIDA PLUS REALTY, LLC
Harbor Hills Country Club
![6120 LANDINGS BLVD, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|2,598 sq ft
|House
6120 LANDINGS BLVD, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS OM722856 • ROBERTS REAL ESTATE INC, Erin Howl... • ROBERTS REAL ESTATE INC
Cresswind at Victoria Gardens
![103 OLD MOSS CIR, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|2 baths
|2,001 sq ft
|House
103 OLD MOSS CIR, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS V4948545 • BEE REALTY CORP, Bee Powell • BEE REALTY CORP
The Villages®
![5556 COLUMBUS CIR, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
3 beds
|3 baths
|1,680 sq ft
|Manufactured Home
5556 COLUMBUS CIR, WILDWOOD, FL, 34785
Community: The Villages®
MLS G5110797 • VILLAGE VALET REALTY LLC, Carolyn ... • VILLAGE VALET REALTY LLC
Cindy Certified
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Alamanda Key
![4050 ALAMANDA KEY DR DRIVE, MELBOURNE, F..., Melbourne, FL 32901]()
3 beds
|2 baths
|1,550 sq ft
|House
4050 ALAMANDA KEY DR DRIVE, MELBOURNE, F...
Community: Alamanda Key
MLS 1075142 • RE/MAX Elite, Theresa Friend • RE/MAX Elite
The Villages®
![17009 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
17009 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
MLS G5111237 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Lakes of Mount Dora
![2359 WAKEFIELD WAY, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,615 sq ft
|House
2359 WAKEFIELD WAY, MOUNT DORA, FL, 3275...
Community: Lakes of Mount Dora
MLS G5111169 • ERA GRIZZARD REAL ESTATE, Scott Mc... • ERA GRIZZARD REAL ESTATE
The Villages®
![324 EMMALEE PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
324 EMMALEE PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5110946 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Breakaway Trails
![59 SHADOWCREEK WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|3,227 sq ft
|House
59 SHADOWCREEK WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
MLS 1225441 • Realty Pros Assured, Terri Wilkinso... • Realty Pros Assured
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.
Arlington Ridge
![27102 CAMERONS RUN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,000 sq ft
|House
27102 CAMERONS RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS OM722565 • DISCOVER FLORIDA REALTY GROUP LLC,... • DISCOVER FLORIDA REALTY GROUP LLC
The Country Club of Mount Dora
![1760 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|3 baths
|3,141 sq ft
|House
1760 EDGEWATER DR, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS G5111131 • DAVE LOWE REALTY, INC., Tony Jacko... • DAVE LOWE REALTY, INC.
Pelican Bay Daytona Beach
![770 PELICAN BAY DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119]()
5 beds
|4 baths
|3,165 sq ft
|House
770 PELICAN BAY DR, DAYTONA BEACH, FL, 3...
Community: Pelican Bay Daytona Beach
MLS V4948597 • RE/MAX SIGNATURE, Stephanie Cathey • RE/MAX SIGNATURE
Arlington Ridge
![4307 BENT CREEK LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,683 sq ft
|House
4307 BENT CREEK LN, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS G5111198 • VANGIE BERRY SIGNATURE REALTY, Ang... • VANGIE BERRY SIGNATURE REALTY
Kings Ridge
![3871 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,327 sq ft
|House
3871 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5110983 • LA ROSA RTY WINTER GARDEN LLC, Wil... • LA ROSA RTY WINTER GARDEN LLC
Traditions at Lake Ruby
![3890 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884]()
4 beds
|3 baths
|2,322 sq ft
|House
3890 BEDFORD AVE, WINTER HAVEN, FL, 3388...
Community: Traditions at Lake Ruby
MLS L4961088 • DREAM REALTY GROUP, Christie Weeks • DREAM REALTY GROUP
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(888) 625-4885
The Villages®
![2033 SALMON WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,939 sq ft
|House
2033 SALMON WAY, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5110991 • LPT REALTY, LLC, Dave Monty • LPT REALTY, LLC
Stonecrest
![17083 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,724 sq ft
|House
17083 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
MLS G5111093 • LPT REALTY, LLC, Lena Morgan • LPT REALTY, LLC
Breakaway Trails
![120 BLACK HICKORY WAY, ORMOND BEACH, FL,..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,931 sq ft
|House
120 BLACK HICKORY WAY, ORMOND BEACH, FL,...
Community: Breakaway Trails
MLS 1225407 • Adams, Cameron & Co., Realtors, Ton... • Adams, Cameron & Co., Realtors
Plantation at Leesburg
![3719 BELLE ROSE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|3 baths
|2,571 sq ft
|House
3719 BELLE ROSE DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5111171 • CHARLES RUTENBERG REALTY ORLANDO, ... • CHARLES RUTENBERG REALTY ORLANDO
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
Westhaven at Ovation - Townes Collection
![12788 SUNSET WALK DR, WINTER GARDEN, FL,..., Winter Garden, FL 34787]()
4 beds
|3 baths
|2,031 sq ft
|Townhouse
12788 SUNSET WALK DR, WINTER GARDEN, FL,...
Community: Westhaven at Ovation - Townes Collection
MLS O6400288 • ORLANDO TBI REALTY LLC, DeVahn Pow... • ORLANDO TBI REALTY LLC
Ridgehaven
![425 BROOKHAVEN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,181 sq ft
|House
425 BROOKHAVEN, ORMOND BEACH, FL, 32174
Community: Ridgehaven
MLS TB8491169 • MERITAGE HOMES OF FL REALTY, Brya... • MERITAGE HOMES OF FL REALTY
Cindy Certified
Indian River Colony Club
![1551 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940]()
3 beds
|2 baths
|1,816 sq ft
|House
1551 INDEPENDENCE AVE, MELBOURNE, FL, 32...
Community: Indian River Colony Club
MLS 1075016 • Four Star Real Estate LLC, Robin St... • Four Star Real Estate LLC
Bridgewater at Viera
![2190 CARAVAN PL, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|3 baths
|2,453 sq ft
|House
2190 CARAVAN PL, MELBOURNE, FL, 32940
Community: Bridgewater at Viera
MLS 1075011 • RE/MAX Aerospace Realty, Kathy Ferd... • RE/MAX Aerospace Realty
Esplanade at Highland Ranch
![1222 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715]()
2 beds
|3 baths
|2,105 sq ft
|House
1222 ZEEK RIDGE ST, CLERMONT, FL, 34715
Community: Esplanade at Highland Ranch
MLS O6398370 • RE/MAX SELECT GROUP, Mike Mondello • RE/MAX SELECT GROUP
Want to learn more about 55+ communities in Winter Park?
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Cindy Certified
Cindy Certified
Lakes of Mount Dora
![2289 HAMDEN WAY, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
3 beds
|2 baths
|1,732 sq ft
|House
2289 HAMDEN WAY, MOUNT DORA, FL, 32757
Community: Lakes of Mount Dora
MLS O6400260 • DR HORTON REALTY OF CENTRAL FLORID... • DR HORTON REALTY OF CENTRAL FLORIDA 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
Plantation at Leesburg
![4967 HERON RUN CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,119 sq ft
|House
4967 HERON RUN CIR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5111091 • CHARLES RUTENBERG REALTY ORLANDO, ... • CHARLES RUTENBERG REALTY ORLANDO
The Lakes at Harmony
![3481 MIDDLEBROOK PL, ST CLOUD, FL, 34773, St Cloud, FL 34773]()
5 beds
|3 baths
|3,467 sq ft
|House
3481 MIDDLEBROOK PL, ST CLOUD, FL, 34773
Community: The Lakes at Harmony
MLS S5147896 • CORCORAN CONNECT LLC, Jeanine Corc... • CORCORAN CONNECT LLC
Lakes of Mount Dora
![3952 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
3 beds
|2 baths
|2,034 sq ft
|House
3952 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
MLS O6400207 • DR HORTON REALTY OF CENTRAL FLORID... • DR HORTON REALTY OF CENTRAL FLORIDA LLC
Bridgewater at Viera
![2509 MILLENNIUM CIR, VIERA, FL, 32940, Viera, FL 32940]()
3 beds
|3 baths
|2,453 sq ft
|House
2509 MILLENNIUM CIR, VIERA, FL, 32940
Community: Bridgewater at Viera
MLS 1074863 • Better Homes & Gardens RE Star, Bar... • Better Homes & Gardens RE Star
Breakaway Trails
![8 FOX CLIFF WAY, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,566 sq ft
|House
8 FOX CLIFF WAY, ORMOND BEACH, FL, 32174
Community: Breakaway Trails
MLS O6400100 • MARK SPAIN REAL ESTATE, Jeff Jones • MARK SPAIN REAL ESTATE
Trilogy® Orlando
![126 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|1,269 sq ft
|House
126 BAYOU BEND RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS O6396580 • FANNIE HILLMAN & ASSOCIATES, Rober... • FANNIE HILLMAN & ASSOCIATES
The Villages®
![1314 SANTA ROSA CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,302 sq ft
|Villa
1314 SANTA ROSA CT, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5110972 • KELLER WILLIAMS CORNERSTONE RE, Ka... • KELLER WILLIAMS CORNERSTONE RE
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The Villages®
![4151 BALCHARAN TER, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|2 baths
|1,539 sq ft
|House
4151 BALCHARAN TER, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5111115 • CENTURY 21 ALTON CLARK, Regina Rod... • CENTURY 21 ALTON CLARK
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.
