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Winter Park, FL 55+ active adult communities & homes for sale - Page 34
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.
The Villages®
![1625 HILTON HEAD BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159]()
2 beds
|2 baths
|1,332 sq ft
|Manufactured Home
1625 HILTON HEAD BLVD, LADY LAKE, FL, 32...
Community: The Villages®
MLS O6408296 • ALL FLORIDA PROPERTY GROUP,INC, Me... • ALL FLORIDA PROPERTY GROUP,INC
Cindy Certified
American Village
![17 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164]()
3 beds
|2 baths
|1,745 sq ft
|House
17 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
MLS FC319276 • GRAND LIVING REALTY, Scott Chappui... • GRAND LIVING REALTY
Cindy Certified
Royal Highlands
![21830 KING EDWARD CT, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,268 sq ft
|House
21830 KING EDWARD CT, LEESBURG, FL, 3474...
Community: Royal Highlands
MLS G5113678 • COLDWELL BANKER HUBBARD HANSEN, Ap... • COLDWELL BANKER HUBBARD HANSEN
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Questions? Call us:
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Cindy Certified
Stonecrest
![16887 SE 110TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,100 sq ft
|House
16887 SE 110TH COURT RD, SUMMERFIELD, FL...
Community: Stonecrest
MLS G5113234 • RE/MAX PREMIER REALTY LADY LK, Cin... • RE/MAX PREMIER REALTY LADY LK
Cindy Certified
Pelican Bay Daytona Beach
![140 GOLDEN EYE DR D, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,242 sq ft
|Condo
140 GOLDEN EYE DR D, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS 1227573 • Compass Florida, LLC, Debra Meyer • Compass Florida, LLC
Del Webb Oasis
![15139 CANOPY COVER DR, WINTER GARDEN, FL..., Winter Garden, FL 34787]()
2 beds
|2 baths
|2,000 sq ft
|House
15139 CANOPY COVER DR, WINTER GARDEN, FL...
Community: Del Webb Oasis
MLS O6415871 • INTERNATIONAL TEAM INC, Jo Costa • INTERNATIONAL TEAM INC
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.
Spring Lake Towers
![700 MIRROR TER 506, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881]()
2 beds
|2 baths
|1,190 sq ft
|Condo
700 MIRROR TER 506, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
MLS P4939037 • JUDY B CLEAVES PROPERTIES INC, Chr... • JUDY B CLEAVES PROPERTIES INC
The Villages®
![562 ALLENWOOD LOOP, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|1,906 sq ft
|House
562 ALLENWOOD LOOP, THE VILLAGES, FL, 32...
Community: The Villages®
MLS OM726346 • ROBERTS REAL ESTATE INC, Diane Tre... • ROBERTS REAL ESTATE INC
Cindy Certified
Kings Ridge
![3675 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,713 sq ft
|House
3675 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5111341 • REAL BROKER, LLC, Diane Rogers • REAL BROKER, LLC
The Villages®
![2446 HOPESPRING LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
2446 HOPESPRING LOOP, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5113681 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Cindy Certified
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
Cindy Certified
The Villages®
![321 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159]()
2 beds
|2 baths
|1,478 sq ft
|House
321 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5113749 • WORTH CLARK REALTY, Nathan Piotrow... • WORTH CLARK REALTY
Legacy of Leesburg
![5304 TREASURE VIEW WAY, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,641 sq ft
|House
5304 TREASURE VIEW WAY, LEESBURG, FL, 34...
Community: Legacy of Leesburg
MLS G5113723 • VANGIE BERRY SIGNATURE REALTY, Ang... • VANGIE BERRY SIGNATURE REALTY
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.
Kings Ridge
![3786 AVON CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS O6416585 • WATSON REALTY CORP., REALTORS, Cur... • WATSON REALTY CORP., REALTORS
Pelican Bay Daytona Beach
![141 GOLDEN EYE DR B, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,237 sq ft
|Condo
141 GOLDEN EYE DR B, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS O6416729 • LOKATION, Donna Lang • LOKATION
The Villages®
![919 WEEPING WILLOW AVE, LADY LAKE, FL, 3..., Lady Lake, FL 32159]()
2 beds
|2 baths
|1,392 sq ft
|Manufactured Home
919 WEEPING WILLOW AVE, LADY LAKE, FL, 3...
Community: The Villages®
MLS G5113268 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Alamanda Key
![543 HEMING WAY, MELBOURNE, FL, 32901, Melbourne, FL 32901]()
MLS 1079965 • RE/MAX Elite, Todd Ostrander • RE/MAX Elite
The Villages®
![1133 DEL TORO DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,332 sq ft
|House
1133 DEL TORO DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5113320 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Cindy Certified
Venetian Bay
![3507 CASALTA CIR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,180 sq ft
|Townhouse
3507 CASALTA CIR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS 1227518 • Oceans Luxury Realty Full Service L... • Oceans Luxury Realty Full Service LLC
Want to learn more about 55+ communities in Winter Park?
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The Villages®
![16840 SE 85TH SAPELO CT, THE VILLAGES, F..., The Villages, FL 32162]()
3 beds
|2 baths
|2,003 sq ft
|House
16840 SE 85TH SAPELO CT, THE VILLAGES, F...
Community: The Villages®
MLS G5113557 • DOWN HOME REALTY, LLLP, Colleen A.... • DOWN HOME REALTY, LLLP
Twin Lakes
![2724 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS S5151662 • WEICHERT REALTORS HALLMARK PRO, Sh... • WEICHERT REALTORS HALLMARK PRO
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.
Bridgewater at Viera
![1764 VELKY LN, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,565 sq ft
|House
1764 VELKY LN, MELBOURNE, FL, 32940
Community: Bridgewater at Viera
MLS 1079901 • Compass Florida LLC, David Andai • Compass Florida LLC
Cindy Certified
Foxwood Lake Estates
![5035 LODGEWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,352 sq ft
|Manufactured Home
5035 LODGEWOOD DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS O6416213 • INVENTURE GROUP LLC, Kevin Atchoo • INVENTURE GROUP LLC
VillageWalk at Lake Nona
![8523 LEATHERLEAF LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
4 beds
|3 baths
|1,720 sq ft
|Townhouse
8523 LEATHERLEAF LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS S5151750 • FIGLOFT INC, Carmen Maysonet • FIGLOFT INC
Tohoqua Reserve
![1973 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
3 beds
|2 baths
|1,701 sq ft
|House
1973 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS O6416082 • MARK SPAIN REAL ESTATE, ARod Rodri... • MARK SPAIN REAL ESTATE
The Villages®
![1312 BAEZ WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|2,044 sq ft
|House
1312 BAEZ WAY, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5113606 • BHHS FLORIDA REALTY, Tess US Udden... • BHHS FLORIDA REALTY
The Villages®
![1534 HILLCREST DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,144 sq ft
|House
1534 HILLCREST DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5113458 • KELLER WILLIAMS CORNERSTONE RE, Ka... • KELLER WILLIAMS CORNERSTONE RE
The Country Club of Mount Dora
![1920 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
5 beds
|4 baths
|4,018 sq ft
|House
1920 EDGEWATER DR, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS G5113449 • ERA GRIZZARD REAL ESTATE, Loretta ... • ERA GRIZZARD REAL ESTATE
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High Vista at Ridgewood Lakes
![215 FITZGERALD LN, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|2 baths
|1,760 sq ft
|House
215 FITZGERALD LN, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS S5151767 • KELLER WILLIAMS REALTY AT THE LAKE... • KELLER WILLIAMS REALTY AT THE LAKES
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.
