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Winter Park, FL 55+ active adult communities & homes for sale - Page 4
98 communities near Winter Park
2,698 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
4.7 rating (18 reviews)
![Solivita]()
$300ks
- $700ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 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
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
$300ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 homes
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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
5 rating (3 reviews)
![Stonecrest]()
$200ks
- $500ks
Stonecrest, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 2024
|
2,224 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)
![Twin Lakes]()
$200ks
- $600ks
Twin Lakes, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
2,000 homes
5 rating (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 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.
$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 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
$200ks
- $800ks
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 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 (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
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$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 homes
5 rating (8 reviews)
![Kings Ridge]()
$200ks
- $400ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 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
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
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.
5 rating (1 reviews)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 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
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
$200ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 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
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
Want to learn more about 55+ communities in Winter Park?
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$100ks
- $200ks
Scottish Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1992
|
653 homes
$300ks
- $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
557 homes
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 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
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
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
$300ks
- $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
216 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
- $300ks
Highland Fairways, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1998
|
660 homes
$400ks
- $1Ms
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
1,300 homes
$100ks
- $300ks
Lakeside Landings, Oxford, FL
New and Resale
|
Age-targeted
|
Built 2005 - present
|
700 homes
Want to learn more about 55+ communities in Winter Park?
55places can help!
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
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
|
545 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.
New
![480 GRAND RESERVE DR, BUNNELL, FL, 32110, Bunnell, FL 32110]()
Cindy Certified
New
![5606 DENNERY BAY RD, KISSIMMEE, FL, 3475..., Kissimmee, FL 34758]()
Cindy Certified
New
Arlington Ridge
![27033 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,323 sq ft
|House
27033 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
MLS G5118630 • LOKATION, Steven Simpkins • LOKATION
New
Venetian Bay
![3131 PORTOFINO BLVD, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168]()
4 beds
|4 baths
|2,338 sq ft
|House
3131 PORTOFINO BLVD, NEW SMYRNA BEACH, F...
Community: Venetian Bay
MLS NS1089429 • EXIT REAL ESTATE PROPERTY SOL, Ca... • EXIT REAL ESTATE PROPERTY SOL
New
The Villages®
![1700 NORFOLK AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,920 sq ft
|House
1700 NORFOLK AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5118627 • RE/MAX PREMIER REALTY, Mark Sevegn... • RE/MAX PREMIER REALTY
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
New
The Villages®
![1234 EAGLE RIDGE DR, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|House
1234 EAGLE RIDGE DR, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5118639 • LPT REALTY, LLC, Karen Seale • LPT REALTY, LLC
New
Stonecrest
![17681 SE 115TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|3 baths
|1,952 sq ft
|House
17681 SE 115TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5118658 • RE/MAX PREMIER REALTY LADY LK, Cin... • RE/MAX PREMIER REALTY LADY LK
New
![3629 MAIDENCAIN ST, CLERMONT, FL, 34714, Clermont, FL 34714]()
Cindy Certified
New
![414 TAFT DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
Cindy Certified
New
Solivita
![532 PASADENA PL, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS O6447298 • LPT REALTY, LLC, Maria Cuffaro • LPT 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.
New
The Villages®
![17115 SE 93RD TELLFIER TER, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|2,036 sq ft
|House
17115 SE 93RD TELLFIER TER, THE VILLAGES...
Community: The Villages®
MLS G5118643 • COLDWELL BANKER VANGUARD LIFESTYLE... • COLDWELL BANKER VANGUARD LIFESTYLE REALTY
New
Royal Highlands
![21736 PRINCESS GRACE CT, LEESBURG, FL, 3..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,233 sq ft
|House
21736 PRINCESS GRACE CT, LEESBURG, FL, 3...
Community: Royal Highlands
MLS G5118588 • FLORIDA PLUS REALTY, LLC, Celie Wh... • FLORIDA PLUS REALTY, LLC
New
The Villages®
![3209 HAMPTON LN, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,640 sq ft
|House
3209 HAMPTON LN, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5118533 • WORTH CLARK REALTY, Madison Waddel... • WORTH CLARK REALTY
New
Lakes of Mount Dora
![7887 CROSSWINDS WAY, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,721 sq ft
|House
7887 CROSSWINDS WAY, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
MLS G5118490 • ERA GRIZZARD REAL ESTATE, Scott Mc... • ERA GRIZZARD REAL ESTATE
New
Lake Ashton
![4227 BERWICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|1,847 sq ft
|House
4227 BERWICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4940050 • LAKE ASHTON REALTY INC., Lori Raat... • LAKE ASHTON REALTY INC.
New
Scottish Highlands
![803 DUNDEE CIR 803, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,436 sq ft
|Condo
803 DUNDEE CIR 803, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5118270 • WEICHERT REALTORS HALLMARK PRO, Be... • WEICHERT REALTORS HALLMARK PRO
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
New
The Villages®
![2459 LAUREL BAY LN, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|House
2459 LAUREL BAY LN, THE VILLAGES, FL, 32...
Community: The Villages®
MLS OM732801 • VAUGHT REALTY, Billy Vaught • VAUGHT REALTY
New
Del Webb Orlando
![533 ARENA DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|2 baths
|1,728 sq ft
|House
533 ARENA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS O6446005 • SERHANT, Jonathan Fadoul • SERHANT
New
Latitude Margaritaville
![459 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
3 beds
|2 baths
|1,848 sq ft
|House
459 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS 1231511 • Bob Hodges and Sons Realty, Kelley ... • Bob Hodges and Sons Realty
New
Plantation at Leesburg
![25078 RIVERWALK DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,549 sq ft
|House
25078 RIVERWALK DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS V4951162 • PROPERTY SHOWCASE HOMES REALTY, Do... • PROPERTY SHOWCASE HOMES 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.
New
![4046 DINNER LAKE WAY, LAKE WALES, FL, 33..., Lake Wales, FL 33859]()
Cindy Certified
New
The Villages®
![1318 BALBOA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|978 sq ft
|Villa
1318 BALBOA CT, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5118646 • LPT REALTY, LLC, LD Black Bowers-B... • LPT REALTY, LLC
New
The Villages®
![16870 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162]()
2 beds
|2 baths
|1,160 sq ft
|House
16870 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
MLS G5118629 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
New
The Villages®
![3033 HILLSIDE LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
2 beds
|2 baths
|1,588 sq ft
|House
3033 HILLSIDE LN, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5118611 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
New
Latitude Margaritaville
![879 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124]()
3 beds
|3 baths
|2,415 sq ft
|House
879 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
Community: Latitude Margaritaville
MLS 1231505 • Realty Hub, Cherri Tindall • Realty Hub
New
Plantation Bay Golf & Country Club
![1015 SUDBURY LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|7 baths
|4,739 sq ft
|House
1015 SUDBURY LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS 1231503 • 386RealEstate.com, Kevin Kling • 386RealEstate.com
New
![1295 KYLAR DR, PALM BAY, FL, 32907, Palm Bay, FL 32907]()
Cindy Certified
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
New
![3068 AVALONIA DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
Cindy Certified
Cresswind at Victoria Gardens
![413 CYPRESS HILLS WAY, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,655 sq ft
|House
413 CYPRESS HILLS WAY, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS V4951629 • LPT REALTY LLC, Sheree Frazier • LPT REALTY LLC
Spruce Creek Country Club
![8573 SE 133RD LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,822 sq ft
|House
8573 SE 133RD LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS O6446200 • INVESTOR'S REAL ESTATE LLC, Susan ... • INVESTOR'S REAL ESTATE 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
The Villages®
![1693 MOUNT CROGHAN TRL, THE VILLAGES, FL..., The Villages, FL 32162]()
3 beds
|2 baths
|1,927 sq ft
|House
1693 MOUNT CROGHAN TRL, THE VILLAGES, FL...
Community: The Villages®
MLS G5118616 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
The Villages®
![9595 SE 171ST ARGYLL ST, THE VILLAGES, F..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
9595 SE 171ST ARGYLL ST, THE VILLAGES, F...
Community: The Villages®
MLS G5118250 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Four Seasons at Orlando
![1999 LIMESTONE TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
3 beds
|2 baths
|2,202 sq ft
|House
1999 LIMESTONE TRL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS O6447154 • VIVA ORLANDO REALTY INC., Susan Ri... • VIVA ORLANDO REALTY INC.
Plantation Bay Golf & Country Club
![409 SEABROOK RD, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,153 sq ft
|House
409 SEABROOK RD, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS V4951651 • KELLER WILLIAMS RLTY FL. PARTN, Tr... • KELLER WILLIAMS RLTY FL. PARTN
Cindy Certified
The Villages®
![5099 NE 124TH PL, OXFORD, FL, 34484, Oxford, FL 34484]()
3 beds
|3 baths
|2,491 sq ft
|House
5099 NE 124TH PL, OXFORD, FL, 34484
Community: The Villages®
MLS G5118148 • COLDWELL BANKER VANGUARD LIFESTYLE... • COLDWELL BANKER VANGUARD LIFESTYLE REALTY
The Villages®
![1648 PENNECAMP DR, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,753 sq ft
|House
1648 PENNECAMP DR, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5118614 • ERA GRIZZARD REAL ESTATE, Jim Rich... • ERA GRIZZARD REAL ESTATE
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
Lake Ashton
![5344 NICKLAUS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884]()
3 beds
|2 baths
|1,680 sq ft
|House
5344 NICKLAUS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
MLS P4940027 • LAKE ASHTON REALTY INC., Lori Raat... • LAKE ASHTON REALTY INC.
Legacy of Leesburg
![5401 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,621 sq ft
|House
5401 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS G5118590 • RE/MAX PREMIER REALTY, Adriana Sko... • 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.
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?
2,698
homes
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REIN updates its listings on a daily basis. Data last updated: Oct 10, 2026.
This application does not include information on all of the properties available for sale at this time.
