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Winter Park, FL 55+ active adult communities & homes for sale - Page 58
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
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
|
Built 2017 - 2025
|
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
|
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 (3 reviews)
![Lake Ashton]()
$200ks
- $500ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
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
|
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
|
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
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
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
|
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
|
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
$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.
Cindy Certified
Heritage Hills
![3550 FAIRWATERS CT D, CLERMONT, FL, 3471..., Clermont, FL 34711]()
2 beds
|2 baths
|1,503 sq ft
|Villa
3550 FAIRWATERS CT D, CLERMONT, FL, 3471...
Community: Heritage Hills
MLS G5107861 • OPTIMA ONE REALTY, INC., Heather W... • OPTIMA ONE REALTY, INC.
Summit Greens
![2390 CALEDONIAN ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,961 sq ft
|House
2390 CALEDONIAN ST, CLERMONT, FL, 34711
Community: Summit Greens
MLS O6384621 • EXP REALTY LLC, Phil Mariani • EXP REALTY LLC
Royal Harbor
![5732 FREEPORT DR, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS G5108407 • BHHS FLORIDA REALTY, Doug Piazza • BHHS FLORIDA REALTY
Cindy Certified
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Lakeside Landings
![5427 COMPASS PT 1, OXFORD, FL, 34484, Oxford, FL 34484]()
2 beds
|2 baths
|1,281 sq ft
|Condo
5427 COMPASS PT 1, OXFORD, FL, 34484
Community: Lakeside Landings
MLS G5108257 • EXP REALTY LLC, Brenda Bell • EXP REALTY LLC
The Villages®
![210 PALERMO PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|3 baths
|2,118 sq ft
|House
210 PALERMO PL, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5108098 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Gatherings of Lake Nona
![7545 LAUREATE BLVD 7301, ORLANDO, FL, 32..., Orlando, FL 32827]()
2 beds
|2 baths
|1,445 sq ft
|Condo
7545 LAUREATE BLVD 7301, ORLANDO, FL, 32...
Community: Gatherings of Lake Nona
MLS O6383756 • KELLER WILLIAMS ADVANTAGE REALTY, ... • KELLER WILLIAMS ADVANTAGE REALTY
Cindy Certified
The Country Club of Mount Dora
![1500 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|3 baths
|2,544 sq ft
|House
1500 EDGEWATER DR, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS O6383176 • UNITED REAL ESTATE PREFERRED, Kay ... • UNITED REAL ESTATE PREFERRED
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
Cindy Certified
The Villages®
![648 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159]()
3 beds
|2 baths
|1,774 sq ft
|House
648 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5108179 • CENTURY 21 ALTON CLARK, Kwynn Nich... • CENTURY 21 ALTON CLARK
Oakview
![1581 OAKVIEW CIR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33880]()
2 beds
|2 baths
|1,220 sq ft
|House
1581 OAKVIEW CIR, WINTER HAVEN, FL, 3388...
Community: Oakview
MLS G5108372 • LPT REALTY, LLC, Vanessa Aybar Bad... • LPT REALTY, LLC
Park Place
![107 PARK PLACE CIR, PALM COAST, FL, 3216..., Palm Coast, FL 32164]()
3 beds
|2 baths
|1,759 sq ft
|House
107 PARK PLACE CIR, PALM COAST, FL, 3216...
Community: Park Place
MLS FC316256 • NEXTHOME NEW BEGINNINGS, Brianne N... • NEXTHOME NEW BEGINNINGS
Alamanda Key
![4220 ALAMANDA KEY DR DRIVE, MELBOURNE, F..., Melbourne, FL 32901]()
3 beds
|2 baths
|1,551 sq ft
|House
4220 ALAMANDA KEY DR DRIVE, MELBOURNE, F...
Community: Alamanda Key
MLS 1069103 • Lokation Real Estate, Cheryld T. Ha... • Lokation Real Estate
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Lake Ashton
![5264 GREEN DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
3 beds
|2 baths
|2,011 sq ft
|House
5264 GREEN DR, WINTER HAVEN, FL, 33884
Community: Lake Ashton
MLS P4937885 • LAKE ASHTON REALTY INC., Lori Raat... • LAKE ASHTON REALTY INC.
The Villages®
![16905 SE 93RD CUTHBERT CIR, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,924 sq ft
|House
16905 SE 93RD CUTHBERT CIR, THE VILLAGES...
Community: The Villages®
MLS NS1087246 • ENGEL & VOLKERS NEW SMYRNA, Josep... • ENGEL & VOLKERS NEW SMYRNA
Grand Haven
![10 RIVER PARK DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
2 beds
|2 baths
|1,828 sq ft
|Townhouse
10 RIVER PARK DR, PALM COAST, FL, 32137
Community: Grand Haven
MLS FC316308 • RE/MAX SELECT PROFESSIONALS, Cryst... • RE/MAX SELECT PROFESSIONALS
The Lakes at Harmony
![3204 OXBOW CT, ST CLOUD, FL, 34773, St Cloud, FL 34773]()
4 beds
|3 baths
|2,361 sq ft
|House
3204 OXBOW CT, ST CLOUD, FL, 34773
Community: The Lakes at Harmony
MLS S5144242 • TIE TEAM REALTY LLC, Chris Woeste • TIE TEAM 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.
Cindy Certified
The Villages®
![1194 MCDONOUGH PL, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
4 beds
|2 baths
|2,028 sq ft
|House
1194 MCDONOUGH PL, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5107637 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Palms at Serenoa
![3465 MEADOW BEAUTY WAY, CLERMONT, FL, 34..., Clermont, FL 34714]()
2 beds
|2 baths
|1,646 sq ft
|House
3465 MEADOW BEAUTY WAY, CLERMONT, FL, 34...
Community: Palms at Serenoa
MLS O6383495 • EXP REALTY LLC, Phil Mariani • EXP REALTY LLC
VillageWalk at Lake Nona
![11831 FAN TAIL LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
2 beds
|2 baths
|1,526 sq ft
|Halfplex
11831 FAN TAIL LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6375764 • LPT REALTY, LLC, Manuel Delgado • LPT REALTY, LLC
Sandpiper Golf & Country Club
![5888 SANDPIPERS DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,852 sq ft
|House
5888 SANDPIPERS DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4959490 • COLDWELL BANKER REALTY, Kelley Bla... • COLDWELL BANKER REALTY
Breakaway Trails
![175 DEEP WOODS WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
5 beds
|3 baths
|2,959 sq ft
|House
175 DEEP WOODS WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
MLS O6381856 • KELLER WILLIAMS CLASSIC, Jorge Mar... • KELLER WILLIAMS CLASSIC
The Villages®
![17723 SE 81ST TIMBERWOOD TER, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|2,027 sq ft
|House
17723 SE 81ST TIMBERWOOD TER, THE VILLAG...
Community: The Villages®
MLS OM718904 • LPT REALTY, LLC, Gary Martin • LPT REALTY, LLC
Want to learn more about 55+ communities in Winter Park?
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Cindy Certified
Esplanade at Westview
![5683 NEVIS TER, KISSIMMEE, FL, 34758, Kissimmee, FL 34758]()
3 beds
|3 baths
|2,372 sq ft
|House
5683 NEVIS TER, KISSIMMEE, FL, 34758
Community: Esplanade at Westview
MLS O6381617 • KELLER WILLIAMS REALTY AT THE PARK... • KELLER WILLIAMS REALTY AT THE PARKS
Royal Highlands
![21849 TARTAN ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,074 sq ft
|House
21849 TARTAN ST, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5108275 • FLORIDA PLUS REALTY, LLC, Tonya Ti... • FLORIDA PLUS 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.
Cindy Certified
Cindy Certified
Esplanade at Westview
![4240 BARBUDA LN, KISSIMMEE, FL, 34758, Kissimmee, FL 34758]()
2 beds
|2 baths
|2,100 sq ft
|House
4240 BARBUDA LN, KISSIMMEE, FL, 34758
Community: Esplanade at Westview
MLS O6381612 • KELLER WILLIAMS REALTY AT THE PARK... • KELLER WILLIAMS REALTY AT THE PARKS
The Villages®
![9711 SE 171ST ARGYLL ST, THE VILLAGES, F..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
9711 SE 171ST ARGYLL ST, THE VILLAGES, F...
Community: The Villages®
MLS G5107046 • KELLER WILLIAMS CORNERSTONE RE, Ka... • KELLER WILLIAMS CORNERSTONE RE
Esplanade at Westview
![4246 BARBUDA LN, KISSIMMEE, FL, 34758, Kissimmee, FL 34758]()
3 beds
|2 baths
|1,923 sq ft
|House
4246 BARBUDA LN, KISSIMMEE, FL, 34758
Community: Esplanade at Westview
MLS O6381620 • KELLER WILLIAMS REALTY AT THE PARK... • KELLER WILLIAMS REALTY AT THE PARKS
American Village
![29 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164]()
3 beds
|2 baths
|1,604 sq ft
|House
29 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
MLS FC316194 • DR HORTON REALTY INC., Charlie Rog... • DR HORTON REALTY INC.
Scottish Highlands
![822 DUNDEE CIR, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,414 sq ft
|House
822 DUNDEE CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5108264 • MORRIS REALTY AND INVESTMENTS, Jo ... • MORRIS REALTY AND INVESTMENTS
Pennbrooke Fairways
![752 OLD OAKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,620 sq ft
|House
752 OLD OAKS LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5108177 • GOLDKEY REAL ESTATE PARTNERS LLC, ... • GOLDKEY REAL ESTATE PARTNERS LLC
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Lakes of Mount Dora
![8301 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,823 sq ft
|House
8301 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS G5108256 • OLYMPUS EXECUTIVE REALTY INC, Kate... • OLYMPUS EXECUTIVE REALTY INC
Spruce Creek South
![9826 SE 178TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,312 sq ft
|House
9826 SE 178TH LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS G5107726 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
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.
