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Winter Park, FL 55+ active adult communities & homes for sale - Page 65
98 communities near Winter Park
2,715 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
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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
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
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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
Royal Palm
![5415 SWORDFERN CT, PORT ORANGE, FL, 3212..., Port Orange, FL 32128]()
3 beds
|3 baths
|1,942 sq ft
|House
5415 SWORDFERN CT, PORT ORANGE, FL, 3212...
Community: Royal Palm
MLS NS1086360 • EXECUTIVE REALTY GROUP LLC, Alire... • EXECUTIVE REALTY GROUP LLC
Cindy Certified
Huntington at Hunter's Ridge
![42 HUNTINGTON PL, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|2 baths
|2,003 sq ft
|House
42 HUNTINGTON PL, ORMOND BEACH, FL, 3217...
Community: Huntington at Hunter's Ridge
MLS V4945587 • RE/MAX SIGNATURE, Rola Michael • RE/MAX SIGNATURE
Cindy Certified
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Highland Lakes
![5616 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS G5103058 • COLDWELL BANKER REALTY, Sara Suthe... • COLDWELL BANKER REALTY
The Villages®
![5371 WARM SPRINGS AVE, WILDWOOD, FL, 347..., Wildwood, FL 34785]()
2 beds
|1 baths
|696 sq ft
|House
5371 WARM SPRINGS AVE, WILDWOOD, FL, 347...
Community: The Villages®
MLS OM711975 • FLORIDA CAPITAL REALTY, Dolly Plan... • FLORIDA CAPITAL REALTY
Venetian Bay
![2937 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
4 beds
|3 baths
|2,070 sq ft
|House
2937 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS O6353959 • DE VIVO REALTY LLC, Alessandro De ... • DE VIVO REALTY LLC
Plantation Bay Golf & Country Club
![1047 KILKENNY LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,081 sq ft
|Townhouse
1047 KILKENNY LN, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS FC313504 • VENTURE DEVELOPMENT REALTY,INC, El... • VENTURE DEVELOPMENT REALTY,INC
Twin Lakes
![2600 MEADOWEDGE LOOP, ST CLOUD, FL, 3477..., St Cloud, FL 34772]()
3 beds
|3 baths
|2,935 sq ft
|House
2600 MEADOWEDGE LOOP, ST CLOUD, FL, 3477...
Community: Twin Lakes
MLS O6346165 • LPT REALTY, LLC, Jessica Snyder • 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.
Stonecrest
![17306 SE 112TH CT RD, SUMMERFIELD, FL, 3..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,955 sq ft
|House
17306 SE 112TH CT RD, SUMMERFIELD, FL, 3...
Community: Stonecrest
MLS G5102892 • CHARLES RUTENBERG REALTY ORLANDO, ... • CHARLES RUTENBERG REALTY ORLANDO
Lakes of Mount Dora
![8860 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,671 sq ft
|House
8860 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS G5103304 • WATSON REALTY CORP, Jody Parks • WATSON REALTY CORP
Halifax Plantation
![3078 SILVERMINES AVE, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,914 sq ft
|House
3078 SILVERMINES AVE, ORMOND BEACH, FL, ...
Community: Halifax Plantation
MLS FC313426 • NEVER 6 PERCENT REALTY INC., Peter... • NEVER 6 PERCENT REALTY INC.
Solivita
![1305 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6350952 • RE/MAX SELECT GROUP, Bridget Daku-... • RE/MAX SELECT GROUP
Lake Ashton
![4004 SABLE LOOP DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859]()
4 beds
|3 baths
|2,937 sq ft
|House
4004 SABLE LOOP DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
MLS P4936596 • GLOBAL LIFESTYLE LLC, Brad Kirwan • GLOBAL LIFESTYLE LLC
Cindy Certified
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Questions? Call us:
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The Villages®
![16946 SE 93RD CUTHBERT CIR, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|2,002 sq ft
|House
16946 SE 93RD CUTHBERT CIR, THE VILLAGES...
Community: The Villages®
MLS OM711180 • DANIEL J MCNULTY PLLC LLC, Dan McN... • DANIEL J MCNULTY PLLC LLC
Sullivan Ranch
![30101 BRETTON LOOP, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757]()
4 beds
|3 baths
|3,452 sq ft
|House
30101 BRETTON LOOP, MOUNT DORA, FL, 3275...
Community: Sullivan Ranch
MLS O6351059 • LA ROSA REALTY PREMIER LLC, Tavis ... • LA ROSA REALTY PREMIER LLC
Grand Haven
![455 RIVERFRONT DR A104, PALM COAST, FL, ..., Palm Coast, FL 32137]()
3 beds
|3 baths
|2,167 sq ft
|Condo
455 RIVERFRONT DR A104, PALM COAST, FL, ...
Community: Grand Haven
MLS FC313284 • COASTAL GATEWAY REAL ESTATE GR, Ma... • COASTAL GATEWAY REAL ESTATE GR
Highland Fairways
![2137 GRAND CYPRESS DR, LAKELAND, FL, 338..., Lakeland, FL 33810]()
3 beds
|2 baths
|1,808 sq ft
|House
2137 GRAND CYPRESS DR, LAKELAND, FL, 338...
Community: Highland Fairways
MLS B4902076 • CRAIG BURKE REAL ESTATE GROUP, LLC... • CRAIG BURKE REAL ESTATE GROUP, 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.
Plantation at Leesburg
![3606 MULBERRY GROVE LOOP, LEESBURG, FL, ..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,664 sq ft
|House
3606 MULBERRY GROVE LOOP, LEESBURG, FL, ...
Community: Plantation at Leesburg
MLS G5102758 • CENTURY 21 MYERS ROSE REALTY, Mary... • CENTURY 21 MYERS ROSE REALTY
Cindy Certified
The Villages®
![939 KOLLER CT, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,880 sq ft
|House
939 KOLLER CT, THE VILLAGES, FL, 32163
Community: The Villages®
MLS O6350238 • REAL PROPERTY INTERNATIONAL, Bob L... • REAL PROPERTY INTERNATIONAL
Pennbrooke Fairways
![615 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
1 beds
|1 baths
|490 sq ft
|Manufactured Home
615 COTTAGE PARK LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS OM710883 • SUNBURST PROPERTIES, Scott Hutchin... • SUNBURST PROPERTIES
The Villages®
![712 JASON DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,292 sq ft
|Manufactured Home
712 JASON DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5102567 • IM REALTY, Ira Miller • IM REALTY
The Villages®
![870 HENDERSON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,375 sq ft
|House
870 HENDERSON LN, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5101221 • CENTURY 21 MYERS ROSE REALTY, Mari... • CENTURY 21 MYERS ROSE REALTY
Plantation Bay Golf & Country Club
![875 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,101 sq ft
|Townhouse
875 PINEWOOD DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC313186 • OLIVE GROVE REAL ESTATE, Sean Tabo... • OLIVE GROVE REAL ESTATE
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Solivita
![507 PRESIDO PARK PL, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
2 beds
|2 baths
|1,302 sq ft
|House
507 PRESIDO PARK PL, KISSIMMEE, FL, 3475...
Community: Solivita
MLS TB8429298 • NHR BROKERAGE LLC, Madalina Tat • NHR BROKERAGE LLC
The Villages®
![1224 DUSTIN DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|912 sq ft
|Manufactured Home
1224 DUSTIN DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS OM707875 • VAUGHT REALTY, Billy Vaught • VAUGHT 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.
Cindy Certified
Cindy Certified
Stonecrest
![17209 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,695 sq ft
|House
17209 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
MLS G5102714 • MORRIS REALTY AND INVESTMENTS, Kim... • MORRIS REALTY AND INVESTMENTS
Spruce Creek Country Club
![9244 SE 128TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|2,130 sq ft
|House
9244 SE 128TH ST, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM710460 • RE/MAX FOXFIRE - SUMMERFIELD, Caro... • RE/MAX FOXFIRE - SUMMERFIELD
The Reserve at Victoria
![1548 LAKE RESERVE DR, DELAND, FL, 32724, Deland, FL 32724]()
4 beds
|3 baths
|2,436 sq ft
|House
1548 LAKE RESERVE DR, DELAND, FL, 32724
Community: The Reserve at Victoria
MLS V4945053 • BEE REALTY CORP, Bee Powell • BEE REALTY CORP
Plantation Bay Golf & Country Club
![945 STONE LAKE DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,910 sq ft
|House
945 STONE LAKE DR, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS FC313035 • VENTURE DEVELOPMENT REALTY,INC, El... • VENTURE DEVELOPMENT REALTY,INC
Colonnades
![4816 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,066 sq ft
|Manufactured Home
4816 GOLDENVIEW LN, LAKELAND, FL, 33811
Community: Colonnades
MLS L4955982 • COLDWELL BANKER REALTY, Lisa Broch... • COLDWELL BANKER REALTY
Cindy Certified
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Plantation Bay Golf & Country Club
![998 DOWNSHIRE LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
5 beds
|4 baths
|5,454 sq ft
|House
998 DOWNSHIRE LN, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS FC312940 • VENTURE DEVELOPMENT REALTY,INC, El... • VENTURE DEVELOPMENT REALTY,INC
Del Webb Minneola
![2761 TOP HILL CT, MINNEOLA, FL, 34715, Minneola, FL 34715]()
2 beds
|2 baths
|1,943 sq ft
|House
2761 TOP HILL CT, MINNEOLA, FL, 34715
Community: Del Webb Minneola
MLS O6345393 • SERHANT, Silvia Kinkela • SERHANT
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?
2,715
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.
