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Winter Park, FL 55+ active adult communities & homes for sale - Page 43
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
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$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
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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.
Halifax Plantation
![3753 MAYO CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|4 baths
|2,863 sq ft
|House
3753 MAYO CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS FC318362 • FLORIDA BEACHES REAL ESTATE, Amand... • FLORIDA BEACHES REAL ESTATE
Plantation Bay Golf & Country Club
![1117 OXBRIDGE LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|5 baths
|5,352 sq ft
|House
1117 OXBRIDGE LN, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS V4949096 • REALTY PROS ASSURED, Bill Navarra • REALTY PROS ASSURED
Pelican Bay Daytona Beach
![128 SPOONBILL CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32119]()
3 beds
|2 baths
|2,056 sq ft
|House
128 SPOONBILL CT, DAYTONA BEACH, FL, 321...
Community: Pelican Bay Daytona Beach
MLS 1226453 • EXP Realty LLC, Kevin Yarina • EXP Realty LLC
High Vista at Ridgewood Lakes
![237 GOLF VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|3 baths
|2,611 sq ft
|House
237 GOLF VISTA DR, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS O6407154 • EXP REALTY LLC, Corinne Defilippis • EXP REALTY LLC
Four Seasons at Orlando
![1691 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
2 beds
|2 baths
|1,557 sq ft
|Villa
1691 KEY BAY TRL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS S5149880 • PROPERTIES IN TOWN, Rabie Georgey • PROPERTIES IN TOWN
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Spruce Creek South
![17814 SE 107TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,450 sq ft
|House
17814 SE 107TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS G5112062 • EXP REALTY LLC, Edalys Ramos • EXP REALTY LLC
Latitude Margaritaville
![396 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,466 sq ft
|House
396 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS 1226433 • Bob Hodges and Sons Realty, Kelley ... • Bob Hodges and Sons Realty
Grand Haven
![200 RIVERFRONT DR D304, PALM COAST, FL, ..., Palm Coast, FL 32137]()
3 beds
|3 baths
|2,015 sq ft
|Condo
200 RIVERFRONT DR D304, PALM COAST, FL, ...
Community: Grand Haven
MLS FC318503 • TRADEMARK REALTY GROUP LLC, Marie ... • TRADEMARK REALTY GROUP LLC
The Villages®
![3541 ROANOKE ST, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
3541 ROANOKE ST, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5112220 • KELLER WILLIAMS CORNERSTONE RE, Ka... • KELLER WILLIAMS CORNERSTONE RE
The Villages®
![1008 VENTURA DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,344 sq ft
|House
1008 VENTURA DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5112229 • KELLER WILLIAMS CORNERSTONE RE, Ka... • KELLER WILLIAMS CORNERSTONE RE
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®
![1795 HAGOOD LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,770 sq ft
|House
1795 HAGOOD LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5112290 • WORTH CLARK REALTY, Margaret Ingmi... • WORTH CLARK REALTY
Kings Ridge
![4390 SAMBOURNE ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,363 sq ft
|House
4390 SAMBOURNE ST, CLERMONT, FL, 34711
Community: Kings Ridge
MLS O6406642 • LPT REALTY, LLC, Lora Feingold • LPT REALTY, LLC
The Villages®
![2696 MIDLAND TER, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|2,133 sq ft
|House
2696 MIDLAND TER, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS O6408111 • FLORIDA PREFERRED REALTY LLC, Marg... • FLORIDA PREFERRED REALTY LLC
Cindy Certified
Plantation Bay Golf & Country Club
![420 WINGSPAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
5 beds
|7 baths
|5,151 sq ft
|House
420 WINGSPAN DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS V4949030 • REALTY PROS ASSURED, Sheriff Guind... • REALTY PROS ASSURED
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Twin Lakes
![2486 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS O6406989 • EXP REALTY LLC, Kristy Cook • EXP REALTY LLC
Cindy Certified
Cindy Certified
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
The Villages®
![2039 TYNTE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|3 baths
|2,473 sq ft
|House
2039 TYNTE TER, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5110849 • LPT REALTY, LLC, Kathy Tucker • LPT REALTY, LLC
The Villages®
![1969 HAGOOD LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|2,000 sq ft
|House
1969 HAGOOD LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5111749 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Cindy Certified
The Villages®
![1648 ABASCO CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
1648 ABASCO CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS TB8508059 • HOMECOIN.COM, Jonathan Minerick • HOMECOIN.COM
Cindy Certified
Want to learn more about 55+ communities in Winter Park?
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Spruce Creek Country Club
![13500 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
2 beds
|3 baths
|2,333 sq ft
|House
13500 SE 97TH TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM724620 • RE/MAX PREMIER REALTY LADY LK, Ter... • RE/MAX PREMIER REALTY LADY LK
The Villages®
![447 FOSTER PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,872 sq ft
|House
447 FOSTER PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5112156 • COLDWELL BANKER VANGUARD LIFESTYLE... • COLDWELL BANKER VANGUARD LIFESTYLE REALTY
The Villages®
![991 BARRYMOORE LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
3 beds
|2 baths
|1,527 sq ft
|House
991 BARRYMOORE LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
MLS OM724672 • SALLY LOVE REAL ESTATE, Star Amado... • SALLY LOVE REAL ESTATE
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.
Venetian Bay
![3604 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168]()
4 beds
|2 baths
|2,050 sq ft
|House
3604 MARIBELLA DR, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
MLS NS1088040 • WATSON REALTY CORP, Terri Lynn Br... • WATSON REALTY CORP
The Villages®
![17167 SE 76TH BOXBURY CT, THE VILLAGES, ..., The Villages, FL 32162]()
2 beds
|2 baths
|1,194 sq ft
|House
17167 SE 76TH BOXBURY CT, THE VILLAGES, ...
Community: The Villages®
MLS TB8505329 • REDFIN CORPORATION, Marc Collazo • REDFIN CORPORATION
Trilogy® Orlando
![115 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736]()
3 beds
|2 baths
|1,856 sq ft
|House
115 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
MLS O6407445 • EXP REALTY LLC, Eddie Lopez • EXP REALTY LLC
The Villages®
![207 DESOTA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,889 sq ft
|House
207 DESOTA CT, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5112093 • COLDWELL BANKER VANGUARD LIFESTYLE... • COLDWELL BANKER VANGUARD LIFESTYLE REALTY
The Villages®
![2561 BIRCH AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,188 sq ft
|Villa
2561 BIRCH AVE, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5112091 • COLDWELL BANKER VANGUARD LIFESTYLE... • COLDWELL BANKER VANGUARD LIFESTYLE REALTY
The Villages®
![1000 KENOVA AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
1000 KENOVA AVE, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5112080 • COLDWELL BANKER VANGUARD LIFESTYLE... • COLDWELL BANKER VANGUARD LIFESTYLE REALTY
The Villages®
![2013 SANTO DOMINGO DR, THE VILLAGES, FL,..., The Villages, FL 32159]()
3 beds
|2 baths
|2,015 sq ft
|House
2013 SANTO DOMINGO DR, THE VILLAGES, FL,...
Community: The Villages®
MLS G5112078 • COLDWELL BANKER VANGUARD LIFESTYLE... • COLDWELL BANKER VANGUARD LIFESTYLE REALTY
The Villages®
![608 DELGADO AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,094 sq ft
|Villa
608 DELGADO AVE, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5112218 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
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The Villages®
![728 PRADO DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,144 sq ft
|Manufactured Home
728 PRADO DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5112113 • RE/MAX FOXFIRE - SUMMERFIELD, Tina... • RE/MAX FOXFIRE - SUMMERFIELD
Royal Highlands
![4841 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,197 sq ft
|House
4841 GLEN COE ST, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5112234 • VANTAGE POINT REALTY CO., Tracie R... • VANTAGE POINT REALTY CO.
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.
