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Winter Park, FL 55+ active adult communities & homes for sale - Page 57
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?
55places can help!
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.
Royal Highlands
![4921 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,414 sq ft
|House
4921 GLEN COE ST, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5108958 • FLORIDA PLUS REALTY, LLC, Tonya Ti... • FLORIDA PLUS REALTY, LLC
Cindy Certified
Cindy Certified
The Villages®
![5255 OXFORD CT, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
3 beds
|2 baths
|1,352 sq ft
|Manufactured Home
5255 OXFORD CT, WILDWOOD, FL, 34785
Community: The Villages®
MLS G5109068 • DOWN HOME REALTY, LLLP, Colleen A.... • DOWN HOME REALTY, LLLP
Cindy Certified
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Questions? Call us:
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The Villages®
![16938 SE 94TH SUNNYBROOK CIR, THE VILLAG..., The Villages, FL 32162]()
2 beds
|2 baths
|1,163 sq ft
|Villa
16938 SE 94TH SUNNYBROOK CIR, THE VILLAG...
Community: The Villages®
MLS G5108710 • RE/MAX PREMIER REALTY LADY LK, Nao... • RE/MAX PREMIER REALTY LADY LK
Sandpiper Golf & Country Club
![669 EAGLE RUN, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,134 sq ft
|House
669 EAGLE RUN, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4959718 • COLDWELL BANKER REALTY, Ginger Qui... • COLDWELL BANKER REALTY
The Villages®
![2946 DUKE TER, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,661 sq ft
|House
2946 DUKE TER, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5109060 • CENTURY 21 ALTON CLARK, Regina Rod... • CENTURY 21 ALTON CLARK
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
Spruce Creek South
![10689 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,008 sq ft
|House
10689 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Spruce Creek South
MLS G5109057 • RE/MAX PREMIER REALTY LADY LK, Ger... • RE/MAX PREMIER REALTY LADY LK
Plantation Bay Golf & Country Club
![1020 SUDBURY LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|4 baths
|3,411 sq ft
|House
1020 SUDBURY LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS V4947604 • RE/MAX ADVANTAGE, Eric Zimmerman • RE/MAX ADVANTAGE
Plantation Bay Golf & Country Club
![1204 SUNNINGDALE LN, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,912 sq ft
|House
1204 SUNNINGDALE LN, ORMOND BEACH, FL, 3...
Community: Plantation Bay Golf & Country Club
MLS 2132808 • DJ & LINDSEY REAL ESTATE, BRITTANY ... • DJ & LINDSEY REAL ESTATE
Esplanade at Highland Ranch
![1282 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715]()
2 beds
|2 baths
|1,710 sq ft
|House
1282 ZEEK RIDGE ST, CLERMONT, FL, 34715
Community: Esplanade at Highland Ranch
MLS G5108850 • WATSON REALTY CORP., REALTORS, Ron... • WATSON REALTY CORP., REALTORS
Cresswind at Victoria Gardens
![109 AVENHAM DR, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,508 sq ft
|House
109 AVENHAM DR, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS O6385448 • NONA LEGACY POWERED BY LA ROSA, Pe... • NONA LEGACY POWERED BY LA ROSA
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
Breakaway Trails
![35 CARRIAGE CREEK WAY, ORMOND BEACH, FL,..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,803 sq ft
|House
35 CARRIAGE CREEK WAY, ORMOND BEACH, FL,...
Community: Breakaway Trails
MLS 1223626 • RE/MAX Signature, Dawn Beltrami • RE/MAX Signature
Spruce Creek Country Club
![9375 SE 125TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,958 sq ft
|House
9375 SE 125TH ST, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM719900 • REALTY ONE GROUP DAVALLS, David St... • REALTY ONE GROUP DAVALLS
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.
Alamanda Key
![3720 ALAMANDA KEY DR DRIVE, MELBOURNE, F..., Melbourne, FL 32901]()
3 beds
|2 baths
|1,729 sq ft
|House
3720 ALAMANDA KEY DR DRIVE, MELBOURNE, F...
Community: Alamanda Key
MLS 1070767 • Ellingson Properties, Jack C Jeffco... • Ellingson Properties
Plantation at Leesburg
![5535 TANGELO ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,040 sq ft
|House
5535 TANGELO ST, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5108923 • CENTURY 21 MYERS ROSE REALTY, Thom... • CENTURY 21 MYERS ROSE REALTY
Cindy Certified
The Villages®
![2000 GOLDENROD CT, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,398 sq ft
|Villa
2000 GOLDENROD CT, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5108940 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Cindy Certified
Cindy Certified
Cindy Certified
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
The Villages®
![5186 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484]()
3 beds
|4 baths
|1,929 sq ft
|House
5186 NE 122ND BLVD, OXFORD, FL, 34484
Community: The Villages®
MLS OM719308 • KELLER WILLIAMS CORNERSTONE RE, Ci... • KELLER WILLIAMS CORNERSTONE RE
Sullivan Ranch
![30337 GIDRAN TER, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|3 baths
|2,307 sq ft
|House
30337 GIDRAN TER, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS G5107968 • OLYMPUS EXECUTIVE REALTY INC, Brya... • OLYMPUS EXECUTIVE REALTY INC
Bridgewater at Viera
![1765 VELKY LN, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
2 beds
|2 baths
|1,565 sq ft
|House
1765 VELKY LN, MELBOURNE, FL, 32940
Community: Bridgewater at Viera
MLS 1070216 • EXP Realty, LLC, David S Jelinek • EXP 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
Latitude Margaritaville
![485 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,308 sq ft
|Villa
485 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Community: Latitude Margaritaville
MLS TB8476795 • KELLER WILLIAMS REALTY- PALM HARB... • KELLER WILLIAMS REALTY- PALM HARBOR
Cindy Certified
Cindy Certified
The Villages®
![1301 FONTANA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|2,106 sq ft
|House
1301 FONTANA CT, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5108697 • PREMIER SOTHEBYS INT'L REALTY, Kei... • PREMIER SOTHEBYS INT'L REALTY
Breakaway Trails
![3 FOREST VIEW WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,737 sq ft
|House
3 FOREST VIEW WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
MLS 1223398 • Realty Pros Assured, Thomas Caffrey • Realty Pros Assured
Spruce Creek Country Club
![12747 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,575 sq ft
|House
12747 SE 97TH TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM719520 • REALTY ONE GROUP DAVALLS, David St... • REALTY ONE GROUP DAVALLS
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
The Villages®
![5288 HURTT ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,642 sq ft
|House
5288 HURTT ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5108670 • WORTH CLARK REALTY, Talia Franchi • WORTH CLARK REALTY
Huntington at Hunter's Ridge
![35 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,850 sq ft
|House
35 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Community: Huntington at Hunter's Ridge
MLS FC316410 • VENTURE DEVELOPMENT REALTY,INC, El... • VENTURE DEVELOPMENT REALTY,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.
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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© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
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.
