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Winter Park, FL 55+ active adult communities & homes for sale - Page 54
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
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 (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.
Del Webb Sunbridge
![2808 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ..., St Cloud, FL 34771]()
3 beds
|3 baths
|2,321 sq ft
|House
2808 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ...
Community: Del Webb Sunbridge
MLS O6387148 • REAL BROKER, LLC, Peter Luu • REAL BROKER, LLC
Cindy Certified
Royal Highlands
![21811 KING HENRY AVE, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,918 sq ft
|House
21811 KING HENRY AVE, LEESBURG, FL, 3474...
Community: Royal Highlands
MLS G5109896 • VANGIE BERRY SIGNATURE REALTY, Ang... • VANGIE BERRY SIGNATURE REALTY
Cindy Certified
Compass Pointe
![620 BROCKTON WAY, MELBOURNE, FL, 32904, Melbourne, FL 32904]()
3 beds
|2 baths
|1,814 sq ft
|House
620 BROCKTON WAY, MELBOURNE, FL, 32904
Community: Compass Pointe
MLS 1072636 • Real Estate Direct of Florida, Andy... • Real Estate Direct of Florida
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Trilogy® Orlando
![329 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736]()
2 beds
|2 baths
|1,808 sq ft
|House
329 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
MLS G5109935 • GODFREY REALTY GROUP, INC., Joe Go... • GODFREY REALTY GROUP, INC.
Twin Lakes
![2388 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS A4683880 • EXPERT REALTY SOLUTIONS INC., Joel... • EXPERT REALTY SOLUTIONS INC.
Heritage Isle
![2952 BODDINGTON WAY, MELBOURNE, FL, 3294..., Melbourne, FL 32940]()
3 beds
|2 baths
|2,034 sq ft
|House
2952 BODDINGTON WAY, MELBOURNE, FL, 3294...
Community: Heritage Isle
MLS 1072582 • One Sotheby's International, Eileen... • One Sotheby's International
Royal Highlands
![5729 KING JAMES AVE, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|3 baths
|2,402 sq ft
|House
5729 KING JAMES AVE, LEESBURG, FL, 34748
Community: Royal Highlands
MLS TB8488786 • HOMECOIN.COM, Jonathan Minerick • HOMECOIN.COM
The Villages®
![5719 SPARTINA TER, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
2 beds
|2 baths
|1,258 sq ft
|Villa
5719 SPARTINA TER, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5109910 • LPT REALTY, LLC, Genie Muldoon • 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.
Park Place
![133 PARK PLACE CIR, PALM COAST, FL, 3216..., Palm Coast, FL 32164]()
3 beds
|2 baths
|1,879 sq ft
|House
133 PARK PLACE CIR, PALM COAST, FL, 3216...
Community: Park Place
MLS FC316937 • REAL BROKER, LLC, Joyce Cunningham • REAL BROKER, LLC
The Villages®
![2129 ZARAGOZA PL, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
3 beds
|2 baths
|1,669 sq ft
|House
2129 ZARAGOZA PL, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5109884 • COLDWELL BANKER REALTY, William Pe... • COLDWELL BANKER REALTY
Four Seasons at Orlando
![7774 FOUR SEASONS BLVD, KISSIMMEE, FL, 3..., Kissimmee, FL 34747]()
3 beds
|2 baths
|1,969 sq ft
|House
7774 FOUR SEASONS BLVD, KISSIMMEE, FL, 3...
Community: Four Seasons at Orlando
MLS O6392299 • VIVA ORLANDO REALTY INC., Susan Ri... • VIVA ORLANDO REALTY INC.
Kings Ridge
![2282 FENTON AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS O6389828 • MERVIN MORGAN REALTY & PROPERTY MA... • MERVIN MORGAN REALTY & PROPERTY MANAGEMENT LLC
The Reserve at Victoria
![899 MEGANO BLVD, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,970 sq ft
|House
899 MEGANO BLVD, DELAND, FL, 32724
Community: The Reserve at Victoria
MLS V4947724 • BEE REALTY CORP, Bee Powell • BEE REALTY CORP
Venetian Bay
![3377 CATERINA DR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
4 beds
|4 baths
|3,882 sq ft
|House
3377 CATERINA DR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS O6391834 • REDFIN CORPORATION, Tammy Shaver • REDFIN CORPORATION
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Cindy Certified
Plantation Bay Golf & Country Club
![534 WINGSPAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|4 baths
|3,713 sq ft
|House
534 WINGSPAN DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC317085 • VENTURE DEVELOPMENT REALTY,INC, El... • VENTURE DEVELOPMENT 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 1224347 • Adams, Cameron & Co., Realtors, Jer... • Adams, Cameron & Co., Realtors
Gatherings of Lake Nona
![7521 LAUREATE BLVD 5306, ORLANDO, FL, 32..., Orlando, FL 32827]()
2 beds
|2 baths
|1,549 sq ft
|Condo
7521 LAUREATE BLVD 5306, ORLANDO, FL, 32...
Community: Gatherings of Lake Nona
MLS O6391661 • THE WILKINS WAY LLC, Pamela Graben... • THE WILKINS WAY 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.
Heritage Hills
![4052 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,672 sq ft
|House
4052 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6392318 • GLOBAL REALTY INTERNATIONAL, Eliza... • GLOBAL REALTY INTERNATIONAL
Vienna Square
![1678 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,158 sq ft
|House
1678 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
MLS L4960316 • COLDWELL BANKER REALTY, Bryan Dick... • COLDWELL BANKER REALTY
Cresswind at Victoria Gardens
![314 BELLINGRATH TER, DELAND, FL, 32724, Deland, FL 32724]()
4 beds
|3 baths
|2,528 sq ft
|House
314 BELLINGRATH TER, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS V4947579 • REALTY PROS ASSURED, Mary Maholias • REALTY PROS ASSURED
The Villages®
![2055 HYDRANGEA AVE, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|1,398 sq ft
|Villa
2055 HYDRANGEA AVE, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5109806 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Latitude Margaritaville
![896 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,563 sq ft
|House
896 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS FC317039 • KELLER WILLIAMS RLTY FL. PARTN, Ta... • KELLER WILLIAMS RLTY FL. PARTN
Sandpiper Golf & Country Club
![6236 RAVEN RUN, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,179 sq ft
|House
6236 RAVEN RUN, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4960274 • XCELLENCE, Mike Holbrook • XCELLENCE
Spruce Creek Country Club
![9003 SE 118TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,850 sq ft
|House
9003 SE 118TH LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM721111 • SELLSTATE NGR- SUMMERFIELD, Virgil... • SELLSTATE NGR- SUMMERFIELD
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Cindy Certified
Grand Haven
![10 RIVER POINT DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
2 beds
|2 baths
|1,828 sq ft
|Townhouse
10 RIVER POINT DR, PALM COAST, FL, 32137
Community: Grand Haven
MLS FC316912 • COLDWELL BANKER PREMIER PROPERTIES... • COLDWELL BANKER PREMIER PROPERTIES
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®
![17353 SE 76TH FLINTLOCK TER, THE VILLAGE..., The Villages, FL 32162]()
2 beds
|2 baths
|1,388 sq ft
|House
17353 SE 76TH FLINTLOCK TER, THE VILLAGE...
Community: The Villages®
MLS G5109722 • DOWN HOME REALTY, LLLP, Kevin Russ... • DOWN HOME REALTY, LLLP
The Villages®
![3258 HOLLEY TER, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
4 beds
|2 baths
|2,028 sq ft
|House
3258 HOLLEY TER, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5109554 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Breakaway Trails
![114 SHADOW CREEK WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,754 sq ft
|House
114 SHADOW CREEK WAY, ORMOND BEACH, FL, ...
Community: Breakaway Trails
MLS 2135298 • HEARTLAND REAL ESTATE SERVICES, JIL... • HEARTLAND REAL ESTATE SERVICES
Latitude Margaritaville
![1002 SEA SHELL CT, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124]()
3 beds
|2 baths
|1,848 sq ft
|House
1002 SEA SHELL CT, DAYTONA BEACH, FL, 32...
Community: Latitude Margaritaville
MLS NS1087658 • EXP REALTY LLC, Geri Davis • EXP REALTY LLC
Spruce Creek Country Club
![12767 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,720 sq ft
|House
12767 SE 97TH TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM720895 • REALTY ONE GROUP DAVALLS, David St... • REALTY ONE GROUP DAVALLS
Harbor Hills Country Club
![6053 SPINNAKER LOOP, LADY LAKE, FL, 3215..., Lady Lake, FL 32159]()
3 beds
|3 baths
|3,024 sq ft
|House
6053 SPINNAKER LOOP, LADY LAKE, FL, 3215...
Community: Harbor Hills Country Club
MLS G5109709 • MORRIS REALTY AND INVESTMENTS, The... • MORRIS REALTY AND INVESTMENTS
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
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.
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.
