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Winter Park, FL 55+ active adult communities & homes for sale - Page 68
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
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.
Vienna Square
![1224 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,118 sq ft
|Villa
1224 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
MLS P4934564 • KELLER WILLIAMS REALTY SMART 1, Do... • KELLER WILLIAMS REALTY SMART 1
Plantation Bay Golf & Country Club
![1009 SUDBURY LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|5 baths
|3,927 sq ft
|House
1009 SUDBURY LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS TB8375913 • ICI SELECT REALTY, Ali Kargar • ICI SELECT REALTY
Cindy Certified
Royal Highlands
![20631 PRINCE RANIER PL, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,070 sq ft
|House
20631 PRINCE RANIER PL, LEESBURG, FL, 34...
Community: Royal Highlands
MLS G5095688 • VANGIE BERRY SIGNATURE REALTY, Ang... • VANGIE BERRY SIGNATURE REALTY
Kings Ridge
![3684 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,552 sq ft
|House
3684 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5095074 • REAL BROKER, LLC, Diane Rogers • REAL BROKER, LLC
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
Spruce Creek Country Club
![9290 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,126 sq ft
|House
9290 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM698604 • SELLSTATE NGR- SUMMERFIELD, Virgil... • SELLSTATE NGR- SUMMERFIELD
Spruce Creek Country Club
![13729 SE 89TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,760 sq ft
|House
13729 SE 89TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS A4646770 • NEW DOOR REAL ESTATE LLC, Alicia A... • NEW DOOR REAL ESTATE LLC
The Wellington
![689 LAKE HOWARD DR 1E, WINTER HAVEN, FL,..., Winter Haven, FL 33880]()
2 beds
|2 baths
|1,050 sq ft
|Condo
689 LAKE HOWARD DR 1E, WINTER HAVEN, FL,...
Community: The Wellington
MLS TB8360466 • RIVERA & ASSOCIATES REALTY, Maria... • RIVERA & ASSOCIATES REALTY
Cindy Certified
Royal Highlands
![20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,224 sq ft
|House
20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
MLS G5094138 • VANGIE BERRY SIGNATURE REALTY, Ang... • VANGIE BERRY SIGNATURE REALTY
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.
Gatherings of Lake Nona
![7517 LAUREATE BLVD 4103, ORLANDO, FL, 32..., Orlando, FL 32827]()
2 beds
|2 baths
|1,549 sq ft
|Condo
7517 LAUREATE BLVD 4103, ORLANDO, FL, 32...
Community: Gatherings of Lake Nona
MLS O6285908 • CASTRO REALTY GROUP, Marcia Castro... • CASTRO REALTY GROUP
Cindy Certified
Carmel Condominium
![1420 HUNTINGTON LN 2101, ROCKLEDGE, FL, ..., Rockledge, FL 32955]()
2 beds
|2 baths
|1,228 sq ft
|Condo
1420 HUNTINGTON LN 2101, ROCKLEDGE, FL, ...
Community: Carmel Condominium
MLS 1038868 • Ellingson Properties, Gregory Ellin... • Ellingson Properties
Vienna Square
![1703 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,164 sq ft
|Villa
1703 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
MLS P4933885 • DGCF REALTY ADVISORS LLC, Austin S... • DGCF REALTY ADVISORS LLC
Heritage Isle
![7174 EGBERT ST, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,770 sq ft
|House
7174 EGBERT ST, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1038008 • Thomas J. O Brien, Thomas J O Brien • Thomas J. O Brien
Plantation Bay Golf & Country Club
![51 BAY POINTE DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,996 sq ft
|House
51 BAY POINTE DR, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS 1209215 • Realty Evolution Inc, Marsha Thayer • Realty Evolution Inc
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
Lakes of Mount Dora
![8456 NORWICH WAY, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
3 beds
|3 baths
|2,460 sq ft
|House
8456 NORWICH WAY, MOUNT DORA, FL, 32757
Community: Lakes of Mount Dora
MLS O6278226 • KELLER WILLIAMS LEGACY, Thomas Hix... • KELLER WILLIAMS LEGACY
Kings Ridge
![3667 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,552 sq ft
|House
3667 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
MLS O6275507 • FLORIDA PRESTIGIOUS HOMES INC, Ian... • FLORIDA PRESTIGIOUS HOMES INC
Venetian Bay
![3088 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
2 beds
|2 baths
|1,003 sq ft
|Townhouse
3088 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS NS1083432 • EXIT REAL ESTATE PROPERTY SOL, Ca... • EXIT REAL ESTATE PROPERTY SOL
The Villages®
![9199 SE 171ST COOPER LOOP, THE VILLAGES,..., The Villages, FL 32162]()
3 beds
|2 baths
|1,850 sq ft
|House
9199 SE 171ST COOPER LOOP, THE VILLAGES,...
Community: The Villages®
MLS G5090513 • 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
Cindy Certified
Vienna Square
![1561 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,231 sq ft
|Villa
1561 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
MLS P4932767 • FLORIDA HOME CHOICE REALTY, Glenda... • FLORIDA HOME CHOICE REALTY
Alhambra Villas Condominiums
![201 N HILL AVE 150, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,090 sq ft
|Condo
201 N HILL AVE 150, DELAND, FL, 32724
Community: Alhambra Villas Condominiums
MLS V4939262 • UNITED REAL ESTATE PREFERRED, Chri... • UNITED REAL ESTATE PREFERRED
Trilogy® Orlando
![119 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736]()
2 beds
|2 baths
|1,556 sq ft
|House
119 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
MLS G5088807 • WEICHERT REALTORS-HALLMARK PR, Bre... • WEICHERT REALTORS-HALLMARK PR
Cindy Certified
Cindy Certified
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
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.
Foxwood Lake Estates
![5013 FOXWOOD BLVD, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,056 sq ft
|Manufactured Home
5013 FOXWOOD BLVD, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS S5108231 • BETTER HOMES & GARDENS RE LIFESTYL... • BETTER HOMES & GARDENS RE LIFESTYLES
Pelican Bay Daytona Beach
![244 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,370 sq ft
|House
244 PALM SPARROW CT, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS 1117527 • Seemore Realty Group Inc., Judy Tin... • Seemore Realty Group Inc.
Twin Lakes
![2410 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS S5103150 • COLDWELL BANKER SOLOMON, Susy Orti... • COLDWELL BANKER SOLOMON
Alhambra Villas Condominiums
![217 N HILL AVE 20, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,090 sq ft
|Condo
217 N HILL AVE 20, DELAND, FL, 32724
Community: Alhambra Villas Condominiums
MLS V4934458 • UNITED REAL ESTATE PREFERRED, Chri... • UNITED REAL ESTATE PREFERRED
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.
