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Winter Park, FL 55+ active adult communities & homes for sale - Page 6
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
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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
Want to learn more about 55+ communities in Winter Park?
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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.
Spruce Creek Country Club
![12407 SE 92ND COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,279 sq ft
|House
12407 SE 92ND COURT RD, SUMMERFIELD, FL,...
Community: Spruce Creek Country Club
MLS OM730385 • JUDY L. TROUT REALTY, Judy Trout • JUDY L. TROUT REALTY
Kings Ridge
![4122 KINGSLEY ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS O6434430 • KELLER WILLIAMS REALTY AT THE LAKE... • KELLER WILLIAMS REALTY AT THE LAKES
Cindy Certified
Spruce Creek Country Club
![11811 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,958 sq ft
|House
11811 SE 91ST CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM730275 • JUDY L. TROUT REALTY, Judy Trout • JUDY L. TROUT REALTY
The Villages®
![301 KLAMUT CT, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,392 sq ft
|House
301 KLAMUT CT, THE VILLAGES, FL, 32163
Community: The Villages®
MLS TB8539766 • EXP REALTY LLC, Jodi Heifner • EXP REALTY LLC
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Del Webb Sunbridge
![6391 SHIMMERING SHORES LN, ST CLOUD, FL,..., St Cloud, FL 34771]()
2 beds
|2 baths
|1,921 sq ft
|House
6391 SHIMMERING SHORES LN, ST CLOUD, FL,...
Community: Del Webb Sunbridge
MLS GC542816 • COASTAL REAL ESTATE PROFESSIONALS ... • COASTAL REAL ESTATE PROFESSIONALS LLC
Highland Fairways
![2240 SEA ISLAND CIR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,241 sq ft
|House
2240 SEA ISLAND CIR, LAKELAND, FL, 33810
Community: Highland Fairways
MLS L4964045 • KELLER WILLIAMS REALTY, Gate Arty • KELLER WILLIAMS REALTY
Cindy Certified
High Vista at Ridgewood Lakes
![919 ASHTON DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|2 baths
|2,081 sq ft
|House
919 ASHTON DR, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS S5155707 • KELLER WILLIAMS REALTY AT THE LAKE... • KELLER WILLIAMS REALTY AT THE LAKES
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.
Scottish Highlands
![1410 NEW ABBEY AVE, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,663 sq ft
|House
1410 NEW ABBEY AVE, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5116578 • OLYMPUS EXECUTIVE REALTY INC, Nanc... • OLYMPUS EXECUTIVE REALTY INC
Sandpiper Golf & Country Club
![6217 RAVEN RUN, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,203 sq ft
|House
6217 RAVEN RUN, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4964278 • REMAX EXPERTS, Steve Harvey • REMAX EXPERTS
Cindy Certified
Pennbrooke Fairways
![1009 FOREST BREEZE PATH, LEESBURG, FL, 3..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,921 sq ft
|House
1009 FOREST BREEZE PATH, LEESBURG, FL, 3...
Community: Pennbrooke Fairways
MLS TB8539740 • COMMUNITY REALTY ASSOCIATES, Doug... • COMMUNITY REALTY ASSOCIATES
Grand Haven
![4 LAKEVIEW LN, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS V4950778 • RE/MAX SIGNATURE, Marc Vigilante • RE/MAX SIGNATURE
Solivita
![778 IRVINE RANCH RD, POINCIANA, FL, 3475..., Poinciana, FL 34759]()
4 beds
|3 baths
|2,326 sq ft
|House
778 IRVINE RANCH RD, POINCIANA, FL, 3475...
Community: Solivita
MLS S5155660 • RIGHT TRACK REALTY, Kelley Spear • RIGHT TRACK REALTY
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Scottish Highlands
![1507 NEW ABBEY AVE, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,324 sq ft
|House
1507 NEW ABBEY AVE, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS OM730555 • COLDWELL BANKER VANGUARD EDGE, Val... • COLDWELL BANKER VANGUARD EDGE
The Villages®
![4986 ELLIE LN, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,184 sq ft
|House
4986 ELLIE LN, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5116520 • LPT REALTY, LLC, John Reed • LPT REALTY, LLC
Cindy Certified
Latitude Margaritaville
![215 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,160 sq ft
|Townhouse
215 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS V4950507 • KELLER WILLIAMS RLTY FL. PARTN, Ca... • KELLER WILLIAMS RLTY FL. PARTN
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.
The Timbers at Everlands
![1592 MIRAFLORES TRL, PALM BAY, FL, 32907, Palm Bay, FL 32907]()
3 beds
|2 baths
|1,436 sq ft
|House
1592 MIRAFLORES TRL, PALM BAY, FL, 32907
Community: The Timbers at Everlands
MLS 1085234 • Lennar Realty, Inc., Jennifer Riche... • Lennar Realty, Inc.
Heritage Hills
![3650 LIMESTONE ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,677 sq ft
|House
3650 LIMESTONE ST, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6433390 • REAL BROKER, LLC, Maureen Nguyen • REAL BROKER, LLC
Cindy Certified
The Villages®
![1596 BIRMINGHAM TER, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
3 beds
|3 baths
|2,021 sq ft
|House
1596 BIRMINGHAM TER, THE VILLAGES, FL, 3...
Community: The Villages®
MLS TB8539534 • COMMUNITY REALTY ASSOCIATES, Doug... • COMMUNITY REALTY ASSOCIATES
Venetian Bay
![538 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,779 sq ft
|House
538 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
MLS O6432872 • OPENDOOR BROKERAGE LLC, Karen Albr... • OPENDOOR BROKERAGE LLC
Royal Palm
![1508 ARECA PALM DR, PORT ORANGE, FL, 321..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,332 sq ft
|House
1508 ARECA PALM DR, PORT ORANGE, FL, 321...
Community: Royal Palm
MLS 1229741 • Realty Pros Assured, Alexandra Tolk... • Realty Pros Assured
Cindy Certified
Want to learn more about 55+ communities in Winter Park?
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The Villages®
![1519 MARTINEZ DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|3 baths
|2,138 sq ft
|Villa
1519 MARTINEZ DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5116395 • RE/MAX PREMIER REALTY, Guy William... • RE/MAX PREMIER REALTY
The Villages®
![449 LAYTON TER, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,108 sq ft
|Villa
449 LAYTON TER, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5115615 • RE/MAX PREMIER REALTY LADY LK, Lyn... • RE/MAX PREMIER REALTY LADY LK
Gatherings of Lake Nona
![7517 LAUREATE BLVD 4303, ORLANDO, FL, 32..., Orlando, FL 32827]()
2 beds
|2 baths
|1,549 sq ft
|Condo
7517 LAUREATE BLVD 4303, ORLANDO, FL, 32...
Community: Gatherings of Lake Nona
MLS TB8539508 • FLORIDA EXECUTIVE REALTY 2, Jerry... • FLORIDA EXECUTIVE REALTY 2
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.
Twin Lakes
![5013 VANTAGE CT, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS O6433971 • EXP REALTY LLC, Charlie Santos • EXP REALTY LLC
The Villages®
![1717 PALM AIRE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,284 sq ft
|Manufactured Home
1717 PALM AIRE DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5116522 • RE/MAX SELECT PARTNERS, Jacob Pfaf... • RE/MAX SELECT PARTNERS
Highland Fairways
![2033 LONG BOAT DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,205 sq ft
|House
2033 LONG BOAT DR, LAKELAND, FL, 33810
Community: Highland Fairways
MLS L4964260 • DALTON WADE INC, Judene Padgett • DALTON WADE INC
Kings Ridge
![4224 SNOWDON ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5116428 • WATSON REALTY CORP., REALTORS, Chr... • WATSON REALTY CORP., REALTORS
Twin Lakes
![2889 MIDSWEET AVE, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS O6434066 • PULTE REALTY OF NORTH FLORIDA LLC,... • PULTE REALTY OF NORTH FLORIDA LLC
Twin Lakes
![2776 BUCKEYE LN, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS O6434062 • PULTE REALTY OF NORTH FLORIDA LLC,... • PULTE REALTY OF NORTH FLORIDA LLC
Preserve at Lakeside Landings
![5852 MARSH LANDING DR, WINTER HAVEN, FL,..., Winter Haven, FL 33881]()
3 beds
|2 baths
|2,091 sq ft
|House
5852 MARSH LANDING DR, WINTER HAVEN, FL,...
Community: Preserve at Lakeside Landings
MLS L4963732 • FLORIDA REAL ESTATE COMPANY, Cyles... • FLORIDA REAL ESTATE COMPANY
Heritage Hills
![3516 KINLEY BROOKE LN, CLERMONT, FL, 347..., Clermont, FL 34711]()
3 beds
|2 baths
|1,879 sq ft
|House
3516 KINLEY BROOKE LN, CLERMONT, FL, 347...
Community: Heritage Hills
MLS O6433965 • BHHS FLORIDA REALTY, Patti Kincaid • BHHS FLORIDA REALTY
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Plantation at Leesburg
![26305 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,512 sq ft
|House
26305 GLEN EAGLE DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5116516 • RE/MAX PREMIER REALTY, Adriana Sko... • RE/MAX PREMIER REALTY
Colonnades
![4983 PLEASANT HOLLOW TRL, LAKELAND, FL, ..., Lakeland, FL 33811]()
2 beds
|2 baths
|1,520 sq ft
|House
4983 PLEASANT HOLLOW TRL, LAKELAND, FL, ...
Community: Colonnades
MLS B4902337 • 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.
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.
