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Winter Park, FL 55+ active adult communities & homes for sale
90 communities near Winter Park
2,487 homes near Winter Park
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4 rating (17 reviews)
![The Villages®]()
<$100k
- $1Ms
The Villages®, The Villages, FL
New and Resale
|
55+ age-restricted
|
Built 1978 - present
|
70,000 homes
4.7 rating (18 reviews)
![Solivita]()
$100Ks
- $600Ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 homes
3.6 rating (48 reviews)
![Latitude Margaritaville]()
$300Ks
- $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2025
|
3,900 homes
5 rating (1 reviews)
![Plantation Bay Golf &...]()
$200Ks
- $4Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1988 - present
|
3,500 homes
4.5 rating (11 reviews)
![Spruce Creek Country Club]()
$200Ks
- $500Ks
Spruce Creek Country Club, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1996 - 2007
|
3,250 homes
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5 rating (2 reviews)
![Plantation at Leesburg]()
$100Ks
- $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2008
|
2,820 homes
5 rating (3 reviews)
![Stonecrest]()
$200Ks
- $500Ks
Stonecrest, Summerfield, FL
New and Resale
|
55+ age-restricted
|
Built 1990 - present
|
2,200 homes
5 rating (7 reviews)
![Kings Ridge]()
$200Ks
- $400Ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
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2,088 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
$300Ks
- $1Ms
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 homes
Download the Ultimate 55+ Homebuying Guide
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$100Ks
- $500Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 homes
4.7 rating (3 reviews)
![Spruce Creek South]()
$100Ks
- $300Ks
Spruce Creek South, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1989 - 1995
|
1,650 homes
5 rating (1 reviews)
![Cypress Lakes]()
$100Ks
- $200Ks
Cypress Lakes, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2016
|
1,604 homes
5 rating (3 reviews)
![Lake Ashton]()
$200Ks
- $800Ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
$200Ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 homes
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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 (2 reviews)
![Heritage Isle]()
$200Ks
- $500Ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
1,500 homes
5 rating (8 reviews)
![Royal Highlands]()
$200Ks
- $500Ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
$300Ks
- $800Ks
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
1,300 homes
5 rating (1 reviews)
![VillageWalk at Lake Nona]()
$300Ks
- $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only
|
Age-targeted
|
Built 2006 - 2016
|
1,300 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.
5 rating (1 reviews)
![Del Webb Sunbridge]()
$300Ks
- $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
1,300 homes
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)
![Sandpiper Golf & Coun...]()
$200Ks
- $400Ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale
|
55+ age-restricted
|
Built 1985 - present
|
1,193 homes
3.6 rating (5 reviews)
![Heritage Hills]()
$200Ks
- $500Ks
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
- $600Ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
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$200Ks
- $700Ks
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 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
$400Ks
- $700Ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
4 rating (4 reviews)
![Lakes of Mount Dora]()
$400Ks
- $900Ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 homes
4 rating (2 reviews)
![Harbor Hills Country Club]()
$200Ks
- $1Ms
Harbor Hills Country Club, Lady Lake, FL
New and Resale
|
Age-targeted
|
Built 1989 - present
|
940 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.
4.8 rating (6 reviews)
![Highland Lakes]()
$100Ks
- $300Ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 homes
4.4 rating (16 reviews)
![Del Webb Orlando]()
$300Ks
- $400Ks
Del Webb Orlando, Davenport, FL
Resale Only
|
55+ age-restricted
|
Built 2007 - 2021
|
937 homes
5 rating (2 reviews)
![Bridgewater at Viera]()
$300Ks
- $600Ks
Bridgewater at Viera, Melbourne, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2023
|
870 homes
$200Ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 homes
4.1 rating (9 reviews)
![Indian River Colony Club]()
$200Ks
- $400Ks
Indian River Colony Club, Melbourne, FL
New and Resale
|
55+ age-restricted
|
Built 1986 - present
|
777 homes
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Questions? Call us:
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3.9 rating (7 reviews)
![Summit Greens]()
$300Ks
- $400Ks
Summit Greens, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2019
|
769 homes
5 rating (1 reviews)
![Royal Harbor]()
$200Ks
- $400Ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
$200Ks
- $600Ks
Lakeside Landings, Oxford, FL
New and Resale
|
Age-targeted
|
Built 2005 - present
|
700 homes
1 rating (1 reviews)
![Sullivan Ranch]()
$300Ks
- $600Ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
Latitude Margaritaville
![770 JOLLYMON WAY, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,681 sq ft
|House
770 JOLLYMON WAY, DAYTONA BEACH, FL, 321...
Community: Latitude Margaritaville
MLS 1216640 • Bob Hodges and Sons Realty, Kelley ...
Carmel Condominium
![1420 HUNTINGTON LN 2304, ROCKLEDGE, FL, ..., Rockledge, FL 32955]()
2 beds
|2 baths
|1,008 sq ft
|Condo
1420 HUNTINGTON LN 2304, ROCKLEDGE, FL, ...
Community: Carmel Condominium
MLS 1039122 • Ellingson Properties, Gregory Ellin...
Solivita
![136 VERONA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5133379 • PELLEGO, LLC, Stan Wilson
Royal Highlands
![21636 KING HENRY AVE, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,642 sq ft
|House
21636 KING HENRY AVE, LEESBURG, FL, 3474...
Community: Royal Highlands
MLS O6279378 • KELLER WILLIAMS WINTER PARK, Lana ...
The Lakes at Harmony
![3436 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773]()
2 beds
|2 baths
|1,637 sq ft
|House
3436 SAGEBRUSH ST, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS S5136072 • CHARLES RUTENBERG REALTY ORLANDO, ...
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Solivita
![154 RANCHO MIRAGE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759]()
3 beds
|4 baths
|2,616 sq ft
|House
154 RANCHO MIRAGE DR, KISSIMMEE, FL, 347...
Community: Solivita
MLS S5133904 • PELLEGO, LLC, Claudia Gimenez-Carl...
Bridgewater at Viera
![992 GREAT BELT CIR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
4 beds
|3 baths
|2,614 sq ft
|House
992 GREAT BELT CIR, MELBOURNE, FL, 32940
Community: Bridgewater at Viera
MLS O6326643 • EXP REALTY LLC, Jamie Rogaliner
Lake Ashton
![4168 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|1,756 sq ft
|House
4168 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4934058 • A+ REALTY LLC, Michael Krigelski
Carlsberg Estates on Lake Suzanne
![524 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
3 beds
|3 baths
|1,718 sq ft
|House
524 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Community: Carlsberg Estates on Lake Suzanne
MLS P4933513 • CENTURY 21 MYERS REALTY LAKE WALES...
Royal Highlands
![20806 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,939 sq ft
|House
20806 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
MLS O6330029 • KELLER WILLIAMS REALTY AT THE PARK...
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.
High Vista at Ridgewood Lakes
![205 CUNNINGHAM DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|2 baths
|2,502 sq ft
|House
205 CUNNINGHAM DR, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS S5136988 • KELLER WILLIAMS REALTY AT THE LAKE...
Halifax Plantation
![1313 RUNABY LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,810 sq ft
|House
1313 RUNABY LN, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS G5103265 • LIST NOW REALTY, LLC, Matt Buttner
VillageWalk at Lake Nona
![12004 ULETA LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
4 beds
|4 baths
|4,114 sq ft
|House
12004 ULETA LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6347169 • MS LAND & BUILDING LLC, Ataide Bra...
Vienna Square
![1709 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,164 sq ft
|Villa
1709 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
MLS P4936273 • CENTURY 21 WATSON & MYERS REALTY, ...
Vienna Square
![1584 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,231 sq ft
|Villa
1584 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
MLS L4955737 • BHHS FLORIDA PROPERTIES GROUP, Joh...
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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...
Vienna Square
![1620 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,329 sq ft
|Villa
1620 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
MLS L4952436 • LPT REALTY, LLC, Paula Aponte
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...
Summit Greens
![890 SUMMIT GREENS BLVD, CLERMONT, FL, 34..., Clermont, FL 34711]()
3 beds
|2 baths
|1,556 sq ft
|House
890 SUMMIT GREENS BLVD, CLERMONT, FL, 34...
Community: Summit Greens
MLS G5100261 • ERA GRIZZARD REAL ESTATE, Olga Jak...
Grand Haven
![17 GRANDVIEW DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
4 beds
|3 baths
|3,395 sq ft
|House
17 GRANDVIEW DR, PALM COAST, FL, 32137
Community: Grand Haven
MLS FC312537 • RE/MAX SELECT PROFESSIONALS, Kari ...
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.
Plantation at Leesburg
![25036 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,095 sq ft
|House
25036 CRANES ROOST CIR, LEESBURG, FL, 34...
Community: Plantation at Leesburg
MLS G5102167 • OLYMPUS EXECUTIVE REALTY INC, Carm...
Royal Highlands
![21202 BRAVEHEART DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,588 sq ft
|House
21202 BRAVEHEART DR, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5104368 • VANGIE BERRY SIGNATURE REALTY, Ang...
Royal Highlands
![5025 ST ANDREWS ARC, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,995 sq ft
|House
5025 ST ANDREWS ARC, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5104158 • LPT REALTY, LLC., Sara Edmundson
Spruce Creek Country Club
![8845 SE 132ND LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,000 sq ft
|House
8845 SE 132ND LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM712444 • JUDY L. TROUT REALTY, Judy Trout
Lakes of Mount Dora
![8860 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,671 sq ft
|House
8860 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS G5103304 • WATSON REALTY CORP, Jody Parks
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Royal Highlands
![20504 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,722 sq ft
|House
20504 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
MLS G5103173 • FLORIDA PLUS REALTY, LLC, Tonya Ti...
Del Webb Orlando
![333 ALMANSA ST, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|2 baths
|1,655 sq ft
|House
333 ALMANSA ST, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS S5136129 • RIDGE REALTY GROUP LLC, Deborah Ba...
Lake James
![8147 LAKE JAMES DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,476 sq ft
|House
8147 LAKE JAMES DR, LAKELAND, FL, 33810
Community: Lake James
MLS L4956503 • REMAX EXPERTS, Becky Lane
Breakaway Trails
![16 FOREST VIEW WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,114 sq ft
|House
16 FOREST VIEW WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
MLS NS1086060 • WEICHERT, REALTORS HALLMARK PR, M...
Royal Highlands
![21829 TARTAN ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,684 sq ft
|House
21829 TARTAN ST, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5100835 • FLORIDA PLUS REALTY, LLC, Tonya Ti...
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.
Lakes of Mount Dora
![8348 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
4 beds
|3 baths
|3,156 sq ft
|House
8348 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS O6328646 • FLORIDA HOME TEAM REALTY LLC, Kris...
Royal Highlands
![6307 BERKSHIRE PASS, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,748 sq ft
|House
6307 BERKSHIRE PASS, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5099468 • FLORIDA PLUS REALTY, LLC, Tonya Ti...
Royal Highlands
![21325 ROYAL TROON DR, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,333 sq ft
|House
21325 ROYAL TROON DR, LEESBURG, FL, 3474...
Community: Royal Highlands
MLS G5098918 • FLORIDA PLUS REALTY, LLC, Tonya Ti...
Royal Highlands
![21850 TARTAN ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,159 sq ft
|House
21850 TARTAN ST, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5093444 • FLORIDA PLUS REALTY, LLC, Tonya Ti...
High Vista at Ridgewood Lakes
![116 FLEMING LN, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|2 baths
|1,776 sq ft
|House
116 FLEMING LN, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS S5135608 • KELLER WILLIAMS REALTY AT THE LAKE...
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The Villages®
![552 SOCIETY HILL CIR, THE VILLAGES, FL, ..., The Villages, FL 32162]()
3 beds
|2 baths
|2,046 sq ft
|House
552 SOCIETY HILL CIR, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5104147 • RE/MAX SELECT PARTNERS, Kimberly V...
Halifax Plantation
![1171 ATHLONE WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,634 sq ft
|House
1171 ATHLONE WAY, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
MLS FC312978 • GRAND LIVING REALTY, MICHAEL HERRO...
Royal Highlands
![21607 REGENCY PARK LN, LEESBURG, FL, 347..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,366 sq ft
|House
21607 REGENCY PARK LN, LEESBURG, FL, 347...
Community: Royal Highlands
MLS G5102512 • VANGIE BERRY SIGNATURE REALTY, Ang...
Four Seasons at Orlando
![2111 LIMESTONE TRL # 504, KISSIMMEE, FL,..., Kissimmee, FL 34747]()
3 beds
|2 baths
|2,189 sq ft
|House
2111 LIMESTONE TRL # 504, KISSIMMEE, FL,...
Community: Four Seasons at Orlando
MLS O6358113 • HOMEVEST REALTY, Erica Diaz
The Lakes at Harmony
![3447 FEATHERGRASS CT, HARMONY, FL, 34773, Harmony, FL 34773]()
5 beds
|4 baths
|3,300 sq ft
|House
3447 FEATHERGRASS CT, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS O6356968 • THE AGENCY ORLANDO, Patrick Lynn
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Want to learn more about 55+ communities in Winter Park?
2,487
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near Winter Park
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REIN updates its listings on a daily basis. Data last updated: Nov 30, 2025.
This application does not include information on all of the properties available for sale at this time.
