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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
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.
$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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5 rating (2 reviews)
![Heritage Isle]()
$200Ks
- $500Ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
1,500 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
- $500Ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
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 (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.
$300Ks
- $800Ks
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - 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
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
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
- $500Ks
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
Pennbrooke Fairways
![642 GLEN OAKS DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,632 sq ft
|House
642 GLEN OAKS DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5100872 • MAXREV LLC, Jayne Marvin
The Villages®
![1712 GALLOWAY DR, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,696 sq ft
|Villa
1712 GALLOWAY DR, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5100770 • REALTY EXECUTIVES IN THE VILLAGES,...
Lake Ashton
![5225 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884]()
3 beds
|2 baths
|2,031 sq ft
|House
5225 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
MLS P4936039 • LAKE ASHTON REALTY INC., Candra Al...
Pennbrooke Fairways
![32831 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,757 sq ft
|House
32831 TIMBERWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5103527 • CENTURY 21 ALTON CLARK, Kathi Hill
Trilogy® Orlando
![100 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736]()
3 beds
|2 baths
|1,564 sq ft
|House
100 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
MLS O6342106 • WATSON REALTY CORP, Julie Sevilla
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Plantation Bay Golf & Country Club
![1047 KILKENNY LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,081 sq ft
|Townhouse
1047 KILKENNY LN, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS FC313504 • VENTURE DEVELOPMENT REALTY,INC, El...
Harbor Hills Country Club
![5066 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
4 beds
|3 baths
|2,544 sq ft
|House
5066 GREENS DR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5103387 • MORRIS REALTY AND INVESTMENTS, Lau...
Arlington Ridge
![27327 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,712 sq ft
|House
27327 ROANOKE DR, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS O6338663 • REAL BROKER, LLC, Abby Anderson Ha...
Venetian Bay
![2937 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
4 beds
|3 baths
|2,070 sq ft
|House
2937 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS O6353959 • DE VIVO REALTY LLC, Alessandro De ...
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...
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 Villages®
![1225 EDGEWATER LN, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,491 sq ft
|House
1225 EDGEWATER LN, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5102754 • BROKER ASSOCIATES REALTY, Wendy La...
Scottish Highlands
![803 DUNDEE CIR, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,436 sq ft
|House
803 DUNDEE CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5103224 • HARRISON REAL PROPERTY GROUP, Aman...
Lakes at Laurel Highlands
![2778 CANYON CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33811]()
3 beds
|2 baths
|1,685 sq ft
|House
2778 CANYON CREST DR, LAKELAND, FL, 3381...
Community: Lakes at Laurel Highlands
MLS L4955797 • KELLER WILLIAMS REALTY SMART, Garr...
Heritage Landings
![2778 CANYON CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33811]()
3 beds
|2 baths
|1,685 sq ft
|House
2778 CANYON CREST DR, LAKELAND, FL, 3381...
Community: Heritage Landings
MLS L4955797 • KELLER WILLIAMS REALTY SMART, Garr...
Pelican Bay Daytona Beach
![320 BOB WHITE CT 3200, DAYTONA BEACH, FL..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,469 sq ft
|Condo
320 BOB WHITE CT 3200, DAYTONA BEACH, FL...
Community: Pelican Bay Daytona Beach
MLS 1217180 • Daytona Beach International Realty ...
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Colonnades
![1774 BIRCHWOOD LOOP, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,193 sq ft
|House
1774 BIRCHWOOD LOOP, LAKELAND, FL, 33811
Community: Colonnades
MLS L4956406 • S & D REAL ESTATE SERVICE LLC, Sol...
The Villages®
![3567 INFINITY RUN, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|2 baths
|2,035 sq ft
|House
3567 INFINITY RUN, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5101262 • EXP REALTY LLC, Dena Manning
Palms at Serenoa
![17386 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714]()
3 beds
|2 baths
|1,621 sq ft
|House
17386 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
MLS G5095939 • LIST NOW REALTY, LLC, Matt Buttner
Harbor Hills Country Club
![38800 HARBORWOODS PL, LADY LAKE, FL, 321..., Lady Lake, FL 32159]()
3 beds
|4 baths
|2,692 sq ft
|House
38800 HARBORWOODS PL, LADY LAKE, FL, 321...
Community: Harbor Hills Country Club
MLS G5103070 • MORRIS REALTY AND INVESTMENTS, Len...
Cresswind at Victoria Gardens
![430 CYPRESS HILLS WAY, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,655 sq ft
|House
430 CYPRESS HILLS WAY, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS V4940009 • KELLER WILLIAMS HERITAGE REALTY, C...
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.
Kings Ridge
![4012 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS O6323263 • COLDWELL BANKER RESIDENTIAL RE, Ke...
Huntington at Hunter's Ridge
![51 WRENDALE LOOP, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,603 sq ft
|House
51 WRENDALE LOOP, ORMOND BEACH, FL, 3217...
Community: Huntington at Hunter's Ridge
MLS V4944327 • REALTY PROS ASSURED, Jonathan Gild...
Halifax Plantation
![3070 SILVERMINES AVE, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,111 sq ft
|House
3070 SILVERMINES AVE, ORMOND BEACH, FL, ...
Community: Halifax Plantation
MLS V4945492 • REALTY PROS ASSURED, Shannon Brook...
Summit Greens
![1180 MESA VERDE CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,508 sq ft
|House
1180 MESA VERDE CT, CLERMONT, FL, 34711
Community: Summit Greens
MLS G5098046 • OLYMPUS EXECUTIVE REALTY INC, Mari...
Heritage Hills
![3550 FAIRWATERS CT D, CLERMONT, FL, 3471..., Clermont, FL 34711]()
2 beds
|2 baths
|1,503 sq ft
|Villa
3550 FAIRWATERS CT D, CLERMONT, FL, 3471...
Community: Heritage Hills
MLS G5097426 • OPTIMA ONE REALTY, INC., Heather W...
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(888) 625-4885
Plantation at Leesburg
![4928 HERON RUN CIR CIR, LEESBURG, FL, 34..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,424 sq ft
|House
4928 HERON RUN CIR CIR, LEESBURG, FL, 34...
Community: Plantation at Leesburg
MLS G5101638 • CHARLES RUTENBERG REALTY ORLANDO, ...
Indian River Colony Club
![1300 MAYFLOWER AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
4 beds
|3 baths
|2,253 sq ft
|House
1300 MAYFLOWER AVE, MELBOURNE, FL, 32940
Community: Indian River Colony Club
MLS 1039051 • Four Star Real Estate LLC, Robin St...
Twin Lakes
![2449 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,464 sq ft
|Villa
2449 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS S5130528 • WEICHERT REALTORS HALLMARK PRO, Sh...
Indian River Colony Club
![1423 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940]()
3 beds
|2 baths
|1,832 sq ft
|House
1423 INDEPENDENCE AVE, MELBOURNE, FL, 32...
Community: Indian River Colony Club
MLS 1045534 • Four Star Real Estate LLC, Robin St...
Grand Haven
![26 PINE HARBOR DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
3 beds
|2 baths
|1,668 sq ft
|House
26 PINE HARBOR DR, PALM COAST, FL, 32137
Community: Grand Haven
MLS 1218606 • Oceans Luxury Realty Full Service L...
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.
Fountain View
![1324 MORNING WALK DR, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
4 beds
|2 baths
|1,882 sq ft
|House
1324 MORNING WALK DR, ORMOND BEACH, FL, ...
Community: Fountain View
MLS 1217221 • A Realty of Florida, LLC, Amy Regan...
Pelican Bay Daytona Beach
![129 BLUE HERON DR A, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
3 beds
|2 baths
|1,347 sq ft
|Condo
129 BLUE HERON DR A, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS FC304769 • ADAMS, CAMERON & CO., REALTORS, Jo...
Stonecrest
![11326 SE 175TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,328 sq ft
|House
11326 SE 175TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS OM703074 • OAK & SAGE REALTY LLC, Patsy Mildn...
Trilogy® Orlando
![251 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736]()
2 beds
|2 baths
|1,900 sq ft
|House
251 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
MLS O6351663 • FLORIDA PLUS REALTY, LLC, Tricia F...
Latitude Margaritaville
![560 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,466 sq ft
|House
560 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1216795 • Bob Hodges and Sons Realty, Susan W...
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Latitude Margaritaville
![914 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,563 sq ft
|House
914 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
Community: Latitude Margaritaville
MLS 1212372 • Bob Hodges and Sons Realty, Kelley ...
Latitude Margaritaville
![638 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,464 sq ft
|House
638 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Community: Latitude Margaritaville
MLS 1219037 • Bob Hodges and Sons Realty, Kelley ...
Solivita
![591 HIGHLANDS HAMMOCK DR, KISSIMMEE, FL,..., Kissimmee, FL 34759]()
2 beds
|2 baths
|2,078 sq ft
|House
591 HIGHLANDS HAMMOCK DR, KISSIMMEE, FL,...
Community: Solivita
MLS S5131599 • ARISTA REALTY GROUP, LLC, Don Broa...
Grand Haven
![2 CHINIER ST, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC307274 • COASTAL GATEWAY REAL ESTATE GR, SU...
Heritage Hills
![3543 FAIRWATERS CT D, CLERMONT, FL, 3471..., Clermont, FL 34711]()
2 beds
|2 baths
|1,503 sq ft
|Villa
3543 FAIRWATERS CT D, CLERMONT, FL, 3471...
Community: Heritage Hills
MLS O6353723 • BHHS FLORIDA REALTY, Andrew Kincai...
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2,487
homes
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.
