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Winter Park, FL 55+ active adult communities & homes for sale - Page 39
90 communities near Winter Park
2,513 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
4.7 rating (18 reviews)
![Solivita]()
$300ks
- $700ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 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
$300ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 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
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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 (3 reviews)
![Stonecrest]()
$200ks
- $500ks
Stonecrest, Summerfield, FL
New and Resale
|
55+ age-restricted
|
Built 1990 - present
|
2,200 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)
![Lake Ashton]()
$200ks
- $500ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
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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
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
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 (7 reviews)
![Kings Ridge]()
$200ks
- $400ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 homes
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$200ks
- $800ks
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 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)
![Twin Lakes]()
$200ks
- $600ks
Twin Lakes, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
2,000 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.
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
$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 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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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
1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
5 rating (2 reviews)
![Heritage Isle]()
$300ks
- $500ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
1,500 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 (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 homes
5 rating (1 reviews)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
$300ks
- $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
557 homes
5 rating (1 reviews)
![Cresswind at Victoria Gar...]()
$200ks
- $600ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
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$100ks
- $200ks
Scottish Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1992
|
653 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
$300ks
- $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
258 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
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.
3.8 rating (5 reviews)
![Traditions at Lake Ruby]()
$200ks
- $300ks
Traditions at Lake Ruby, Winter Haven, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
552 homes
$200ks
- $400ks
The Lakes at Harmony, Harmony, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
400 homes
$200ks
- $400ks
Summer Trees, Port Orange, FL
Resale Only
|
55+ age-restricted
|
Built 1976 - 2005
|
500 homes
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
$100ks
- $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
|
545 homes
Kings Ridge
![2066 DOBSON ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5105932 • RE/MAX TITANIUM GROUP, Kimberly Jo...
Latitude Margaritaville
![887 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,786 sq ft
|House
887 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Community: Latitude Margaritaville
MLS 1221608 • Realty Pros Assured, Sandra Cook
Plantation at Leesburg
![25735 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,652 sq ft
|House
25735 GLEN EAGLE DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5106539 • HARRISON REAL PROPERTY GROUP, Aman...
Plantation at Leesburg
![25120 CLIFFORD HL, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,349 sq ft
|Manufactured Home
25120 CLIFFORD HL, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5106540 • HOAD REALTY GROUP LLC, John Hoad
Plantation Bay Golf & Country Club
![21 SOUTHAMPTON ST, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,643 sq ft
|Townhouse
21 SOUTHAMPTON ST, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS FC315221 • VENTURE DEVELOPMENT REALTY,INC, De...
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Tohoqua Reserve
![1880 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
2 beds
|2 baths
|1,559 sq ft
|House
1880 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS S5141218 • LA ROSA REALTY KISSIMMEE, Vivian P...
Spruce Creek South
![9493 SE 173RD LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
3 beds
|2 baths
|1,720 sq ft
|House
9493 SE 173RD LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS OM716427 • DALTON WADE INC, Tammy Luce
Twin Lakes
![2463 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS S5141394 • FLORIDA INT'NL REAL ESTATE LLC, Li...
Venetian Bay
![3362 MARSILI AVE, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|1,952 sq ft
|House
3362 MARSILI AVE, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS NS1086940 • EXP REALTY LLC, Jennifer Waldo
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.
Tohoqua Reserve
![1909 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
2 beds
|2 baths
|1,545 sq ft
|Halfplex
1909 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS O6372925 • OPENDOOR BROKERAGE LLC, Karen Albr...
Plantation at Leesburg
![4552 PEACH TREE ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,709 sq ft
|House
4552 PEACH TREE ST, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5106405 • CENTURY 21 MYERS ROSE REALTY, Mary...
Heritage Landings
![2805 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811]()
3 beds
|2 baths
|1,711 sq ft
|House
2805 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Heritage Landings
MLS L4958438 • COLDWELL BANKER REALTY, Kelley Bla...
Lakes at Laurel Highlands
![2805 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811]()
3 beds
|2 baths
|1,711 sq ft
|House
2805 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Lakes at Laurel Highlands
MLS L4958438 • COLDWELL BANKER REALTY, Kelley Bla...
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Lakes of Mount Dora
![3003 NEW HAVEN PL, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
3 beds
|2 baths
|1,794 sq ft
|House
3003 NEW HAVEN PL, MOUNT DORA, FL, 32757
Community: Lakes of Mount Dora
MLS O6372744 • WATSON REALTY CORP, Lisa Rewis
Halifax Plantation
![3639 MALLOW DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,176 sq ft
|House
3639 MALLOW DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS FC315218 • REALTY PROS ASSURED, Mike Metzger
Del Webb Sunbridge
![3007 MIRAGE PL, ST CLOUD, FL, 34771, St Cloud, FL 34771]()
3 beds
|3 baths
|2,309 sq ft
|House
3007 MIRAGE PL, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS L4958461 • LA ROSA REALTY PRESTIGE, Erica Ros...
Solivita
![432 BEL AIR WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5141469 • BELLA VERDE REALTY LLC, Miguel Elv...
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
![4900 HERON RUN CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,289 sq ft
|House
4900 HERON RUN CIR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5106484 • CENTURY 21 MYERS ROSE REALTY, Cary...
The Villages®
![7788 SE 168TH LONE OAK LOOP, THE VILLAGE..., The Villages, FL 32162]()
3 beds
|2 baths
|1,923 sq ft
|House
7788 SE 168TH LONE OAK LOOP, THE VILLAGE...
Community: The Villages®
MLS G5106324 • REALTY EXECUTIVES IN THE VILLAGES,...
Trilogy® Orlando
![321 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|1,269 sq ft
|House
321 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS G5106424 • COMMUNITY ELITE REALTY, Diana Ston...
Solivita
![1001 UMBRIA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6372622 • CHARLES RUTENBERG REALTY ORLANDO, ...
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Spruce Creek South
![17770 SE 95TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,726 sq ft
|House
17770 SE 95TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS OM716213 • JUDY L. TROUT REALTY, Diane Stende...
The Villages®
![619 SAINT ANDREWS BLVD, THE VILLAGES, FL..., The Villages, FL 32159]()
2 beds
|2 baths
|936 sq ft
|Manufactured Home
619 SAINT ANDREWS BLVD, THE VILLAGES, FL...
Community: The Villages®
MLS G5106472 • SELLSTATE SUPERIOR REALTY, Willi M...
Royal Highlands
![21623 REGENCY PARK LN, LEESBURG, FL, 347..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,909 sq ft
|House
21623 REGENCY PARK LN, LEESBURG, FL, 347...
Community: Royal Highlands
MLS O6372801 • CASTRO REALTY GROUP, Marcia Castro...
Venetian Bay
![3070 TIGER PALM WAY, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168]()
5 beds
|5 baths
|3,349 sq ft
|House
3070 TIGER PALM WAY, NEW SMYRNA BEACH, F...
Community: Venetian Bay
MLS W7881982 • MALTBIE REALTY GROUP, Bill Maltbie
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.
Venetian Bay
![3143 TIGER PALM WAY, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168]()
4 beds
|4 baths
|3,136 sq ft
|House
3143 TIGER PALM WAY, NEW SMYRNA BEACH, F...
Community: Venetian Bay
MLS W7881981 • MALTBIE REALTY GROUP, Bill Maltbie
Venetian Bay
![125 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168]()
4 beds
|3 baths
|2,208 sq ft
|House
125 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
MLS W7881979 • MALTBIE REALTY GROUP, Bill Maltbie
Venetian Bay
![3139 TIGER PALM WAY, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168]()
4 beds
|3 baths
|2,208 sq ft
|House
3139 TIGER PALM WAY, NEW SMYRNA BEACH, F...
Community: Venetian Bay
MLS W7881976 • MALTBIE REALTY GROUP, Bill Maltbie
Venetian Bay
![3135 TIGER PALM WAY, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|1,898 sq ft
|House
3135 TIGER PALM WAY, NEW SMYRNA BEACH, F...
Community: Venetian Bay
MLS W7881972 • MALTBIE REALTY GROUP, Bill Maltbie
Sullivan Ranch
![22020 BELGIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
3 beds
|2 baths
|1,587 sq ft
|House
22020 BELGIAN CT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS O6372752 • KUNERT REALTY INC, Andreas Kunert
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Venetian Bay
![3147 TIGER PALM WAY, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168]()
5 beds
|3 baths
|3,184 sq ft
|House
3147 TIGER PALM WAY, NEW SMYRNA BEACH, F...
Community: Venetian Bay
MLS W7881968 • MALTBIE REALTY GROUP, Bill Maltbie
Latitude Margaritaville
![237 SAND BAR LN, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,681 sq ft
|House
237 SAND BAR LN, DAYTONA BEACH, FL, 3212...
Community: Latitude Margaritaville
MLS 1221562 • Realty Hub, Cherri Tindall
Breakaway Trails
![15 CIRCLE CREEK WAY, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,875 sq ft
|House
15 CIRCLE CREEK WAY, ORMOND BEACH, FL, 3...
Community: Breakaway Trails
MLS V4946676 • OCEANS LUXURY REALTY FULL SVC, Did...
Stonecrest
![12384 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,110 sq ft
|House
12384 SE 176TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
MLS OM715851 • RE/MAX FOXFIRE - SUMMERFIELD, Chri...
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®
![620 NUEVO LEON LN, THE VILLAGES, FL, 321..., The Villages, FL 32159]()
2 beds
|2 baths
|1,210 sq ft
|Villa
620 NUEVO LEON LN, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5106487 • ERA GRIZZARD REAL ESTATE, Melissa ...
Lakes of Mount Dora
![2154 WALLINGFORD LOOP, MOUNT DORA, FL, 3..., Mount Dora, FL 32757]()
2 beds
|2 baths
|1,958 sq ft
|House
2154 WALLINGFORD LOOP, MOUNT DORA, FL, 3...
Community: Lakes of Mount Dora
MLS O6372764 • DIAMOND REAL ESTATE GROUP, George ...
The Villages®
![518 SAINT ANDREWS BLVD, LADY LAKE, FL, 3..., Lady Lake, FL 32159]()
2 beds
|2 baths
|1,248 sq ft
|Manufactured Home
518 SAINT ANDREWS BLVD, LADY LAKE, FL, 3...
Community: The Villages®
MLS G5106347 • REALTY EXECUTIVES IN THE VILLAGES,...
High Vista at Ridgewood Lakes
![245 FITZGERALD LN, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|2 baths
|1,388 sq ft
|House
245 FITZGERALD LN, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS S5141441 • KELLER WILLIAMS REALTY AT THE LAKE...
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Summit Greens
![916 WOLF CREEK ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,872 sq ft
|House
916 WOLF CREEK ST, CLERMONT, FL, 34711
Community: Summit Greens
MLS G5106184 • REAL LIVING R E SOLUTIONS, William...
Grand Haven
![455 RIVERFRONT DR A302, PALM COAST, FL, ..., Palm Coast, FL 32137]()
3 beds
|2 baths
|1,779 sq ft
|Condo
455 RIVERFRONT DR A302, PALM COAST, FL, ...
Community: Grand Haven
MLS 2124530 • CENTURY 21 INTEGRA, PATRICIA MARGAR...
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2,513
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REIN updates its listings on a daily basis. Data last updated: Apr 10, 2026.
This application does not include information on all of the properties available for sale at this time.
