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Winter Park, FL 55+ active adult communities & homes for sale - Page 57
90 communities near Winter Park
2,377 homes near Winter Park
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4 rating (17 reviews)
![The Villages®]()
<$100k
- $2Ms
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
|
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
Download the Ultimate 55+ Homebuying Guide
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$300Ks
- $1Ms
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 homes
$100Ks
- $400Ks
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
- $400Ks
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
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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
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
- $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2022
|
1,500 homes
Download the Ultimate 55+ Homebuying Guide
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5 rating (8 reviews)
![Royal Highlands]()
$200Ks
- $400Ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
$400Ks
- $1Ms
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
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
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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)
![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
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
- $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
- $800Ks
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
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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
- $800Ks
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
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.
4.1 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
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]()
$300Ks
- $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
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1 rating (1 reviews)
![Sullivan Ranch]()
$200Ks
- $700Ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
Huntington at Hunter's Ridge
![23 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|1,852 sq ft
|House
23 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Community: Huntington at Hunter's Ridge
MLS FC313604 • REALTY PROS ASSURED, Terri Wilkins...
Lakes at Laurel Highlands
![1829 PRISTINE LOOP, LAKELAND, FL, 33811, Lakeland, FL 33811]()
4 beds
|2 baths
|1,867 sq ft
|House
1829 PRISTINE LOOP, LAKELAND, FL, 33811
Community: Lakes at Laurel Highlands
MLS L4955000 • XCELLENCE REALTY, INC, Annette Col...
Indian River Colony Club
![1484 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940]()
3 beds
|2 baths
|1,728 sq ft
|House
1484 INDEPENDENCE AVE, MELBOURNE, FL, 32...
Community: Indian River Colony Club
MLS 1060790 • Four Star Real Estate LLC, Robin St...
Poinsettia Heights
![1818 SAN SALVADOR CT, WINTER HAVEN, FL, ..., Winter Haven, FL 33881]()
2 beds
|2 baths
|1,271 sq ft
|House
1818 SAN SALVADOR CT, WINTER HAVEN, FL, ...
Community: Poinsettia Heights
MLS P4935578 • KELLER WILLIAMS REALTY SMART 1, Br...
Sullivan Ranch
![22035 BELGIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
3 beds
|2 baths
|1,663 sq ft
|Villa
22035 BELGIAN CT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS O6356010 • SPARROW REALTY & RENTALS, Marc Spe...
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The Villages®
![16900 SE 81ST ELLERSLIE CT, THE VILLAGES..., The Villages, FL 32162]()
2 beds
|2 baths
|1,160 sq ft
|Villa
16900 SE 81ST ELLERSLIE CT, THE VILLAGES...
Community: The Villages®
MLS OM711133 • KELLER WILLIAMS CORNERSTONE RE, Cr...
Silver Lakes
![2206 SILVER LAKES DR, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
3 beds
|2 baths
|1,597 sq ft
|House
2206 SILVER LAKES DR, LAKELAND, FL, 3381...
Community: Silver Lakes
MLS L4956889 • REMAX EXPERTS, Kara Severit
Twin Lakes
![2585 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,464 sq ft
|Villa
2585 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS O6343239 • EXP REALTY LLC, Dawn Grigsby
Summit Greens
![993 EVEREST ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS S5121766 • CENTURY 21 WOLF'S CROSSING 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.
Lake Ashton
![4028 BIRKDALE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|1,706 sq ft
|House
4028 BIRKDALE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4936811 • LAKE ASHTON REALTY INC., Lori Raat...
Plantation Bay Golf & Country Club
![5 JASMINE RUN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,386 sq ft
|House
5 JASMINE RUN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC311584 • CLAIRE HUNTER REALTY, Brian Hunter
Plantation Bay Golf & Country Club
![21 JASMINE RUN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,424 sq ft
|House
21 JASMINE RUN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS 1216701 • Venture Development Realty, Inc, Sc...
Lakes at Laurel Highlands
![1823 PRISTINE LOOP, LAKELAND, FL, 33811, Lakeland, FL 33811]()
3 beds
|2 baths
|1,711 sq ft
|House
1823 PRISTINE LOOP, LAKELAND, FL, 33811
Community: Lakes at Laurel Highlands
MLS T3520599 • CENTURY 21 ROSA LEON, Maribel Calz...
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Harbor Hills Country Club
![39517 HILLRISE LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
4 beds
|3 baths
|2,532 sq ft
|House
39517 HILLRISE LN, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5103664 • MORRIS REALTY AND INVESTMENTS, Cra...
Spruce Creek South
![10683 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,620 sq ft
|House
10683 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Spruce Creek South
MLS G5096056 • HANSON REAL ESTATE GROUP, INC., Je...
Sullivan Ranch
![30101 BRETTON LOOP, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757]()
4 beds
|3 baths
|3,452 sq ft
|House
30101 BRETTON LOOP, MOUNT DORA, FL, 3275...
Community: Sullivan Ranch
MLS O6351059 • LA ROSA REALTY PREMIER LLC, Tavis ...
Highland Fairways
![3130 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,210 sq ft
|House
3130 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
MLS TB8407029 • LAND MERCHANTS REAL ESTATE SERVIC...
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
![25800 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,653 sq ft
|House
25800 BELLE HELENE, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5096683 • SCATES REALTY & INVESTMENT PRO, Ei...
Spruce Creek South
![17855 SE 99TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,678 sq ft
|House
17855 SE 99TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS OM689620 • JUDY L. TROUT REALTY, Jennifer Tra...
Tohoqua Reserve
![1873 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
3 beds
|2 baths
|1,559 sq ft
|Villa
1873 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS S5133310 • EXP REALTY LLC, Carlos Nolte
Del Webb at Viera
![3113 TIDEPOOL PL, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,655 sq ft
|House
3113 TIDEPOOL PL, MELBOURNE, FL, 32940
Community: Del Webb at Viera
MLS 1060119 • EXP Realty, LLC, Peggy Page
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Plantation at Leesburg
![4242 LEAFWAY CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|2,297 sq ft
|House
4242 LEAFWAY CIR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6354460 • WYNNMORE REALTY LLC, Taylor McKinl...
Solivita
![432 GRAND CANAL DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5130686 • BORCHINI REALTY, Charles Borchini
Oakview
![1518 OAKVIEW CIR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33880]()
2 beds
|2 baths
|1,438 sq ft
|House
1518 OAKVIEW CIR, WINTER HAVEN, FL, 3388...
Community: Oakview
MLS L4956282 • FLORIDA REALTY INVESTMENT FIRM, El...
Summit Greens
![793 SUMMIT GREENS BLVD, CLERMONT, FL, 34..., Clermont, FL 34711]()
2 beds
|2 baths
|1,731 sq ft
|House
793 SUMMIT GREENS BLVD, CLERMONT, FL, 34...
Community: Summit Greens
MLS G5101007 • TRINITY REAL ESTATE SALES LLC, Rob...
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®
![5371 WARM SPRINGS AVE, WILDWOOD, FL, 347..., Wildwood, FL 34785]()
2 beds
|1 baths
|696 sq ft
|House
5371 WARM SPRINGS AVE, WILDWOOD, FL, 347...
Community: The Villages®
MLS OM711975 • FLORIDA CAPITAL REALTY, Dolly Plan...
Trilogy® Orlando
![105 CUPANIA CT, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|1,469 sq ft
|House
105 CUPANIA CT, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS G5096238 • WATSON REALTY CORP., REALTORS, Mic...
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
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 ...
Spruce Creek South
![9645 SE 173RD PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
3 beds
|2 baths
|1,450 sq ft
|House
9645 SE 173RD PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS G5095488 • TEAM WYN REALTY LLC, Gloria Wyning...
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Pelican Bay Daytona Beach
![149 BLUE HERON DR C, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,192 sq ft
|Condo
149 BLUE HERON DR C, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS S5123673 • LPT REALTY, LLC, Yomari Ayala
Foxwood Lake Estates
![5026 FOXWOOD BLVD, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,456 sq ft
|Manufactured Home
5026 FOXWOOD BLVD, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS L4955800 • KELLER WILLIAMS REALTY SMART, Casa...
Lake Ashton
![4568 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|1,847 sq ft
|House
4568 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4936702 • GLOBAL LIFESTYLE LLC, Brad Kirwan
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 ...
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 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...
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...
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...
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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...
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...
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2,377
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REIN updates its listings on a daily basis. Data last updated: Jan 11, 2026.
This application does not include information on all of the properties available for sale at this time.
