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Winter Park, FL 55+ active adult communities & homes for sale - Page 50
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
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
- $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
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)
![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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Questions? Call us:
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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
Stonecrest
![17209 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,695 sq ft
|House
17209 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
MLS G5102714 • MORRIS REALTY AND INVESTMENTS, Kim...
Highland Lakes
![5609 ROSEWALL CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|3 baths
|2,251 sq ft
|House
5609 ROSEWALL CIR, LEESBURG, FL, 34748
Community: Highland Lakes
MLS G5103638 • COLDWELL BANKER REALTY, Sara Suthe...
Spruce Creek South
![10442 SE 179TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,652 sq ft
|House
10442 SE 179TH PL, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS G5096885 • IM REALTY, Ira Miller
Lake Ashton
![4124 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
2 beds
|2 baths
|1,682 sq ft
|House
4124 MUIRFIELD LOOP, LAKE WALES, FL, 338...
Community: Lake Ashton
MLS P4935581 • LAKE ASHTON REALTY INC., Candra Al...
The Villages®
![1314 LAJOLLA CIR, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,094 sq ft
|Villa
1314 LAJOLLA CIR, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5100553 • RE/MAX PREMIER REALTY, Tammy Freil...
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Tohoqua Reserve
![1855 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
2 beds
|2 baths
|1,559 sq ft
|Villa
1855 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS O6360691 • EXP REALTY LLC, Amy Moline
Stonecrest
![17243 SE 116TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,729 sq ft
|House
17243 SE 116TH COURT RD, SUMMERFIELD, FL...
Community: Stonecrest
MLS G5103549 • BASSETT PREMIER REALTY INC, Sharon...
Lake Ashton
![6165 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884]()
3 beds
|2 baths
|2,045 sq ft
|House
6165 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
MLS P4937082 • GLOBAL LIFESTYLE LLC, Brad Kirwan
Solivita
![680 PORTOFINO DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5137088 • BORCHINI REALTY, Valerie Williams
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.
Harbor Hills Country Club
![5235 ISLAND TERRACE CT, LADY LAKE, FL, 3..., Lady Lake, FL 32159]()
3 beds
|3 baths
|2,446 sq ft
|House
5235 ISLAND TERRACE CT, LADY LAKE, FL, 3...
Community: Harbor Hills Country Club
MLS G5097748 • CHARLES RUTENBERG REALTY ORLANDO, ...
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
![2343 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884]()
3 beds
|2 baths
|1,948 sq ft
|House
2343 SALZBURG LOOP, WINTER HAVEN, FL, 33...
Community: Vienna Square
MLS P4936926 • COLDWELL BANKER REALTY, Wanda Dick...
Legacy of Leesburg
![27111 NOSTALGIA DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,477 sq ft
|House
27111 NOSTALGIA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS O6338390 • HOGAN REALTY GROUP INC, Kaitlin Si...
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Halifax Plantation
![1318 ASHER CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,684 sq ft
|House
1318 ASHER CT, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS FC313470 • WATSON REALTY CORP, Bogdana Subach...
Twin Lakes
![2476 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,346 sq ft
|Villa
2476 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS S5134447 • WEICHERT REALTORS HALLMARK PRO, Sh...
The Villages®
![903 RAMOS DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,836 sq ft
|House
903 RAMOS DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS O6358859 • REALTY HUB, Gordon Veling
The Villages®
![732 PALMA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,374 sq ft
|House
732 PALMA DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS O6319952 • REALTY HUB, Gordon Veling
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.
Royal Harbor
![5305 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778]()
3 beds
|2 baths
|1,824 sq ft
|House
5305 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
MLS V4941959 • ROUND TABLE REALTY INC., Roxanne L...
The Villages®
![4434 SHOCKOE CIR, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,950 sq ft
|House
4434 SHOCKOE CIR, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5103310 • FLORIDA REALTY INVESTMENTS, Katie ...
Solivita
![1423 HARBOR RIDGE DR, POINCIANA, FL, 347..., Poinciana, FL 34759]()
2 beds
|2 baths
|1,703 sq ft
|House
1423 HARBOR RIDGE DR, POINCIANA, FL, 347...
Community: Solivita
MLS TB8329416 • NHR BROKERAGE LLC, Madalina Tat
Halifax Plantation
![3908 TANO DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|2 baths
|2,038 sq ft
|House
3908 TANO DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS FC313308 • COASTAL GATEWAY REAL ESTATE GROUP,...
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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...
The Villages®
![17238 SE 94TH COULTS CIR, THE VILLAGES, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,558 sq ft
|House
17238 SE 94TH COULTS CIR, THE VILLAGES, ...
Community: The Villages®
MLS G5095911 • BHHS FLORIDA REALTY, Dawn Bush
Sullivan Ranch
![21632 HIDDEN CRK, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|4 baths
|3,853 sq ft
|House
21632 HIDDEN CRK, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS A4673135 • SAVVY AVENUE, LLC, Moe Mossa
Del Webb Sunbridge
![6553 ROVER WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771]()
3 beds
|3 baths
|2,038 sq ft
|House
6553 ROVER WAY, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS O6351448 • KELLER WILLIAMS ADVANTAGE III, Kat...
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 Bay Golf & Country Club
![1221 HARWICK LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,151 sq ft
|House
1221 HARWICK LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC306494 • ADAMS, CAMERON & CO., REALTORS, Ry...
Foxwood Lake Estates
![5027 FOREST CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,248 sq ft
|Manufactured Home
5027 FOREST CREST DR, LAKELAND, FL, 3381...
Community: Foxwood Lake Estates
MLS L4957092 • KELLER WILLIAMS REALTY SMART, Dani...
Four Seasons at Orlando
![7632 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747]()
2 beds
|2 baths
|1,437 sq ft
|Villa
7632 SAND PIERRE CT, KISSIMMEE, FL, 3474...
Community: Four Seasons at Orlando
MLS O6351213 • LOKATION, Eddy Rodriguez
Plantation Bay Golf & Country Club
![1009 SUDBURY LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|5 baths
|3,927 sq ft
|House
1009 SUDBURY LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS TB8375913 • ICI SELECT REALTY, Ali Kargar
The Villages®
![1507 E SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159]()
2 beds
|2 baths
|1,040 sq ft
|Manufactured Home
1507 E SCHWARTZ BLVD, LADY LAKE, FL, 321...
Community: The Villages®
MLS TB8411863 • LISTED SIMPLY, Sinan Zakaria
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Lake Ashton
![5201 GREEN DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
3 beds
|2 baths
|1,845 sq ft
|House
5201 GREEN DR, WINTER HAVEN, FL, 33884
Community: Lake Ashton
MLS TB8441806 • LA ROSA REALTY LLC, Francis Alvar...
Pennbrooke Fairways
![432 RANCHWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,336 sq ft
|House
432 RANCHWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5105001 • SALLY LOVE REAL ESTATE, Carol Juli...
Kings Ridge
![4326 HAMMERSMITH DR, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|3 baths
|1,722 sq ft
|House
4326 HAMMERSMITH DR, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5104371 • WATSON REALTY CORP., REALTORS, Chr...
Summer Trees
![128 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128]()
3 beds
|2 baths
|1,268 sq ft
|House
128 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
MLS V4944401 • ADAMS, CAMERON & CO., REALTORS, Ma...
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.
Arlington Ridge
![4671 SPRING GROVE LN, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,558 sq ft
|House
4671 SPRING GROVE LN, LEESBURG, FL, 3474...
Community: Arlington Ridge
MLS G5095980 • FLORIDA REALTY INVESTMENTS, Bonnie...
Pennbrooke Fairways
![32942 RAMBLING OAKS CT, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,869 sq ft
|House
32942 RAMBLING OAKS CT, LEESBURG, FL, 34...
Community: Pennbrooke Fairways
MLS G5099019 • CENTURY 21 ALTON CLARK, Regina Rod...
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...
Spruce Creek South
![17830 SE 95TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,734 sq ft
|House
17830 SE 95TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS G5101267 • RE/MAX PREMIER REALTY LADY LK, Ger...
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Venetian Bay
![3328 MARSILI AVE, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|1,423 sq ft
|House
3328 MARSILI AVE, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS FC314384 • KELLER WILLIAMS RLTY FL. PARTN, BJ...
Solivita
![779 VIA COMO ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5139075 • PELLEGO, LLC, Stan Wilson
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2,377
homes
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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.
