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Winter Park, FL 55+ active adult communities & homes for sale - Page 58
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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1 rating (1 reviews)
![Sullivan Ranch]()
$200Ks
- $700Ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
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...
Grand Haven
![2 CHINIER ST, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC307274 • COASTAL GATEWAY REAL ESTATE GR, SU...
Royal Harbor
![5837 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS G5101897 • KELLER WILLIAMS ELITE PARTNERS III...
Pennbrooke Fairways
![32218 SWEET BRIAR CT, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,272 sq ft
|House
32218 SWEET BRIAR CT, LEESBURG, FL, 3474...
Community: Pennbrooke Fairways
MLS G5101998 • CARLINO REAL ESTATE GROUP INC, San...
Arlington Ridge
![26807 BULL RUN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,962 sq ft
|House
26807 BULL RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS O6304952 • COLDWELL BANKER RESIDENTIAL RE, Ke...
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Solivita
![861 BELLA VIANA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5135913 • PELLEGO, LLC, Stan Wilson
Carlsberg Estates on Lake Suzanne
![260 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
2 beds
|2 baths
|1,321 sq ft
|House
260 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Community: Carlsberg Estates on Lake Suzanne
MLS K4903100 • LEGACY REAL ESTATE CENTER INC, Vic...
Lake Ashton
![4004 SABLE LOOP DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859]()
4 beds
|3 baths
|2,937 sq ft
|House
4004 SABLE LOOP DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
MLS P4936596 • GLOBAL LIFESTYLE LLC, Brad Kirwan
Colonnades
![4829 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,182 sq ft
|House
4829 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
MLS L4947890 • REGAL REAL ESTATE LLC, Tammy Stori...
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.
Pennbrooke Fairways
![615 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
1 beds
|1 baths
|490 sq ft
|Manufactured Home
615 COTTAGE PARK LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS OM710883 • SUNBURST PROPERTIES, Scott Hutchin...
Alhambra Villas Condominiums
![201 N HILL AVE 150, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,090 sq ft
|Condo
201 N HILL AVE 150, DELAND, FL, 32724
Community: Alhambra Villas Condominiums
MLS V4939262 • UNITED REAL ESTATE PREFERRED, Chri...
Spruce Creek Country Club
![13822 SE 85TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,540 sq ft
|House
13822 SE 85TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM710156 • REALTY ONE GROUP DAVALLS, David St...
Solivita
![159 VENTANA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5120654 • FAIRWAY REALTY OF SOLIVITA, Bonnie...
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The Villages®
![3812 NOTTINGHAM LOOP, THE VILLAGES, FL, ..., The Villages, FL 32163]()
3 beds
|2 baths
|1,559 sq ft
|House
3812 NOTTINGHAM LOOP, THE VILLAGES, FL, ...
Community: The Villages®
MLS OM685882 • RE/MAX PREMIER REALTY LADY LK, Don...
Lake Ashton
![3834 LITCHFIELD LOOP, LAKE WALES, FL, 33..., Lake Wales, FL 33859]()
2 beds
|2 baths
|1,792 sq ft
|House
3834 LITCHFIELD LOOP, LAKE WALES, FL, 33...
Community: Lake Ashton
MLS P4936538 • GLOBAL LIFESTYLE LLC, Brad Kirwan
The Villages®
![4908 NE 123RD LN, OXFORD, FL, 34484, Oxford, FL 34484]()
4 beds
|4 baths
|1,912 sq ft
|House
4908 NE 123RD LN, OXFORD, FL, 34484
Community: The Villages®
MLS G5101496 • BLACK TIE REALTY, INC., Alex Scopi...
Silver Lakes
![6341 SILVER LAKES DR, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
3 beds
|2 baths
|1,637 sq ft
|House
6341 SILVER LAKES DR, LAKELAND, FL, 3381...
Community: Silver Lakes
MLS L4955861 • COLDWELL BANKER REALTY, Kelley Bla...
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
![4489 STRATHMORE DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859]()
2 beds
|2 baths
|1,530 sq ft
|House
4489 STRATHMORE DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
MLS P4936248 • GLOBAL LIFESTYLE LLC, Brad Kirwan
Legacy of Leesburg
![27437 DESERT ROSE CT, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,115 sq ft
|House
27437 DESERT ROSE CT, LEESBURG, FL, 3474...
Community: Legacy of Leesburg
MLS O6339748 • COLDWELL BANKER RESIDENTIAL RE, Mi...
The Villages®
![15102 SANDALWOOD DR # 102, WILDWOOD, FL,..., Wildwood, FL 34785]()
3 beds
|2 baths
|1,474 sq ft
|Condo
15102 SANDALWOOD DR # 102, WILDWOOD, FL,...
Community: The Villages®
MLS G5100208 • DOWN HOME REALTY, LLLP, Melanie Mo...
Twin Lakes
![2516 PICKETT AVE, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,208 sq ft
|House
2516 PICKETT AVE, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS S5106768 • GODWIN REALTY GROUP, Melissa Godwi...
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American Village
![31 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164]()
4 beds
|2 baths
|1,986 sq ft
|House
31 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
MLS FC313292 • DR HORTON REALTY INC., Charlie Rog...
Plantation at Leesburg
![3606 MULBERRY GROVE LOOP, LEESBURG, FL, ..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,664 sq ft
|House
3606 MULBERRY GROVE LOOP, LEESBURG, FL, ...
Community: Plantation at Leesburg
MLS G5102758 • CENTURY 21 MYERS REALTY, Mary Jane...
The Villages®
![13103 SANDALWOOD DR # 13103, WILDWOOD, F..., Wildwood, FL 34785]()
2 beds
|1 baths
|1,000 sq ft
|Condo
13103 SANDALWOOD DR # 13103, WILDWOOD, F...
Community: The Villages®
MLS G5089886 • FLAMINGO REAL ESTATE & MNGMT, Kody...
The Villages®
![1737 LAUREN LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,392 sq ft
|House
1737 LAUREN LN, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5102847 • FLAMINGO REAL ESTATE & MNGMT, Robb...
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.
Solivita
![555 PRESIDO PARK PL, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
3 beds
|2 baths
|1,610 sq ft
|House
555 PRESIDO PARK PL, KISSIMMEE, FL, 3475...
Community: Solivita
MLS S5121580 • ARISTA REALTY GROUP, LLC, Douglas ...
The Villages®
![4406 CREIGHTON LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163]()
3 beds
|2 baths
|2,061 sq ft
|House
4406 CREIGHTON LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5100580 • WORTH CLARK REALTY, Nathan Piotrow...
Stonecrest
![17867 SE 115TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,597 sq ft
|House
17867 SE 115TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS GC532918 • WATSON REALTY CORP, Faylene Welcom...
The Country Club of Mount Dora
![1521 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
3 beds
|3 baths
|3,028 sq ft
|House
1521 EDGEWATER DR, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS O6339213 • UNITED REAL ESTATE PREFERRED, Kay ...
Solivita
![243 NEW RIVER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5135378 • BELLA VERDE REALTY LLC, Miguel Elv...
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Solivita
![1329 DEL MAR DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5131377 • PELLEGO, LLC, Stan Wilson
Spruce Creek Country Club
![9290 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,126 sq ft
|House
9290 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM698604 • SELLSTATE NGR- SUMMERFIELD, Virgil...
Four Seasons at Orlando
![1890 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
2 beds
|2 baths
|1,557 sq ft
|Villa
1890 FLORA PASS PL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS TB8392113 • COMPASS FLORIDA LLC, Stella Sheri...
Twin Lakes
![5043 VANTAGE CT, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,365 sq ft
|House
5043 VANTAGE CT, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS S5117701 • WEICHERT REALTORS HALLMARK PRO, Sh...
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.
Halifax Plantation
![1510 KINNARD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,695 sq ft
|Townhouse
1510 KINNARD DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS FC306681 • VENTURE DEVELOPMENT REALTY,INC, El...
Plantation Bay Golf & Country Club
![998 DOWNSHIRE LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
5 beds
|4 baths
|5,454 sq ft
|House
998 DOWNSHIRE LN, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS FC312940 • VENTURE DEVELOPMENT REALTY,INC, El...
Venetian Bay
![440 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,779 sq ft
|House
440 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
MLS O6342352 • TOPSKY REALTY INC, Sammi Li
Twin Lakes
![2419 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,261 sq ft
|Villa
2419 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS S5130508 • CENTURY 21 EDGE, Juan Hidalgo
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The Villages®
![1224 DUSTIN DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|912 sq ft
|Manufactured Home
1224 DUSTIN DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS OM707875 • VAUGHT REALTY, Billy Vaught
Stonecrest
![17435 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,682 sq ft
|House
17435 SE 112TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS OM706907 • RE/MAX PREMIER REALTY LADY LK, Don...
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2,377
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REIN updates its listings on a daily basis. Data last updated: Jan 10, 2026.
This application does not include information on all of the properties available for sale at this time.
