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Winter Park, FL 55+ active adult communities & homes for sale - Page 54
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 (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 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 (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
1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 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
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.
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
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 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
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
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
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
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
- $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
258 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
The Villages®
![1619 W SCHWARTZ BLVD, THE VILLAGES, FL, ..., The Villages, FL 32159]()
2 beds
|2 baths
|1,300 sq ft
|Manufactured Home
1619 W SCHWARTZ BLVD, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5102602 • RE/MAX PREMIER REALTY LADY LK, Jos...
Plantation at Leesburg
![4949 SAWGRASS LAKE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,133 sq ft
|House
4949 SAWGRASS LAKE CIR, LEESBURG, FL, 34...
Community: Plantation at Leesburg
MLS G5102655 • CENTURY 21 MYERS ROSE REALTY, Mary...
Solivita
![507 PRESIDO PARK PL, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
2 beds
|2 baths
|1,302 sq ft
|House
507 PRESIDO PARK PL, KISSIMMEE, FL, 3475...
Community: Solivita
MLS TB8429298 • NHR BROKERAGE LLC, Madalina Tat
The Villages®
![2054 PALO ALTO AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159]()
3 beds
|2 baths
|2,312 sq ft
|House
2054 PALO ALTO AVE, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5102696 • COLDWELL BANKER REALTY, William Pe...
Latitude Margaritaville
![253 COMPASS ROSE DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|3 baths
|2,067 sq ft
|House
253 COMPASS ROSE DR, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS 1218430 • RE/MAX Signature, Janet Fuller
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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
Del Webb Oasis
![13846 FRESH IVY ST, WINTER GARDEN, FL, 3..., Winter Garden, FL 34787]()
2 beds
|3 baths
|2,108 sq ft
|House
13846 FRESH IVY ST, WINTER GARDEN, FL, 3...
Community: Del Webb Oasis
MLS O6346706 • REAL BROKER, LLC, Ken Pozek
Stonecrest
![11037 SE 173RD PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,328 sq ft
|House
11037 SE 173RD PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5102718 • RE/MAX FOXFIRE - SUMMERFIELD, Donn...
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...
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
![3713 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS O6348405 • FLORIDA PRESTIGIOUS HOMES INC, Ian...
The Villages®
![3338 QUEENSWAY TER, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|2 baths
|2,013 sq ft
|House
3338 QUEENSWAY TER, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5102624 • BERKSHIRE HATHAWAY HS FLORIDA, Jim...
Spruce Creek Country Club
![9244 SE 128TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|2,130 sq ft
|House
9244 SE 128TH ST, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM710460 • RE/MAX FOXFIRE - SUMMERFIELD, Caro...
Arlington Ridge
![26925 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,254 sq ft
|House
26925 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
MLS G5102632 • LOKATION, Steven Simpkins
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The Villages®
![3818 INFINITY RUN, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|2 baths
|1,501 sq ft
|House
3818 INFINITY RUN, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5102409 • REALTY EXECUTIVES IN THE VILLAGES,...
Stonecrest
![12321 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,815 sq ft
|House
12321 SE 176TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
MLS G5101659 • RE/MAX PREMIER REALTY LADY LK, Cin...
Del Webb Sunbridge
![6375 TRAILBLAZE BND, ST CLOUD, FL, 34771, St Cloud, FL 34771]()
4 beds
|4 baths
|2,781 sq ft
|House
6375 TRAILBLAZE BND, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS O6347477 • LPT REALTY, LLC, Manuel Delgado
Plantation Bay Golf & Country Club
![945 STONE LAKE DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,910 sq ft
|House
945 STONE LAKE DR, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS FC313035 • VENTURE DEVELOPMENT REALTY,INC, El...
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.
Cypress Lakes
![2247 CYPRESS CROSS LOOP, LAKELAND, FL, 3..., Lakeland, FL 33810]()
2 beds
|2 baths
|768 sq ft
|Manufactured Home
2247 CYPRESS CROSS LOOP, LAKELAND, FL, 3...
Community: Cypress Lakes
MLS L4956160 • KELLER WILLIAMS REALTY SMART, Casa...
Colonnades
![4816 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,066 sq ft
|Manufactured Home
4816 GOLDENVIEW LN, LAKELAND, FL, 33811
Community: Colonnades
MLS L4955982 • COLDWELL BANKER REALTY, Lisa Broch...
Heritage Isle
![3130 LE CONTE ST, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
2 beds
|2 baths
|1,394 sq ft
|Townhouse
3130 LE CONTE ST, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1058050 • Blue Marlin Real Estate, Sarah Reka...
The Villages®
![1717 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,143 sq ft
|Villa
1717 CAMPOS DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5102399 • RE/MAX FOXFIRE - SUMMERFIELD, Kell...
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Solivita
![243 NEW RIVER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5135378 • BELLA VERDE REALTY LLC, Miguel Elv...
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...
Lake Ashton
![4195 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
3 beds
|2 baths
|2,039 sq ft
|House
4195 MUIRFIELD LOOP, LAKE WALES, FL, 338...
Community: Lake Ashton
MLS P4936379 • GLOBAL LIFESTYLE LLC, Brad Kirwan
Vienna Square
![2470 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884]()
3 beds
|2 baths
|1,935 sq ft
|House
2470 SALZBURG LOOP, WINTER HAVEN, FL, 33...
Community: Vienna Square
MLS O6344501 • PREMIUM REAL ESTATE SERVICES, Nere...
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
![428 BEL AIR WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5134079 • BELLA VERDE REALTY LLC, Miguel Elv...
Trilogy® Orlando
![277 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736]()
3 beds
|2 baths
|1,839 sq ft
|House
277 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
MLS G5102140 • COMMUNITY ELITE REALTY, Nancy Aitk...
Del Webb Sunbridge
![6213 CITRUS GROVE CT, ST CLOUD, FL, 3477..., St Cloud, FL 34771]()
3 beds
|3 baths
|2,269 sq ft
|House
6213 CITRUS GROVE CT, ST CLOUD, FL, 3477...
Community: Del Webb Sunbridge
MLS O6346549 • PULTE REALTY OF NORTH FLORIDA LLC,...
Stonecrest
![12163 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,645 sq ft
|House
12163 SE 176TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
MLS G5102452 • RE/MAX FOXFIRE - SUMMERFIELD, Cher...
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...
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Stonecrest
![11246 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,312 sq ft
|House
11246 SE 175TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5102326 • CHARLES RUTENBERG REALTY ORLANDO, ...
Grand Haven
![200 RIVERFRONT DR B303, PALM COAST, FL, ..., Palm Coast, FL 32137]()
3 beds
|2 baths
|1,762 sq ft
|Condo
200 RIVERFRONT DR B303, PALM COAST, FL, ...
Community: Grand Haven
MLS FC312912 • TRADEMARK REALTY GROUP LLC, Bruce ...
Latitude Margaritaville
![221 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,503 sq ft
|House
221 ISLAND BREEZE AVE, DAYTONA BEACH, FL...
Community: Latitude Margaritaville
MLS 1218111 • Bob Hodges and Sons Realty, Susan W...
Latitude Margaritaville
![944 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,558 sq ft
|House
944 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Community: Latitude Margaritaville
MLS 1218107 • Realty Hub, Aimee Aballo
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®
![1712 MORELOS RD, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,193 sq ft
|Villa
1712 MORELOS RD, THE VILLAGES, FL, 32159
Community: The Villages®
MLS W7879135 • LISTWITHFREEDOM.COM, Ralph Harvey
Arlington Ridge
![26939 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,631 sq ft
|Villa
26939 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
MLS G5102246 • HOAD REALTY GROUP LLC, Lisa Hoad
Heritage Hills
![3524 LITCHFIELD CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
4 beds
|3 baths
|2,293 sq ft
|House
3524 LITCHFIELD CT, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6344422 • BHHS FLORIDA REALTY, Patti Kincaid
Del Webb Minneola
![2761 TOP HILL CT, MINNEOLA, FL, 34715, Minneola, FL 34715]()
2 beds
|2 baths
|1,943 sq ft
|House
2761 TOP HILL CT, MINNEOLA, FL, 34715
Community: Del Webb Minneola
MLS O6345393 • SERHANT, Silvia Kinkela
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Del Webb Minneola
![2763 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715]()
2 beds
|2 baths
|1,395 sq ft
|House
2763 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
MLS O6345207 • AGENT TRUST REALTY CORPORATION, Mi...
Stonecrest
![11276 SE 170TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,000 sq ft
|House
11276 SE 170TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5102089 • WORTH CLARK REALTY, Jim McDonald
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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.
