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Islamorada Luxury Real Estate, Luxury Homes For Sale

(162) PROPERTIES

ISLAMORADA, FL 33036
$8,900,000
ISLAMORADA, FL 33036
87961 Old

8 Beds 9 Baths Square Ft: 7855
Single Family Home - MLS#: 559023
Community: Plant Beach - Mile Marker (MM) 87.5

Spectacular offering! Two adjacent ocean front estate properties in Islamorada with fabulous main house, guest house with pool, attached garage, wide open porches with endless ocean views...and adjacent…

MLS 559023

ISLAMORADA, FL 33036
$6,000,000
ISLAMORADA, FL 33036
87961 Old

6 Beds 7 Baths Square Ft: 5791
Single Family Home - MLS#: 560918
Community: Plant Beach - Mile Marker (MM) 87.5

Oceanfront estate on 4 acres with exquisite wide open water views. Private gated long driveway entrance to Main house 4 bedrooms ensuite baths. Two bedroom guest home connected by covered breezeways.…

MLS 560918

ISLAMORADA, FL 33036
$5,799,000
ISLAMORADA, FL 33036
220 Plantation Blvd

4 Beds 5 Baths Square Ft: 4600
Single Family Home - MLS#: 555172
Community: Plant Beach - Mile Marker (MM) 87.5

This bayfront home has it ALL! Spacious home for a large family has elevator and 3rd floor master suite. Room for all your boats and water toys. 5.05 acres plus .52 acres of deeded baybottom with an irreplaceable…

MLS 555172

ISLAMORADA, FL 33036
$5,500,000
ISLAMORADA, FL 33036
85261 Old

3 Beds 2 Baths Square Ft: 1839
Single Family Home - MLS#: 549574
Community: Misc Windley Key - Mile Marker (MM) 85.0

HUGE OCEANFRONT PARCEL IN ISLAMORADA offering a deep water basin...rare for oceanfront! 200' on the ocean! You will enjoy this gated compound with a remodeled ground level home with many extras including…

MLS 549574

ISLAMORADA, FL 33036
$3,800,000
ISLAMORADA, FL 33036
423 & 427 Palm

6 Beds 5 Baths Square Ft: 4667
Single Family Home - MLS#: 560916
Community: Safety Harbor - Mile Marker (MM) 74.0

Great family compound or corporate retreat. 2 homes on almost 1 acre with 400' of waterfrontage and deep water protected dockage. Main house is a stunning contemporary 4 bed/3 bath, second house is a…

MLS 560916

ISLAMORADA, FL 33070
$3,600,000
ISLAMORADA, FL 33070
169 Indian Mound

3 Beds 3.1 Baths Square Ft: 4400
Single Family Home - MLS#: 559230
Community: Indian Harbor - Mile Marker (MM) 89.0

It's A Lifestyle. Magnificent bayfront pool home with gracious entertaining space throughout. Custom designed by renowned architect 3BR/3.5BA + office + entertainment area + gym. Everything top of the…

MLS 559230

ISLAMORADA, FL 33070
$3,500,000
ISLAMORADA, FL 33070
88547 Old

4 Beds 3 Baths Square Ft: 5023
Single Family Home - MLS#: 558232
Community: Key Heights - Mile Marker (MM) 88.5

DEEP WATER 5 feet 400 Foot NEW PIER, 3 NEW boat lifts.Direct Oceanfront gatedEstate.Custom Designed concrete 4/3 multi-level fully furnished house. The pool,secluded driveway,covered parking,screened…

MLS 558232

ISLAMORADA, FL 33036
$3,200,000
ISLAMORADA, FL 33036
76180 Overseas

16 Beds 14 Baths Square Ft: 7785
Single Family Home - MLS#: 556818
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Bay front compound offers 7 residences comprised of 2 duplexes and 3 homes on over 1.5acres of prime Islamorada real estate. Immediate back country & offshore access. Dockage for multiple vessels from…

MLS 556818

ISLAMORADA, FL 33036
$3,000,000
ISLAMORADA, FL 33036
87963 Old Hwy

3 Beds 3.1 Baths Square Ft: 2064
Single Family Home - MLS#: 560917
Community: Plant Beach - Mile Marker (MM) 87.5

Charming Old-Florida style oceanfront home with substantial boat basin offering 2 lifts, well protected dockage for multiple boats! Long private drive, with lovely grounds, in ground pool. Huge open air…

MLS 560917

ISLAMORADA, FL 33036
$2,975,000
ISLAMORADA, FL 33036
1008 Venetian

5 Beds 4.1 Baths Square Ft: 4308
Single Family Home - MLS#: 558116
Community: Venetian Shores - Mile Marker (MM) 86.0

EXTRAORDINARY BAYFRONT HOME IN VENETIAN SHORES situated on a lot and a half offering 105' of concrete deep water dockage and a superior roof-top deck to capture the beautiful views. Tri-level home offers…

MLS 558116

ISLAMORADA, FL 33036
$2,950,000
ISLAMORADA, FL 33036
88060 Overseas

6 Beds 7 Baths Square Ft: 4999
Single Family Home - MLS#: 559233
Community: Plant Beach - Mile Marker (MM) 87.5

Gracious family home on the Bay in Islamorada. With 6 bedrooms and 7 full baths there is plenty of room for a large family or corporate entertaining. Walk from the dock with 2 boatlifts to the sandy beach…

MLS 559233

ISLAMORADA, FL 33036
$2,950,000
ISLAMORADA, FL 33036
77521 Overseas Hwy , Unit #11

4 Beds 4.1 Baths Square Ft: 3382
Single Family Home - MLS#: 543669
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

MLS 543669

ISLAMORADA, FL 33036
$2,950,000
ISLAMORADA, FL 33036
77521 Overseas Hwy , Unit #12

4 Beds 4.1 Baths Square Ft: 3382
Single Family Home - MLS#: 543670
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

MLS 543670

ISLAMORADA, FL 33036
$2,950,000
ISLAMORADA, FL 33036
77521 Overseas Hwy , Unit #1

4 Beds 4.1 Baths Square Ft: 3382
Single Family Home - MLS#: 543659
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

MLS 543659

ISLAMORADA, FL 33070
$2,800,000
ISLAMORADA, FL 33070
138 N Rolling Hill

5 Beds 4.1 Baths Square Ft: 4646
Single Family Home - MLS#: 561042
Community: High Point - Mile Marker (MM) 89.0

OPEN WATER 5BD/4.5BA ESTATE HOME with GUEST COTTAGE, deep DOCKAGE & 2 BOAT LIFTS in ISLAMORADA. Enjoy watercolor sunsets from this gated estate on the open bay with sweeping open water views throughout.…

MLS 561042

ISLAMORADA, FL 33036
$2,800,000
ISLAMORADA, FL 33036
322 Tollgate Shores

5 Beds 5 Baths Square Ft: 4643
Single Family Home - MLS#: 560537
Community: Toll Gate Shores - Mile Marker (MM) 73.5

Magnificent bay front home situated on over an acre point lot. Surrounded by water on 3 sides with deep water dockage to accomodate large yachts. Offering 5 bedrooms, 5 baths, elevator, pool, beach, 2…

MLS 560537

ISLAMORADA, FL 33070
$2,675,000
ISLAMORADA, FL 33070
432 S Coconut Palm

3 Beds 3.1 Baths Square Ft: 2903
Single Family Home - MLS#: 554419
Community: Plant Key Colony - Mile Marker (MM) 90.0

Privacy abounds at this resort like residence. Water frontage on 2 sides offers seclusion that is hard to find. Totally updated home provides 2 master suites in nearly 3000 sq. ft. Gourmet kitchen with…

MLS 554419

ISLAMORADA, FL 33036
$2,650,000
ISLAMORADA, FL 33036
77521 Overseas Hwy , Unit Unit 2

4 Beds 4 Baths Square Ft: 2895
Single Family Home - MLS#: 543660
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

MLS 543660

ISLAMORADA, FL 33036
$2,650,000
ISLAMORADA, FL 33036
77521 Overseas Hwy , Unit #10

4 Beds 4 Baths Square Ft: 2895
Single Family Home - MLS#: 543668
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

MLS 543668

ISLAMORADA, FL 33036
$2,500,000
ISLAMORADA, FL 33036
18 Pen Key Club

3 Beds 3 Baths Square Ft: 2609
Single Family Home - MLS#: 552388
Community: Penn Key Club - Mile Marker (MM) 83.0

Islamorada's private, secluded gated community on the Bay, with pool, and boat dockage for each homeowner. This beautiful ground level home was completely rebuilt from the ground up in 2006. Travertine…

MLS 552388

ISLAMORADA, FL 33036
$2,499,000
ISLAMORADA, FL 33036
76001 Overseas

5 Beds 4 Baths Square Ft: 3172
Single Family Home - MLS#: 554412
Community: Matecumbe Ocean Bay - Mile Marker (MM) 75.0

Tranquil 2 +/- acre estate, featuring 2 homes. Main is a 3 bedroom 3 bath with attached garage and carport. 2nd home is a large 2 bedroom 1 bath located above a huge 2 car garage. Both homes are all concrete…

MLS 554412

ISLAMORADA, FL 33036
$2,325,000
ISLAMORADA, FL 33036
77521 Overseas Hwy , Unit #6

4 Beds 4 Baths Square Ft: 2736
Single Family Home - MLS#: 543664
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

MLS 543664

ISLAMORADA, FL 33036
$2,325,000
ISLAMORADA, FL 33036
77521 Overseas Hwy , Unit #7

4 Beds 4 Baths Square Ft: 2736
Single Family Home - MLS#: 543665
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

MLS 543665

ISLAMORADA, FL 33036
$2,325,000
ISLAMORADA, FL 33036
77521 Overseas Hwy , Unit #5

4 Beds 4 Baths Square Ft: 2719
Single Family Home - MLS#: 543663
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

MLS 543663

ISLAMORADA, FL 33036
$2,325,000
ISLAMORADA, FL 33036
77521 Overseas Hwy , Unit #8

4 Beds 4 Baths Square Ft: 2719
Single Family Home - MLS#: 543666
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

MLS 543666

ISLAMORADA, FL 33036
$2,325,000
ISLAMORADA, FL 33036
77521 Overseas Hwy , Unit #4

4 Beds 4 Baths Square Ft: 2719
Single Family Home - MLS#: 543662
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

MLS 543662

ISLAMORADA, FL 33036
$2,300,000
ISLAMORADA, FL 33036
75761 Overseas

3 Beds 2.2 Baths Square Ft: 3011
Single Family Home - MLS#: 559846
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Beautiful sunrises and open water views await you at this spectacular Key West style estate. Walk the natural sand beach or enjoy the pool set amongst the lush landscape. This exceptional residence features…

MLS 559846

ISLAMORADA, FL 33036
$2,300,000
ISLAMORADA, FL 33036
150 Stromboli

6 Beds 4 Baths Square Ft: 4016
Single Family Home - MLS#: 559872
Community: Venetian Shores - Mile Marker (MM) 86.0

Looking for perfection? Elegant, spacious, extremely well maintained home located in prestigious Venetian Shores, offering 6 bedrooms, 4 full baths, fireplace in master and living room, formal dining…

MLS 559872

ISLAMORADA, FL 33036
$2,295,000
ISLAMORADA, FL 33036
423 Palm

4 Beds 3 Baths Square Ft: 3200
Single Family Home - MLS#: 553318
Community: Safety Harbor - Mile Marker (MM) 74.0

Contemporary home on 200' waterfront - deep water protected dockage - 2 boat lifts (24K & 12K) - a boater's dream. The house is also a dream. Great room with cork floors, wet bar, dining area, kitchen…

MLS 553318

ISLAMORADA, FL 33036
$2,295,000
ISLAMORADA, FL 33036
137 Bayview Isle

4 Beds 3.2 Baths Square Ft: 3376
Single Family Home - MLS#: 558283
Community: Venetian Shores - Mile Marker (MM) 86.0

LOCATION! LOCATION! This is a property you will fall in love with located directly on Snake Creek. Spacious tri-level all concrete home with 105' concrete dock, screened porch, roof-top deck to enjoy…

MLS 558283

ISLAMORADA, FL 33036
$2,279,000
ISLAMORADA, FL 33036
77071 Overseas Hwy

3 Beds 2 Baths Square Ft: 1900
Single Family Home - MLS#: 560705
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

A winding brick-pavered drive leads you to your more than 1 acre oceanfront oasis. This beautiful home offers spectacular views of the Atlantic and a large screened balcony runs the width of the home…

MLS 560705

ISLAMORADA, FL 33036
$2,249,000
ISLAMORADA, FL 33036
75240 Overseas

3 Beds 3 Baths Square Ft: 1241
Single Family Home - MLS#: 556308
Community: Lower Mat Harbor - Mile Marker (MM) 75.0

Gorgeous Bay Front Property with 'cut in' boat basin! Free form pool with walk in entry and hot tub. 1 Bedroom 1 bath up and two seperate ''Guest'' bedrooms and baths down. Owner is a Real Estate Professional.

MLS 556308

ISLAMORADA, FL 33036
$2,199,000
ISLAMORADA, FL 33036
74049 Overseas Hwy

4 Beds 3 Baths Square Ft: 2714
Single Family Home - MLS#: 549979
Community: Lower Mat Bch - Mile Marker (MM) 74.0

BAREFOOT ON THE BEACH! A truly beachfront property in Islamorada, offering 3 bdr and 2 ba on the upper level with 1 bdr 1 ba lower level guest quarters. Spacious living and dining area, new gourmet stainless/granite…

MLS 549979

ISLAMORADA, FL 33070
$2,100,000
ISLAMORADA, FL 33070
428 S Coconut Palm

3 Beds 3 Baths Square Ft: 2623
Single Family Home - MLS#: 560629
Community: Plant Key Colony - Mile Marker (MM) 90.0

Sunset Splendor in Islamorada - FL Keys! This is the perfect home, in the perfect location to watch the sun go down over Florida Bay. Open floor plan, custom Maple cabinets and designer touches throughout.…

MLS 560629

ISLAMORADA, FL 33036
$1,999,000
ISLAMORADA, FL 33036
75804 Overseas

4 Beds 4.1 Baths Square Ft: 2696
Single Family Home - MLS#: 557734
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Custom Built Pool Home With Gorgeous Sunset Views, Pool & Spa, Dockage, Beach, Tennis, Plus Private Guest Suite! Located in premiere, gated, Islamorada Bonefish Bay,when nothing but the best will do!…

MLS 557734

ISLAMORADA, FL 33036
$1,995,000
ISLAMORADA, FL 33036
166 Bayview

4 Beds 4 Baths Square Ft: 2478
Single Family Home - MLS#: 556306
Community: Safety Harbor - Mile Marker (MM) 74.0

This property is a lot and a lot with a house! Alternate key # for the lot is 9081021. Drop dead gorgeous sunsets and bayviews! You need to see this as it is one of the best bay front properties on the…

MLS 556306

ISLAMORADA, FL 33036
$1,995,000
ISLAMORADA, FL 33036
138 Leoni

5 Beds 3 Baths Square Ft: 4209
Single Family Home - MLS#: 560742
Community: Venetian Shores - Mile Marker (MM) 86.0

170 ft. of dockage in Venetian Shores! Spacious family home, beautifully remodeled and expanded. This home has it all including an elevator and giant garage and workshop. The main level has 3 bedrooms…

MLS 560742

ISLAMORADA, FL 33070
$1,976,000
ISLAMORADA, FL 33070
334 Woods

5 Beds 4 Baths Square Ft: 3836
Single Family Home - MLS#: 560063
Community: Lake Harbor - Mile Marker (MM) 89.5

Solid concrete home in a secluded area in Plantation Key, at the end of the street with a lot of privacy, facing the Lake of San Pedro with instant access to the bay. 6'Depth control for big boats. House…

MLS 560063

ISLAMORADA, FL 33036
$1,950,000
ISLAMORADA, FL 33036
102 Plantation

3 Beds 2 Baths Square Ft: 1362
Single Family Home - MLS#: 558608
Community: Plant Beach - Mile Marker (MM) 87.5

Quintessential Florida Keys Cottage! Located on the bay with fabulous views and your own beach just steps away. This home will take you back to a simpler time and a slower pace. Keep it and update or…

MLS 558608

ISLAMORADA, FL 33036
$1,950,000
ISLAMORADA, FL 33036
181 Ridge

3 Beds 3 Baths Square Ft: 2447
Single Family Home - MLS#: 560829
Community: Plant Ridge - Mile Marker (MM) 87.0

Panaromic Ocean Views from this Modern designer home completely renovated. Custom built in kitchen with top of the line stainless steel appliances,wine cooler, convection oven,adjoining bar. Walnut floors…

MLS 560829

ISLAMORADA, FL 33036
$1,950,000
ISLAMORADA, FL 33036
193 Sunset

3 Beds 2 Baths Square Ft: 1255
Single Family Home - MLS#: 558969
Community: Lower Mat Bch - Mile Marker (MM) 74.0

NO SHOES REQUIRED!!! 3 bedroom, 2 bath home is located on the best beach in the Keys. Gorgeous sugar-sand beach with endless ocean views from every room. Relax your day away in the hammock beneath the…

MLS 558969

ISLAMORADA, FL 33036
$1,945,000
ISLAMORADA, FL 33036
75751 Overseas Hwy

3 Beds 3.1 Baths Square Ft: 4121
Single Family Home - MLS#: 545875
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Possible short sale. Impeccable ocean front 3/3/1 custom built by owner on Matecumbe Ocean Bay Beach.Top floor boasts 2 bed 2 full baths,office & media room opens to spectacular 3rd floor ocean front…

MLS 545875

ISLAMORADA, FL 33036
$1,899,000
ISLAMORADA, FL 33036
134 Milano

5 Beds 5 Baths Square Ft: 3576
Single Family Home - MLS#: 556366
Community: Venetian Shores - Mile Marker (MM) 86.0

ISLAMORADA VENETIAN SHORES waterfront 5BD/5BA with 100' DOCK and BOAT LIFT, custom POOL with spa & waterfall, ELEVATOR and private master suite on the 3rd floor. Instant big boat access to both the ocean…

MLS 556366

ISLAMORADA, FL 33036
$1,895,000
ISLAMORADA, FL 33036
75731 Overseas

4 Beds 4 Baths Square Ft: 2644
Single Family Home - MLS#: 556695
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

CLASSIC KEY WEST IN ISLAMORADA - Oceanfront with sandy beach. Main house has 3BR/3BA, plus third floor lofted study. Beachfront cabana house gives you an additional 1BR/1BA guest room. Lush landsscaping,…

MLS 556695

ISLAMORADA, FL 33036
$1,875,000
ISLAMORADA, FL 33036
75851 Overseas

5 Beds 5 Baths Square Ft: 3604
Single Family Home - MLS#: 560880
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Spectacular Ocean Front Home!!! Breathtaking views and breezes from this Tri level Matecumbre Gem!! Grand open living areas, luxurious master suite with Jacuzzi, gourmet kitchen, huge family room, wrap…

MLS 560880

ISLAMORADA, FL 33036
$1,850,000
ISLAMORADA, FL 33036
423 Palm

4 Beds 3 Baths Square Ft: 3108
Single Family Home - MLS#: 560944
Community: Safety Harbor - Mile Marker (MM) 74.0

Comtemporary home on 100' waterfront - deep water protected dockage - 2 boat lifts (24K & 12K) - a boater's dream. The house is also a dream. Great room with cork floors, wet bar, dining area, kitchen…

MLS 560944

ISLAMORADA, FL 33036
$1,795,000
ISLAMORADA, FL 33036
75831 Overseas

4 Beds 3 Baths Square Ft: 2080
Single Family Home - MLS#: 560302
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Islamorada Beach! OPEN OCEANFRONT ESTATE with expansive white sand BEACH, POOL and open OCEAN VIEWS on nearly an ACRE of land. This custom concrete home is a 3/2 upstairs with a 1/1 guest apt. down. Enjoy…

MLS 560302

ISLAMORADA, FL 33070
$1,790,000
ISLAMORADA, FL 33070
174 Indian Mound

4 Beds 3.1 Baths Square Ft: 3452
Single Family Home - MLS#: 558943
Community: Indian Waterways - Mile Marker (MM) 89.0

WATERFRONT CANAL HOME WITH ROOF TOP DECK WITH PANORAMIC BAY VIEW. 4 bedroom 3.5 bath with den. Large custom kitchen with granite counter tops and formal dining room. 80' concrete dock with boat lift &…

MLS 558943

ISLAMORADA, FL 33070
$1,775,000
ISLAMORADA, FL 33070
432 S Coconut Palm

3 Beds 3.1 Baths Square Ft: 2903
Single Family Home - MLS#: 560381
Community: Plant Key Colony - Mile Marker (MM) 90.0

Beautiful bayfront home.Quiet location at end of street offering privacy.Totally updated provides 2 master suites in nearly 3000 sq ft. Gourmet kitchen with granite countertops and stainless steel appliances.Deep…

MLS 560381

ISLAMORADA, FL 33036
$1,750,000
ISLAMORADA, FL 33036
75808 Overseas

4 Beds 4.1 Baths Square Ft: 2696
Single Family Home - MLS#: 557846
Community: Mat Ocean Bay - Mile Marker (MM) 75.0

Prestigous Bonefish Bay home offers 4 bedrooms, 4 1/2 baths, including separate guest quarters. This 2 story has as custom wood flooring throughout, gourmet kitchen, master suite & large bath on main…

MLS 557846



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The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of the Florida Keys Board of Realtors Florida Keys MLS, Inc. Real estate listings held by brokerage firms other than (Shoreline Properties) are marked with the MLS Log and detailed information about them included the name of the listing brokers office.

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