Summerland Key, FL Homes

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  /2

  Est $197,352 Not Listed For Sale

  281 Pelican Ln, Big Pine Key, FL 33043

  • Studio

  281 Pelican Ln, Big Pine Key, FL 33043

  Last Sold Summary

  • 93% Below List Price

  Last Sold Price $102,000

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.
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  /52

  $1,449,000

  • 3 Beds
  • 3 Baths
  • 1,820 Sq Ft

  845 Pirates Rd, Summerland Key, FL 33042

  Discover waterfront living in Jolly Roger Estates on Little Torch Key. This beautifully maintained 3 bedroom, 3 bathroom canal-front home offers quick boating access to open water, making it ideal for fishing and island adventures.Designed for the Florida Keys lifestyle, the property features a private pool, tiki hut, and spacious outdoor entertaining areas overlooking the canal. Boaters will

  Sandra Dolowy KeyIsle Realty

  845 Pirates Rd, Summerland Key, FL 33042
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  /51

  $1,100,000 Sold May 02, 2025

  27984 Barton Ave, Little Torch Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,225 Sq Ft
  • Built 1993

  Last Sold Summary

  • 8% Below List Price
  • $898/SF
  • 126 Days On Market

  Current Estimated Value $1,116,570

  Last Listing Agent Steven Koleno Beycome of Florida, LLC

  27984 Barton Ave, Little Torch Key, FL 33042
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  /46

  Est $1,906,259 Not Listed For Sale

  271 W Indies Dr, Ramrod Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,358 Sq Ft
  • Built 2023

  271 W Indies Dr, Ramrod Key, FL 33042

  Last Sold Summary

  • $806/SF
  • 342 Days On Market

  Last Sold Price $1,900,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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  /49

  $1,450,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 1,740 Sq Ft

  16823 E Point Dr, Summerland Key, FL 33042

  Nestled in the prestigious South Point neighborhood of Sugarloaf Shores, this waterfront home offers the perfect blend of coastal tranquility and convenient access to Key West--just a short 15-minute drive away. Set on an expansive 12,500 sq. ft. lot, the property captures the relaxed elegance of island living.The 3-bedroom residence features 1,740 sq. ft. of living space, highlighted by a bright

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  16823 E Point Dr, Summerland Key, FL 33042
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  /2

  $1,400,000 Sold Sep 17, 2025

  491 W Indies Dr, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,204 Sq Ft
  • Built 2020

  Last Sold Summary

  • $1,163/SF
  • 0 Days On Market

  Current Estimated Value $1,398,195

  Last Listing Agent Mark Gable Engel & Volkers Marathon

  491 W Indies Dr, Ramrod Key, FL 33042
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  /35

  Not Listed For Sale

  701 Spanish Main Dr Unit 48, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 849 Sq Ft
  • Built 1992

  701 Spanish Main Dr Unit 48, Cudjoe Key, FL 33042

  Last Sold Summary

  • $854/SF
  • 191 Days On Market

  Last Sold Price $725,000

  Last Listing Agent Michael Sorah Truman & Co. (KW)
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  /47

  $1,200,000

  • 3 Beds
  • 2 Baths
  • 1,250 Sq Ft

  43 Venetian Way, Summerland Key, FL 33042

  Beautifully updated 3 bedroom 2 bath home, with effective build date of 2015 and completely renovated in 2018 including New Electrical, Plumbing, HVAC, Roof, Tankless Water heater, Flooring, Kitchen, Bathrooms, Windows, & Doors, landscaping/sprinkler system, TESLA charging station and an amazing new paved driveway installed in 2021. This is a split floor plan for privacy with amazing screened in

  Lori Cameron Buy The Keys

  43 Venetian Way, Summerland Key, FL 33042
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  /40

  $1,350,000 Sold May 15, 2025

  31254 Hollerich Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,315 Sq Ft
  • Built 2025

  Last Sold Summary

  • 8% Below List Price
  • $1,027/SF
  • 6 Days On Market

  Current Estimated Value $1,258,183

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  31254 Hollerich Dr, Big Pine Key, FL 33043
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  /58

  Est $1,644,383 Not Listed For Sale

  1106 Thatch Ln, Summerland Key, FL 33042

  • 4 Beds
  • 3.5 Baths
  • 2,548 Sq Ft
  • Built 2016

  1106 Thatch Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 2% Below List Price
  • $657/SF
  • 50 Days On Market

  Last Sold Price $1,675,000

  Last Listing Agent Aryl and Pati Robison RE/MAX
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  /40

  $1,190,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,204 Sq Ft

  857 Caribbean Dr E, Summerland Key, FL 33042

  HOME is where the BOAT IS!Discover effortless access to world-class boating on one of the widest, deepest, and most desirable canals in the Lower Keys. Your 17,000-lb boat lift sits on a pristine flow-through canal--meaning clean, clear water and quick access. In just minutes, you can be fishing the Atlantic, exploring the backcountry in the Gulf, or gliding toward a perfect Key West sunset.This

  Donna Pezzi Keller Williams Key West Compass Realty

  857 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /23

  $710,000 Sold Aug 20, 2025

  19603 Seminole St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2014

  Last Sold Summary

  • 3% Below List Price
  • $598/SF
  • 5 Days On Market

  Current Estimated Value $723,874

  Last Listing Agent Steven Koleno Beycome of Florida, LLC

  19603 Seminole St, Summerland Key, FL 33042
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  /6

  Not Listed For Sale

  Lot 27 Angelfish Rd, Ramrod Key, FL 33042

  Lot 27 Angelfish Rd, Ramrod Key, FL 33042

  Last Sold Summary

  • 291 Days On Market

  Last Sold Price $105,000

  Last Listing Agent Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)
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  /44

  $1,149,000

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  27426 Martinique Ln, Summerland Key, FL 33042

  Oceanside canal-front opportunity in Ramrod Key. This 3-bedroom, 2-bath home with a pool is ideally located near Looe Key Reef and Picnic Island, and is just a 10-minute walk to the local watering hole, The Tiki.The property includes an additional buildable lot, creating a rare opportunity to construct a second residence, guest house, or future income-producing property--significantly enhancing

  Kasey Fey Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  27426 Martinique Ln, Summerland Key, FL 33042
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  /30

  $628,000 Sold Sep 05, 2025

  31256 Avenue H, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Below List Price
  • $549/SF
  • 106 Days On Market

  Current Estimated Value $633,349

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  31256 Avenue H, Big Pine Key, FL 33043
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  /30

  Est $732,815 Not Listed For Sale

  124 Yardarm Rd, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 2023

  124 Yardarm Rd, Cudjoe Key, FL 33042

  Last Sold Summary

  • 1% Below List Price
  • $695/SF
  • 22 Days On Market

  Last Sold Price $740,000

  Last Listing Agent The Spottswood Team Truman & Co. (KW)
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  /35

  $1,099,000

  • 3 Beds
  • 3 Baths
  • 2,143 Sq Ft

  1615 Fern Ave, Big Pine Key, FL 33043

  Don't settle for small spaces! Welcome to this spacious and beautifully updated 3-bedroom, 2.5-bath home nestled on a rare 12,000 sq. ft. double lot in the heart of Big Pine Key. Fully renovated, this two-story home feels open, airy, and inviting throughout.Inside, you'll find a large living room filled with natural light, offering plenty of space for family gatherings. A versatile office/den

  Taron Wirth Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  1615 Fern Ave, Big Pine Key, FL 33043
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  /73

  $809,300 Sold Aug 18, 2025

  547 Heck Ave, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1991

  Last Sold Summary

  • $736/SF
  • 39 Days On Market

  Current Estimated Value $824,976

  Last Listing Agent Litney Ellis Dalton Wade Inc

  547 Heck Ave, Little Torch Key, FL 33042
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  /17

  Not Listed For Sale

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 770 Sq Ft
  • Built 1978

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

  Last Sold Summary

  • $695/SF
  • 43 Days On Market

  Last Sold Price $535,000

  Last Listing Agent Suzanne Washburn Coldwell Banker Schmitt Real Estate Co. (KW)
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  /21

  $1,099,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  325 Pirates Rd, Summerland Key, FL 33042

  *POOL PLANS IN HAND FOR 12X22 POOL, WITH POOL QUOTE*Escape to paradise with this incredible waterfront property located on a deep boating canal in the heart of the Lower Florida Keys. Perfectly suited for boating enthusiasts and water lovers, this home offers dockage and a boat lift, and direct, easy access to the open waters of the Atlantic Ocean and Gulf of Mexico, making it a dream come true

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  325 Pirates Rd, Summerland Key, FL 33042
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  /18

  $250,000 Sold Feb 24, 2026

  138 Sands Rd, Big Pine Key, FL 33043

  • 1 Bed
  • 1 Bath
  • 442 Sq Ft
  • Built 1969

  Last Sold Summary

  • 9% Below List Price
  • $566/SF
  • 16 Days On Market

  Last Listing Agent Tracy Shields KeyIsle Realty

  138 Sands Rd, Big Pine Key, FL 33043
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  /41

  Not Listed For Sale

  701 Spanish Main Dr Unit 94, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft
  • Built 2004

  701 Spanish Main Dr Unit 94, Cudjoe Key, FL 33042

  Last Sold Summary

  • $1,173/SF
  • 84 Days On Market

  Last Sold Price $1,009,000

  Last Listing Agent Terri Spottswood Truman & Co. (KW)
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  /68

  $879,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042

  This Truly Spectacular Oceanfront Property offers the ultimate waterfront lifestyle and is a one of a kind, featuring an impressive 98' seawall. Designed to capture the best of coastal living, the property combines 72' of concrete seawall along a protected canal with 26' of direct Atlantic Ocean Frontage, delivering both tranquility and open-ocean beauty. A waterfront lovers dream, the canal side

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042
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  /41

  $1,350,000 Sold Aug 18, 2025

  20735 5th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1985

  Last Sold Summary

  • 7% Below List Price
  • $853/SF
  • 16 Days On Market

  Current Estimated Value $1,341,932

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  20735 5th Ave W, Summerland Key, FL 33042
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  /33

  Est $842,488 Not Listed For Sale

  22918 Cudjoe Dr, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,431 Sq Ft
  • Built 2016

  22918 Cudjoe Dr, Cudjoe Key, FL 33042

  Last Sold Summary

  • 16% Above List Price
  • $507/SF
  • 175 Days On Market

  Last Sold Price $725,000

  Last Listing Agent Pamela Stangler Expert Realty LLC
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  /33

  $949,000 Pending

  • 2 Beds
  • 3 Baths
  • 1,140 Sq Ft

  151 Cutthroat Dr, Summerland Key, FL 33042

  Move-in ready waterfront 2-bedroom, 2.5-bath home located in desirable Cudjoe Key. The open floor plan features a spacious living and dining area complemented by an upgraded kitchen with new cabinetry, granite countertops, and modern stainless-steel appliances. The main level offers two bedrooms and 1.5 baths, while a permitted full second bath is conveniently located downstairs with easy access

  Heather Bennett Keller Williams Key West Compass Realty

  151 Cutthroat Dr, Summerland Key, FL 33042
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  /36

  $1,215,000 Sold Apr 09, 2025

  17246 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 2020

  Last Sold Summary

  • 12% Below List Price
  • $844/SF
  • 23 Days On Market

  Current Estimated Value $1,200,399

  Last Listing Agent Stephen Hachey

  17246 Jamaica Ln, Summerland Key, FL 33042
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  /65

  Est $292,144 Not Listed For Sale

  701 Spanish Main Dr Unit 620, Cudjoe Key, FL 33042

  • 1 Bed
  • Built 1980

  701 Spanish Main Dr Unit 620, Cudjoe Key, FL 33042

  Last Sold Summary

  • 15% Above List Price
  • $405/SF
  • 154 Days On Market

  Last Sold Price $255,000

  Last Listing Agent PATRICIA BRUMMER Waterfront Keys Realty Inc.
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  /41

  $800,000

  • Land

  33000 Old State Road 4a, No Name Key, FL 33043

  YOU CAN HELP SAVE THE FLORIDA KEYS REEFS..!!THIS 20 ACRE PARCEL WITH A 17 ACRE SALTWATER LAKE WAS RECENTLY MARKETED AS A PRIVATE LAKE FOR PERSONAL USE. IT MAY STILL BE USED FOR THAT. THIS PROPERTY CANNOT BE DEVELOPED...!!!! NO HOME, NO COMMERCIAL USE. HOWEVER IN RECENT MONTHS RESEARCHERS FROM FLORIDA INTERNATIONAL UNIVERSITY HAVE BEEN STUDYING THE GROWTH OF SPIDER CRABS THAT THRIVE ON ALGAE. THE

  Tony Paterniti Tony Paterniti

  33000 Old State Road 4a, No Name Key, FL 33043
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  /37

  $725,000 Sold Jan 14, 2026

  27394 Saint Lucie Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,078 Sq Ft
  • Built 1994

  Last Sold Summary

  • $673/SF
  • 19 Days On Market

  Current Estimated Value $738,389

  Last Listing Agent Casey Arnold eXp Realty LLC

  27394 Saint Lucie Ln, Summerland Key, FL 33042
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  /2

  Est $813,494 Not Listed For Sale

  1547 Narcissus Ave, Big Pine Key, FL 33043

  • 4 Beds
  • 2 Baths
  • 1,575 Sq Ft
  • Built 1991

  1547 Narcissus Ave, Big Pine Key, FL 33043

  Last Sold Summary

  • 25% Below List Price
  • $413/SF

  Last Sold Price $650,000

  Last Listing Agent Jane Wasmund RE/MAX
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  /4

  $1,050,000

  • 3 Beds
  • 2.5 Baths
  • 1,954 Sq Ft

  27403 Antigua Ln, Summerland Key, FL 33042

  Waterfront value-add opportunity in the Florida Keys with direct ocean access and no fixed bridges - perfect for serious boaters with vessels up to 60 feet. Situated on an oversize 18,000 SF lot, this property offers rare space, flexibility and future potential not commonly found in the Keys. The elevated concrete home features a spacious layout, multiple balconies, and abundant natural light

  Sonia Petraitis Caffroni Capital Intl Realty LLC

  27403 Antigua Ln, Summerland Key, FL 33042
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  /47

  $945,000 Sold Oct 03, 2025

  29487 Ranger Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Built 1996

  Last Sold Summary

  • 3% Below List Price
  • $751/SF
  • 99 Days On Market

  Current Estimated Value $1,016,630

  Last Listing Agent Melissa Gibbins Expert Realty LLC (HQ)

  29487 Ranger Ave, Big Pine Key, FL 33043
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  /2

  Est $704,536 Not Listed For Sale

  1791 Narcissus Ave, Big Pine Key, FL 33043

  • 4 Beds
  • 2 Baths
  • 1,575 Sq Ft
  • Built 1993

  1791 Narcissus Ave, Big Pine Key, FL 33043

  Last Sold Summary

  • 8% Below List Price
  • $413/SF

  Last Sold Price $650,000

  Last Listing Agent Jane Wasmund RE/MAX
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  /28

  $758,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  3856 Donna Rd, Big Pine Key, FL 33043

  30k Price Improvement, Priced to SELL, Motivated Seller, Bring all Offers. Sportsman Paradise. 2 Bedroom House with Permitted Concrete BOAT RAMP, concrete sea wall, concrete fish cleaning table with Permitted downstairs bathroom. Real short idle to open water. Back country fishing, lobster diving/snorkel and stone crabs right in your back yard. Easy access to to Atlantic & Looe Key. Lots of

  Alan Ballas Alan Ballas Realty

  3856 Donna Rd, Big Pine Key, FL 33043
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  /49

  $750,000 Sold Jul 24, 2025

  25121 Center St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 2008

  Last Sold Summary

  • 14% Below List Price
  • $781/SF
  • 72 Days On Market

  Current Estimated Value $755,038

  Last Listing Agent Gregory Sullivan BYOWNER.COM

  25121 Center St, Summerland Key, FL 33042
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  /2

  Est $875,300 Not Listed For Sale

  29530 Enterprise Ave, Big Pine Key, FL 33043

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • Built 1969

  29530 Enterprise Ave, Big Pine Key, FL 33043

  Last Sold Summary

  • 9% Below List Price
  • $383/SF

  Last Sold Price $805,000

  Last Listing Agent Jennifer Weeks Select Properties of NWFL
• 

  

  /25

  $619,500

  • 3 Beds
  • 2 Baths
  • 1,204 Sq Ft

  31243 E Ave E, Big Pine Key, FL 33043

  **Price Enhancement** OPEN HOUSE SUN MAR 29TH 1PM - 3PM SELLER SAYS BRING ALL OFFERS!!! Welcome to your slice of paradise in Big Pine Key! This charming 3-bedroom, 2-bath home is an ideal opportunity for families or first-time homebuyers seeking the quintessential Florida Keys lifestyle. Step inside to discover a comfortable and inviting living space, perfect for creating lasting

  Sabre Mendoza Coldwell Banker Schmitt RE Co.

  31243 E Ave E, Big Pine Key, FL 33043
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  /45

  $710,000 Sold Feb 05, 2026

  27163 Mariposa Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 2018

  Last Sold Summary

  • 10% Below List Price
  • $477/SF
  • 238 Days On Market

  Current Estimated Value $743,935

  Last Listing Agent Jessica Roden Ocean Sotheby's International Realty

  27163 Mariposa Rd, Summerland Key, FL 33042
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  /2

  Est $744,493 Not Listed For Sale

  677 Heck Ave, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 875 Sq Ft
  • Built 1977

  677 Heck Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 10% Below List Price
  • $949/SF

  Last Sold Price $830,000

  Last Listing Agent Monika Rydzak eXp Realty LLC KW Branch

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