Southport, CT Homes for Sale

• 

  

  

  /22

  $589,000

  $10K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,337 Sq Ft

  245 Oakwood Dr, Fairfield, CT 06824

  An amazing opportunity to own in a highly desirable University neighborhood - Welcome home to 245 Oakwood Drive. Distinguishable features include a picture perfect move in ready home, hardwood floors, an updated kitchen with granite countertops, freshly painted cabinetry and natural sunlight that brightens daily living. The main level presents beautifully with a bright and inviting living room,

  

  Austin Reid

  William Raveis Real Estate

  245 Oakwood Dr, Fairfield, CT 06824
• 

  

  

  /40

  $949,000

  • 3 Beds
  • 3.5 Baths
  • 2,304 Sq Ft

  25 Beaumont St, Fairfield, CT 06824

  Spectacular luxury townhouse with a sophisticated New York loft feel! This stunning 3-bedroom, 3.5-bath residence showcases custom finishes throughout, hardwood flooring on the upper levels, and heated tile flooring on the entry level. A private elevator services all floors, providing effortless access from the tandem 2-car garage with additional storage. The chef's kitchen features premium

  

  Patricia Moreggi

  Coldwell Banker Realty

  25 Beaumont St, Fairfield, CT 06824
• 

  

  

  /36

  $2,997,000

  • 5 Beds
  • 4 Baths
  • 3,255 Sq Ft

  4 Bradley St, Westport, CT 06880

  Just 383 steps from the sands of Compo Beach, this storied 1920s residence claims one of Westport's most sought-after addresses. Approximately 3,255 square feet hold five bedrooms and four baths. An open, updated kitchen with top-tier appliances flows into the living and gathering areas. The primary suite is a generous retreat with vaulted ceilings, a spa bath, and a walk-in closet. Four

  

  Hyleri Katzenberg

  Compass Connecticut, LLC

  4 Bradley St, Westport, CT 06880
• 

  

  

  /37

  $755,000

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,524 Sq Ft

  241 Old Stratfield Rd, Fairfield, CT 06825

  !!!ASSUMABLE 3% VA LOAN - APPROX. $468,000 BALANCE!!! A rare opportunity to secure a substantial portion of your financing at just 3% on this fully renovated Fairfield two-family! Current rents total $4,650/month and are believed to be below market, creating a compelling opportunity for owner-occupants and investors alike. Live in one unit and let the other help offset your housing costs or add a

  

  Andrei Balaj

  Higgins Group Real Estate

  241 Old Stratfield Rd, Fairfield, CT 06825
• 

  

  

  /36

  $950,000

  • 3 Beds
  • 1.5 Baths
  • 2,100 Sq Ft

  102 Geneva Terrace, Fairfield, CT 06824

  Rare opportunity in Fairfield's highly sought-after Beach Area! This 3-bedroom, 1,400 SF ranch offers an exceptionally rare combination of location, lot, and future potential. Just a short walk to South Pine Creek Beach and only a quarter mile from the prestigious Sasco Hill neighborhood, you'll also enjoy easy access to downtown Fairfield, the train station, restaurants, shops, and beaches.

  

  Judy Szablak

  Coldwell Banker Realty

  102 Geneva Terrace, Fairfield, CT 06824
• 

  

  /36

  $2,395,000

  $100K PRICE DROP

  • 6 Beds
  • 5.5 Baths
  • 3,700 Sq Ft

  40 Richmondville Ave, Westport, CT 06880

  Built in 2022, this 6-bedroom, 5.5-bath home offers four finished levels of flexible living just minutes from downtown Westport. Open-concept main level features high ceilings, oversized windows, and a Thermador kitchen with large island, walk-in pantry, and mudroom with built-ins. Upstairs includes a primary suite with heated floors, soaking tub, and oversized shower. Two bedrooms share a Jack

  Jessica Lane

  Serhant Connecticut LLC

  40 Richmondville Ave, Westport, CT 06880
• 

  

  /19

  $1,625,000

  $74K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,450 Sq Ft

  173 Puritan Rd, Fairfield, CT 06824

  Located in the highly desirable beach area of Fairfield, this charming and beautifully maintained 3-bedroom Cape, situated on a corner lot, offers the perfect blend of classic character and modern convenience. The newly remodeled eat-in kitchen features granite countertops and stylish finishes throughout. Enjoy entertaining in the formal dining room with beautiful built-in hutches or relax in the

  

  Glenn Marr

  Marr Caruso Realty Group

  173 Puritan Rd, Fairfield, CT 06824
• 

  

  /3

  $450,000

  • Land
  • 6,969 Sq Ft
  • $2,812,500 per Acre

  37 Bartram Ave, Bridgeport, CT 06605

  St Mary's by the Sea flat and cleared building lot. Single family and multifamily possible at this location. Beautiful tree lined street close to the water.

  

  David Krasnoff

  Compass Connecticut, LLC

  37 Bartram Ave, Bridgeport, CT 06605
• 

  

  /36

  $3,550,000

  • 6 Beds
  • 6.5 Baths
  • 6,751 Sq Ft

  9 N Ridge Rd, Westport, CT 06880

  In today's world, there is nothing more important than having a place to gather. This private retreat with a stunning residence and amazing recreational facilities can become your own private sanctuary with a tennis court, heated Gunite pool and separate pool house set among lush, meticulously curated grounds on almost 2.4 acres. This 6,700-square-foot shingle-style residence offers refined

  

  Susan Lieberman

  The Riverside Realty Group

  9 N Ridge Rd, Westport, CT 06880
• 

  

  /17

  $7,926,000

  New Construction

  • 6 Beds
  • 7 Baths
  • 7,200 Sq Ft

  0 Clapboard Hill Rd Unit (New Build), Westport, CT 06880

  Set within Westport's most prestigious private estate enclave, surrounded by grand coastal estates and quintessential antique treasures, this exceptional Greens Farms 2+ acre* new construction offering is poised to become one of Fairfield County's most coveted addresses. Perfectly positioned, moments from beaches, downtown boutiques, vibrant dining scene, and just an express train to Manhattan,

  

  Brett Lieberman

  The Riverside Realty Group

  0 Clapboard Hill Rd Unit (New Build), Westport, CT 06880
• 

  

  /7

  $995,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,000 Sq Ft

  53 Sterling St, Fairfield, CT 06825

  New construction townhome built by a respected local builder known for quality craftsmanship and clean, modern design. This residence offers approximately 2,300 square feet of above-grade living plus a finished lower level, thoughtfully laid out across three levels. The main floor features an open-concept design anchored by a well-appointed kitchen with white and white oak cabinetry, quartz

  Jessica Lane

  Serhant Connecticut, LLC

  53 Sterling St, Fairfield, CT 06825
• 

  

  /7

  $995,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,000 Sq Ft

  45 Sterling St, Fairfield, CT 06825

  New construction townhome built by a respected local builder known for quality craftsmanship and clean, modern design. This residence offers approximately 2,300 square feet of above-grade living plus a finished lower level, thoughtfully laid out across three levels. The main floor features an open-concept design anchored by a well-appointed kitchen with white and white oak cabinetry, quartz

  Jessica Lane

  Serhant Connecticut, LLC

  45 Sterling St, Fairfield, CT 06825
• 

  /2

  $2,275,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,744 Sq Ft

  75 Spinning Wheel Rd, Fairfield, CT 06824

  Another exceptional new construction by a well-known local builder! Now is the perfect opportunity to meet with the builder and customize this beautifully designed home to suit your lifestyle. Offering approximately 2700 square feet of thoughtfully designed living space, plus additional finished space in the basement, this home features 4 levels of living, 4 spacious bedrooms, and 3.5 luxurious

  

  Bette Gigliotti

  William Raveis Real Estate

  75 Spinning Wheel Rd, Fairfield, CT 06824
• 

  

  /7

  $995,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,000 Sq Ft

  51 Sterling St, Fairfield, CT 06825

  New construction townhome built by a respected local builder known for quality craftsmanship and clean, modern design. This residence offers approximately 2,300 square feet of above-grade living plus a finished lower level, thoughtfully laid out across three levels. The main floor features an open-concept design anchored by a well-appointed kitchen with white and white oak cabinetry, quartz

  Jessica Lane

  Serhant Connecticut, LLC

  51 Sterling St, Fairfield, CT 06825
• 

  

  /7

  $995,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,000 Sq Ft

  47 Sterling St, Fairfield, CT 06825

  New construction townhome built by a respected local builder known for quality craftsmanship and clean, modern design. This residence offers approximately 2,300 square feet of above-grade living plus a finished lower level, thoughtfully laid out across three levels. The main floor features an open-concept design anchored by a well-appointed kitchen with white and white oak cabinetry, quartz

  Jessica Lane

  Serhant Connecticut, LLC

  47 Sterling St, Fairfield, CT 06825
• 

  

  /37

  $2,399,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,950 Sq Ft

  96 Clinton St, Fairfield, CT 06824

  One of only two new construction homes currently available in Fairfield's coveted Beach neighborhood, an incredible opportunity w/ outstanding market value & just steps to the beach - Welcome Home to 96 Clinton Street. 4 levels of living w/ 2950 sf, elevator shaft ready, 4 bedrooms, 3.5 bath & high end finishes throughout. The open concept main level features custom finishes w/ a chef's kitchen

  

  Jackie Davis

  William Raveis Real Estate

  96 Clinton St, Fairfield, CT 06824
• 

  

  /19

  $4,250,000

  New Construction

  • 6 Beds
  • 9 Baths
  • 7,499 Sq Ft

  6 Janson Dr, Westport, CT 06880

  Exceptional new construction by AR Luxury Homes with 7,500+/- square feet of thoughtfully designed living space across four finished levels in a prime Westport location. This 6-bedroom, 6 full and 3 half bath residence blends refined craftsmanship with modern functionality, featuring an open-concept layout ideal for both everyday living and entertaining. The heart of the home is a custom-designed

  

  Brett Lieberman

  The Riverside Realty Group

  6 Janson Dr, Westport, CT 06880
• 

  

  /31

  $890,000

  • 10 Beds
  • 5 Baths
  • 3,530 Sq Ft

  80-82 Poplar St, Bridgeport, CT 06605

  Exceptional investment opportunity in Bridgeport's desirable Black Rock neighborhood! This well-maintained three-family property offers strong cash flow with a current gross monthly rental income of $8,600, making it an excellent addition to any investor's portfolio or an ideal owner-occupied opportunity. The first and second floor units each feature 3 bedrooms and 1 full bathroom, while the

  Alexia Andrade US Asset Realty

  80-82 Poplar St, Bridgeport, CT 06605
• 

  

  /40

  $2,999,000

  New Construction

  • 6 Beds
  • 6 Baths
  • 4,922 Sq Ft

  36 E Main St, Westport, CT 06880

  Nestled in the heart of Westport, Connecticut, this stunning new construction residence redefines elegant suburban living with unparalleled sophistication, timeless grace and is complete and ready for immediate occupancy. Boasting six generous bedrooms and six luxurious bathrooms, the home features soaring nine-foot ceilings that bathe its expansive interiors in natural light and create an

  Paul Plonsky Realty ONE Group Connect

  36 E Main St, Westport, CT 06880
• 

  

  /38

  $3,695,000

  • 4 Beds
  • 4.5 Baths
  • 3,744 Sq Ft

  110 Judson Rd, Fairfield, CT 06824

  Nestled on one of Fairfield Beach's most coveted streets, this exceptional new construction blends timeless coastal architecture with sophisticated design in a location that's simply hard to duplicate. Just moments from the beach, town, train, schools, and parks, 110 Judson offers the rare convenience today's buyers seek without sacrificing privacy or tranquility. Thoughtfully positioned at a

  Cindy Raney Coldwell Banker Realty

  110 Judson Rd, Fairfield, CT 06824
• 

  

  /40

  $4,500,000

  $490K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 4,144 Sq Ft

  1149 Fairfield Beach Rd, Fairfield, CT 06824

  A rare opportunity to own a premier BEACHFRONT residence offering compelling value in today's luxury market with updated guest home....All BEAUTIFULLY appointed & MOVE IN READY! 60 MINS to NYC! BEACHFRONT Home~1149 Walk-Out-To-Sand Waterfront AND Guest Home ~1148 fun & updated (2022) just steps to your Private BEACH. Enjoy true beachfront living w/no steps from your main level family room to an

  Christine Magliocco Higgins Group Real Estate

  1149 Fairfield Beach Rd, Fairfield, CT 06824
• 

  

  /37

  $6,495,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,260 Sq Ft

  16 Westport Ave, Westport, CT 06880

  Experience the future of coastal living in this brand-new smart home located just steps from the sands of Compo Beach. This is the only just-completed residence on the Compo Beach side of Westport delivered as a fully integrated, self-monitoring home: rooftop solar power w/battery storage, intelligent load management, leak detection w/automatic water shutoff, energy-recovery ventilation, radiant

  Karen Scott Compass Connecticut, LLC

  16 Westport Ave, Westport, CT 06880
• 

  

  /6

  $455,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,210 Sq Ft

  141 Berwick Ave, Fairfield, CT 06825

  Situated on a quiet dead-end street in the desirable town of Fairfield, this well-maintained 3-bedroom, 2 full-bath single-family home offers comfort, efficiency, and convenience. With approximately 1,200 square feet of living space, the home features a functional layout with bright, inviting rooms throughout. The first-floor living room includes a wood-burning stove, creating a warm and

  Derek Greene Derek Greene

  141 Berwick Ave, Fairfield, CT 06825
• 

  

  /23

  $1,575,000

  • 5 Beds
  • 3.5 Baths
  • 3,596 Sq Ft

  35 S Benson Commons, Fairfield, CT 06824

  Nestled on a quiet cul-de-sac just minutes from town, train, and beach, this beautifully crafted Colonial offers the perfect blend of elegance, comfort, and convenience. A charming front porch welcomes you into a light-filled home featuring a dramatic two-story foyer, a chef's kitchen, granite countertops, and premium Viking, Wolf, and Sub-Zero stainless steel appliances. The adjoining family

  Katie O'Grady Compass Connecticut, LLC

  35 S Benson Commons, Fairfield, CT 06824
• 

  

  /20

  $550,000

  • 8 Beds
  • 3 Baths
  • 2,679 Sq Ft

  18-20 Clinton Ave, Bridgeport, CT 06605

  This very large 2,679 sqft 2 family property is perfect for any home owner or investor. The 1st floor unit consists of 3 bedrooms and 1 bathroom. The 2nd unit is a very spacious two floor apartment that has 5 bedrooms and 2 bathrooms that was recently updated. Conveniently located just minutes from I-95 and I-91. Schedule your showing today!!!

  Thomas Payne Century 21 Scala Group

  18-20 Clinton Ave, Bridgeport, CT 06605
• 

  

  /40

  $8,450,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 9,893 Sq Ft

  10 Beltas Farm Ln, Westport, CT 06880

  Extraordinary New Construction home on one of Westport's newest premier cul-de-sacs. Offering nearly 10,000 SF of impeccably finished living space, this exceptional home blends timeless elegance w/ modern luxury & showcases the finest craftsmanship throughout.Designed with an uncompromising attention to detail, features include exquisite millwork, stunning custom cabinetry, spectacular ceiling

  Linda Skolnick Coldwell Banker Realty

  10 Beltas Farm Ln, Westport, CT 06880
• 

  

  /9

  $3,750,000

  New Construction

  • 5 Beds
  • 5.5 Baths
  • 5,000 Sq Ft

  22 Brett Rd, Fairfield, CT 06824

  Greenfield Hill proposed new construction on a 2.65-acre lot along a Town-designated Scenic Road, to be built by award-winning design-builder Bonnie Paige in collaboration with Vicente Burin Architects. The proposed residence is based on a design sold in Southport Village; interested buyers may tour similar homes and meet the team to tailor plans, finishes, and timeline. The property sits among

  Andrew Whiteley Brown Harris Stevens

  22 Brett Rd, Fairfield, CT 06824
• 

  

  /40

  $11,995,000

  New Construction

  • 5 Beds
  • 7 Baths
  • 6,050 Sq Ft

  14 Owenoke Park, Westport, CT 06880

  Summer starts here. Set on prestigious Owenoke Park steps from Compo Beach, this brand-new 6,050 sqft coastal masterpiece delivers the ultimate Westport lifestyle - pool and spa, Gray's Creek waterfront access, Long Island Sound views throughout, and a rare 3-car garage. Five ensuite bedrooms, double-island kitchen with scullery, elevator, primary suite sauna, and a lower-level loggia built for

  Deirdre Andreoli Compass Connecticut, LLC

  14 Owenoke Park, Westport, CT 06880
• 

  

  /11

  $699,900

  $89K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,195 Sq Ft

  225 Winnepoge Dr, Fairfield, CT 06825

  Endless opportunities clean up, move in, expand or build your new dream house. Lake Hills Association...enjoy all the beautiful beaches, kayaking, swimming, etc.

  Stacey DiDio Coldwell Banker Realty

  225 Winnepoge Dr, Fairfield, CT 06825
• 

  

  /32

  $1,999,900

  $250K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,381 Sq Ft

  125 Battery Park Dr, Bridgeport, CT 06605

  Perched on a quiet cul-de-sac, this exceptional home offers breathtaking 220-degree panoramic views of Long Island Sound, Black Rock Harbor, and Fayerweather lighthouse. Designed for effortless main-level living, the residence captures stunning water views from the living room, dining room, and luxurious primary bedroom suite. The remodeled primary bath features elegant marble flooring with

  Gail Robinson William Raveis Real Estate

  125 Battery Park Dr, Bridgeport, CT 06605
• 

  /2

  $950,000

  • 6 Beds
  • 6 Baths
  • 5,304 Sq Ft

  50 Carleton Ave, Bridgeport, CT 06604

  On the market for the first time in nearly 20 years. This legal 6 family is a cash cow with loads of growth potential. Each unit boasts a living room, dining room, eat-in-kitchen, one bedroom and a full bathroom. There is potential to convert each unit into a two bedroom. The property is currently fully occupied, so new owners will have immediate cash flow. The long standing tenants are currently

  Thomas Chanaca Chanaca Real Estate

  50 Carleton Ave, Bridgeport, CT 06604
• 

  /2

  $699,000

  • Land
  • 16,117 Sq Ft
  • $1,889,189 per Acre

  1 Battery Park Dr, Bridgeport, CT 06605

  Welcome to an exceptional opportunity in the highly sought after enclave at Black Rock! Nestled on a .37 acre lot this parcel boasts unparrelled vistas of the majestic Long Island Sound a canvas for your visionary masterpiece. This prime location beckons investors and builders alike to sieze the potential of coastal living at its finest. Edmbrace the allur of seaside living and capitalize on this

  Steven Koleno Beycome of Connecticut

  1 Battery Park Dr, Bridgeport, CT 06605
• 

  

  /40

  $6,795,000

  • 7 Beds
  • 6.5 Baths
  • 9,209 Sq Ft

  21 Compo Pkwy, Westport, CT 06880

  A rare offering in Westport's coveted Compo Beach neighborhood, this extraordinary estate sits on a prized double lot just moments from Compo Beach, Longshore Club, train & vibrant downtown. Featured in Westport Magazine, the property masterfully blends the charm of a beautifully preserved historic residence from 1928 w/ a remarkable 6,000 sq ft addition completed in 2008. The result is a

  Sarah Fair William Raveis Real Estate

  21 Compo Pkwy, Westport, CT 06880
• 

  

  /38

  $1,999,000

  • 5 Beds
  • 3.5 Baths
  • 2,864 Sq Ft

  110 Cross Hwy, Westport, CT 06880

  Experience modern luxury in this beautifully reimagined home, set on 1.57 scenic, park-like acres. Thoughtfully renovated, this 2,864 sq ft residence offers open-concept living spaces filled with natural light and sophisticated finishes throughout. The designer kitchen features a stunning island and premium cabinetry, flowing seamlessly into the dining and living areas with a dramatic linear

  Stephanie Ferreira BHGRE Gaetano Marra Homes

  110 Cross Hwy, Westport, CT 06880
• 

  

  /39

  $2,699,000

  $251K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 2,188 Sq Ft

  1235 Fairfield Beach Rd, Fairfield, CT 06824

  TWO incredible waterside opportunities await! That's right, not one, but TWO fantastic beach area homes are offered! With their direct waterfront locations (1235 - beachfront/LI Sound; 1236 - canal side), both homes have amazing water views, beach access and a convenient, fantastic location all in one! Both homes also offer excellent investment/rental opportunities. #1235 is rented for the

  John Foran Compass Connecticut, LLC

  1235 Fairfield Beach Rd, Fairfield, CT 06824
• 

  

  /5

  $369,900

  Coming Soon

  • 2 Beds
  • 1.5 Baths
  • 1,340 Sq Ft

  41 Calderwood Ct, Bridgeport, CT 06605

  Location, Location, Location! Great opportunity to live just steps to Seabright Beach on Black Rock Harbor and Long Island Sound. This affordable two bedroom, 1.5 bathroom half duplex with a finished lower level family room is located between Captain's Cove Seaport, Fayerweather Yacht Club, Port 5 Naval Veterans Club, S.S. Norden Club and the Black Rock Yacht Club, a boater's paradise. Enjoy the

  John Kleps Berkshire Hathaway NE Prop.

  41 Calderwood Ct, Bridgeport, CT 06605
• 

  

  /40

  $12,000,000

  • 7 Beds
  • 10 Baths
  • 9,129 Sq Ft

  4800 Congress St, Fairfield, CT 06824

  This offering is for 4800 Congress St, a one of a kind estate consists of main residence on 10.92 acres, pool, barn pool house/gym, heated paddle court, and an office pavilion. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street,offering seclusion with proximity to NYC. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century

  Leslie Razook William Pitt Sotheby's Int'l

  4800 Congress St, Fairfield, CT 06824
• 

  

  /19

  $10,500,000

  • 4 Beds
  • 5.5 Baths
  • 10,522 Sq Ft

  47 Charcoal Hill Rd, Westport, CT 06880

  Designed by renowned architect and builder Frazier Forman Peters, this stone estate is set on nearly 3.5 private, meticulously landscaped acres in Westport. Crafted over more than two decades, the residence reflects exceptional artistry, scale, and craftsmanship. A gated entry and winding stone drive arrive at a stately porte-cochere and attached two-car garage, establishing a grand sense of

  Jonathan Ducharme Serhant Connecticut, LLC

  47 Charcoal Hill Rd, Westport, CT 06880
• 

  

  /36

  $5,995,000

  $504K PRICE DROP

  • 5 Beds
  • 7 Baths
  • 6,189 Sq Ft

  775 Sasco Hill Rd, Fairfield, CT 06824

  775 Sasco Hill Road is an extraordinary estate where timeless elegance meets modern luxury. Impeccably renovated and beautifully curated by the current owners, this sophisticated residence offers three full levels of refined living set across five private, park-like acres. A dramatic cathedral foyer and soaring 9-foot ceilings create an immediate sense of scale and light, while the thoughtfully

  Suzy Ryan William Raveis Real Estate

  775 Sasco Hill Rd, Fairfield, CT 06824
• 

  

  /22

  $625,000

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft

  439 Stillson Rd, Fairfield, CT 06824

  Ideally situated in a highly convenient location, this home offers easy access to shopping, dining, schools, parks, transportation and everyday essentials within easy reach. Enjoy the ideal balance of comfort and accessibility, with everything you need just moments from your front door. This home has an open floor plan that connects the kitchen to the dining area with an easy entrance from the

  Rima Bishuti William Raveis Real Estate

  439 Stillson Rd, Fairfield, CT 06824

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