Madison, CT Homes

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  $2,375,000

  • 4 Beds
  • 4.5 Baths
  • 4,637 Sq Ft

  132 Summer Hill Rd, Madison, CT 06443

  Welcome to your dream home, where thoughtful design meets high-end craftsmanship. This newly built four-bedroom, four-and-a-half bathroom house offers the perfect blend of style and comfort. Inside, an open floor plan creates a seamless flow from room to room, anchored by a soaring two-story great room with a stunning gas fireplace. Large oversized doors spill out onto a 580 SF covered deck where

  Diane Dupont William Pitt Sotheby's Int'l

  132 Summer Hill Rd, Madison, CT 06443
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  /24

  $3,900 per month

  • 3 Beds
  • 2 Baths
  • 2,034 Sq Ft
  • House for Rent

  90 Boston Post Rd, Madison, CT 06443

  AVAILABLE NOW! Charming Downtown Madison Rental. Enjoy gorgeous salt marsh views from this lovely 3-bedroom home available for a yearly lease starting this September. The main level offers two spacious bedrooms with a shared full bath, while the private upstairs primary suite features vaulted ceilings, a gas fireplace, full bath, and a balcony with sweeping marsh views. A sunny living room opens

  Kate Jasko Coldwell Banker Realty

  90 Boston Post Rd, Madison, CT 06443
• 

  $705,000 Sold Aug 22, 2025

  • 2,424 Sq Ft
  • $291/SF
  • 5 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1968

  310 Opening Hill Rd, Madison, CT 06443

  *Please submit offers by 7 pm Wednesday, 7/16/25. Welcome to this charming and extensively updated colonial home that embodies comfort and style. With a wealth of improvements completed in 2014, including new windows, roof, driveway and a beautiful kitchen, this home is move-in ready. Recent enhancements in 2024 include an updated primary bath and half bath, making it even more inviting for you

  Barbara Goetsch William Pitt Sotheby's Int'l

  310 Opening Hill Rd, Madison, CT 06443
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  Est $707,959 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,248 Sq Ft

  15 Bentwater Ln, Madison, CT 06443

  15 Bentwater Ln, Madison, CT 06443
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  $849,900

  • 4 Beds
  • 5 Baths
  • 3,986 Sq Ft

  16 Yankee Peddler Path, Madison, CT 06443

  This fully renovated and expanded Farmhouse Colonial offers nearly 4,000 sq ft of luxurious living space on a private 1.6-acre lot, blending timeless charm with modern upgrades. Every detail has been thoughtfully updated from roof to flooring, including new HVAC system, electrical, plumbing, a gourmet kitchen with center island and huge walk-in pantry, stylish bathrooms, and more. With 4 spacious

  Linda Toscano Coldwell Banker Realty

  16 Yankee Peddler Path, Madison, CT 06443
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  /26

  $3,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,638 Sq Ft
  • House for Rent

  39 Circle Beach Rd, Madison, CT 06443

  Academic Furnished Rental with direct ocean views and private sandy beach. Experience coastal living at its finest in this modern 3-bedroom, 2.5-bath fully furnished residence, available for academic rental from September 10, 2025 through May 30, 2026. Built in 2014 with energy efficiency in mind, this stylish and well-appointed home offers an open-concept first floor that seamlessly connects the

  Jessica Kimball William Raveis Real Estate

  39 Circle Beach Rd, Madison, CT 06443
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  $1,585,000 Sold Aug 22, 2025

  • 6,010 Sq Ft
  • $264/SF
  • 73 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 2007

  61 Governors Way, Madison, CT 06443

  Elegant 4-Bedroom Colonial on Prestigious Cul-de-Sac in Madison, CT. Experience the pinnacle of suburban living in this exquisite 4-bedroom Colonial, built in 2007, boasting a generous 4,400+ SF of living space, with an additional 1,600+ SF of a finished basement. Nestled on almost 1 acre of landscaped grounds, this home is on a private and respected cul-de-sac, offering the perfect neighborhood

  Kirsten Adams William Pitt Sotheby's Int'l

  61 Governors Way, Madison, CT 06443
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  Est $574,541 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,354 Sq Ft

  Unlisted Address

  Unlisted Address
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  /16

  $800,000

  • 3 Beds
  • 2.5 Baths
  • 2,112 Sq Ft

  677 Durham Rd, Madison, CT 06443

  Stunning 3-Bed, 2.5-Bath Home Built in 2022 - Immaculate and Move-In Ready! Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home, built in 2022 and designed for modern living. From the moment you step inside, you'll be impressed by the open floor plan that seamlessly blends living, dining, and kitchen spaces-perfect for both everyday life and entertaining. Custom built-ins

  Meig Walz Newcomb Coldwell Banker Realty

  677 Durham Rd, Madison, CT 06443
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  /23

  $2,800 per month

  • 2 Beds
  • 2 Baths
  • 1,684 Sq Ft
  • House for Rent

  52 Overshores E, Madison, CT 06443

  ACADEMIC RENTAL AVAILABLE - September 8, 2025 to May 31, 2026. Comfortable and nicely decorated, this home has 2 bedrooms upstairs that share a newer renovated full bath. This home is located in a private association with access to the Overshores Beach, one of the nicest association beaches on Neck Road. Recently renovated kitchen, newer mud room, newer first floor full bath, laundry room on 1st

  Kirsten Adams William Pitt Sotheby's Int'l

  52 Overshores E, Madison, CT 06443
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  $739,000 Sold Aug 22, 2025

  • 3,892 Sq Ft
  • $190/SF
  • 111 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1968

  94 Sportsman Hill Rd, Madison, CT 06443

  Welcome to 94 Sportsman Hill Road! Nestled on a 1.66-acre lot on a quiet cul-de-sac, this newly renovated colonial offers over 3,800 sq ft of versatile living space with 5 bedrooms, 3.5 bathrooms, a family room, an entertainment room, and more. Step inside to a bright center hall with a neutral palette and gleaming hardwood floors throughout. The kitchen features a center island with storage and

  Alejandro Pabon-Rey mygoodagent

  94 Sportsman Hill Rd, Madison, CT 06443
• 

  Est $590,128 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,928 Sq Ft

  1956 Durham Rd, Madison, CT 06443

  1956 Durham Rd, Madison, CT 06443
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  /40

  $799,000 Open Sun 11AM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 4,879 Sq Ft

  48 Shepherds Trail, Madison, CT 06443

  This one-of-a-kind Contemporary Colonial home features 4 bedrooms, 2.5 baths, and a versatile floor plan designed for both grand entertaining and everyday comfort. Step into the impressive foyer, where an expansive living room and formal dining area set the stage for large gatherings. At the heart of the main level, the kitchen shines with granite countertops, stainless steel appliances, and a

  Erin Connelly Coldwell Banker Realty

  48 Shepherds Trail, Madison, CT 06443
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  /8

  $4,000 per month

  • 1 Bath
  • 490 Sq Ft
  • House for Rent

  141 Middle Beach Rd, Madison, CT 06443

  The studio is graced with stunning views of Fence Creek, providing a picturesque backdrop to your daily living. Just steps away from the sandy shores of East Wharf Beach and the vibrant Madison town center, you'll have the best of coastal living right at your fingertips. Designed with efficiency in mind, the space features a queen bed that effortlessly converts into a couch, allowing you to

  Sue Knapp William Pitt Sotheby's Int'l

  141 Middle Beach Rd, Madison, CT 06443
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  $670,000 Sold Aug 21, 2025

  • 2,096 Sq Ft
  • $320/SF
  • 97 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1984

  5 Dover Ln, Madison, CT 06443

  Elegant Colonial on Pristine Corner Lot. Nestled on a generous 1.34-acre corner lot in the charming town of Madison, CT, this exquisite 4-bedroom, 2.5-bath colonial home offers a harmonious blend of comfort and outdoor space. The property's curb appeal is immediately apparent with a stone wall & garden area (backyard) and newer walkway to the front door. As you step inside, the entire interior

  Kirsten Adams William Pitt Sotheby's Int'l

  5 Dover Ln, Madison, CT 06443
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  Est $704,743 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,323 Sq Ft

  25 Summit Ln, Madison, CT 06443

  25 Summit Ln, Madison, CT 06443
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  $875,000

  • 3 Beds
  • 4 Baths
  • 2,235 Sq Ft

  3 Arrowhead Rd, Madison, CT 06443

  Newly Priced! Embrace the enchantment of Shoreline Living at its finest with this sun-drenched haven at 3 Arrowhead, a jewel nestled in a quaint community with the river at your doorstep. As you step into this radiant abode, you're welcomed by a symphony of natural light and the serene melodies of local birdsong. The home's design harmoniously blends the outdoors with the indoors, creating a

  Diana Hartman William Pitt Sotheby's Int'l

  3 Arrowhead Rd, Madison, CT 06443
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  /31

  $7,800 per month

  • 4 Beds
  • 3 Baths
  • 1,869 Sq Ft
  • House for Rent

  43 Soundview Ave, Madison, CT 06443

  Fabulous academic rental available Sept 8th through May 31st 2026. This direct waterfront four bedroom home set on a one of kind property with access to a private beach. Enjoy fabulous views from your deck, large yard and tidal pool. Plenty of space for everyone with a bedroom with full bath on the main level, Primary en suite on the second floor with private balcony and two additional bedrooms

  Sue Knapp William Pitt Sotheby's Int'l

  43 Soundview Ave, Madison, CT 06443
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  $456,500 Sold Aug 20, 2025

  • 1,468 Sq Ft
  • $311/SF
  • 39 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1958

  20 Robin Ridge Dr, Madison, CT 06443

  Welcome to 20 Robin Ridge Drive, a charming ranch-style home located in the highly sought-after Robin Ridge neighborhood! Ideally located just over 2 miles from Downtown Madison and approximately 3 miles to the Madison Beach Hotel, West Wharf Beach, and the Surf Club, this property combines comfort, convenience, and coastal living. This inviting home offers 3 generously sized bedrooms with

  Anne Marie Straka Compass Connecticut, LLC

  20 Robin Ridge Dr, Madison, CT 06443
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  Est $775,622 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,614 Sq Ft

  272 County Rd, Madison, CT 06443

  272 County Rd, Madison, CT 06443
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  /40

  $1,098,000 Open Sat 11AM - 1PM

  • 5 Beds
  • 3 Baths
  • 2,781 Sq Ft

  8 Highview Rd, Madison, CT 06443

  One-of-a-kind home in a small, sought-after subdivision close to the heart of charming Madison, CT. This architecturally distinctive residence features soaring cathedral ceilings and brand new skylights in the living room, vaulted ceilings in the dining room, and a striking shiplap ceiling in the expansive family room. Two wood-burning fireplaces create cozy focal points in both living and family

  Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  8 Highview Rd, Madison, CT 06443
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  /32

  $3,500 per month

  • 4 Beds
  • 2 Baths
  • 1,956 Sq Ft
  • House for Rent

  99 Horse Pond Rd, Madison, CT 06443

  Available for unfurnished annual rental - this beautifully restored circa 1870 home is located in the heart of historic Madison and seamlessly blends classic charm with modern convenience. Recent updates include freshly painted interiors, refinished hardwood floors, new stamped concrete patios, and a newly installed driveway. Enjoy the comfort of central A/C, an automatic full-house generator,

  Rose Ciardiello William Raveis Real Estate

  99 Horse Pond Rd, Madison, CT 06443
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  $325,000 Sold Aug 19, 2025

  • 1,332 Sq Ft
  • $244/SF
  • 34 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1986

  2 Brantwood Dr, Madison, CT 06443

  Welcome to this move in ready townhouse located just a short walk to downtown Madison. Newly installed sidewalks make it convenient to visit everything Madison has to offer - shopping, movie theater, restaurants, farmers market and Sunday evening concerts. This unit offers 2 bedrooms, 1.2 baths with over 1300 s.f. The updated kitchen has shaker cabinets, granite countertops and stainless steel

  Rebecca Ferguson Coldwell Banker Realty

  2 Brantwood Dr, Madison, CT 06443
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  Est $674,370 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,040 Sq Ft

  237 County Rd, Madison, CT 06443

  237 County Rd, Madison, CT 06443
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  /7

  $1,450,000 New Construction

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft

  1339 Boston Post Rd Unit 2-5, Madison, CT 06443

  Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

  Vinny Valentino Advise Realty Services

  1339 Boston Post Rd Unit 2-5, Madison, CT 06443
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  $580,000 Sold Aug 19, 2025

  • 2,256 Sq Ft
  • $257/SF
  • 31 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1985

  73 Legend Hill Rd, Madison, CT 06443

  Welcome to this beautifully maintained two-bedroom, 2.1-bath townhouse condominium in Madison's sought-after Legend Hill community. Set within an 88-acre private enclave of 90 homes, Legend Hill is rich in history and charm, with residences thoughtfully arranged around the historic Northam Manor. Perched on one of the highest elevations between Boston and the New York shoreline, the community

  Dana Weinstein Coldwell Banker Realty

  73 Legend Hill Rd, Madison, CT 06443
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  Est $719,671 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,954 Sq Ft

  31 Lakewood Dr, Madison, CT 06443

  31 Lakewood Dr, Madison, CT 06443
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  /7

  $1,450,000 New Construction

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft

  1339 Boston Post Rd Unit 2-6, Madison, CT 06443

  Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

  Vinny Valentino Advise Realty Services

  1339 Boston Post Rd Unit 2-6, Madison, CT 06443
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  $1,927,500 Sold Aug 19, 2025

  • 2,700 Sq Ft
  • $714/SF
  • 8 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1924

  44 E Wharf Rd, Madison, CT 06443

  PRIVATE AND PERFECT! Tucked away on a quiet lane with only two other houses is 44 East Wharf Rd, a charming oasis that's a short walk to both town and East Wharf Beach. The first floor includes a spacious, vaulted ceiling primary suite, a living room with wood burning fireplace, French doors leading to a large heated porch with a hip ceiling and a gas fireplace overlooking a gorgeous private yard

  Margaret Muir William Pitt Sotheby's Int'l

  44 E Wharf Rd, Madison, CT 06443
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  Est $744,091 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 3,146 Sq Ft

  35 Lakewood Dr, Madison, CT 06443

  35 Lakewood Dr, Madison, CT 06443
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  /7

  $1,450,000 New Construction

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft

  1339 Boston Post Rd Unit 3-1, Madison, CT 06443

  Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

  Vinny Valentino Advise Realty Services

  1339 Boston Post Rd Unit 3-1, Madison, CT 06443
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  $212,000 Sold Aug 15, 2025

  • 647 Sq Ft
  • $328/SF
  • 19 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  26 North St, Madison, CT 06443

  Madison Connecticut - By the sea, literally! Beautifully framed cottage is evident here! Character in exposed wood and wooden beamed vaulted ceilings. Tons of sunlight stream into this beautiful home! Sunny living room, bedroom/den, and patio. This CORNER lot provides easy parking, a darling patio, exceptional large wooden shed, professionally landscaped lawn! Location offers an easy one mile

  Laurie McCann William Pitt Sotheby's Int'l

  26 North St, Madison, CT 06443
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  Est $841,838 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,025 Sq Ft

  235 Devonshire Ln, Madison, CT 06443

  235 Devonshire Ln, Madison, CT 06443
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  $1,450,000 New Construction

  • 2 Beds
  • 2 Baths
  • 1,230 Sq Ft

  1339 Boston Post Rd Unit 3-2, Madison, CT 06443

  Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

  Vinny Valentino Advise Realty Services

  1339 Boston Post Rd Unit 3-2, Madison, CT 06443
• 

  $1,200,000 Sold Aug 15, 2025

  • 4,437 Sq Ft
  • $270/SF
  • 50 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1820

  479 Opening Hill Rd, Madison, CT 06443

  You won't want to miss this move-in ready Colonial-style home, completely renovated in 2021! The property offers over 4,000 square feet of living space, is on more than 3 acres of land, and is conveniently located minutes from the heart of Madison, schools, shopping, I-95 and famous Madison beaches. This 4-bedroom, 2.5-bath home combines traditional charm with beautiful modern updates. The

  Erin Connelly Coldwell Banker Realty

  479 Opening Hill Rd, Madison, CT 06443
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  Est $916,100 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,259 Sq Ft

  834 Summer Hill Rd, Madison, CT 06443

  834 Summer Hill Rd, Madison, CT 06443
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  /7

  $1,450,000 New Construction

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft

  1339 Boston Post Rd Unit 3-3, Madison, CT 06443

  Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

  Vinny Valentino Advise Realty Services

  1339 Boston Post Rd Unit 3-3, Madison, CT 06443
• 

  $935,570 Sold Aug 14, 2025

  • 2,728 Sq Ft
  • $343/SF
  • 42 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1854

  109 Boston Post Rd, Madison, CT 06443

  Built in 1854 for the Chittenden family, this historic Madison home sits on a beautifully landscaped, level one-acre lot and blends classic New England charm with modern upgrades. The main residence features three bedrooms on the second floor, plus a finished third-floor loft that serves as a fourth bedroom, office, or playroom. A highlight is the detached oversized garage with a connected studio

  Jack Hill Seabury Hill REALTORS

  109 Boston Post Rd, Madison, CT 06443
• 

  Est $616,719 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,404 Sq Ft

  640 Summer Hill Rd, Madison, CT 06443

  640 Summer Hill Rd, Madison, CT 06443
• 

  

  /8

  $1,450,000 New Construction

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft

  1339 Boston Post Rd Unit 3-5, Madison, CT 06443

  Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

  Vinny Valentino Advise Realty Services

  1339 Boston Post Rd Unit 3-5, Madison, CT 06443

Showing Results 81 - 120, Page 3 of 18