Woodbury, CT Homes

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  $2,195,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,551 Sq Ft

  382 Weekeepeemee Rd, Woodbury, CT 06798

  The Jesse Peck Lambert Homestead, built in 1805 & thoughtfully restored, provides a seamless blend of historic charm & modern comfort. Set on 6.42 acres in Northern Woodbury on the Washington border just 2 hours from NYC, this 4-bedroom/3.5-bath home provides a serene escape with timeless appeal. The newly designed kitchen is a chef's dream, featuring custom rift-sawn white oak cabinets, oiled

  Jeff Phillips William Pitt Sotheby's Int'l

  382 Weekeepeemee Rd, Woodbury, CT 06798
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  $302,500 Sold Jul 09, 2025

  8 Highpoint Ct, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $208/SF
  • 33 Days On Market

  Current Estimated Value $314,404

  Last Listing Agent Tom Greto William Raveis Real Estate

  8 Highpoint Ct, Woodbury, CT 06798
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  Est $471,928 Not Listed For Sale

  24 Joshua Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 2,072 Sq Ft
  • Built 1997

  24 Joshua Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 11% Above List Price
  • $206/SF
  • 128 Days On Market

  • Last Sold Price $427,000
  • Mar 01, 2024

  Last Listing Agent Karen Dibble-flaherty Keller Williams Realty
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  /17

  $479,900

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  34 Transylvania Rd, Woodbury, CT 06798

  Price Improvement for this Charming Country Retreat- A perfect alternative to Condo Living! Nestled on a serene 3 acre lot with picturesque stream, this property offers the tranquility of country living while maintaining easy access to nearby amenities. One level living- enjoy the convenience of the primary bedroom with spacious walk-in closet on the same level as the open floor plan

  Betsy Rosa Berkshire Hathaway NE Prop.

  34 Transylvania Rd, Woodbury, CT 06798
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  $539,000 Sold Jul 18, 2025

  54 Barnhill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 1,675 Sq Ft
  • Built 1985

  Last Sold Summary

  • 2% Above List Price
  • $322/SF
  • 3 Days On Market

  Current Estimated Value $574,242

  Last Listing Agent Joseph Racanelli William Raveis Real Estate

  54 Barnhill Rd, Woodbury, CT 06798
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  Est $464,570 Not Listed For Sale

  9 Orenaug Ave, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 2,058 Sq Ft
  • Built 1912

  9 Orenaug Ave, Woodbury, CT 06798

  Last Sold Summary

  • 18% Above List Price
  • $192/SF
  • 233 Days On Market

  • Last Sold Price $395,000
  • Dec 18, 2024

  Last Listing Agent Gary Smith eXp Realty
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  $400,000

  • Land
  • 22,215 Sq Ft
  • $784,314 per Acre

  1545 Main St N, Woodbury, CT 06798

  Rare Main Street commercial property available in Woodbury, CT. The land and the building upon it are being sold in "as is, where is" condition. Neither the probate court system, the attorney, or the broker have any knowledge as to any deficiencies on the property or if they even exist Located in the OS 60 zone, interested parties should consult with the planning and zoning to verify their

  Mario Longobucco Coldwell Banker Commercial NRT

  1545 Main St N, Woodbury, CT 06798
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  $600,000 Sold Nov 20, 2025

  36 Heritage Dr, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,032 Sq Ft
  • Built 1968

  Last Sold Summary

  • 5% Below List Price
  • $295/SF
  • 60 Days On Market

  Current Estimated Value $625,026

  Last Listing Agent Justin Bette Century 21 Bette Real Estate

  36 Heritage Dr, Woodbury, CT 06798
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  Est $1,287,264 Not Listed For Sale

  45 Birchwood Ln, Woodbury, CT 06798

  • 5 Beds
  • 5.5 Baths
  • 5,956 Sq Ft
  • Built 2004

  45 Birchwood Ln, Woodbury, CT 06798

  Last Sold Summary

  • 12% Above List Price
  • $193/SF
  • 15 Days On Market

  • Last Sold Price $1,150,000
  • Jul 07, 2023

  Last Listing Agent Dawn Grabover Keller Williams Realty
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  /27

  $212,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,150 Sq Ft

  126 Sherman Hill Rd Unit C14, Woodbury, CT 06798

  Beautifully updated 1st floor end unit with plenty of parking. Fantastic 2 bedroom with brand new bathroom, updated kitchen, large custom built-ins, wood burning fireplace, sliders that open to private patio and garden just steps from pool.HOA includes heat, water and basic cable. Plenty of storage in unit and private storage close by. Quiet complex conveniently located to shopping and minutes to

  Gena Ruocco-Lockery GRL & Realtors, LLC

  126 Sherman Hill Rd Unit C14, Woodbury, CT 06798
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  $1,225,000 Sold Nov 16, 2025

  68 Whittlesey Rd, Woodbury, CT 06798

  • 4 Beds
  • 4 Baths
  • 4,682 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Above List Price
  • $262/SF
  • 44 Days On Market

  Current Estimated Value $1,246,395

  Last Listing Agent Michael Caporizzo William Pitt Sotheby's Int'l

  68 Whittlesey Rd, Woodbury, CT 06798
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  Est $189,660 Not Listed For Sale

  229 Bacon Pond Rd Unit 443, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft
  • Built 1971

  229 Bacon Pond Rd Unit 443, Woodbury, CT 06798

  Last Sold Summary

  • 1% Below List Price
  • $209/SF
  • 8 Days On Market

  • Last Sold Price $191,000
  • Aug 20, 2024

  Last Listing Agent Ann Gerschefski William Raveis Real Estate
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  $272,500

  • 2 Beds
  • 2.5 Baths
  • 1,182 Sq Ft

  23 Lower Commons Unit 23, Woodbury, CT 06798

  RECENTLY REFURBISHED and move-in-ready! Notice the tile entry. The Kitchen has new S.S. appliances. The Kitchen layout is "chef-friendly" w/plenty of cabinet storage. The first floor includes the convenience of laundry and a 1/2 Bath. Hardwood floors in the living room adds to the inviting ambiance. There is a fireplace: it can easily become working with the insert of a Pellet or Wood-burning

  Terry Lee Adams Adams & Adams Real Estate

  23 Lower Commons Unit 23, Woodbury, CT 06798
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  $300,000 Sold Dec 30, 2025

  9 Heather Ct Unit 9, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,723 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Above List Price
  • $174/SF
  • 33 Days On Market

  Current Estimated Value $307,848

  Last Listing Agent Ann Micacci Berkshire Hathaway NE Prop.

  9 Heather Ct Unit 9, Woodbury, CT 06798
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  Est $670,470 Not Listed For Sale

  97 Hard Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 2 Baths
  • 3,022 Sq Ft
  • Built 1981

  97 Hard Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 6% Above List Price
  • $209/SF
  • 91 Days On Market

  • Last Sold Price $632,500
  • Nov 12, 2024

  Last Listing Agent Erik Sousa William Raveis Real Estate
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  /22

  $214,900 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft

  47 Woods Way Unit 47, Woodbury, CT 06798

  This Country House model, end unit in Woodbury's Woodlake community offers two spacious bedrooms, with their own full baths, a detached one car garage and open floor plan on the main level. The Woodlake community provides non-motorized boating on the lake, hiking trails, basketball, tennis courts, and a playground area to name a few. The full unfinished basement offers more storage space. New

  Katherine Parlato Drakeley Real Estate, Inc.

  47 Woods Way Unit 47, Woodbury, CT 06798
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  $130,000 Sold Oct 01, 2025

  Lot 64 Highpoint Rd, Woodbury, CT 06798

  • Land
  • 35,283 Sq Ft
  • $160,494 per Acre

  Last Sold Summary

  • 8% Above List Price
  • 88 Days On Market

  Last Listing Agent Justin Bette Century 21 Bette Real Estate

  Lot 64 Highpoint Rd, Woodbury, CT 06798
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  Est $433,305 Not Listed For Sale

  40 Pilgrim Trail, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft
  • Built 1966

  40 Pilgrim Trail, Woodbury, CT 06798

  Last Sold Summary

  • 10% Above List Price
  • $155/SF
  • 85 Days On Market

  • Last Sold Price $395,000
  • Dec 11, 2024

  Last Listing Agent Patricia Forbes Berkshire Hathaway Home Services
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  $200,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,150 Sq Ft

  126 Sherman Hill Rd Unit B12, Woodbury, CT 06798

  This second level unit offers a living and dining combo, kitchen, two bedrooms and one full bath. Upstairs units have vaulted ceilings & additional windows that allow for even more daylight and sense of space. A floor to ceiling brick fireplace will draw you in the winter and a modern curved wall, as you enter the door, adds so much character. The complex offers an in-ground pool. HOA Includes

  Tiffany Clark RE/MAX Right Choice

  126 Sherman Hill Rd Unit B12, Woodbury, CT 06798
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  $775,000 Sold Nov 13, 2025

  6 Strong Field Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 2024

  Last Sold Summary

  • 8% Below List Price
  • $298/SF
  • 103 Days On Market

  Current Estimated Value $799,214

  Last Listing Agent Mary Ann Bennett Drakeley Real Estate, Inc.

  6 Strong Field Rd, Woodbury, CT 06798
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  Est $360,420 Not Listed For Sale

  274 Minortown Rd, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 914 Sq Ft
  • Built 1989

  274 Minortown Rd, Woodbury, CT 06798

  Last Sold Summary

  • 9% Above List Price
  • $361/SF
  • 0 Days On Market

  • Last Sold Price $330,000
  • Jul 25, 2023

  Last Listing Agent Amy Mosley Elevated Life Realty LLC
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  $450,000 Coming Soon

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

  89 Lighthouse Rd, Woodbury, CT 06798

  Tucked away on 4.99 serene wooded acres in picturesque Woodbury, this solidly built Cape Cod offers privacy, charm, and endless potential. Surrounded by mature trees and peaceful natural beauty, the property provides a true country setting with room to create gardens, walking trails, or space for animals and hobby farm interests. Inside, the home features 3 bedrooms, 1.5 baths, beautiful hardwood

  Heather Crabtree RE/MAX RISE

  89 Lighthouse Rd, Woodbury, CT 06798
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  $592,750 Sold Feb 05, 2026

  94 Old Town Farm Rd, Woodbury, CT 06798

  • 6 Beds
  • 3 Baths
  • 4,245 Sq Ft
  • Built 1900

  Last Sold Summary

  • 21% Below List Price
  • $140/SF
  • 175 Days On Market

  Current Estimated Value $620,517

  Last Listing Agent Michael Caporizzo William Pitt Sotheby's Int'l

  94 Old Town Farm Rd, Woodbury, CT 06798
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  Est $463,117 Not Listed For Sale

  99 Flanders Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 2,664 Sq Ft
  • Built 1956

  99 Flanders Rd, Woodbury, CT 06798

  Last Sold Summary

  • 40% Above List Price
  • $124/SF
  • 337 Days On Market

  • Last Sold Price $330,000
  • May 29, 2020

  Last Listing Agent Joyce Drakeley Drakeley Real Estate, Inc.
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  $314,900

  • 2 Beds
  • 1.5 Baths
  • 1,920 Sq Ft

  439 Washington Rd, Woodbury, CT 06798

  Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can potentially be converted into a single family residential ranch overlooking the babbling Sprain Brook below. Across the brook, with road frontage and access off of Hoop Pole Hill Rd, lies the majority of the acreage with a dry,

  Matthew Amatruda Drakeley Real Estate, Inc.

  439 Washington Rd, Woodbury, CT 06798
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  $810,000 Sold Apr 28, 2026

  148 Flanders Rd, Woodbury, CT 06798

  • 3 Beds
  • 4 Baths
  • 3,082 Sq Ft
  • Built 1987

  Last Sold Summary

  • 5% Below List Price
  • $263/SF
  • 103 Days On Market

  Current Estimated Value $840,781

  Last Listing Agent Ron Nettleton William Raveis Real Estate

  148 Flanders Rd, Woodbury, CT 06798
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  Est $287,617 Not Listed For Sale

  49 Clubhouse Dr, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,316 Sq Ft
  • Built 1972

  49 Clubhouse Dr, Woodbury, CT 06798

  Last Sold Summary

  • 30% Above List Price
  • $169/SF
  • 24 Days On Market

  • Last Sold Price $222,000
  • Aug 02, 2023

  Last Listing Agent Terry Lee Adams Adams & Adams Real Estate
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  $499,999

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

  110 Brushy Hill Rd, Woodbury, CT 06798

  Experience the charm of this classic Cape Cod style property, featuring 3 bedrooms and 2 cozy fireplaces that invite warm gatherings on 1 acre of land perfect for outdoor enjoyment. This country eclectic home blends timeless architecture with modern comfort, offering a serene retreat that captures the essence of country living. Whether you're relaxing by the fire or exploring the great outdoors,

  Jacqueline Voegeli Manzi Real Estate

  110 Brushy Hill Rd, Woodbury, CT 06798
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  $765,000 Sold Sep 29, 2025

  34 Hollow Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 1,675 Sq Ft
  • Built 1750

  Last Sold Summary

  • 4% Below List Price
  • $457/SF
  • 103 Days On Market

  Current Estimated Value $785,767

  Last Listing Agent Lorraine Consiglio BHGRE Gaetano Marra Homes

  34 Hollow Rd, Woodbury, CT 06798
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  Est $180,292 Not Listed For Sale

  229 Bacon Pond Rd Unit 241, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft
  • Built 1971

  229 Bacon Pond Rd Unit 241, Woodbury, CT 06798

  Last Sold Summary

  • $197/SF
  • 34 Days On Market

  • Last Sold Price $180,000
  • Mar 06, 2025

  Last Listing Agent Taner Genc Coldwell Banker Realty
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  /40

  $949,900

  • 4 Beds
  • 5 Baths
  • 3,865 Sq Ft

  8 Curtiss Meadows, Woodbury, CT 06798

  Beautiful Colonial set on a private 3+ acre lot in sought-after Curtiss Meadows, ideally located on the southern end of Woodbury abutting the Southbury line. Set back from the cul-de-sac entryway, this well-cared-for home offers a wonderful blend of privacy, comfort, convenience, and thoughtful updates. The level, light-filled driveway provides easy access, while the peaceful setting creates a

  Joyce Drakeley Drakeley Real Estate, Inc.

  8 Curtiss Meadows, Woodbury, CT 06798
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  $370,000 Sold Nov 18, 2025

  4 Hazel Plain Rd, Woodbury, CT 06798

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft
  • Built 1949

  Last Sold Summary

  • 8% Above List Price
  • $344/SF
  • 6 Days On Market

  Current Estimated Value $378,438

  Last Listing Agent Gary Smith eXp Realty

  4 Hazel Plain Rd, Woodbury, CT 06798
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  Est $694,267 Not Listed For Sale

  60 Main St S, Woodbury, CT 06798

  • 4 Beds
  • 2 Baths
  • 3,068 Sq Ft
  • Built 1829

  60 Main St S, Woodbury, CT 06798

  Last Sold Summary

  • 12% Above List Price
  • $203/SF
  • 14 Days On Market

  • Last Sold Price $622,500
  • Apr 29, 2024

  Last Listing Agent Joyce Drakeley Drakeley Real Estate, Inc.
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  $475,000 Under Contract

  • 4 Beds
  • 1 Bath
  • 1,836 Sq Ft

  242 Bacon Pond Rd, Woodbury, CT 06798

  Charming antique home in the heart of Woodbury with a separate legal 700 sq. ft. apartment over the detached 2-car garage, offering excellent rental income potential. Full of vintage character, this special property features wide board antique flooring, original details, built-ins, and three fireplaces, including one in the cozy eat-in kitchen. Set on a gorgeous long, treed in-town lot, the

  Tim Drakeley Drakeley Real Estate, Inc.

  242 Bacon Pond Rd, Woodbury, CT 06798
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  $280,000 Sold May 28, 2025

  22 Woods Way Unit 22, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,482 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $189/SF
  • 69 Days On Market

  Last Listing Agent Joan Junga CB Country to Coast Realty

  22 Woods Way Unit 22, Woodbury, CT 06798
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  Est $759,995 Not Listed For Sale

  194 Washington Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 3,182 Sq Ft
  • Built 1836

  194 Washington Rd, Woodbury, CT 06798

  Last Sold Summary

  • 3% Above List Price
  • $231/SF
  • 78 Days On Market

  • Last Sold Price $735,000
  • Jan 17, 2025

  Last Listing Agent Kevin Hickey William Pitt
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  $1,850,000

  • 4 Beds
  • 4.5 Baths
  • 3,324 Sq Ft

  55 Good Hill Rd, Woodbury, CT 06798

  Step into History with Modern Comfort Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character with today's modern conveniences. Inside, the open floor plan creates a warm and inviting flow, with three cozy sitting rooms

  Stacey Matthews W. Raveis Lifestyles Realty

  55 Good Hill Rd, Woodbury, CT 06798
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  $385,000 Sold Jul 02, 2025

  59 Arrowhead Way, Woodbury, CT 06798

  • 5 Beds
  • 2 Baths
  • 1,693 Sq Ft
  • Built 1964

  Last Sold Summary

  • 4% Below List Price
  • $227/SF
  • 26 Days On Market

  Current Estimated Value $405,692

  Last Listing Agent Shawna Mucherino Coldwell Banker Realty

  59 Arrowhead Way, Woodbury, CT 06798
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  Est $835,523 Not Listed For Sale

  82 Bear Run, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 3,158 Sq Ft
  • Built 1998

  82 Bear Run, Woodbury, CT 06798

  Last Sold Summary

  • 86% Above List Price
  • $142/SF
  • 53 Days On Market

  • Last Sold Price $450,000
  • Jun 26, 2020

  Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.
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  $805,000 Sold Aug 07, 2025

  59 Davids Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,475 Sq Ft
  • Built 1979

  Last Sold Summary

  • 6% Above List Price
  • $325/SF
  • 16 Days On Market

  Current Estimated Value $837,049

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  59 Davids Hill Rd, Woodbury, CT 06798

Showing Results 161 - 200, Page 5 of 18