Woodbury, Connecticut is a charming New England town known for its antique shops, historic homes, and beautiful countryside. With its picturesque streets lined with 18th and 19th-century buildings, Woodbury is a popular destination for tourists and locals alike. Visitors can enjoy a variety of outdoor activities, including hiking, fishing, and picnicking in nearby state parks.

Best Choice of Shopping

  1. Antique Market Place: Offering a vast selection of antiques and collectibles from over 200 dealers, Antique Market Place is a must-visit for anyone interested in unique, high-quality pieces.
  2. LaBonne's Market: This upscale grocery store offers an extensive selection of gourmet foods, wines, and spirits, as well as a deli and bakery.
  3. The Golden Button: A boutique gift shop featuring locally made art and crafts, as well as jewelry and home decor items.
  4. New Morning Market: A natural foods store with an extensive selection of organic and locally sourced produce, meat, and dairy products, as well as supplements and wellness products.
  5. Connecticut Antique Machinery Association: Not your typical shopping destination, but a fascinating place to explore vintage machinery and learn about Connecticut's industrial history.

Most Luxurious Hotels

  1. The Curtis House Inn: A historic bed and breakfast dating back to the 1730s, featuring elegant rooms with fireplaces and four-poster beds.
  2. The Mayflower Inn & Spa: A luxury hotel and spa set on 58 acres of lush gardens and woodlands, offering elegant accommodations, fine dining, and a full-service spa.
  3. The Inn at Mount Pleasant: A picturesque bed and breakfast offering comfortable rooms and suites with period decor and modern amenities, as well as a relaxing outdoor pool.
  4. The Guest House at Norwalk Inn: A stylish and modern boutique hotel featuring spacious rooms and suites with luxury amenities, as well as a restaurant and bar.
  5. Delamar Southport: A chic and sophisticated hotel with plush rooms and suites, a full-service spa, and a rooftop bar with stunning views of the Long Island Sound.

Excellent Dining

  1. The Good News Cafe: An eclectic eatery offering creative, farm-to-table dishes and artisanal cocktails in a cozy and intimate atmosphere.
  2. Market Place Kitchen & Bar: A trendy restaurant featuring upscale New American cuisine and an extensive wine list, as well as a lively bar scene.
  3. John's Cafe: A family-owned restaurant serving classic American dishes and seafood in a casual and welcoming setting.
  4. The Copper Beech Inn: A historic inn and restaurant offering refined New England cuisine and an extensive wine list in an elegant and romantic atmosphere.
  5. The Irons Restaurant & Bar: A sleek and modern restaurant located at the Hilton Mystic, featuring farm-to-table cuisine, craft cocktails, and panoramic views of Mystic.

World Class Residence

  1. Chateau Soleil: A stunning French-inspired estate featuring a private lake, tennis court, pool, and guest house, as well as luxurious living spaces and exquisite architectural details.
  2. The Oaks: A grand and stately colonial-style mansion set on 20 acres of pristine woodland, featuring a pool, tennis court, and elegant living spaces.
  3. Cedar Hill Estate: A magnificent waterfront property with sweeping views of Long Island Sound, featuring a private beach, pool, tennis court, and elegant living spaces.
  4. Twin Ponds Estate: A sprawling property set on over 20 acres of picturesque countryside, featuring a main house, guest house, pool, tennis court, and lush gardens.
  5. Deer Run Farm: A peaceful and private retreat set on 80 acres of rolling hills and woodlands, featuring a stunning main house, guest house, barn, pool, and tennis court.
Step through the doors of history and into one of Connecticut's most treasured colonial residences.
$1,495,000
Courtesy of William Pitt Sotheby's Int'l
Rare opportunity to own a spectacular 40 acre equestrian estate designed for exceptional horse care, training, and country living.
$1,800,000
Courtesy of William Raveis Real Estate
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.
$1,995,000
Courtesy of W. Raveis Lifestyles Realty
Prime commercial opportunity on Main Street South in Woodbury, adjacent to the well known 1754 House restaurant.
$1,350,000
Courtesy of Drakeley Real Estate, Inc.
Open Meadow Farm, a beautifully maintained property offering a blend of rural charm and modern conveniences.
$1,675,000
Courtesy of Klemm Real Estate Inc
Discover this beautifully updated ranch style home ideally situated on over an acre of level, private land.
$549,000
Courtesy of West View Properties, LLC
One of Woodbury's last remaining homes built in the late 1600s.
$874,900
Courtesy of Berkshire Hathaway NE Prop.
Welcome to Upper Grassy Hill Living !
$895,000
Courtesy of William Pitt Sotheby's Int'l
Charming Gentleman's Farm on 5.
$799,000
Courtesy of RE/MAX RISE
Recently renovated from the studs up, this single family ranch on the Woodbury Roxbury town line offers the rare chance to own a truly like new home with immediate availability.
$759,900
Courtesy of Drakeley Real Estate, Inc.
Located in picturesque Woodbury, voted Most Charming Town in CT by Reader's Digest in 2018, 2020 and 2024 and featured by Travel Leisure among the 10 Best Places to Live.
$699,000
Courtesy of BHGRE Gaetano Marra Homes
Discover the charm of this beautiful antique home in the heart of Woodbury !
$999,900
Courtesy of Drakeley Real Estate, Inc.
Welcome to Woodbury, a quintessential New England town.
$1,100,000
Courtesy of Showcase Realty, Inc.
Need space ! This elegant Colonial in Carriage Hills features approximately 5700 sqft of living space, including a walk out lower level suitable for an in law suite or for ...
$999,900
Courtesy of Klemm Real Estate Inc
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