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.
Welcome to this charming, single level ranch style home in idyllic Woodbury, one of Litchfield County's most desirable towns.
$559,900
Courtesy of Drakeley Real Estate, Inc.
Charming Country Retreat A perfect alternative to Condo Living !
$499,000
Courtesy of Berkshire Hathaway NE Prop.
Looking for peace, privacy and small town charm ?
$445,000
Courtesy of Drakeley Real Estate, Inc.
Beautifully Spacious Colonial in the Heart of Woodbury.
$799,900
Courtesy of Drakeley Real Estate, Inc.
Tucked away in the picturesque hills of Litchfield County, right on the desirable Woodbury Roxbury line, this stunning Colonial Contemporary residence offers an unparalleled blend of privacy, natural beauty, and ...
$1,275,000
Courtesy of Houlihan Lawrence
Charming Gentleman's Farm on 5.
$799,000
Courtesy of Coldwell Banker Realty
Fall in love with this colonial in a tranquil private setting on over 5 acres, yet close to everything.
$675,000
Courtesy of Coldwell Banker Realty
Wonderful Ca 1840's Colonial on 3 acres with wrap around porch.
$649,000
Courtesy of Klemm Real Estate Inc
Welcome to a piece of New England history an 1835 Farmhouse lovingly updated for today's living while preserving all its timeless charm.
$760,000
Courtesy of Coldwell Banker Realty
Step into this well cared for 3 bedroom, 2 bath Victorian offering just over 2, 000 sq.
$499,900
Courtesy of Drakeley Real Estate, Inc.
Wonderful, spacious 3 bedroom 2.
$629,900
Courtesy of Joseph Bette REALTORS Inc
If you are looking for peace and tranquility, you will find it here in this expansive cape.
$675,000
Courtesy of BHGRE Gaetano Marra Homes
Experience the charm of Woodbury's most desirable condominium community at 18 Woodbury Hill.
$559,900
Courtesy of Drakeley Real Estate, Inc.
The Tomlinson House, built in 1786, offers a rare chance to own a piece of Woodbury's history.
$895,000
Courtesy of William Pitt Sotheby's Int'l
Discover this beautifully updated ranch style home ideally situated on over an acre of level, private land, backing onto a tranquil nature preserve in the heart of Woodbury.
$549,000
Courtesy of BHGRE Gaetano Marra Homes
Tucked away in absolute privacy, yet centrally located, this exceptional estate offers 6, 300 square feet of refined living space that seamlessly blends country sophistication modern luxuries.
$1,800,000
Courtesy of Keller Williams Realty Prtnrs.
Welcome to a rare find in scenic Woodbury, CT !
$600,000
Courtesy of Coldwell Banker Realty
The epitome of where Contemporary Design, open spaces, light and efficiency meet the true warmth and pride of local master craftsman.
$595,000
Courtesy of Drakeley Real Estate, Inc.
Built in 1900 as a barn and converted to a home in 1990, the architecture fuses countryside charm and mid century design two contrasting genres married to create an interesting ...
$698,000
Courtesy of William Pitt Sotheby's Int'l
Experience elevated New England living at 6 Strong Field Road, an exceptional 2024 custom built Cape Cod residence set on a private, manicured 1 acre lot in one of Woodbury's ...
$799,900
Courtesy of Drakeley Real Estate, Inc.
Lovely well maintained colonial just minutes to town.
$995,000
Courtesy of W. Raveis Lifestyles Realty
Welcome to Upper Grassy Hill Living !
$915,000
Courtesy of William Pitt Sotheby's Int'l
PRICE IMPROVEMENT ! ! ! !
$899,900
Courtesy of William Raveis Real Estate
NEW PRICE ! Don't wait ! This ranch style home might be the perfect fit !
$599,000
Courtesy of Klemm Real Estate Inc
Charming antique home in the heart of Woodbury !
$565,000
Courtesy of Coldwell Banker Realty
Welcome to Woodbury, a quintessential New England town.
$1,100,000
Courtesy of Showcase Realty, Inc.
Welcome to your North Woodbury bucolic retreat !
$624,900
Courtesy of Berkshire Hathaway NE Prop.
Presenting a rare opportunity to acquire a 23 acre parcel that has been held within a family for generations.
$675,000
Courtesy of William Pitt Sotheby's Int'l
A Real Classic ! Beautifully renovated with many original features.
$899,900
Courtesy of Berkshire Hathaway NE Prop.
Custom built. This unique home is made for entertaining.
$1,275,000
Courtesy of William Raveis Real Estate
An Antique home with two large barns that offers a unique opportunity for a mixed use development.
$699,900
Courtesy of Drakeley Real Estate, Inc.
Discover refined country living in this remarkable Woodbury estate set on 33.
$1,998,000
Courtesy of Klemm Real Estate Inc
VIEWS Wonderful views for a home site or farm.
$400,000
Courtesy of W. Raveis Lifestyles Realty
Come home to a unique 3082 sqft, one of a kind custom built Colonial home all set on 5 secluded acres.
$899,900
Courtesy of William Raveis Real Estate
Discover the charm of this beautiful antique home in the heart of Woodbury !
$699,900
Courtesy of Drakeley Real Estate, 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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