Woodbury Real Estate

Recently Sold Listings in Woodbury, CT

Welcome to your dedicated resource for viewing Sold listings in Woodbury, CT. As local Woodbury, CT agents, Dave Jones Realty specializes in the unique market dynamics of this area, offering insights home values, selling strategies, and options like cash offers. Start exploring the most recent sold properties in Woodbury, CT below, or if you are looking to sell a home in Woodbury, CT contact a local agent to discuss the possibilities.

< Back to all Homes for Sale in Woodbury, CT

Be the First to Know About New Woodbury Homes

Stay ahead with real-time updates — no searching required.

See Homes Before Everyone Else

Woodbury Real Estate Map Search

Search by Lifestyle
  Advanced Search   Market Reports   Home Value   Connect

All Recently Sold in Woodbury, CT

$1,540,000
4 Beds ⋅ 6 Baths ⋅ 24005954 MLS
Unwind and create lasting memories in your private sanctuary at 55 Good Hill Road, nestled in historic Woodbury. This meticulously crafted residence, boasting 4-beds and 4.5-baths, transcends mere function; it offers a haven of gracious living imbued with enduring charm. Step beyond the grand facade and discover a world of comfort and sophistication. Antique hardwood floors flow throughout, inviting exploration of each elegant space. Imagine grand entertaining in the thoughtfully appointed rooms, each one whispering tales of a rich heritage. Sparkling sunlight dances on the surface of the inviting pool, beckoning you to take a refreshing dip. Unwind afterwards in the soothing spa, or gather with loved ones in the charming pool house for meals and laughter. The expansive 3.67-acre grounds offer endless possibilities for outdoor recreation. 55 Good Hill Road transcends the ordinary. It's a legacy property, where history melds seamlessly with modern luxury. The exquisite chef's kitchen, adorned with top-of-the-line appliances and custom cabinetry, awaits your culinary creations. A beautiful center-cut fireplace serves as a focal point for warmth and togetherness, while a detached garage and large barn with a finished second level offer additional functionality. This exceptional estate beckons discerning buyers seeking a haven of refined taste, enduring charm, and the opportunity to create lasting memories.

55 Good Hill Rd, Woodbury
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 24160616 MLS
Rare opportunity to own a spectacular 40-acre estate designed for exceptional horse care, training, and country living-while also offering the flexibility to create a private escape tucked away from it all. This remarkable property features a 150' x 80' indoor riding arena with excellent lighting and three overhead doors, along with an immaculate 9-stall barn complete with concrete floors and mats, stall windows, mounted hay racks, a hay chute, three cross-tie areas, and convenient hay storage with a conveyor system. Additional equestrian amenities include an outdoor wash stall, a 200' x 150' outdoor riding arena with stadium jumps, cross-country jumps woven throughout the property, and a 130' x 65' dressage arena. Five paddocks, 13 outdoor stalls, and ample room for expansion make this an exceptional setup for horse enthusiasts, trainers, or boarding operations. Thoughtfully sited to capture breathtaking views, the custom-built home overlooks the picturesque grounds from a stunning 90-foot wraparound deck. Inside, the cathedral-ceiling great room with a cozy wood stove flows into the kitchen, dining area, and bright sunroom, with French doors opening to the expansive deck for seamless indoor-outdoor living. The main level includes a bedroom and full bath, while the second-floor primary suite offers a walk-in closet and spa-like bath featuring a clawfoot soaking tub.

76 Cowles Rd, Woodbury
$1,400,000
4 Beds ⋅ 5 Baths ⋅ 24168051 MLS
Gloriously Peaceful, Private, Magnificent views...This exceptional residence among similar spectacular homes welcomes you with a dramatic two-story entry - designed for both refined entertaining and comfortable living. The heart of the home is a beautifully appointed chef's kitchen featuring porcelain countertops with waterfall island and slab backsplash. New 48' Sub-Zero refrigerator & a Sub-Zero 136-bottle wine fridge. Plus built-in professional expresso machine, a coffee-lover's dream! All Wolf appliance suite including a 6-burner gas cooktop, double ovens and microwave. The sun-filled breakfast nook flows effortlessly into the comfortable, inviting family room, where a striking marble fireplace and expansive bay window frame picturesque views of the property and distant hills. A set of sliders open to a large lawn-level deck for summer enjoyment and entertaining. The second floor is highlighted by an extraordinary primary suite designed as a private retreat. Luxurious space features a fireplace, an elegant sitting room, a spa-inspired bathroom with soaking tub, his & hers walk-in closets. Three additional bedrooms with en-suite bathrooms and a large Flex room complete upstairs. Dramatically transformed and enhanced to include all new 7" hardwood radiant floors. The spacious flat, fully fenced yard hosts a beautiful Gunite, heated, salt-water pool and hot-tub waterfall while enjoying the beautiful distant views. Extraordinary - Must See.

48 Coach Light Dr, Woodbury
Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.