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.

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All Recently Sold in Woodbury, CT

$975,000
3 Beds 3 Baths 24037167 MLS
A rare find, this ca 1860 cape sits on 2+ acres just outside of town and includes a cottage, in-ground pool, pool cabana, workshop, and potting shed. The home itself is the perfect size with three bedrooms and two full and one-half baths. The living room is highlighted by built-ins and exposed beams. The dining room with exposed beams has corner cupboard and French door to a stone terrace perfect for al fresco dining or a morning coffee. A fireplace adorns the eat-in kitchen and there is a 5-burner gas stove top, Bosch double oven and Subzero refrigerator. The primary bedroom is conveniently located on the main level and has a vaulted ceiling, spacious full bath and French door to rear patio. Upstairs you'll find the two other bedrooms, a full bath and foyer perfect for a reading nook or office area. The main level also includes a foyer, mudroom and laundry room. Beautiful hardwood floors throughout the home. The many updates include a generator (services house & cottage) and smart systems for thermostat and security. The grounds are lovely with mature perennial gardens, multiple patios, stonewalls and walkways, and a fenced in raised bed vegetable garden. There is a detached two bay garage and a detached 1 bay stone garage. The lovely 768 sq ft cottage is set away from the main residence & has kitchen, living/dining combo, two bedrooms, full bath on main level and lower level with half bath and laundry room. List of upgrades/updates available.

151 Flanders Rd, Woodbury

$970,000
4 Beds 4 Baths 24107125 MLS
Live your best life in Woodbury, CT, where charm, history, and natural beauty intertwine! The "Antiques Capital of CT", with a picturesque Main Street, historic homes, festivals, and scenic preserves. Imagine living in the heart of this idyllic setting! This 2005 home, on 4.5 acres, is meant for life, living, and entertaining. Upstairs, you'll find 4 generously sized bedrooms and 3 well-appointed bathrooms; 2 of which are ensuite, along with a convenient laundry area. On the main floor, there are living, dining, and family rooms, a half-bath, study, a dinette, and kitchen. There is a large attic and a bright walkout full basement which is partially finished with all walls and future rooms fully framed. Step outside and be amazed by the 40' in-ground heated pool, a spectacular custom-built pavilion and pool house with living-space, loft, a half bath, and a glorious outdoor shower. The star of the show is the full outdoor Viking kitchen & bar. Providing unforgettable experiences for gatherings of any size; Simple dinners or awesome larger celebrations! The expansive grounds offer the perfect mix of level terrain and picturesque hills, for outdoor fun in every season. Swimming, ATV, ball games, sledding and much more! 25 Curtiss Meadows is a camp-like getaway for close ones and friends and an immensely profound and treasured home for its residents. This gem is an absolute must-see. Don't miss the opportunity, schedule your private showing today and begin your next chapter

25 Curtiss Mdws, Woodbury

$952,000
4 Beds 5 Baths 24059188 MLS
Tucked away on a sought-after cul-de-sac, this open-layout home is crafted for exceptional entertaining. The light-filled, two-story foyer is framed by two sets of French doors: one opening to an office & the other leading to a living room that flows seamlessly into the dining room-an ideal setup for holiday gatherings. The custom kitchen, equipped with granite countertops, a center island, gas cooktop, walk-in pantry & dining area, overlooks the pool & patio. Adjacent to the kitchen is a sitting room & spacious family room featuring a fireplace & built-in bookcase. A generous 20x35 recreation room further enhances the home's entertainment options with a custom bar, vaulted ceiling, full bath & two sets of sliding doors that open to the pool, spa & patio area, creating a perfect indoor-outdoor experience. The upper level boasts a primary suite with a spacious bath & walk-in closet along with two additional bedrooms connected by a Jack & Jill bath. This floor also includes a craft/yoga room & laundry room. On the 3rd floor, a private fourth bedroom with a full bath provides an ideal space for nanny quarters or guests. The lower level offers 715 square feet of flexible finished space, perfect for a workout area with room for a golf simulator & includes ample storage & access to the 3-car garage. Outside, the grounds are complete with a gunite pool, spa, fire pit, stone wall & a fenced area, creating a tranquil oasis for relaxation & entertainment-all just minutes from town!

5 Bear Run, Woodbury

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