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382 Weekeepeemee Rd, Woodbury
$2,050,000
4 Beds ⋅ 4 Baths ⋅ 24159893 MLS
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 soapstone counters, a Sub-Zero fridge, Wolf 6-burner range & burnished nickel Waterworks fixtures. Every detail has been carefully curated, from soft-close drawers to premium finishes. Historic touches abound, including heartwood floors, an open hearth fireplace with a beehive oven & original millwork with hand-forged cast iron hardware. The primary bath is a spa-like retreat with a cast iron soaking tub, stone surround & custom vanity, while modern updates enhance the other baths with style & practicality. All new custom Anderson 400 Series windows flood every room with light while preserving the home's historic proportions. The large flat property invites outdoor enjoyment with a tranquil pond, mature 200-year-old trees & fenced-in vegetable garden. A restored English barn with a loft, 11-foot custom insulated steel barn doors, insulated and propane-heated garage, floor drains & updated electrical systems provide space for projects, storage, or entertaining.

382 Weekeepeemee Rd, Woodbury
509 Main St N, Woodbury
$1,752,500
6 Beds ⋅ 8 Baths ⋅ 24121221 MLS
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. Crafted w/warmth & character throughout, the home boasts wide board hardwood floors, coffered ceilings, French doors, exposed beams, & built-ins. With 13 thoughtfully designed rooms, the home features 6 generous bedrooms, 6 full bathrooms, & two 1/2 baths. Each bath w/radiant heated floors for comfort. Primary suite has 2 walk-in closets, & office space. At the heart of the home is a stunning, brand-new custom kitchen featuring handcrafted cabinetry, an 8-burner gas range, built-in coffee bar, & an elegant butler's pantry. The floor plan offers multiple spaces to live and unwind: a formal living room w/fireplace, a media/game room on the lower level, a dedicated home gym, & two convenient laundry areas. Additional fireplaces can be found in the eat in kitchen, primary suite, & lower level. Heated 2-car garage w/EV charging station & unfinished space above for future customization. The two-story barn offers storage & creative use. The beautifully manicured grounds are a celebration of nature: stone walls & lush gardens frame multiple outdoor living spaces. There are stone patios/walkways, covered porches, & the built-in grill is perfect for entertaining. Tap maple trees for syrup in winter, tend bees & gardens in summer, or press cider in the fall... this home is a year round experience!

509 Main St N, Woodbury
225 Old Sherman Hill Rd, Woodbury
$1,700,000
4 Beds ⋅ 5 Baths ⋅ 24072926 MLS
Discover refined country living in this remarkable Woodbury estate set on 33.98 private acres in sought-after Litchfield County. The 4,517 sq ft residence features 4 bedrooms, 4.1 baths, and bright, open interiors designed to capture serene views of distant hills. A spacious deck overlooks the sparkling saltwater gunite pool, creating an ideal setting for relaxation or entertaining. Equestrians will appreciate the immaculate 8-stall stable, 14 lush paddocks, and generous riding spaces surrounded by pastoral beauty. Completing the property is a 4-car garage and the peace and privacy that define Woodbury's countryside. This rare offering combines elegance, comfort, and the timeless appeal of New England living.

225 Old Sherman Hill Rd, Woodbury
76 Cowles 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
112 W Lake Rd Unit 112, Woodbury
$1,495,000
2 Beds ⋅ 2 Baths ⋅ 24185479 MLS ⋅ Woodlake BLDG.
Just 2 hours from New York City, this exceptional lakefront retreat offers a rare blend of privacy, natural beauty & turnkey luxury. Tucked at the end of West Lake Rd and bordered by the protected woodlands of Flanders Nature Center Preserve, the property enjoys sweeping, unobstructed views across pristine Lake Quassapaug to historic Tranquillity Farm, designed by McKim, Mead & White. Lake Quassapaug is a private lake with no public access & a 10-mph speed limit, creating an ideal setting for boating, fishing, swimming & year-round recreation. Private beach & dock provide direct water access, while the renovated lakeside cabana offers flexible space for a home office, fitness studio or retreat. Outdoor KIT, BBQ area & multiple patios, including a waterfront terrace, are perfect for entertaining. Renovated in 2020, the home features a beautifully appointed gourmet KIT with premium finishes & seamless flow to inviting living spaces. One of only a select few lakefront homes in Woodbury, it benefits from the town's favorable tax structure while being minutes to historic Main St, acclaimed restaurants & antique shops. Town of Woodbury recognizes 112 West Lake Road and a few other neighboring properties as condominium units. All other homes on the Lake are in Middlebury CT. Rare opportunity to own a fully renovated waterfront home with exceptional privacy, spectacular views & an unparalleled lake lifestyle.

112 W Lake Rd Unit 112, Woodbury
48 Coach Light Dr, 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
46 Grassy Hill Rd, Woodbury
$1,275,000
4 Beds ⋅ 4 Baths ⋅ 24188752 MLS
Beautifully updated and impeccably maintained, this custom Colonial offers timeless New England charm in a private setting with gorgeous views of a picturesque waterfall and babbling brook. Set on beautifully landscaped grounds with an additional lot included, the home features wide-board hardwood floors, crown molding, custom built-ins, plantation shutters, French doors, and three fireplaces. The eat-in kitchen offers granite countertops, premium appliances, and opens to warm, inviting living spaces including formal living and dining rooms, a family room with fireplace, private den/office, and screened porch. The spacious primary suite includes a fireplace, walk-in closet, and ensuite bath, with three additional bedrooms and updated bathrooms. The finished walk-out lower level provides flexible space for a recreation room, gym, media room, or guests. Outdoor living is exceptional with a wraparound porch, Trex deck, extensive stone patios, mature landscaping, scenic trails, and the soothing sights and sounds of the cascading waterfall. A rare offering combining privacy, elegance, upgrades, and natural beauty just minutes from town.

46 Grassy Hill Rd, Woodbury
68 Whittlesey Rd, Woodbury
$1,225,000
4 Beds ⋅ 4 Baths ⋅ 24130861 MLS
This magnificent Woodbury colonial, adjacent to 42 acres of open space, offers an unparalleled blend of elegance and tranquility. Surrounded by hiking trails, park like grounds and a serene brook. A light filled interior with soaring nine foot ceilings, graceful arches and an open flowing floor plan. The wraparound mahogany deck invites you to relax and take in the peace and quiet. The back patio, crafted with premium ipe decking, features tiered rock walls and a circular fire pit-perfect for entertaining or quiet evenings under the stars. Designed with quality and comfort in mind this home boasts I-beam construction, two wells, enhanced insulation, and durable HardiePlank siding, ideal for those who value sustainable, low maintenance living. Turn off the outside noise and rest assure this sanctuary will welcome you home with open arms.

68 Whittlesey Rd, Woodbury
101 Old Grassy Hill Rd, Woodbury
$1,200,000
4 Beds ⋅ 5 Baths ⋅ 24135665 MLS
"Where Luxury Meets the Landscape." Welcome to a home where nature and craftsmanship converge in breathtaking harmony. Nestled on five professionally landscaped acres, this country manor is a sanctuary of serenity and sophistication. A statuesque quarry of stone lines one side of the property, perfectly balanced by a tranquil body of water-inviting you to kayak, canoe, or skate through the seasons or perhaps just enjoy the resident eagles or osprey who make the area their home during some of the year. As you enter, the grand open staircase is the centerpiece of a 2-story wrap-around Foyer that sets the stage for the comfortable elegance this home inspires. Step inside and experience the artistry of design. Sunlight pours through expansive windows, illuminating exquisite millwork: coffered ceilings, oversized crown and baseboard moldings, solid raised paneling, and wide-board hardwood floors. Every detail speaks to the builder's commitment to timeless quality. The grounds are thoughtfully engineered for beauty and function-featuring a level yard with industrial grade drainage, a low-maintenance milled crushed stone driveway, double-tiered decking, and a refreshing outdoor shower along with new stone seating area, walkways in the backyard.

101 Old Grassy Hill Rd, Woodbury
61 Silver Brook Ln, Woodbury
$1,069,900
4 Beds ⋅ 4 Baths ⋅ 24177448 MLS
Exceptional Colonial in one of Woodbury's finest developments, beautifully set among similar distinguished homes at the end of Silver Brook Lane. Thoughtfully updated over the past five years with high-quality materials and careful attention to detail, this 4,000+ square foot residence offers an ideal blend of elegance, comfort, and modern convenience. The heart of the home is the stunning remodeled eat-in kitchen, complete with a large center island and all the features expected in a gourmet kitchen. The kitchen opens seamlessly to a generous family room with fireplace, coffered ceiling, and access to the rear level deck, creating a wonderful flow for everyday living and entertaining. The main level also includes a private office, formal living room, and formal dining room, all enhanced by hardwood floors and moldings. Upstairs, the luxurious primary suite features a dressing room or office, two walk-in closets, a soaking tub, and a custom tiled shower. Three additional bedrooms complete the upper level, including two with en-suite baths and one with an open stairway leading to a third floor sleeping area.

61 Silver Brook Ln, Woodbury
40 Main St N, Woodbury
$1,000,000
24154908 MLS
Prime Commercial Real Estate along Main Street Woodbury. 11800 sq feet of retail, medical and office space. Excellent investment opportunity!

40 Main St N, Woodbury
25 Curtiss Mdws, 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
35 Coach Light Dr, Woodbury
$925,000
4 Beds ⋅ 6 Baths ⋅ 24158582 MLS
This exceptional residence welcomes you with a dramatic two-story entry and is designed for both refined entertaining and comfortable everyday living, just minutes from town. There is a formal living and dining room with rich hardwood flooring, creating a sophisticated setting for gatherings. The heart of the home is a beautifully appointed chef's kitchen featuring granite countertops, a breakfast bar, and KitchenAid and Thermador appliances. The sun-filled breakfast nook flows effortlessly into the inviting family room, where a striking stone fireplace and expansive bay window frame picturesque views of the property. A set of sliders open to a large composite deck for summer enjoyment. The second floor is highlighted by an extraordinary primary suite designed as a private retreat. This luxurious space features a spa-inspired bath, two walk-in closets, and an elegant sitting room with fireplace and built-ins, along with a private office or dressing room. Three additional en-suite bedrooms-including one currently used as a gym-offer comfort and privacy for family and guests. The partially finished walk-out lower level is filled with natural light, offering impressive 9+ foot ceilings and exceptional versatility. Anchored by a beautiful stone fireplace, the space includes two additional finished rooms and a full bath-ideal for recreation, guest accommodations, or extended living. There is a relaxing patio, peach trees, pear trees and raspberries. A must see!

35 Coach Light Dr, Woodbury
52 Steeple View Ln, Woodbury
$922,000
4 Beds ⋅ 3 Baths ⋅ 24145387 MLS
Nestled within an established enclave of Woodbury-a quintessential New England town-this 2001 four-bedroom Colonial offers a refined blend of understated, classic architecture, and modern comfort. Ideally located just five minutes from Main Street, the home is privately sited at the end of a quiet cul-de-sac, bordered by tranquil woodlands. The interior showcases richly layered trim details, including deep crown moldings, wainscoting, and substantial baseboards in the formal spaces, creating an elegant and tailored aesthetic. The home thoughtfully balances formal entertaining areas with an open-concept layout. The gracious foyer, flanked by a formal Dining Room and a Living Room featuring custom woodworking, leads into the expansive, sun-filled Kitchen and Family Room. Designed for entertaining, the formal Dining Room features a beautiful custom built-in and a charming bay window and connects to the Kitchen via a functional hallway ideal for use as a butler's pantry or bar. This hallway provides access to a combined mudroom/Laundry Room and Half Bath. The Kitchen and Family Room form the heart of the home, featuring a cozy gas fireplace, a six-burner Wolf range, and direct access to a private Deck and stone terrace-perfect for outdoor dining and summer gatherings.

52 Steeple View Ln, Woodbury
557 Upper Grassy Hill, Woodbury
$885,000
4 Beds ⋅ 4 Baths ⋅ 24158380 MLS
Welcome to Upper Grassy Hill Living!

557 Upper Grassy Hill, Woodbury
99 Plumb Brook Rd, Woodbury
$850,000
4 Beds ⋅ 3 Baths ⋅ 24138603 MLS
Tucked away in a private and peaceful setting, this beautifully appointed Colonial offers an exceptional blend of comfort, style and functionality. Hardwood floors and custom millwork are showcased throughout, creating a warm and refined atmosphere. A dramatic two-story foyer welcomes you and is flanked by a first-floor office with transom-topped French doors for privacy. Opposite, a double opening with a transom window leads to the formal dining room, which flows seamlessly into the formal living room-ideal for entertaining. The spacious eat-in kitchen is thoughtfully designed with stainless steel appliances, granite countertops, a center island, and a dining area with sliders leading to a large patio-perfect for effortless indoor-outdoor living and entertaining. The kitchen opens to a generous family room featuring a fireplace and custom built-in bookcases, creating a comfortable and inviting gathering space. A half bath and convenient mudroom complete the main level. Upstairs, the home offers four bedrooms, all with wall-to-wall carpeting, including a spacious primary suite with tray ceiling and a full bath with double vanities, a soaking tub, and a walk-in shower. A dedicated laundry room enhances everyday convenience. The unfinished lower level provides excellent potential for future living space, allowing the next owner to tailor it to their needs. Enjoy a large, level yard ideal for recreation, gardening or gatherings.. Your peaceful retreat awaits!

99 Plumb Brook Rd, Woodbury
17 Curtiss Rd, Woodbury
$825,000
3 Beds ⋅ 3 Baths ⋅ 24192675 MLS
Welcome to 17 Curtiss Road! This one-of-a-kind 1.8-acre property offers the perfect blend of historic charm and modern convenience, featuring a well-maintained 1900 single-family home, an attached 2-car garage, and an impressive detached 24' x 50' heated 3-car garage built in 2022. Step inside the home and be welcomed by a charming foyer leading to wide-board hardwood floors and six mini-split systems (2019) that provide efficient heating and cooling throughout. The inviting living room features custom built-ins and flows seamlessly into the spacious kitchen, complete with stainless steel appliances, ample cabinetry, recessed lighting, a pantry closet, and basement access. Just off the kitchen is an updated half bath with tile flooring and laundry hookups. Off the kitchen the elegant dining room offers crown molding and plenty of space for entertaining. Completing the main level is a spacious primary suite with double closets and a beautifully updated full bath boasting heated tile floors, a skylight, recessed lighting, chair rail molding, and a linen closet. An adjoining den with custom built-ins provides the perfect space for a home office, reading room, etc. Upstairs, you'll find two generously sized bedrooms, each with walk-in closets and shared access to a Jack-and-Jill bathroom featuring a dual-sink marble vanity. The basement includes 200-amp electrical service, Energy Star hot water heater, well tank (2018), and additional laundry hookups. Outside, enjoy

17 Curtiss Rd, Woodbury
670 Main St N, Woodbury
$825,000
2 Baths ⋅ 24105595 MLS
PRICE IMPROVEMENT !!!! Own an Iconic Connecticut Restaurant. This family run restaurant and adjacent residence has been under the same ownership since the 1950s. This turnkey operation offers great potential to continue current operations or a new culinary vision. Generations of Success, over 70 years in operation, built on community trust and steady clientele. Well-appointed kitchen, dining area, and full-service facilities. NDA and Proof of funds Required: Confidential information available upon signing. Don't miss this unique chance to own a time-tested restaurant and property combo. Reach out today.

670 Main St N, Woodbury
148 Flanders Rd, Woodbury
$810,000
3 Beds ⋅ 4 Baths ⋅ 24149131 MLS
Country Living Abounds with this unique custom built one of a kind Cape nestled on 5 secluded acres. This home features an open floor plan with post and beam construction, beamed ceilings, oak floors, Plaster Walls, fully applianced Kitchen with breakfast bar, a spacious Family Room with brick fireplace, built-ins, & slider leading to back deck. The Living Room with fireplace is adjacent to a spacious Dining Room area & slider leading to large deck with access to side yard. Enjoy some quiet time in the cozy Library with fireplace and built-ins. First floor also has an Office as well as a full Bathroom. As you ascend the stairs to the second floor you will marvel at the unique lighted brick archway. Second floor boasts of a lovely Primary Bedroom Suite with brick fireplace & raised hearth, walk-in closets, Full Bath with tub, shower & vanities, and slider leading to balcony, and Two other large Bedrooms with skylights, Full hallway Bathroom, & Laundry Room with utility sink. With In-law/apartment the total living space is 3882 sqft. This home is convenient to Woodbury's town center, shops, top restaurants, antiquing, and recreation with hiking trails & nearby lake. This property has so much to offer!

148 Flanders Rd, Woodbury
6 Strong Field Rd, Woodbury
$775,000
4 Beds ⋅ 3 Baths ⋅ 24115107 MLS
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 most desirable enclaves. Designed for discerning buyers, this 4-bedroom, 2.5-bath masterpiece blends architectural sophistication with everyday comfort. Inside, you're welcomed by an airy open-concept floor plan, enhanced by dramatic vaulted ceilings, expansive windows, and finely crafted wide-plank hardwood flooring throughout. At the heart of the home is a designer gourmet kitchen-a showcase of form and function-featuring premium quartz countertops, custom cabinetry, a professional-grade appliance suite, and an oversized island perfect for hosting or gathering. The adjoining great room offers a warm, elegant atmosphere anchored by serene views and refined finishes. The first-floor primary suite is a luxurious retreat with a spa-style bath, dual vanities, walk-in glass shower, and a generous walk-in closet. A main level office is idle for work-from-home living. Upstairs, three additional bedrooms and a full bath accompany a spacious loft, perfect for a media lounge or reading retreat. Tucked at the end of a quiet cul-de-sac, just minutes from historic Woodbury's shops, dining, nature preserves, and top-rated schools, this home is a rare opportunity to enjoy elevated country living with modern convenience. Unmatched style, craftsmanship, and comfort-schedule your private showing at 6 Strong Field

6 Strong Field Rd, Woodbury
62 Heritage Dr, Woodbury
$765,000
4 Beds ⋅ 3 Baths ⋅ 24185801 MLS
Beautifully renovated 4-bedroom, 2.5-bath ranch set on a spacious corner lot in one of Woodbury's most desirable locations. Just two streets from Woodbury's nationally recognized Main Street, this home offers the perfect combination of modern updates, comfortable living, and exceptional outdoor entertaining. The complete interior renovation began in 2023 and has recently been completed, creating a truly move-in-ready home. At the heart of the property is a stunning open-concept kitchen featuring stylish finishes and thoughtful design, seamlessly flowing into the dining area and living room-ideal for both everyday living and hosting family and friends. The private primary suite offers beautiful views of the backyard retreat, while three additional generously sized bedrooms and a fully renovated full bathroom provide plenty of space for family and guests. Every bathroom in the home has been tastefully updated, complementing the home's fresh, modern feel. Step outside to your own backyard oasis. The expansive outdoor space features a large in-ground swimming pool, dedicated BBQ area, and ample lawn space for entertaining, yard games, and summer gatherings. Whether you're hosting a crowd or enjoying a quiet evening at home, this outdoor setting is sure to impress. Adding even more versatility is the separate pool house, complete with accommodations that offer endless possibilities for guests, extended family, a home office, or private retreat.

62 Heritage Dr, Woodbury
393 Middle Road Tpke, Woodbury
$765,000
4 Beds ⋅ 4 Baths ⋅ 24123798 MLS
The Tomlinson House, built in 1783, offers a rare chance to own a piece of Woodbury's history. Set on 5+ acres along Middle Road Turnpike, with an additional .87-acres across the street, this 4-bedroom Colonial combines period charm with enduring potential. Historic character is evident throughout-restored wide-board hardwood floors, original millwork, and four (non-working) fireplaces, including a dramatic walk-in hearth with beehive oven. The floor plan provides the best of both worlds: a welcoming open flow between the kitchen and family room for gatherings around the hearth, balanced with dedicated dining and living rooms for more traditional entertaining. A main-level office/bedroom and screened porch add versatility. Upstairs, front and back staircases lead to three spacious bedrooms, two full baths, and a third-floor office with half bath. Recently refinished hardwood floors continue across the upper levels, preserving the home's warmth and continuity. The level property is a highlight...park-like and pastoral, with stone walls, a brook, pond, mature plantings, screened porch and a bluestone patio for outdoor living. A two-car garage with attached shed offers workshop or storage space. With strong bones, timeless appeal, and room to grow, the Tomlinson House is a unique offering in one of Woodbury's most desirable corridors

393 Middle Road Tpke, Woodbury
54 Bear Run, Woodbury
$750,000
4 Beds ⋅ 3 Baths ⋅ 24160410 MLS
HIGHEST & BEST OFFERS DUE BY NOON ON MONDAY, 4/13/26 - Fantastic opportunity to own this beautifully maintained 4-bedroom, 2.5-bath Colonial on lovely cul-de-sac neighborhood, privately set back on a wooded lot which backs up to Land Trust in sought-after Bear Run Estates. Proudly offered by its original owners, this home features numerous updates including a high-efficiency propane furnace (2023), central A/C (2024), and whole-house Generac generator (2023). A welcoming 2-story foyer leads to a fantastic eat-in kitchen with granite countertops, tiled backsplash, stainless steel appliances, breakfast bar, under-cabinet lighting, and pantry. The desirable open floor plan flows into the inviting family room with a propane fireplace and custom bookshelves. A private home office with a wall of built-ins, formal dining room, separate living room, and powder room with laundry complete the main level, all with beautiful hardwood flooring. Upstairs, the spacious primary bedroom suite offers exposed beams, walk-in closet, and renovated bath with soaking tub, tiled walk-in shower, and heated floors. Three additional generously sized bedrooms share a full bath. The walk-out lower level provides flexible finished space for a recreation room, gym, or guest area, plus additional unfinished storage space for future expansion. Professionally landscaped grounds feature a storage shed and maintenance-free Trex deck, perfect for outdoor entertaining.

54 Bear Run, Woodbury
118 Good Hill Rd, Woodbury
$750,000
4 Beds ⋅ 3 Baths ⋅ 24132227 MLS
Beautifully Spacious Colonial in the Heart of Woodbury. This inviting in-town colonial offers the perfect balance of charm and convenience-just 5 minutes from town parks, top-rated Woodbury schools, shopping, and restaurants. Freshly refinished hardwood floors bring a warm glow throughout the home's 3,200 sq. ft. of well-crafted living space. The main level features a sun-filled kitchen and great room with 9-foot ceilings, a center island, eat-in area, and a cozy fireplace. A welcoming living and dining room, a practical mud/laundry room, and a private office with elegant French doors complete the first floor. Upstairs, you'll find three generously sized bedrooms, along with a primary suite with a walk-in closet and luxurious bath. A versatile recreation room with built-in bookshelves-accessible from both the main hall and the primary suite-offers the perfect space for a library, playroom, or studio. Set on a level lot, the home invites outdoor enjoyment with a private back deck, a charming front porch, and ample room for weekend gatherings.

118 Good Hill Rd, Woodbury
17 Carriage Ln, Woodbury
$740,000
5 Beds ⋅ 4 Baths ⋅ 24171620 MLS
Center Hall Colonial with Full In-Law! This majestic brick facing home flaunts its location atop a private lot overlooking sprawling scenic views. Main level features a two-story foyer, formal dining room w/hardwoods & pocket doors leading to a high-end kitchen w/stainless steel appliances including a gas stove. The kitchen delivers with granite tops, upscale cabinetry, breakfast bar, & eat-in area facing French doors opening to a welcoming living room w/hardwood, vaulted ceilings & brick fireplace. The family room/study pulls in the strength of hardwoods, tray ceiling & plenty of natural lighting. The main level bedroom/office & guest bathroom complete this central level. Continuing the journey upstairs & you will be greeted by spectacular views from the transom window aloft the staircase. The path to the primary bedroom suite introduces a tray ceiling, large walk-in closet & full bath w/whirlpool tub, shower stall & skylight. The three additional bedrooms are generous in size while the laundry room, common full bath w/double sink vanity & tub/shower concludes this upper level. The main level full in-law is a desirable focal point showcasing a separate entry, remodeled eat-in kitchen, living room w/vaulted ceiling, gas fireplace, large bedroom, remodeled full bath, laundry closet & staircase to garage w/private basement. Exterior features two new A/C condenser units, custom retaining walls, large deck & three car garage. This sought-after home exceeds all expectations!

17 Carriage Ln, Woodbury
289 Main St S, Woodbury
$732,200
6 Baths ⋅ 24125766 MLS
The iconic Lewis Building is in a prime location at the intersection of Rt 6 and Rt 317, next to the town office buildings and library. Can't beat this location! It offers a valuable opportunity for those looking to leverage the growth and vibrancy of the area. MSD zoning offers 3 commercial rentals and 3 residential rentals. Fully occupied with little turnaround. Rents generate a great income. Well maintained with recent upgrades. With excellent visibility this investment opportunity is not to be missed.

289 Main St S, Woodbury
432 Quassapaug Rd, Woodbury
$725,000
4 Beds ⋅ 4 Baths ⋅ 24137870 MLS
Welcome to Eastfield Farms Etates. This Colonial features an open floor plan for comfortable everyday living an entertaining alike. The large foyer flows to both the formal living room with french doors and formal dining room. Both with crown molding and accent lighting. Just down the hall step into the spacious kitchen with center island, granite counter tops stainless appliances. The dining area flows to the family room with stone wood burning fireplace and french doors leading the the back deck. The laundry room is conveniently located on the main level through the mud room. Round out the first floor with a half bath. Hardwood floors throughout the first floor. The upper level offers primary bedroom with four closets and a large bathroom with jetted tub and double sink vanity. The second bedroom is large enough to have its own seating area. There are two other bedrooms and a large bathroom. The attic has pull-down stairs. The basement is unfinished with plenty of storage. You will enjoy this lovely level landscaped spacious yard, two car attached garage and full shed. Convenielty located to Watertown and Middlebury, 90 minutes to NY City.

432 Quassapaug Rd, Woodbury
58 Good Hill Rd, Woodbury
$710,000
3 Beds ⋅ 4 Baths ⋅ 24155513 MLS
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. This stately circa 1845 home blends historic character with comfortable living. Set along scenic Good Hill Road and surrounded by lush, established gardens, featuring a black bottom gunite pool, private terrace, welcoming front porch, and charming potting shed, creating a peaceful retreat. Inside, a sun-filled front-to-back living room offers elegant moldings, custom built-ins, and a wood-burning fireplace. The adjacent study, with built-in bookcases and a second wood-burning fireplace, provides an ideal home office or quiet sitting room. The warm and functional kitchen includes solid wood, custom cabinetry, a brand-new Thor stove, and a breakfast nook. A versatile side room, with full bath, offers flexibility for a pantry, office, or first-floor bedroom. The dining room, just beyond the wet bar, overlooks the terrace and is perfect for gatherings. Upstairs are three spacious bedrooms and two full baths, including a primary bedroom with fireplace, wall of closets and private en-suite. Cedar-lined closets are found throughout. A classic two-story barn provides three-car parking plus ample storage or hobby space and an area to lounge by the pool. Central air and a whole-house generator complete this idyllic country retreat. Good Hill leads directly to Main St. and Hollow Park, road construction ends in May

58 Good Hill Rd, Woodbury
19 Hillview Ln, Woodbury
$707,000
3 Beds ⋅ 4 Baths ⋅ 24147161 MLS
Nestled within the exclusive South Brook community, 19 Hill View Lane offers timeless New England charm paired with exceptional craftsmanship. This beautifully appointed 3 bedroom, 3.5 bath cape colonial is rich in architectural detail, featuring refined millwork, quality finishes, and a thoughtful layout designed for both everyday living and elegant entertaining. The main living spaces flow effortlessly, filled with natural light and a warm, inviting ambiance that immediately feels like home. Beneath the main living area lies a space designed purely for enjoyment. The finished lower level features a Roman-style sauna, wet bar, recreation room, and a full bath, creating the perfect space for entertaining, relaxing, or unwinding at the end of the day. Set on a picturesque lot within a quiet, well maintained neighborhood, this home offers a rare blend of privacy and community. Residents enjoy award-winning dining, entertainment and boutique shopping within just a quarter mile from home. Located just minutes from the historic town center of Woodbury, scenic parks and highly regarded schools all while being centrally positioned for easy access throughout Litchfield County. A truly special home where classic design meets refined living. Association rules apply.

19 Hillview Ln, Woodbury
43 Mill Rd, Woodbury
$705,000
3 Beds ⋅ 3 Baths ⋅ 24152365 MLS
Experience the ease of single-level living in this lovingly maintained residence. Nestled on a private lot bordering acres of open space, this home is a study in thoughtful design and architectural detail. The interior is defined by a sense of scale and light, featuring hardwood floors, elegant tray ceilings, and custom crown moldings. At the heart of the home, the spacious living room is anchored by a classic fireplace and handsome built-ins. The eat-in kitchen invites warmth with the "chestnut glow" of its cabinetry, beautifully paired with polished granite countertops and a convenient breakfast bar. Seamlessly blending indoor and outdoor living, the home features a three-season sunroom, complete with a "family room" style fireplace-the perfect setting for crisp New England evenings. Designed for ultimate privacy, the "split-wing" floor plan separates the guest quarters-where the bedrooms share a refined marble-clad bath-from the expansive primary suite. This sanctuary features a walk-in closet and a versatile in-room nook, perfect for a private seating area or workspace. For the professional, a dedicated separate office rounds out the living areas.

43 Mill Rd, Woodbury

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