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6 Easy St, Woodbury
$250,000
3 Beds ⋅ 2 Baths ⋅ 24179875 MLS
** INVESTORS TAKE NOTICE! ** Nestled in the desirable town of Woodbury, this 3 bedroom, 1.5 bath Colonial presents a unique opportunity to restore and reimagine a property full of charm and potential. Featuring hardwood flooring throughout the majority, spacious interiors, newer appliances, and some more recently installed mechanicals, this home offers a solid foundation for renovation and personalization. A remarkable oversized barn/garage adds tremendous value and versatility. This space is ideal for contractors, collectors, a workshop space, storage, hobbyists, and many other possibilities. The peaceful setting, mature landscape, and generous lot size create the perfect backdrop for a thoughtful transformation. Whether you're an investor, flipper, or buyer with a vision, this property offers the chance to unlock significant potential in a highly sought-after Woodbury location. Property is being conveyed as-is. BUYER/BUYERS AGENT TO DO DUE DILLIGENCE - SELLER/SELLER'S AGENT HAS NO PERSONAL KNOWLEDGE OF THE PROPERTY AS IT IS AN ESTATE

6 Easy St, Woodbury
520 Washington Rd, Woodbury
$547,500
3 Beds ⋅ 2 Baths ⋅ 24191493 MLS
Classic 1800s vintage Colonial in Connecticut's most charming town! Located within a short drive of all major conveniences, area private/public schools and parks, this three bedroom, two bath home has something for everyone! Situated on a beautifully level lot, enjoy your 1.55 acres by throwing the ball around, entertaining on your slate side patio or terrace area. The backyard barn, named the "Carriage House", is a unique feature of the property that is just waiting for you to cultivate your favorite hobby. On the main level of the home you will find a spacious country kitchen with hook up for a woodstove. The formal dining room can fit the relatives for the upcoming holiday season, and the formal living room, with center fireplace, beams with natural light! Rounding out the first floor is a study with custom-built bookcases and a full bath off the kitchen. Upstairs are spacious bedrooms, a full bath with clawfoot tub, and a bonus room, currently used as another bedroom. Lastly, the walk up attic is fully floored and highly functional for your storage needs or other use. Come and appreciate how this property reflects Woodbury's 19th century antique flair!

520 Washington Rd, Woodbury
18 South St, Woodbury
$629,000
4 Beds ⋅ 3 Baths ⋅ 24188362 MLS
Sited privately on 2.7 scenic acres in Woodbury's desirable Cardinal Hill neighborhood, this classic four-bedroom Colonial offers a perfect blend of quiet country living and everyday functionality. As part of a low-fee, self-managed neighborhood association, residents enjoy a wonderful sense of privacy and peace of mind. The main level features a traditional flow, including a formal living room and a separate dining room ideal for gatherings. Across the back of the home, a comfortable, open living space connects the eat-in kitchen-complete with a center island bar-to a cozy family room centered around a fireplace. This bright living area looks out to serene, elevated treetop views. A spacious pantry, dedicated laundry room, and a half bath complete the well-organized first floor. Upstairs, the primary bedroom suite features a private full bath and a spacious walk-in closet. Three additional bedrooms are nicely proportioned and share a full hallway bath. A traditional home in a peaceful, established setting just a short drive from the vibrant shops, eateries, and historic charm of downtown Woodbury.

18 South St, Woodbury
2 S Mdws Unit 2, Woodbury
$347,000
3 Beds ⋅ 3 Baths ⋅ 24156207 MLS ⋅ Woodlake BLDG.
New Price-Point on this lovely upscale residence! Don't miss the opportunity for a vacation at home "Woodlake Life Style" Each room is thoughtfully purposed and decorated with classy features.A spacious "open" concept kitchen includes "Corian" countertops. Cherry toned flooring adds a warm welcome to the first floor, as does the working fireplace. The 1st., floor powder room is oversized & updated. Upstairs, the primary bedroom bath is thoughtfully renovated: notice the addition of the "closet system". You will also note the convenient feature of the laundry - in close proximity to the primary bedroom. The Lower Level is finished and provides ample storage. The garage is partitioned from the other garage units. You will love exploring Woodbury and all it has to offer. Recently voted CT's Best Small Town by The Boston Globe and Reader's Digest. There are Restaurants galore, many featuring farm to table cuisine. Woodbury is home to two Main Street Greens & lovely period homes. Woodbury is part of CT's Antique and wine trail. Shop Boutiques & Garden Ctrs. Hollow Park, Flanders Nature Ctr., Learning & Performing Art Centers, The Glebe House Museum & hiking trails, are just a few suggestions that make Woodbury Special. Close to private schools. The Commute east or west on I-84 is easy! Its time to plan your 2026 move! 2025 New Heat Pump and Attic "Blown-in" insulation, keeps this residence toasty warm. Stay tuned for info on Woodlake's Community Room Reopening!plan your tour soo

2 S Mdws Unit 2, Woodbury
16 Cross Brook Rd, Woodbury
$612,500
3 Beds ⋅ 2 Baths ⋅ 24177873 MLS
Fantastic Potential in this home. Three bedroom Cape Cod sitting on 5.50 acre lot with a giant barn that has great potential living space to convert into an in-laws set up, office, studio space or music studio to fit your lifestyle. Home freshly painted interior and exterior. Renovated kitchen with all new countertops and Italian farmhouse sink, floors, Pantry, refreshed cabinets. All newer energy star appliances. Updated bathrooms- new vanities, tile, floor, and walk-in shower in upstairs bath. Walk out into your large screened in porch to enjoy the beautiful quiet and nature surrounding you in your lovely home. Giving you a peaceful retreat. New roof 2022. New heat pump hot water heater 2022 . New water holding tank 2025. Mini Splits installed in 2020. Entire house water filtration system. New cast iron woodstove installed in 2021 with refaced fireplace. Lots of space to run and play. Private hiking and biking trails with a campsite at the top of the property complete with fire pit. Grow a Beautiful garden of vegetables, with pretty flowers and flowering trees surrounding you. The lot is large enough for poultry or livestock for those of you with Love of animals? The two car garage has electric car outlet. 9.8 kW Solar array installed 2020.Seller owned Solar panels on the property for those energy saving consumers. So much potential, so much to see, schedule your tour soon!

16 Cross Brook Rd, Woodbury
4 Woods Way Unit 4, Woodbury
$230,000
2 Beds ⋅ 2 Baths ⋅ 24178857 MLS ⋅ Woodlake BLDG.
Nestled in the desirable Woodlake community, this townhouse at 4 Woods Way offers the perfect blend of comfort, convenience, and cozy living. The inviting layout features a bright and spacious living area with hardwood floors, a brick wood burning fireplace, open-concept dining, and easy access to a private deck-perfect for relaxing or entertaining. The kitchen offers generous cabinet storage and a functional design. Just off kitchen is a nook great for reading, coffee or an office. Upstairs, the primary bedroom includes carpet, ample closet space and a private bath, including a main bath with tub, while the second bedroom provides comfort and privacy for guests. An unfinished lower level with tall ceiling offers endless possibilities for future expansion, storage, or recreation space. Laundry hook-up is located in this area. Enjoy all that Woodlake has to offer, including scenic walking trails, lake, tennis court, clubhouse (currently under construction) and beautifully maintained grounds. This year-round living delivers the ideal Woodbury lifestyle. Minutes from Southbury and Main Street shops. Commutable having I-84 a few miles away.

4 Woods Way Unit 4, Woodbury
134 Old Sherman Hill Rd, Woodbury
$430,000
3 Beds ⋅ 2 Baths ⋅ 24179907 MLS
Welcome home to this charming 3-bedroom, 2-bath ranch, perfectly situated on a lovely lot. This home offers comfortable one-level living with a bright and inviting floor plan designed for everyday living and entertaining. The spacious living areas flow seamlessly into the kitchen and dining space, while three generously sized bedrooms provide ample room for family, guests, or a home office. Enjoy the convenience of two full baths and the beauty of the outdoor setting, featuring a private backyard ideal for relaxing, gardening, or hosting gatherings. The oversized two car garage allows for plenty of storage. This is your chance to live in the beautiful and desirable town of Woodbury. This home is being sold AS IS.

134 Old Sherman 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
38 Mountain Rd, Woodbury
$477,000
3 Beds ⋅ 3 Baths ⋅ 24174440 MLS
Welcome to 38 Mountain Road, a perfect blend of functional living space and privacy while still offering a close proximity to town. Upon entering you are greeted with a warm and welcoming living room. This space flows into the dining room which is right next to the remodeled kitchen making dinner hosting a breeze! The kitchen offers a view of your private back yard from the window and beautiful granite and tile. Easily transition from in home cooking to grilling outside with the backyard just a step away. The first floor is completed with a family room featuring a slider door leading out to your brand new patio. This family room enjoys the same private view as the kitchen and includes a cozy fireplace. A half bath with laundry, an over sized closet for storage and access to your two car garage completes this level. Upstairs you will find a generous sized primary bedroom with a walk in closet and private full bathroom. Two more bedrooms offering ample space and another full bath complete this level. Hardwood floors, beautiful trim work, and an abundance of natural light are just a few features that you may enjoy. Home was reinsulated in 2023 making it more energy efficient.

38 Mountain Rd, Woodbury
3 Tamarack Ln Unit 3, Woodbury
$276,375
2 Beds ⋅ 3 Baths ⋅ 24162115 MLS ⋅ Condos At Woodlake BLDG.
Welcome to this well-maintained condo offering comfortable living in a desirable Woodbury location. This inviting unit features a bright and open layout with spacious living areas, an updated kitchen, and generously sized bedrooms. Enjoy the ample storage and a private outdoor space perfect for relaxing or entertaining. Nestled in a quiet, well-kept complex close to local shops, dining, and major routes, this home offers a perfect blend of comfort, convenience, and low-maintenance living.

3 Tamarack Ln Unit 3, Woodbury
437 Middle Road Tpke, Woodbury
$517,000
3 Beds ⋅ 2 Baths ⋅ 24173270 MLS
Everything has already been done for you. Just move in, unpack, and enjoy the ease of single-floor living in this beautifully renovated ranch with endless potential below. Completely renovated and truly move-in ready, this home offers effortless living with every major updated already completed. From the brand-new HVAC system and newly installed septic to new windows, lighting, interior and exterior paint, driveway, and front walkway, this property has been thoughtfully upgraded from top to bottom. At the heart of the home is a stunning new kitchen that opens seamlessly to the dining and living areas, creating the perfect flow for both everyday comfort and entertaining. The beautifully updated fireplace with new stonework and a floating mantel adds warmth and character, while all-new bathrooms bring a fresh, modern feel throughout. And don't let the size fool you - the expansive unfinished basement significantly increases the home's potential. Complete with a newly updated half bath, this lower level offers an incredible opportunity to create additional living space, whether you envision a family room, home office, gym, guest suite, or playroom. Outside, the expansive yard provides plenty of space to relax, entertain, or enjoy the outdoors. Turnkey, low-maintenance, and full of future possibilities, this home offers the perfect combination of comfort, convenience, and room to grow.

437 Middle Road Tpke, Woodbury
104 Hard Hill Rd, Woodbury
$452,000
3 Beds ⋅ 1 Baths ⋅ 24178085 MLS
Nestled along a country road on a cul-de-sac, this charming home offers the perfect blend of warmth, comfort, and convenience. A welcoming entry greets you with soaring ceilings, wood floors, and a propane stove that adds both character and cozy ambiance. The spacious country kitchen is designed for gathering, featuring vaulted ceilings, a large center island, stainless steel appliances, and an open feel ideal for entertaining family and friends. Just off the dining area, step down to an expansive patio - the perfect setting for morning coffee, summer picnics, or outdoor entertaining. Set on a full acre, the private front and back yards provide plenty of space for gardening, recreation, and relaxing in a peaceful setting. Just a few steps upstairs, the oversized primary bedroom offers generous space along with plumbing already in place for a future full bath. A large walk-in closet completes this inviting retreat. The full bathroom is conveniently located at the top of the stairs, easily accessible for guests and everyday living. A spacious two-car garage and nearby laundry area add to the home's functionality and convenience. Pride of ownership shines throughout this lovingly maintained, one-owner home. Enjoy country living with the convenience of being just minutes from shopping, schools, and commuter routes. Highest and best by Friday, 5/29 8PM.

104 Hard Hill Rd, Woodbury
23 Lower Commons, Unit 23, Woodbury
$263,000
2 Beds ⋅ 3 Baths ⋅ 24160938 MLS ⋅ Woodlake BLDG.
Note New Price-point! REFURBISHED, fresh paint, move in ready W/tile entry. The Kitchen has new S.S. appliances, loads of cabinet storage, spacious workspace for the chef! The first floor includes the convenience of laundry and a 1/2 Bath. Hardwood floors in the living room adds to the inviting ambiance. There is a fireplace: it can easily become working with the insert of a Pellet or Wood-burning stove insert. The Woodlake Office will guide you w/the easy permit process. New carpet upstairs. The Primary Bedroom is ensuite and offers plenty of closet space. The lower level is a spacious "clean" canvas; finish to suit your needs... perhaps a media room, home office, work out room, storage etc. Please see Prop. Disclosures RE: Fee structure. With HOA, WTD & Town of Woodbury. Note with new budgets pending: the stated fees may change July 1st, 2026. Woodbury is a quintessential Town: Recently voted the Best Small Town In CT: by the Boston Globe and Readers Digest. Main Street is picturesque with period homes and two village greens. Activities at Hollow Park, Flanders Nature Center, Antique and boutique browsing, The CT wine trail, The Glebe House Museum, learning and performing arts centers, not to be missed; fabulous restaurants to suit everyones palate. You will enjoy living the vacation at home, "Woodlake Life Style". A gem of a community with on-site management to ensure needs are promptly addressed. Watch for the summer of 2026 reopening of the Clubhouse Community Center

23 Lower Commons, Unit 23, Woodbury
20 Stagecoach Rd, Woodbury
$635,000
4 Beds ⋅ 3 Baths ⋅ 24184647 MLS
Summer opportunity in a highly sought-after neighborhood featuring a private inground pool and backyard retreat. This one checks all the boxes-from cul-de-sac living to privacy and a great setting. Spacious 4-bedroom Colonial with hardwood floors, fireplace, and a partially finished walkout lower level. Sold strictly as-is and priced aggressively for a quick sale. Sellers have secured their next home and must move quickly. Needs very little to shine: strong bones, great location, and immediate equity potential. Opportunities like this don't last.

20 Stagecoach Rd, Woodbury
207 Grassy Hill Rd, Woodbury
$650,000
3 Beds ⋅ 2 Baths ⋅ 24173939 MLS
Nestled on a picturesque 2+ acre park-like setting, this beautifully maintained 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and natural beauty-with the ease of one-level living. Designed with both style and functionality in mind, the sun-filled open layout is enhanced by vaulted ceilings, skylights, and elegant bay windows, creating a bright and airy atmosphere throughout. The heart of the home features a chef's kitchen with a large island that flows seamlessly into the family room, with stone gas fireplace making it perfect for both everyday living and entertaining and adds warmth and character. A formal dining room and living room offer additional space for gatherings. The main level includes a spacious primary suite with a full bath, along with two additional bedrooms and a full hall bath. Enjoy peaceful mornings and relaxing evenings in the charming three-season room overlooking the private, scenic grounds, surrounded by nature and tranquility. The finished lower level provides exceptional additional living space, complete with a second stone fireplace-ideal for a recreation room, home office, or guest retreat. Plenty of storage in the walk-up attic with expansion possibilities. Set in a serene country setting yet just minutes from shopping, dining, and commuter routes, this home truly offers the best of both worlds.

207 Grassy Hill Rd, 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
338 Good Hill Rd, Woodbury
$580,000
4 Beds ⋅ 2 Baths ⋅ 24179676 MLS
Nestled on 1.53 acres and set back from the road, this charming Cape Cod style home offers the perfect blend of comfort, character and New England charm. The interior features 2 bedrooms and a full bath on the main and upper level. An inviting Living Room showcases a fireplace with an energy efficient woodburning insert, creating a warm and cozy gathering space. The dining area provides access to the 14x8 rear deck, ideal for outdoor entertaining or relaxing while enjoying the peaceful surroundings. The kitchen includes an island, LVP flooring and ample workspace. Hardwood floors throughout most of the home. Additional highlights include a newer propane heating system with on demand hot water, full basement with interior and garage access, Generator-ready wired for peace of mind and 2 car under house garage with auto door openers. Outside you'll find a 10x10 storage shed and recently paved driveway. Just minutes from Woodbury's vibrant Main Street is easy access to enjoy shopping, dining, the library, post office, parks and scenic land preserves for outdoor activities. Whether you're seeking full-time residence or a weekend getaway, this property offers a great opportunity in one of Connecticut's picturesque communities and "Antique Capitol". Ideally situated roughly 80 miles from NYC approximately 140 miles from Boston.

338 Good 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
557 Upper Grassy Hill, Woodbury
$885,000
4 Beds ⋅ 4 Baths ⋅ 24158380 MLS
Welcome to Upper Grassy Hill Living!

557 Upper Grassy Hill, Woodbury
63 Woodbury Hill, Unit 63, Woodbury
$525,000
2 Beds ⋅ 3 Baths ⋅ 24171961 MLS ⋅ Woodbury Hill BLDG.
Exceptionally private, Putnam Loft model in the sought after Woodbury Hill! This unit is located in a secluded part of the community with woods behind and only sounds of the nearby babbling brook. This well-cared for unit features hardwood floors throughout, vaulted ceilings, floor to ceiling gas fireplace, a large dining room and remodeled kitchen. The primary bedroom suite is on the main level and includes, full bath, walk-in closet with access to the washer/dryer as well as the garage. Upstairs find a large loft perfect as a reading room, study or home office, which offers great natural light pouring through its skylights. An additional full bath and bedroom are located on this level to easily accommodate an out of town guest or another family member. Recent updates include a new HVAC system and fireplace gas insert. The currently unfinished basement with walk out to the stone patio can be used for storage or can be easily finished with its suitable ceiling height and built-in windows and slider. There is additional storage in the upstairs eaves of the second bedroom or off the loft area. Schedule your showing now while this stunning and private unit is still available!

63 Woodbury Hill, Unit 63, Woodbury
674 Middle Road Tpke, Woodbury
$699,000
3 Beds ⋅ 3 Baths ⋅ 24185444 MLS
Meticulously maintained and handsomely set on a picturesque lot in charming Woodbury, Connecticut, this classic Colonial offers the perfect blend of timeless character, comfort, and outdoor beauty. From the moment you arrive, the home makes a lasting impression with its mature tree-lined setting, stone walls, flowering gardens, cobblestone and bluestone walkway, and inviting front entry. Inside, sun-drenched rooms create a warm and welcoming atmosphere, giving the home an immediate sense of comfort and ease. Thoughtful details, generous living spaces, and a graceful floor plan make this a home that feels both elegant and truly livable. The inviting living and dining areas flow beautifully for everyday living and entertaining, while the bedrooms offer peaceful retreats filled with natural light. The primary suite is a special highlight, featuring its own Romeo and Juliet balcony overlooking the gardens and professionally maintained grounds. It is the kind of private, charming detail that gives the home a rare sense of romance and character. Outdoor living is just as impressive. Enjoy a private bluestone patio, beautifully framed by stonework and landscaping, along with a spacious Trex back deck designed for relaxing, dining, and entertaining. Whether enjoying morning coffee, summer gatherings, or quiet evenings surrounded by nature, the property offers a peaceful country setting while still being close to the charm, shops, restaurants, and conveniences of Woodbury.

674 Middle Road Tpke, Woodbury
12 Walker Rd, Woodbury
$540,000
3 Beds ⋅ 3 Baths ⋅ 24179773 MLS
Would you like to live in beautiful Woodbury Connecticut. Set on 1.95 acres of peaceful, private grounds, this beautifully updated 3-bedroom, 2.1-bath home sits gracefully on a gentle rise at the top of the driveway, partially framed by classic white post and rail fencing that enhances its New England charm. The entire home-interior, exterior, trim, and baseboards-has been freshly painted, move-in-ready feel. Inside, you'll find hardwood flooring throughout, complemented by brand new LVP flooring in the expansive kitchen, central air and a Generac generator system. The kitchen offers an abundance of dining and workspace, a walk-in pantry, and brand-new stove and dishwasher. An oversized two car garage with newer doors provides excellent storage and convenience. The full, unfinished basement offers tremendous potential, complete with two additional storage rooms ideal for organization or future expansion. Outdoors, the setting is serene and usable, with mature trees, open lawn space, and two bonus structures: an additional shed and a separate garage building, perfect for hobbies, equipment, or extra storage. Located in picturesque Woodbury-known for its antique charm, farm to table dining, and scenic countryside-this property offers privacy, updates, and room to grow. Trustee selling, so no disclosures - being sold "AS IS" Cameras in use do NOT go onto the property without an appointment - Under ground Oil tank was discovered will be removed by closing

12 Walker 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
89 Lighthouse Rd, Woodbury
$440,000
3 Beds ⋅ 3 Baths ⋅ 24174349 MLS
** Multiple offers highest and best 5/17 5pm**Tucked away on 4.99 serene wooded acres in picturesque Woodbury, this solidly built Cape Cod offers privacy, charm, and endless potential. Surrounded by mature trees and peaceful natural beauty, the property provides a true country setting with room to create gardens, walking trails, or space for animals and hobby farm interests. Inside, the home features 3 bedrooms, 1.5 baths, beautiful hardwood floors, and a warm, inviting layout filled with timeless character. Whether you envision restoring its classic charm or creating your own private retreat, this property offers a rare opportunity to own nearly five acres in one of Litchfield County's most sought-after towns.

89 Lighthouse Rd, Woodbury
9 Highpoint Ct Unit 116E, Woodbury
$245,000
2 Beds ⋅ 2 Baths ⋅ 24147973 MLS ⋅ Woodlake BLDG.
New price point! Come take a look at this lovely home! A perfect 1st or 2nd. home. Included: one car garage, plus one assigned parking space, a deck and patio for grilling. Notice the wooded privacy in the back. Inside a convenient kitchen, a breakfast nook (Or computer area etc.) There is a large living/dining room combo. The Fireplace is sealed shut for safety. However, w/permits, you can easily install a pellet or wood-burning stove insert. Upstairs are two bedrooms and bathrooms w/updated vanities and flooring. The Lower Level is clean, dry and spacious. It contains the laundry and can easily be finished to suit your needs. The Monthly HOA of $359.13 = Roofing, decking carpentry services, landcare, snow shoveling, onsite staff, maintenance & management, insurance, pest control, etc. The Woodlake Municipal Tax service fee: (WTD) $925.66 paid each Qtr. For sewer, water, roads, trash & snow removal, common lighting, fire hydrants, storm drains, Snow removal, staff & vehicles, pond maintenance, etc. WTD was set up to allow the owner tax deductions for this service tax. Ck with your accountant for your deductions. The Town of Woodbury Tax: $3193.00 Are you traveling East or West on I84? You will reach the interstate in minutes! Visit this value packed condo and award winning Woodbury soon. Woodbury was recently rated the CT's best small Town by the Readers Digest and the Boston Globe. Great restaurants, boutiques, parks, hiking, Ct. wine trail...The list goes on

9 Highpoint Ct Unit 116E, Woodbury
34 Transylvania Rd, Woodbury
$465,000
3 Beds ⋅ 3 Baths ⋅ 24132918 MLS
Price Improvement for this Charming Country Retreat- A perfect alternative to Condo Living! Nestled on a serene 3 acre lot with picturesque stream, this property offers the tranquility of country living while maintaining easy access to nearby amenities. One level living- enjoy the convenience of the primary bedroom with spacious walk-in closet on the same level as the open floor plan kitchen/dining/livingroom. The lower level offers 1008 sq ft-above grade on three sides, with a full bath, large family room, office, and two additional bedrooms. Plenty of room to entertain family and friends. Both levels of the home are walkouts allowing for easy access to the outdoors and parking available at each level. Equipped with new high efficiency propane furnace and electric hot water heater, this home ensures reasonable energy costs and long-term reliability. Enjoy clean, safe drinking water with a reverse osmosis 5 filter water system at the kitchen sink. Custom built, 12' x 24' shed/garage with an overhead door that provides extra storage, workspace, or vehicle storage. This property is perfect for those seeking a peaceful lifestyle without the constraints of condo living. Whether you're looking to downsize or simply want a quiet retreat, this home offers the best of both worlds.

34 Transylvania Rd, 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
5 Westwood Rd, Woodbury
$570,000
3 Beds ⋅ 2 Baths ⋅ 24175070 MLS
Classic early-1900s colonial in the heart of Woodbury with 3 bedrooms, 2 full baths, and over 1,900 square feet of living space. The home offers a comfortable mix of older-home character and practical updates, with hardwood floors, good natural light, and a layout that works well for everyday living. The updated kitchen features white cabinetry, granite counters, stainless steel appliances, recessed lighting, and a breakfast bar area. It has a clean, bright feel with plenty of cabinet and counter space. The living room offers a warm, traditional setting with hardwood floors, a brick fireplace, and large windows overlooking the property. Outside, the home sits back from the road with a large paved driveway and a detached 2-car garage. The garage provides great storage, parking, and separate workspace potential. Additional features include a full basement, newer well, and a whole-house generator. This is a solid Woodbury home with historic charm, useful updates, and a convenient location close to town, shops, restaurants, and area amenities.

5 Westwood 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
7 Highpoint Ct Unit 7, Woodbury
$284,500
3 Beds ⋅ 3 Baths ⋅ 24174377 MLS ⋅ Condos At Woodlake BLDG.
Welcome to this spacious three-bedroom, two and a half bath townhouse located in the desirable Woodlake Community. The living room and dining areas offer an open-concept floor plan, making it perfect for both everyday living and entertaining guests. Sliding glass doors from the dining room lead to a private deck, which looks out upon a wooded area that offers serene views. The primary bedroom includes its own en-suite bath, while a second full bathroom serves the additional two bedrooms. In addition to the main floor living space, this unit has a partially finished basement and clean laundry space. With a newer HVAC system you can enjoy comfort throughout the year. This townhouse presents a wonderful opportunity for those seeking ample space, comfort and a peaceful setting. Residents of Woodlake. benefit from scenic walking trails and a serene natural environment. The community is conveniently located just minutes from the historic downtown Woodbury and I-84, making it easy to access shopping, dining and parks. Discover the convenience of living the Woodlake lifestyle and schedule your private showing today. Owner installing front screen door prior to closing.

7 Highpoint Ct Unit 7, Woodbury

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