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229 Bacon Pond Rd Unit 451, Woodbury
$189,200
2 Beds ⋅ 1 Baths ⋅ 24175688 MLS ⋅ Town In Country BLDG.
Step into condo living in this freshly painted two bedroom unit with new vinyl plank flooring in the foyer, living room and dining room. Curl up in front of your fireplace on cool nights or walk a few steps to the in-ground pool to cool off in the summer. The kitchen features a stainless steel glasstop range and brand new dishwasher. Both generously-sized bedrooms feature fresh paint and brand new carpet with crown molding in the primary bedroom. Enjoy your coffee or evening beverage on your private patio off the dining room accessible via sliding glass doors. This unit features new thermalpane windows and slider and custom blinds throughout. The heating and cooling is via a Heil energy efficient heat pump. Town In Country Condos are just off the beaten path providing the privacy you desire but minutes by car to restaurants, shopping and everything downtown Woodbury has to offer. All you need to do to enjoy this home is move your furniture in!

229 Bacon Pond Rd Unit 451, Woodbury
54 School St, Woodbury
$625,000
3 Beds ⋅ 2 Baths ⋅ 24170889 MLS
Timeless Elegance in the Heart of the Historic District . Step back in time without sacrificing modern convenience in this enchanting 1750s colonial, perfectly situated on a premier corner lot within the town's coveted Historic District. This home isn't just a place to live; it's a piece of local history loaded with "old world" character. From the moment you step inside, the rich wide plank hardwood floors and period details whisper stories of the past. The layout seamlessly blends cozy historic proportions with functional spaces designed for today's lifestyle. The kitchen features new cabinetry and appliances with adjoining stone floored sun room. Bright and airy rooms featuring original architectural charm. 2 well-appointed bedrooms offer peaceful retreats with a 3rd suitable as a nursery or office space. 1.5 baths include a convenient main-floor powder room. An expansive utility and mudroom provides ample storage and organizational space-a rare find in a home of this vintage. A lovely level corner lot is the perfect setting for this in town charmer. New 1250 gallon septic tank 2025. 24 hour notice for all showings please.

54 School St, 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
2 Judd Hill Rd, Woodbury
$575,000
3 Beds ⋅ 2 Baths ⋅ 24172678 MLS
Charm and modern comfort come together in this beautifully renovated 3-bedroom, 2-bath home set on nearly an acre along a quiet country road in Woodbury. Thoughtfully updated and move-in ready, this inviting home blends classic New England character with practical improvements throughout, including a fully insulated attic and insulated walls added by the current owner for enhanced comfort and efficiency. The main level features a warm living room with fireplace, a spacious first-floor bedroom, and a full bath, offering flexibility for guests or convenient one-level living. The newly updated kitchen opens to the dining area and leads directly to a brand-new deck overlooking a private, level backyard with distant pond and mountain views. The yard has been cleared and extends to a peaceful meadow that backs to a wooded preserve, creating a serene and private setting. A recent expansion added an oversized two-car garage, extra deep with high ceilings and potential for a loft, workshop, or additional storage. The full basement offers tall ceilings, ample storage, and rear exterior access to the leveled backyard. Adjacent to the basement door is an additional versatile room, ideal for outdoor storage, tools, hobbies, or a creative workspace.

2 Judd Hill Rd, Woodbury
14 Meadow Crest Dr, Woodbury
$500,000
3 Beds ⋅ 2 Baths ⋅ 24149855 MLS
Opportunity knocks! Your chance to reside in an exclusive cul-de-sac area of north Woodbury! Homes on this street rarely come on the market. Situated on almost 4.5 acres and within a short drive of Woodbury and Watertown centers, including prestigious, private Taft School, this three bedroom, 1.5 bath colonial awaits its new owners! Exterior features include a chicken coop, above ground pool, jacuzzi, mature plantings and an extended process driveway making a portion of the back acreage accessible. Upon entering the home, you are greeted by a classic center hall foyer. Spacious dining and family rooms surround the foyer, along with a cozy sitting room, and a sun-filled bonus room with walk out to the side patio. A remodeled half bath and a country-kitchen, with newer appliances, complete the first floor. On the second level, find three spacious bedrooms, an additional room for home office or crafting space, and a remodeled full bath with walk-in shower and soaking tub. The lower level offers partially finished space, a laundry area, and plenty of room for storage. The two car attached garage has floored loft space for your additional storage needs. Some minor finishing touches are needed in the home. Get ready to enjoy the quiet life, where the only sounds you will hear are the ones that nature provides!

14 Meadow Crest Dr, Woodbury
5 Kimberly Ln, Woodbury
$470,000
3 Beds ⋅ 3 Baths ⋅ 24168924 MLS
Welcome to this beautifully maintained 3-bedroom, 3-bath high ranch nestled in the picturesque New England town of Woodbury. This inviting home offers a perfect blend of comfort, functionality, and modern updates. The upper level features gleaming hardwood floors throughout and an updated kitchen that flows seamlessly into an open-concept dining and living area-ideal for both everyday living and entertaining. New windows and a sliding glass door fill the space with natural light while providing easy access to the outdoors. Downstairs, you'll find a versatile lower level with durable laminate flooring, a full bathroom, and a private sauna-perfect for relaxation after a long day. Additional highlights include central air conditioning, an attached two-car garage, and a spacious primary bedroom complete with its own full bath. Set in a charming and desirable location, this home offers the best of New England living with modern conveniences.

5 Kimberly Ln, Woodbury
9 Upper Commons Unit 9, Woodbury
$275,000
2 Beds ⋅ 2 Baths ⋅ 24154890 MLS ⋅ Woodlake BLDG.
Welcome to 9 Upper Commons, Woodbury - Tucked away in a quiet, well-maintained community surrounded by mature trees and walking trails, this inviting 2-bedroom townhouse offers three levels for a comfortable, functional lifestyle. The main level features a spacious open-concept floor plan, ideal for everyday living or entertaining. Sliding doors off the dining area leads to your private deck/patio overlooking a serene, wooded backdrop-perfect for morning coffee or unwinding at the end of the day. The kitchen offers ample cabinet space and a practical layout designed for efficiency and ease. The family room features a fireplace, creating a warm and cozy atmosphere during the colder months. The lower-level provides flexibility for a home office, gym, music room, or extra storage. Upstairs, both bedrooms are generously sized and include walk-in closets. The primary bedroom offers the added convenience of an en-suite bath, while a second full bath serves the additional bedroom. Additional highlights include central air conditioning for year-round comfort and a detached garage for parking and storage. The Woodlake Condominium community offers privacy while remaining just minutes from shopping, dining, and major commuter routes. This is a wonderful opportunity for those seeking space, comfort, and a quiet setting-schedule your private showing today!

9 Upper Commons Unit 9, Woodbury
43 Bethwood Ln, Woodbury
$513,999
3 Beds ⋅ 2 Baths ⋅ 24171809 MLS
If you're looking for your own piece of heaven, this may be it. Hard to find and full of potential, this modest single-level home is set on a secluded 5+ acre parcel of gorgeous open meadow. Located on a private road near the Woodbury/Bethlehem line, the home offers three bedrooms, an eat-in kitchen, dining room, living room with fireplace, breezeway, and an attached two-car garage. With only a step or two from parking to the living area, the layout provides easy single-level living. The home is set back from the road, providing distant views, abundant meadowland, and wonderful privacy from neighbors. The property is ideal for raising animals, building a workshop, creating expansive gardens, or simply enjoying the peace and open space. While the interior needs some TLC, the current owners have already upgraded several major items, including a new roof, new furnace, and new oil tank. For the right person, the remaining work is manageable, and the outcome could be a true gem for years to come.

43 Bethwood Ln, Woodbury
360 Old Sherman Hill Rd, Woodbury
$426,500
3 Beds ⋅ 1 Baths ⋅ 24159136 MLS
Come view this charming 3 bedroom, 2 full bath, single family home in beautiful Woodbury! Enjoy an above ground pool with a deck wrapped around it-perfect for relaxing year round while taking in the sweeping natural views out back. A spacious 2 car detached garage sits in the middle of a large private semi-circular driveway, offering plenty of parking and storage. Upon entering the front of the home, you'll find yourself in a stunning living area featuring unique skylights, sliding glass doors that open to the rear deck, and a wall of windows that fills the space with natural light. On the right corner a cozy wood stove adds the perfect touch of warm ambiance. The living area opens seamlessly into a spacious eat-in kitchen boasting stainless steel appliances, a center island, and a skylight, lending additional natural lighting. Past the kitchen is a hallway leading into a bedroom with beautiful built in shelving and a closet. Just past this room is the primary bedroom featuring sliding glass doors that open to the deck on the left, large windows overlooking the expansive backyard, and two skylights set into its vaulted ceiling. The home includes two newly remodeled full bathrooms-one on the main level and one on the lower level. The partially finished full basement offers extra living or storage space and includes a dedicated laundry room. The home is heated with an oil-fueled boiler. Make your appointment today to see this beautiful home in the desirable Woodbury area.

360 Old Sherman Hill Rd, Woodbury
43 Woodbury Hill, Unit 43, Woodbury
$430,000
2 Beds ⋅ 2 Baths ⋅ 24170943 MLS ⋅ Woodbury Hill BLDG.
Rarely is a ranch style available at Woodbury Hill as there are only 7 in total, This one is almost self standing-neighbor's one car garage is adjacent to this two car garage. There is an additional 640 sq.ft. in the heated lower level with a laundry room, closets, half bath and a separate work area and all with sliders to the yard. The beamed living/dining room is cathedral in the living room section with a two story window and lovely fireplace. A nice sunny den is nearby and down the hallway is the MBR with a slider to the wrap around deck. There are two full baths on the main floor. The large kitchen also has a slider to the oversized deck that shows beautiful views of the grounds. Keep in mind that Woodbury Hill is in walking distance to the center of Woodury which includes the library, stores, post office, parks, community center for exercise classes and lectures. Take advantage of the outdoor pool, tennis court and gatherings at the gazebo. Enjoy the award winning restaurants, golf courses, nature centers, community theater, art galleries and antique shops. Remember you are only minutes from major routes and 1 1/2 hours to NYC by car and 1/2 hour to the train. This lovingly cared for home is easy to show and well worth it. Woodbury was listed as No.3 in the 10 places to live in Connecticut according to Travel and Leisure as seen in the May issue of Ct. Magazine.

43 Woodbury Hill, Unit 43, Woodbury
242 Bacon Pond Rd, Woodbury
$513,000
4 Beds ⋅ 2 Baths ⋅ 24162107 MLS
Charming antique two-family property in the heart of Woodbury featuring a main residence plus a separate legal apartment over the detached 2-car garage-ideal for rental income, in-law setup, or owner-occupant flexibility. The main home offers 3 bedrooms, 1 bath, wide board antique flooring, original built-ins, and three fireplaces, including one in the cozy eat-in kitchen. The apartment provides approximately 700 sq ft of additional living space with a full bath and private setting. Set on a beautiful 1.46-acre treed lot with gardens, irrigation, and open space. Convenient in-town location close to shopping, dining, and commuter routes.

242 Bacon Pond Rd, Woodbury
126 Sherman Hill Rd Unit APT B12, Woodbury
$200,000
2 Beds ⋅ 1 Baths ⋅ 24146084 MLS ⋅ Heritage Hills BLDG.
This second level unit offers a living and dining combo, kitchen, two bedrooms and one full bath. Upstairs units have vaulted ceilings & additional windows that allow for even more daylight and sense of space. A floor to ceiling brick fireplace will draw you in the winter and a modern curved wall, as you enter the door, adds so much character. The complex offers an in-ground pool. HOA Includes Heat, Hot Water and Cable. Unit comes with a 6x7 storage located in the lower breezeway along with a share laundry just a few steps up from the unit. Experience the magic of New England sunsets from the comfort of your living room or second-level balcony. Embrace the rich heritage of Woodbury from this idyllic hillside retreat in Heritage Hills. Immerse yourself in the towns antique charm, with its quaint restaurants & shops! Come take a look! Unit will be sold "as is"

126 Sherman Hill Rd Unit APT B12, Woodbury
123 Cross Brook Rd, Woodbury
$590,000
1 Beds ⋅ 2 Baths ⋅ 24153133 MLS
Offered for the first time, this custom-built Cape was carefully designed with a vision for both comfortable living and future expansion. Currently configured for easy one-level living, the home features a spacious, well-built layout with hardwood floors and generously proportioned rooms throughout. Upstairs, a blank canvas awaits-ready to become additional bedrooms, a full bath, and expanded living space above the two-car garage. Whether you follow the original plans or create your own vision, the possibilities here are truly exceptional. Set on over 3 acres in one of Woodbury's most sought-after locations, the property is rich with character-featuring classic fieldstone walls, mature gardens, and enduring curb appeal with a composite slate roof and low-maintenance exterior. Unwind on the three-season porch, or gather by the fireplace and enjoy the warmth of a home designed to grow with you. This is a rare chance to create something special in a beautiful setting.

123 Cross Brook Rd, 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
4 Deer Hill Ct Unit 4, Woodbury
$290,000
3 Beds ⋅ 3 Baths ⋅ 24163426 MLS ⋅ Woodlake BLDG.
Welcome to this spacious 3 bedroom, 2.5 bath townhouse in the highly sought-after Woodlake community in Woodbury. Upon entering the unit, you will find a spacious foyer complete with a coat closet and a half bath. The rest of the main level features a large eat-in kitchen, open living room with allocated dining area and a set of sliding doors that lead to a private deck overlooking the tranquil wooded surroundings. The primary suite, located on the second floor, offers ample closet space and a full bath. The remaining two bedrooms are generous in size and the second floor also contains an additional full bath providing flexibility for the whole family. New windows (2022), new hot water heater (2025), and newer HVAC systems (2018) enhance energy efficiency. The windows also include a lifetime warranty that is transferable to the new owner, providing additional peace of mind. The basement adds approximately 732 square feet of space that can easily be finished to create a family room, gym, or office. Additional highlights include a garage and an assigned outside parking space. Residents of Woodlake enjoy scenic walking trails and a peaceful natural setting, just minutes from historic downtown Woodbury and I-84.

4 Deer Hill Ct Unit 4, Woodbury
13 Clubhouse Dr Unit 13, Woodbury
$299,000
2 Beds ⋅ 4 Baths ⋅ 24157849 MLS ⋅ Woodlake BLDG.
Welcome to this well-maintained 3-level condo in the desirable Woodlake community. This spacious unit offers 2 bedrooms, 3 full baths and 1 half bath, plenty of natural light, and a large private deck off the main living area. The kitchen features stainless steel appliances, with washer and dryer conveniently located on the upper level. A fully finished walkout lower level with a full bathroom provides flexible space for a family room, office, guest area, or potential in-law setup. Central air and two assigned parking spaces included. Enjoy Woodlake amenities including tennis courts, basketball court, scenic lake, and walking trails.

13 Clubhouse Dr Unit 13, Woodbury
126 Sherman Hill Rd Unit C14, Woodbury
$215,000
2 Beds ⋅ 1 Baths ⋅ 24168260 MLS ⋅ Heritage Hills BLDG.
Beautifully updated 1st floor end unit with plenty of parking. Fantastic 2 bedroom with brand new bathroom, updated kitchen, large custom built-ins, wood burning fireplace, sliders that open to private patio and garden just steps from pool.HOA includes heat, water and basic cable. Plenty of storage in unit and private storage close by. Quiet complex conveniently located to shopping and minutes to I84.

126 Sherman Hill Rd Unit C14, Woodbury
24 Fox Run, Unit 24, Woodbury
$293,000
2 Beds ⋅ 2 Baths ⋅ 24159700 MLS ⋅ Woodlake BLDG.
Motivated seller!! Price drop 22k! Don't cry over high mortgage rates!! This unit offers an assumable 2.99% mortgage for those who qualify. Lowers your monthly payments substantially!! This renovated 2-bedroom, 2-bath townhouse with over 1,500 square feet has so much to offer. Don't wait! This end unit features white kitchen cabinets and stainless appliances, gleaming hardwood floors, semi finished lower level and a private deck. This home is perfect for comfort and relaxation. Complex offers walking trails, tennis courts, and clubhouse. Come enjoy a quiet, rural setting just minutes from local shops, dining, and easy commuting. A rare opportunity-schedule your visit today!

24 Fox Run, Unit 24, Woodbury
229 Bacon Pond Rd Unit 312, Woodbury
$120,000
2 Beds ⋅ 1 Baths ⋅ 24150943 MLS ⋅ Town In Country BLDG.
Waiting for your personal touch! This Town In Country lower level unit features a Living Room/Dining Room combo with Fireplace and slider leading to your own private Patio, Fully applianced Kitchen, 2 spacious Bedrooms, and Full Bath. Unit freshly painted with new carpet. Convenient to complex's in-ground pool and laundry. Minutes to Woodbury's town center with its shopping, top restaurants, & local parks. Affordable living! Ready for immediate occupancy!

229 Bacon Pond Rd Unit 312, Woodbury
229 Bacon Pond Rd Unit 453, Woodbury
$145,000
2 Beds ⋅ 1 Baths ⋅ 24171771 MLS ⋅ Town In Country BLDG.
Light-filled upper-level unit featuring hardwood floors throughout, located near Woodbury Town Center. The living room offers a fireplace, vaulted ceilings, and sliders to a private deck overlooking park-like grounds. The kitchen opens to the dining area with bar seating and an open floor plan. Spacious bedrooms include large closets, and the full bath offers a tub/shower. Close to the in-ground pool and picnic area, with convenient access to dining, shops, parks, and more. Laundry is a short walk away. As-Is condition.

229 Bacon Pond Rd Unit 453, Woodbury
47 Woods Way Unit 47, Woodbury
$212,500
2 Beds ⋅ 2 Baths ⋅ 24158329 MLS ⋅ Woodlake BLDG.
This Country House model, end unit in Woodbury's Woodlake community offers two spacious bedrooms, with their own full baths, a detached one car garage and open floor plan on the main level. The Woodlake community provides non-motorized boating on the lake, hiking trails, basketball, tennis courts, and a playground area to name a few. The full unfinished basement offers more storage space. New HVAC system replaced in 2025. This well-maintained community provides a responsive on-site property management company. Enjoy the major conveniences provided by proximity to the two town centers of Woodbury and Southbury! Unit is being sold as is, this is an excellent opportunity to live in Woodbury for the price!

47 Woods Way Unit 47, 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
13 Park Ln, Woodbury
$650,000
3 Beds ⋅ 3 Baths ⋅ 24147278 MLS
Set on a picturesque lot with mature landscaping and gorgeous outdoor spaces, this beautifully maintained home offers a flexible layout designed for both entertaining and everyday living. The front entry opens to a bright and inviting living room with built-ins and gas fireplace. The kitchen blends style and function with granite countertops, stainless appliances, and a natural flow into the dining room that makes everyday gathering effortless. A glass door from the dining room leads to a stunning sunroom that connects directly to the two-car garage and provides access to the fenced backyard through both a standard door and a pet door. The living spaces are accompanied by a private primary suite with a walk-in closet and full bath, along with two guest bedrooms and a well-appointed full bath. Upstairs, a spacious family/rec room with a half bath creates a versatile retreat for play, relaxation, or visiting guests. The setting is exceptional. The rear of the property borders preserved parkland with woodland trails, while the land across the street is also protected, creating a tranquil backdrop and long-term privacy. Despite the peaceful surroundings, the home is only a short walk to Woodbury's town center, an uncommon blend of nature and convenience that is hard to replicate. With thoughtful updates, a flexible floor plan, and an outstanding location, 13 Park Lane offers a lifestyle that feels both connected and tucked away, an exceptional offering in the heart of Woodbury.

13 Park Ln, Woodbury
74 Middle Quarter Rd, Woodbury
$665,000
4 Beds ⋅ 3 Baths ⋅ 24160671 MLS
Welcome to 74 Middle Quarter Rd-minutes from downtown, a charming antique colonial home that has been truly loved and thoughtfully maintained, offering the perfect blend of character, space, and everyday comfort. From the moment you step inside, you'll feel the warmth of the main level, featuring a farmhouse-style kitchen with an eat-in area and a cozy wood-burning stove-the kind of space where everyone naturally gathers. The oversized family room, formal dining room, and inviting living room provide plenty of room to spread out, while the central conversation lounge creates a unique and welcoming heart of the home. Upstairs, you'll find four generously sized bedrooms, including a primary suite with a walk-in closet and full bath. An extra living space offers flexibility for a playroom, den, or TV room-whatever fits your lifestyle. The upstairs laundry room is as practical as it is spacious, complete with abundant storage, a wash sink, and even a cedar closet. Need more space? The walk-up attic includes a partially finished area perfect for a home office, creative space, or additional storage. Set on 4.7 peaceful acres, this property invites you to slow down and enjoy quiet evenings and the beauty of nature. The 3-car garage includes an unfinished upper level with endless potential, plus two additional sheds for even more storage. And the surprise you didn't know you needed-owned solar panels keeping electric costs incredibly low (avg just $20/month). Book your showing

74 Middle Quarter Rd, Woodbury
40 Church St, Woodbury
$436,000
3 Beds ⋅ 2 Baths ⋅ 24163332 MLS
Highest and Best by 04/07 at 5:00pm. Beautiful 3-bedroom, 2-bath home located in the heart of Woodbury. Currently the only raised ranch on the market, this property offers a wonderful opportunity in a highly desirable area. The home features a level yard, perfect for outdoor enjoyment, along with a fully finished basement complete with a full bath-ideal for entertaining or providing comfortable space for guests. The main level includes three generously sized bedrooms, a welcoming living room with a fireplace, and a dining area filled with natural light. Additional highlights include a 2-car garage and central air for year-round comfort. Conveniently located near schools and shopping, this home is set in a truly quiet neighborhood-let's just say the neighbors won't be making much noise.

40 Church St, Woodbury
14 Tamarack Ln Unit 14, Woodbury
$261,000
2 Beds ⋅ 3 Baths ⋅ 24153247 MLS ⋅ Woodlake BLDG.
Opportunity awaits in this end unit tucked away in the Woodlake Complex. While in need of some work & new paint colors, there are some nice improvements already in place such as newer windows, wood & tile flooring, & kitchen cabinets. This unit has both a deck & patio overlooking the treed rear yard. Both are accessible from rear sliders. The lower level is finished & has a half bath within the laundry room. Expansive bright area for a guest room, man cave, or teen. Bring your ideas & a paint brush! This is the lowest priced unit in the complex. Woodlake has a quarterly district tax of $1,050 ($4,200 annually). Woodbury, also known as the antiques capital of the state, is also home to several 5 star restaurants & in close proximity to Lake Quassapaug Amusement Park!

14 Tamarack Ln Unit 14, Woodbury
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

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