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$209,900
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24206004 MLS ⋅ Town In Country BLDG.
Move right into this beautifully renovated upper end unit in Woodbury's desirable in-town Town & Country condominium complex. Tastefully updated throughout, this light-filled unit features an open floor plan with a completely renovated kitchen flowing into the living room with fireplace and built-ins. Updates include new windows, luxury vinyl plank flooring, interior doors, lighting, switches, outlets, and electrical finishes throughout. Ideally located toward the rear of the complex, the unit overlooks the pool and landscaped grounds, offering a peaceful setting with added privacy. One of the standout units in the complex, this turnkey property combines quality updates, an excellent location, and the convenience of being within walking distance to shops, restaurants, and everything historic Woodbury has to offer.

229 Bacon Pond Rd Unit 313, Woodbury
$555,000
5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24206024 MLS
BACK ON THE MARKET with a NEW SEPTIC being installed, NEW WELL, and MORE. This generous 5-bedroom home offers a generous footprint to put your personal touches on. Boasting wood flooring and newer windows throughout, the main level features a spacious living room, formal dining room, an eat-in kitchen, a cozy family room with fireplace, a private home office, and a full bathroom. Upstairs, you'll find five sizable bedrooms, including a primary suite complete with a walk-in closet and en-suite bath. The remaining four bedrooms share a large full bathroom equipped with a double vanity. The expansive walk-out lower level adds incredible value with over 1,000 square feet of finished, heated living space. It includes a den with fireplace, a possible game room or in-law suite as light streams through a large picture window with views of the backyard. This finished area includes an additional guest room and half-bath. Outside, a circular driveway frames the property amidst mature, private landscaping, while the back deck is primed for summer grilling. Complete with an oversized two-car garage featuring a dedicated work area and abundant storage closets. Bring your design ideas and unlock this gem's full potential.

33 Hurds Hill Rd, Woodbury
$289,900
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24205036 MLS ⋅ Woodlake BLDG.
Welcome to sought-after Woodlake Estates! A peaceful, resort-like community surrounded by nature and recreational amenities. This spacious Townhouse-style end unit offers 9 rooms, 3+ bedrooms, 2.5 baths, a finished basement, and a detached 1-car garage. The main level features a generous sized living room with sliders leading to your private deck, kitchen with separate dining area, convenient home office nook, and half bath. Upstairs, the primary bedroom offers its own full bath, along with two additional bedrooms and another full bath. The finished lower level provides valuable additional living space with two rooms that can easily adapt to your needs- ideal for a family room, home office, gym, or potential additional bedrooms-plus a dedicated laundry area. Newer central A/C adds peace of mind. This townhouse offers an exciting opportunity for the buyer with vision to add personal touches and updates, bringing out its full potential and building instant equity. Enjoy the tranquil setting of Woodlake Estates with scenic walking and hiking trails, a pond for canoeing and fishing, tennis courts, grove area for picnics and plenty of opportunities to simply relax and unwind on your private deck. Perfectly situated for both convenience and lifestyle with an array of fine dining and shopping options just minutes away. Enjoy easy access to major highways for commuting, only 30 mins from Danbury and less than 2 hours from NYC! Come see it before it's gone!

6 Upper Commons Unit 6, Woodbury
$765,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24203113 MLS
Newly re-imagined and completely renovated single level jewel box on quiet country lane with tree-lined driveway and long seasonal views. The open-concept living areas are designed for effortless entertaining with soaring vaulted ceilings, exposed beams, a floor-to-ceiling brick double-sided fireplace and a fabulous dedicated bar room. A new series of skylights creates a bright and airy space filled with all day sunlight. Eat-in chef's kitchen features bespoke cabinetry and premium appliances. A delightful 3-season dining/living porch with wood stove leads to an expansive stone patio overlooking the large level lawn. Stunning primary suite with vaulted ceiling and beams has a large walk-in closet and a gorgeous bathroom with double sinks and over-sized shower. The second bedroom is served by a handsome full hall bath. Convenient mud and laundry room. All new mechanicals, roof and shingle siding. Detached 2-car garage. Be the first to own this mint condition home peacefully nestled in the sought-after Flanders section of the quintessential New England town of Woodbury. Perfection!

31 Bethwood Ln, Woodbury
$699,900
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204212 MLS
Imagine starting your morning with a cup of coffee on the gorgeous wraparound front porch as you take in the view of Radey Pond or spending warm summer evenings entertaining family and friends in this beautiful and private setting.Situated on 2.31 acres, this charming 3/4-bedroom, 2.5-bath Cape/Colonial offers the perfect combination of classic New England character, comfortable living space, and a flexible floor plan. At the heart of the home is the spacious eat-in kitchen, offering plenty of counter and cabinet space and flowing naturally into the inviting family room with a cozy fireplace. Whether you're entertaining a crowd or enjoying a quiet evening at home, this warm and welcoming space is made for gathering.A separate living room and office/den provide additional options for relaxing, working from home, or creating a space that fits your lifestyle.Upstairs, the spacious primary suite is a true retreat with a large closet and private full bath featuring a spa tub and separate shower. Two additional generously sized bedrooms share another well-appointed full bathroom.Need even more room? The finished third floor offers wonderful flexibility and can easily become a fourth bedroom, private home office. Hardwood floors throughout add timeless appeal, while a new roof offers peace of mind.Outside, the 2.31-acre private lot and beautiful pond views create a setting that feels removed from it all, while still being conveniently located near amenities, and major highways

201 Transylvania Rd, Woodbury
$699,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24200785 MLS
Some homes make their impression at the front door. This one begins long before it. Set nearly out of sight on almost three acres, the home is approached by a long driveway that opens to a circular drive and generous garage parking, a gracious arrival that feels worlds away. Inside, the floor plan delivers more than expected: a sunlit living room, formal dining room, updated white kitchen with breakfast space, and a generous family room anchored by a dramatic stone fireplace. Upstairs are three bedrooms and two full baths, while the finished walkout lower level adds a recreation room, flex room, and dedicated laundry space that can shift with the way you live. The outdoor experience is equally considered, with three distinct places to gather: a welcoming front patio, elevated rear deck, and lower-level patio leading toward the in-ground pool. Framed by bluestone, open lawn, and mature woods, the pool feels less like an amenity and more like a private summer destination. Yet this retreat is only minutes from Woodbury's Main Street celebrated for its restaurants, local shops, and antiques and close to trails and open space at Minortown Road Preserve and Orenaug Park. Private without being remote, flexible without feeling ordinary, this is a home designed for quiet mornings, effortless entertaining, and unforgettable weekends.

61 Minortown Rd, Woodbury
$420,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24203216 MLS
Welcome to 34 Pilgrim Trail, a home thoughtfully cared for and enjoyed for 25.5 years. This peaceful Woodbury property features granite kitchen countertops, a tiled backsplash, stainless-steel appliances, and a ceramic kitchen floor. Solid pine doors throughout the home add warmth and character. The upstairs bathroom has been beautifully updated, including the tub and a solid-rock vanity countertop. The upper bedroom/closet offers flexible use and can easily be converted back to a bedroom. Additional improvements include updated closet systems, a refreshed closet near the upstairs bathroom, and a roof installed in 2011. The home is generator-ready, with the generator located outside. Enjoy the tranquility of the property while remaining just minutes from Main Street, shopping, and New Morning Market. Nearby schools and everyday conveniences make this a wonderful place to call home.

34 Pilgrim Trl, Woodbury
$1,200,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24202077 MLS
Fabulous Center Hall Colonial......Don't be one of those people who drive by and sum it up. This home was built in "The Era". The era I'm speaking of is truly the way homes used to be built. It's the way life used to be lived. It was elegant yet simple. It was colorful but not garish. In all honesty it's a home that knows the correctness of living life. The floor plan will tell you that. The construction will tell you that. The small-scale parlors, four fireplaces, large kitchen, entertaining living and dining will tell you that. Even the Dutch doors, cozy den and perfect bedrooms and the best laundry room ever created on the level of the hang out room with a fireplace will tell you that. One thing I will tell you is that the construction of the pool and professional gardens, growing room and terraces will last lifetimes. Whoever built this home had the brains and the expertise in the way to live a beautiful life. I rest my case.

90 Sage Rd, Woodbury
$589,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24200605 MLS
Welcome home! The details of this home are what make it unique. From the gigantic hydrangeas to the appetizing peach and pear trees, this home will continue to exceed expectations. Inside is remodeled and immaculate with the great elasticity that so many lack. The finely scaled rooms are so versatile, the home really allows you to figure out what works for you. For instance, the dining room, could be an office, the great room a dining room, you choose. Upstairs the bedrooms are a wonderful scale and ready for you to bring your toothbrush. Downstairs, this is where it really gets interesting! Downstairs is a clean and unfinished basement AND a huge room under the addition (which could be made into an in-law with separate entrance), with a deck outside. So much potential OR just enjoy as is! This home is truly a turn-key pleasure. Must see!

323 Upper Grassy Hill, Woodbury
$875,000
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24200842 MLS
Original owner, large Colonial Home with 4 room, private entry inlaw suite on the main level. Close to town center and schools. 4180 s/f plus the 750 s/f inlaw! Bring on the big multi-generational family! Natural sun filtered house has front and back staircases, large rooms, 9'ceilings, and mostly hardwood. Granite kitchen/ great room open to breakfast nook, family room w fireplace and french doors to rear decking. Formal dining room and living room are a must in this classic style. The entertaining space is oversized so host all the holiday gatherings with ease. Primary suite is HUGE, walk in plus another closet and luxury bath. 3 additional bedrooms and an office. A separate 2nd floor laundry room, also very generous in size. Very level usable yard with a large area off the back deck fenced for dogs. (used to have a pool). Brand new central AC unit, refinished hardwood and fresh paint on the main level. In-law apartment is propane heat/ac

132 Good Hill Rd, Woodbury
$309,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24200604 MLS ⋅ Condos At Woodlake BLDG.
PRETTY AND SO PRIVATE!! Enjoy nature right from your back door in this spacious, freshly painted 3-bedroom home! Imagine relaxing with a cup of coffee on your private deck. Kitchen is nicely updated with large pantry, stainless appliances, dining area and ceiling fan. The living room features a warming fireplace with Pellet Stove for an economical heat source. and the dining room boasts sliders that open to the rear deck. Upstairs, you'll find three comfortable bedrooms and two full baths, plus there's an extra room in the finished lower level, perfect for office, media room or workout room. You'll love all the amenities Woodlake has to offer, like walking trails, a pond for canoeing, picnic areas, and a playground. The town of Woodbury itself is fantastic, with a wine trail, excellent restaurants, and charming antique shops to explore. Plus, it's super convenient to the highway, shops, and schools. Woodlake is such a wonderful community.

8 Woods Way Unit 8, Woodbury
$1,600,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24199540 MLS
Turnkey Equestrian Facility on 21 Acres. A rare opportunity to own a fully operational equestrian property offering the perfect blend of functionality, comfort, and income potential. Set on 21 acres, this established working horse boarding facility features 21 stalls, a heated indoor riding arena with viewing area, heated tack rooms, two wash stalls, private storage lockers, two outdoor riding arenas, and newer RAM fencing throughout the property. The spacious 4-bedroom Colonial offers comfortable living with a primary suite featuring its own fireplace, two additional fireplaces with woodstoves, and a screened-in porch overlooking the property. The home provides plenty of space for both everyday living and entertaining. Adding even more versatility is the 2-bedroom apartment above the garage, ideal for a barn manager or helper, guest accommodations, or additional rental income. Whether you're looking to continue the existing boarding operation, create your own private equestrian retreat, or take advantage of the property's multiple income-producing possibilities, this exceptional horse property is ready to welcome its next owner.

138 Minortown Rd, Woodbury
$699,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24194243 MLS
Classic 1930s Colonial set along Main Street in Woodbury, offering the timeless character and craftsmanship of the era. Thoughtfully set back from the road on an expansive lawn, the home features hardwood floors throughout, high ceilings, detailed moldings, interior French doors, charming built-ins, a generous foyer, and a graceful central staircase. The front-to-back living room is anchored by a brick fireplace and opens to a spacious covered porch, creating an inviting setting for everyday living and entertaining. The kitchen and both bathrooms have been updated, blending modern convenience with the home's original character. A beautiful 34' x 27' post-and-beam barn provides exceptional space for a workshop, studio, storage, or other uses. Located within Woodbury's Main Street Design District, the property also offers the flexibility to combine residential living with a business use, subject to applicable regulations. A distinctive property with room to live, work, and enjoy the best of classic Woodbury.

126 Main St N, Woodbury
$620,000
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24198134 MLS ⋅ South Brook BLDG.
Classic New England style village with 21 free standing homes in a luxurious condominium setting on 37 acres. Lighted walkways, open spaces and hiking trails. Upscale homes with all the charm of yesteryear with todays appointments. Master bedroom on the first floor with full bath and large walk in closet, dining room, living room and huge country kitchen with sitting area and fireplace. Hardwood floors throughout plus a large basement. Private patio area is a welcome site. Rarely is a South Brook home available and its location is perfect with quick access to coffee shops, library, senior center, shopping, hiking trails to the town tower and so much more.

13 Hillview Ln, Woodbury
$199,900
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24197977 MLS ⋅ Town In Country BLDG.
Welcome to 229 Bacon Pond Rd Unit 312 - located in the Town In Country complex, this 2 bed/1 bath unit has been remodeled from top to bottom featuring a brand new kitchen, new flooring, and central air. Inside you'll find an open floor plan perfect for entertaining - the kitchen has been completely redesigned featuring new cabinets, quartz countertops, and stainless steel appliances. The modern flooring flows from the kitchen to the fireplace, offering a perfect place for family gatherings. Around the corner you'll find two bedrooms and 1 full bath - the bathroom has been updated and modernized featuring a brand new vanity and tiled shower. The slider door leads to a private patio which is just a short walk down to the in ground pool. Enjoy everything Woodbury has to offer - Rt. 6 is minutes away offering plenty of restaurants and shopping, with I84 just a short drive away. Whether you enjoy laying by the pool or hiking through a number of trails this is the perfect location for the discerning consumer.

229 Bacon Pond Rd Unit 312, Woodbury
$599,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24194640 MLS
Exceptional value and opportunity on 3.5 gorgeous acres! Bring this home back to its original charm. Features hardwood floors throughout and a cozy front porch. The upper level includes 3 bedrooms, a full bath, and access to a walk-up attic from the primary bedroom. The main level offers a half bath and a functional, open layout. Additional property highlights include a separate 962 sq. ft., 2-bedroom guest house-offering incredible potential for an in-law suite or rental income once renovated (appears to be separately metered). The property also features two massive, 2-story barns that appear to have electricity. Tremendous upside potential for an end-user, investor, or multi-generational living. Subject to probate approval. Property sold as-is; no disclosures.

153 Old Sherman Hill Rd, Woodbury
$600,000
9 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24195107 MLS
Rare mixed-use investment opportunity on over an acre along Woodbury's desirable Main Street South. This unique property features a seven-unit residential building, a detached garage with an additional apartment above, and a separate commercial building offering approximately 2,000 square feet with its own dedicated entrance and access. Three of the residential units are currently occupied, while the remaining units present an opportunity for renovation and value-add potential. The separate commercial building offers flexibility for a variety of business, office, or retail uses, creating multiple income opportunities on a single property. Properties offering this combination of residential and commercial space in such a prime Woodbury location rarely become available. Whether you're looking to expand your investment portfolio or reimagine a mixed-use property with significant upside, this is an opportunity not to be missed. Property is being sold as-is.

137 & 141 Main St S, Woodbury
$510,000
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24188214 MLS ⋅ Woodbury Hill BLDG.
Welcome to beautiful Woodbury, CT! Beautiful 2 BR, 2 1/2 bath condo in sought after Woodbury Hill Condos. Park like grounds with only 78 condos, featuring a saltwater pool and a tennis/pickleball court. Well maintained condo features the main level with a Living room with vaulted ceiling and a wood-burning fireplace, dining room w/bow window, a half bath with granite vanity, an updated kitchen w/granite counters and an eating area. Sliders lead out to an oversized private deck with awning and a fantastic view! Primary BR on main level w/full updated bath w/marble vanity, walk-in closet, and an additional slider that leads out to the deck, complete with stairs down to back yard. Upper level features an interior balcony that overlooks the living room below, has a loft and a generous sized 2nd bedroom w/walk-in closet. Lots of closets space and walk in attic eve storage as well. This level also has a full bathroom with granite vanity. Lower level features a large family room with built-ins and walk out slider to the back yard, a separate play room and a large laundry room w/slop sink. Recent updates include, new LG French Door refrigerator (3/26), new hot water heater (2025), new water pump (2025). Exterior home and deck freshly painted June/July 2026. Don't miss seeing this one!

35 Woodbury Hill, Unit 35, Woodbury
$959,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24188039 MLS
Timeless Elegance & Immaculate Detail. Welcome to The Naramore House, a piece of living history. Lovingly preserved since 1898, this pristine colonial home seamlessly blends grand historic character with immaculate, turnkey maintenance. A classic wraparound front porch invites you through a charming dutch door into a formal, stately foyer featuring high ceilings and original pocket doors. The massive living room serves as the heart of the home, offering incredible square footage for multiple seating arrangements, media setups, and a cozy fireplace. Host effortlessly in the grand formal dining room and eat-in kitchen, complete with a generous pantry, a charming secondary rear staircase, and screened in sun porch. A luxurious primary retreat featuring a fireplace, private en-suite bath and massive 10x7 foot closet/dressing room. Three additional bright and spacious bedrooms include a versatile room-ideal for a dedicated home office, nursery, or library. The home has a huge attic with potential for expansion. A private patio, stunning formal garden with pagoda and mature trees offer the perfect setting for outdoor enjoyment. A recently renovated barn includes new structural beans and flooring. This lovely home offers in town conveniences like walking to restaurants, shops and local parades while set off of Main Street. Enjoy the beautiful historic architecture with the peace of mind that comes from a property that has been meticulously cared for inside and out.

11 Pleasant St, Woodbury
$329,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24195376 MLS ⋅ Woodbury Place BLDG.
Move right into this beautifully updated 3-bedroom, 2-bath townhouse offering style, comfort, and low-maintenance living. Gleaming hardwood floors flow throughout the home, complemented by vaulted ceilings, a skylight providing abundant natural light. The updated galley kitchen features tasteful tile backsplash and efficient design, opening to a spacious living and dining area highlighted by a cozy electric fireplace and ceiling fan. Sliding glass doors lead to a private patio with peaceful ideal setting for morning coffee, birdwatching, entertaining or simply relaxing. A convenient outdoor storage shed adds extra functionality. The main level offers two generously sized bedrooms with ample closet space, a full bath a including washer and dryer closet. Upstairs, a dramatic open loft overlooks the living area and leads to a spacious primary suite featuring a unique barn-door closet, walk-in closet, and an updated full custom tiled shower with double vanity, skylight and elegant cabinetry. Wake up to seasonal lake views from the primary bedroom suite. Central Air & updated blown in insulation are just some additional perks. A detached two-car garage provides additional storage and convenience along with an additional dedicated parking space. Ideally located with easy access to I-84, charming shops, a plethora of dining and so much that Southbury and Woodbury have to offer. This exceptional home combines comfort, convenience, and scenic surroundings in desirable Woodbury Place.

22 Woodbury Pl Unit 22, Woodbury
$1,395,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192284 MLS
Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden views. Step through the screened stone-and-timber breezeway to a newly expanded patio and custom firepit crafted directly from native fieldstone, all beneath a classic wood-shingle and copper roof. The surrounding grounds function as a true New England compound. A separate two-bedroom carriage house offers built-in guest quarters with a covered porch and an oversized 2.5-car garage. Nearby, a newer two-story 40'x28' barn provides flexible space for a creative studio, vehicle storage, or livestock, complemented by two additional storage sheds. Recent improvements include, but are not limited to, a new cedar-shingle roof with copper downspouts (2025), new A/C, fresh interior paint throughout (2026), and refinished flooring. It is an unmistakable rural sanctuary with abundant room for hosting friends and extended family.

509 Weekeepeemee Rd, Woodbury
$250,000
ACTIVE Status ⋅ 24192651 MLS
An exceptional opportunity to own 76.9 +/- acres in one of Woodbury's most desirable locations. This unique offering includes two contiguous parcels to be sold together, consisting of this 14.9-acre parcel and the adjoining 62-acre parcel (MLS #24192209). *The 14.9 is land-locked and can not be sold separate). Featuring a charming 3-bedroom home, the property offers a rare combination of rolling meadows, mature woodlands, mountain laurel, stone walls, and open fields, creating endless possibilities for the next owner. Whether you're seeking a private country estate, equestrian property, family compound, recreational retreat, hunting property, or a prime development opportunity, this expansive acreage provides the flexibility to bring your vision to life. Surrounded by the natural beauty of Woodbury while offering convenient access to local amenities, this is a truly remarkable opportunity to invest in one of Litchfield County's most sought-after communities. A rare offering where privacy, scenic landscapes, and future potential come together.

Hoop Pole Hill, Woodbury
$1,000,000
ACTIVE Status ⋅ 24192209 MLS
An exceptional opportunity to own 76.9 acres in one of Woodbury's most desirable locations. This unique offering includes two contiguous parcels to be sold together, consisting of 14.9-acre parcel (MLS# 24192651) and this adjoining 62-acre parcel Featuring a charming 3-bedroom home, the property offers a rare combination of rolling meadows, mature woodlands, and open fields, creating endless possibilities for the next owner. Whether you're seeking a private country estate, equestrian property, family compound, recreational retreat, hunting property, or a prime development opportunity, this expansive acreage provides the flexibility to bring your vision to life. Surrounded by the natural beauty of Woodbury while offering convenient access to local amenities, this is a truly remarkable opportunity to invest in one of Litchfield County's most sought-after communities. A rare offering where privacy, scenic landscapes, and future potential come together.

245 Hoop Pole Hill Rd, Woodbury
$1,100,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24192457 MLS
Spacious Colonial in desirable Carriage Hills offers approximately 5,700 square feet of living space, including a walk-out lower level that is well suited for an in-law suite or au pair quarters. The main level features wood floors, formal living and dining rooms, an eat-in kitchen, a bedroom, a full bath, and a family room with a fireplace that opens to an oversized deck. Upstairs, you'll find three bedrooms, a full bath, and a spacious primary suite with a spa-like bath and loft area. The walk-out lower level includes three finished rooms plus a full bath, offering flexible space for guests, extended living, recreation, or work-from-home needs. The private backyard is surrounded by trees and accented with perennial gardens. NEW Roof June 2026. Located in Woodbury-one of Connecticut's most beloved small towns-the home is close to charming shops, antique stores, coffee shops, and restaurants, all just about 90 minutes from New York City.

16 Gate Post Ln, Woodbury
$599,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192145 MLS
Exceptional opportunity to renovate and create your dream country estate on 12.69 private acres in the heart of Woodbury. Privately sited along a quiet country road with seasonal long views, this 2,972 sq. ft. contemporary offers an outstanding combination of acreage, privacy, and potential rarely found at this price point. Designed for comfortable living, the home features a dramatic sunken living room with soaring vaulted ceilings, a fireplace, and walls of windows overlooking the surrounding landscape. The main level includes a spacious primary suite, private office, butler's pantry, and access to expansive decks that invite outdoor entertaining. Upstairs are 3 additional bedrooms and an open den, while the unfinished walk-out lower level offers endless possibilities for future living space. The property's 12.69 acres provide a beautiful backdrop with open land, mature trees, and a four-stall barn, offering flexibility for a variety of country lifestyles. Priced to reflect the opportunity for renovation and updating, this is an exceptional chance for investors, builders, or buyers looking to customize a solidly built home in one of Woodbury's most desirable locations. With great bones, an outstanding setting, and significant upside potential, this property is ready for its next chapter. Sold as is.

348 Hoop Pole Hill Rd, Woodbury
$895,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24172964 MLS
QUAIL RUN On the cul de sac - 4 NEW HOMES ALL ON FLAT LOTS! They might be what you have been looking for - SMALLER & SMARTER new homes with PRICES TO MATCH. Beautiful 1 acre+ lots on shared common drives surrounded by 12 ACRES OF PRIVATE OPEN SPACE. This is QUINTESSENTIAL WOODBURY - Quiet, woodsy, and BEAUTIFUL! 2 homes IN CONTRACT, 1 home available for FALL DELIVERY and this new build to start in later summer/early fall for SPRING DELIVERY 2027.

96 Quail Run Rd, Woodbury
$395,000
ACTIVE Status ⋅ 24187054 MLS
Nestled along one of Woodbury's finest country roads, this exceptional 2.53-acre parcel offers a rare masterclass in privacy and natural beauty. Located just moments from the Roxbury town line, the gently rolling landscape is framed by mature trees and directly abuts the Arthur Miller Preserve and the Frank and Ellen McCort protected Land Trust. Positioned just two homes away from the historic Calder Estate, the setting creates an extraordinary sense of quietude and absolute seclusion. The property features a magnificent all-season running stream with its own natural waterfall, dramatically enhancing the native wildlife and scenic beauty of the area. Enveloped by the timeless allure of Litchfield County, this land offers an ideal canvas for an architectural masterpiece, a private weekend retreat, or a magnificent legacy estate. Its pristine setting, open spaces, and dramatic yet intimate feel provide the perfect balance of country elegance and everyday livability. Peerless privacy, a coveted location, protected surroundings, and an immediate neighborhood of significant homes make this a compelling opportunity in one of Connecticut's most desirable country settings-just minutes from the refined charm of Roxbury and Washington, and approximately 90 minutes from NYC.

133 Painter Hill Rd, Woodbury
$415,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24099709 MLS
Nestled in the highly desirable town of Woodbury, this charming Cape offers just over 2,000 square feet of comfortable living space with endless potential. The home features 3 bedrooms, 2.5 bathrooms, and beautiful hardwood floors throughout. A dedicated home office with custom built-in shelving provides the perfect space for working from home or studying. The inviting living room includes a cozy pellet stove, creating the perfect gathering space. The bright dining room features a large picture window that fills the space with natural light. A spacious mudroom with vaulted ceilings, laundry hookups, and a large walk-in pantry provides exceptional everyday convenience. Step outside to enjoy the 1.5 acre private setting, complete with an in-ground pool and safety fence-ideal for relaxing, entertaining, or making the most of New England summers. Whether you're looking to restore its original charm or add your own personal touches, this home presents an excellent opportunity to build equity in one of Litchfield County's most sought-after communities. New windows, siding and gutters in 2024. The property is being sold "as is." Priced to sell! Don't miss your chance to make this Woodbury property your own!

241 Hoop Pole Hill Rd, Woodbury
$1,795,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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
$1,590,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24184948 MLS
It's rare to find a vintage estate tucked away from a main road, but this one sits at the end of a private lane, opening to 6.3 enchanting acres framed by stone walls, manicured gardens, and a charming vintage home. The property includes a large custom two-story pole barn, inground pool, detached three-bay garage, and an adorable potting shed. The great room flows into a kitchen with handmade cabinetry, butler's pantry, soapstone counters, and a Vulcan stove, all centered around a brick fireplace flanked by double French doors leading to a shady brick patio. Off the kitchen, a spacious screened porch surrounded with stone walls, offers a peaceful spot to enjoy the seasons. The formal living room, currently an office, boasts a light-filled five-window bay, while two front entry rooms serve as a den and library. The primary suite, in its own wing above the great room, features a private living room, full bath, sleeping area, and views of Perkins Ponds. Three additional bedrooms, accessed via a second staircase, are bright, charming, and surprisingly well-appointed with closets. The impressive barn offers tandem bays for vehicles, a heated workshop, and two upper rooms perfect for future studio spaces. Relax by the pool, take in the flowers, and enjoy the chorus of birds. POTENTIAL FOR ADDITIONAL TWO LOTS SPLIT OFF OR SECONDARY HOME TO BE BUILT. BUYERS MUST DO THEIR OWN DUE DILIGENCE.

40 Ruffin Rd, Woodbury

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