Refine Search
Map
Sort by
$2,995,000
4 Beds ⋅ 6 Baths ⋅ 24163576 MLS
Warren's Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home offers four bedrooms, timeless architectural details, spacious rooms, 4 fireplaces and custom built-ins. The impressive six-barn complex provides exceptional flexibility, featuring a retail shop, extensive equipment storage, a two-car garage, pool cabana and pool equipment building. A newly constructed temperature controlled 3,800-square-foot post-and-beam barn with a half bath and laundry room at the rear of the property further expand the property's possibilities. There are also an equipment/horse barn and riverside cabin. Outdoor living is equally remarkable with a stunning new in-ground gunite pool surrounded by lush landscaping. Designed for both relaxation and entertaining, the grounds include a custom "summer kitchen" with a European-style outdoor pizza oven, gas grill, and screened dining pavilion-perfect for hosting gatherings or enjoying quiet evenings. The 18.3-acre setting includes mature trees, open meadows, scenic walking trails, and frontage along the protected Pomperaug River, creating a private and picturesque retreat. Rich in history yet thoughtfully updated, this rare estate offers an exceptional combination of beauty, functionality, and enduring charm. A comprehensive list of recent improvements is available upon request. Buyer must do due diligence with the town for possible uses.

920 Main St S, Woodbury
$1,795,000
2 Beds ⋅ 2 Baths ⋅ 24185479 MLS ⋅ Woodlake BLDG.
Just 2 hours from New York City, this exceptional lakefront retreat offers a rare blend of privacy, natural beauty & turnkey luxury. Tucked at the end of West Lake Rd and bordered by the protected woodlands of Flanders Nature Center Preserve, the property enjoys sweeping, unobstructed views across pristine Lake Quassapaug to historic Tranquillity Farm, designed by McKim, Mead & White. Lake Quassapaug is a private lake with no public access & a 10-mph speed limit, creating an ideal setting for boating, fishing, swimming & year-round recreation. Private beach & dock provide direct water access, while the renovated lakeside cabana offers flexible space for a home office, fitness studio or retreat. Outdoor KIT, BBQ area & multiple patios, including a waterfront terrace, are perfect for entertaining. Renovated in 2020, the home features a beautifully appointed gourmet KIT with premium finishes & seamless flow to inviting living spaces. One of only a select few lakefront homes in Woodbury, it benefits from the town's favorable tax structure while being minutes to historic Main St, acclaimed restaurants & antique shops. Town of Woodbury recognizes 112 West Lake Road and a few other neighboring properties as condominium units. All other homes on the Lake are in Middlebury CT. Rare opportunity to own a fully renovated waterfront home with exceptional privacy, spectacular views & an unparalleled lake lifestyle.

112 W Lake Rd Unit 112, Woodbury
$1,790,000
4 Beds ⋅ 5 Baths ⋅ 24136657 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. Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character with today's modern conveniences. Inside, the open floor plan creates a warm and inviting flow, with three cozy sitting rooms surrounding the impressive central hearth. The chef's kitchen features a large center island, breakfast bar, and sweeping views of the expansive lawn-perfect for both everyday living and entertaining. Original details abound, including hand-hewn beams, wide king's board flooring, and the historic cooking fireplace that anchors the heart of the home. Recent upgrades include a new HVAC system with humidification and numerous other enhancements (see attachments for the full list). A new mahogany deck overlooks the level backyard, leading toward a picturesque bridge, sparkling pool, and inviting cabana. Two barns sit near the parking area-one offering garage space and the other ready for your imagination: ideal for a future guest house, studio, or recreation room, this barn has new propane heat, water and electric service. This extraordinary home offers the rare opportunity to own a piece of history-beautifully updated for modern living.

55 Good Hill Rd, Woodbury
$1,600,000
4 Beds ⋅ 3 Baths ⋅ 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
$1,590,000
4 Beds ⋅ 3 Baths ⋅ 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
$1,450,000
3 Beds ⋅ 3 Baths ⋅ 24139312 MLS
Open Meadow Farm, a beautifully maintained property offering a blend of rural charm and modern conveniences. Set on 9.88 picturesque acres, this property features three fenced fields, ideal for horses or other livestock and a two-story barn equipped with four stalls, a tack room, gravel storage area and a gleaming concrete main floor. Recent updates include a paved driveway with turnaround, back patio, new heating system, a powerful 20KW whole house generator and four energy efficient mini-splits ensuring year-round comfort. Enjoy the beautifully landscaped gardens, several tranquil ponds, a babbling brook and perennial flower beds. This spacious home boasts three bedrooms and three full baths, a well-appointed kitchen, office space, a full basement and both attached and detached garages. Relax on the screened porch overlooking the ponds and bring your four-legged friends-this property is ready for you to move right in. Come enjoy the charming little town of Woodbury, only 90 minutes to NYC

819 Main St N, Woodbury
$1,395,000
3 Beds ⋅ 3 Baths ⋅ 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
$1,395,000
5 Beds ⋅ 5 Baths ⋅ 24168618 MLS
Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional preservation and character, having been featured in Early American Life magazine and Historic Homes magazine-an honor that speaks to its authenticity and enduring appeal. This stately five bedroom home showcases original architectural details that collectors and history enthusiasts dream about. Seven fireplaces anchor the home's character across its generous 4,800+ square feet. Five beautifully paneled rooms reveal the craftsmanship of a bygone era, while antique wide-board flooring runs throughout, whispering stories of centuries past beneath every footstep.

30 Hollow Rd, Woodbury
$1,200,000
4 Beds ⋅ 5 Baths ⋅ 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
$1,150,000
24177403 MLS
East Meadowbrook Farm presents a rare opportunity to own a legacy New England property offered for the first time since 1918. Encompassing 42 acres, including 15 rolling, sun-drenched acres of open fields, this former dairy and Christmas tree farm is bordered by 250 acres of protected Flanders Nature Center conservation land, creating an extraordinary sense of privacy and permanence. A quarter mile of frontage along Flanders Road, classic stone walls, pristine streams, established culvert crossings, and abundant wildlife define the landscape, while private trails invite walking, hiking, and outdoor recreation. Just 90 minutes from New York City and 10 minutes from Woodbury's shops and historic antique trail, East Meadowbrook Farm offers a peaceful country sanctuary with limitless potential for a premium estate, hobby farm, or family compound.

Flanders Road, Woodbury
$1,100,000
4 Beds ⋅ 4 Baths ⋅ 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
$1,000,000
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
$999,900
3 Beds ⋅ 3 Baths ⋅ 24146826 MLS
Discover the charm of this beautiful antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this vintage gem is being restored by the current owner and is just a 2-minute stroll from coffee shops, top-notch restaurants, and the historic Main Street. The home will be meticulously updated from the ground up, featuring wide board antique flooring, a stunning great room with a cathedral ceiling and fireplace, and formal living and dining rooms, each with its own fireplace. Upstairs, the primary suite boasts a vaulted ceiling with exposed beams, accompanied by two additional bedrooms and a walk-up attic. This will be a brand new house when complete; new mechanicals, new insulation, new wiring, new plumbing, new kitchen and baths - a new home with the charm of old. The exterior could be equally impressive, offering two post-and-beam barns, and a beautifully landscaped level lot. The Middle Quarter zoning adds extra versatility, allowing you to run a business from home and even expand the living space into the barns. This is truly one of the best locations in Woodbury!

27 Middle Quarter Rd, Woodbury
$959,000
4 Beds ⋅ 3 Baths ⋅ 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
$895,000
4 Beds ⋅ 3 Baths ⋅ 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
$895,000
4 Beds ⋅ 3 Baths ⋅ 24172742 MLS
Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, features wide-plank flooring and exposed hand-hewn beams that anchor the home's historic character. The rooms are designed for both intimacy and entertaining. A cozy sitting room and a dedicated office/library-complete with a classic fireplace-offer quiet retreats. For larger gatherings, the front-to-back living room, with windows on three sides, is bathed in natural light. At the heart of the home is the remodeled kitchen, which opens to the dining room centered around the original refurbished center core fireplace. Upstairs, four bedrooms await. The primary bedroom offers a new ensuite bath detailed with custom tile. The three additional bedrooms share a fully renovated bathroom with a soaking tub/shower combo. Thoughtfully curated, professionally designed interior furniture and fixtures are available upon request. The property has benefited from extensive renovations that include new bathrooms and kitchen, floor refinishing, a new well, upgraded septic, and more; a substantial list is available upon request.

253 Bacon Pond Rd, Woodbury
$875,000
4 Beds ⋅ 3 Baths ⋅ 24202477 MLS
Set on 3.29 picturesque acres bordering conservation land, this beautifully maintained and thoughtfully remodeled country Cape is filled with character, custom craftsmanship and modern amenities. The estate-like grounds and versatile floor plan offer privacy, comfort and functionality, including options for multigenerational living. At the heart of the home, the custom country kitchen features granite countertops, a farmhouse sink, stainless steel appliances and handcrafted cabinetry, opening to a sun-filled sitting/living room with a propane fireplace/stove. The generously sized dining room has its own fireplace, distinctive checkerboard wood floors and a bay window, with the versatility to serve as another living area if desired. The main level includes a primary bedroom with private full bath, a second bedroom, remodeled powder room and separate office or craft room. At the rear, the mudroom incorporates laundry and antique chestnut cabinetry, one of the many details that give this home its individual character. Upstairs are two spacious bedrooms, an updated full bath, built-in storage and a large walk-in attic with the potential for future finished space. The walk-out finished lower level adds another dimension to the home, with a fireplace and antique reclaimed pine cupboards and built-ins. This comfortable area lends itself to recreation, a home office or simply relaxing. A substantial unfinished basement provides abundant storage. The grounds are equally impressive.

385 Middle Road Tpke, Woodbury
$875,000
5 Beds ⋅ 4 Baths ⋅ 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
$850,000
4 Beds ⋅ 2 Baths ⋅ 24183601 MLS
Built in 1854, this 5.91 acre property offers an incredible value impossible to replicate today for the price. The property includes an Italianate stone home with an approx 675 sq foot retail/office room with a separate entrance at the driveway, a 28' x 53' post and beam barn with a full walkout lower level, a large pond, stone walls, incredible perennial garden surround, and a 21' x 45' accessory building with heat - great guest house or in-law potential. Inspired by Tuscan villas, Italianate style homes, usually square and symmetrical, were popular in the late 19th C. in New England. Park-like grounds; large pond has goldfish (see pics). The 3532 square foot main home has potential for an in-home business, or retail shop as it once was. Other potential uses in this highly-visible location include using the barn for farm animals and/or horses. Home has 4 bedrooms, 2 full bathrooms, 3 fireplaces, and approx 435 sq foot foot, renovated, eat-in, sunny kitchen with leathered granite counters and stainless appliances. New oil furnace 2026. Septic recently maintained (new pump, piping, and floats in 2022 by Garrity, no problems since). 50 gallon water heater Oct 2022. Substantial moldings and built-ins, front and back staircases, specialty stainless skylights, and a rooftop belvedere, which looks beautiful lit up at night, atop the well maintained copper roof. Minutes to three towns centers of Woodbury, Watertown, and Bethlehem. Guesthouse has elec.

1917 Main St N, Woodbury
$819,000
3 Beds ⋅ 2 Baths ⋅ 24182784 MLS
Live Stress-Free in This Income-Producing Equestrian Retreat! Enjoy the best of country living while generating income from your property. Rental revenue from a separate 1 BR apartment and 4 of the 10 horse stalls offers a rare opportunity to offset ownership costs! Situated on 5.76 level acres of open pasture and riding space, this equestrian property is ideal for horse enthusiasts, trainers, or anyone seeking a peaceful rural lifestyle. The horse facilities include 4 barns with a total of 10 stalls, 2 wash stalls, and a 20 x 60-meter riding arena with premium stone dust and sand footing. The grounds offer ample space for turnout, training, recreation, and relaxation, creating the perfect balance of functionality and tranquility. At the heart of the property is a charming 3-bedroom, 2-bath ranch home featuring a windowed kitchen, spacious dining room for entertaining, vaulted ceilings, 2 fireplaces with wood stoves, a WIC, and an oversized lower-level bonus room. Step outside to a private backyard designed for gatherings and enjoyment, complete with a thriving vegetable garden. The 1 BR apartment is currently rented, but can easily serve as an in-law suite or guest quarters. There is also a 3 car garage for the car enthusiast! The possibilities are endless! The present owners, Serenity Farm Horse Rescue, have lovingly cared for this property for years. As their rescue continues to grow, they are seeking a larger facility to support their expansion. Shown by private appt.

92 Minortown Rd, Woodbury
$775,000
4 Beds ⋅ 4 Baths ⋅ 24138386 MLS
The Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's lifestyle. History surrounds you with wide board flooring, library built-ins, two fireplaces and 1850 barn. This four -bedroom home offers spacious rooms, three finished levels and hidden delights. Enjoy picnics under the mature trees on your own fenced-in level yard. Sidewalks take you everywhere on Main St where you can enjoy the Library, antique and retail shops, schools, churches, great restaurants and coffee shops. Parks and the Senior Center are all nearby. Only 90 minutes to NYC. Named by Reader's Digest as one of CT most charming towns. Come call Woodbury home!

28 School St, Woodbury
$769,900
4 Beds ⋅ 3 Baths ⋅ 24185801 MLS
Beautifully renovated 4-bedroom, 2.5-bath ranch set on a spacious corner lot in one of Woodbury's most desirable locations. Just two streets from Woodbury's nationally recognized Main Street, this home offers the perfect combination of modern updates, comfortable living, and exceptional outdoor entertaining. The complete interior renovation began in 2023 and has recently been completed, creating a truly move-in-ready home. At the heart of the property is a stunning open-concept kitchen featuring stylish finishes and thoughtful design, seamlessly flowing into the dining area and living room-ideal for both everyday living and hosting family and friends. The private primary suite offers beautiful views of the backyard retreat, while three additional generously sized bedrooms and a fully renovated full bathroom provide plenty of space for family and guests. Every bathroom in the home has been tastefully updated, complementing the home's fresh, modern feel. Step outside to your own backyard oasis. The expansive outdoor space features a large in-ground swimming pool, dedicated BBQ area, and ample lawn space for entertaining, yard games, and summer gatherings. Whether you're hosting a crowd or enjoying a quiet evening at home, this outdoor setting is sure to impress. Adding even more versatility is the separate pool house, complete with accommodations that offer endless possibilities for guests, extended family, a home office, or private retreat.

62 Heritage Dr, Woodbury
$765,000
2 Beds ⋅ 2 Baths ⋅ 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
$765,000
3 Beds ⋅ 3 Baths ⋅ 24159088 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! Construction has begun with completion possible in early October. #86 is a 3 BR, 2.5 BA Cape with FULL FRONT PORCH, 2 car attached garage and OPEN BUT LIVABLE floor plan. LL set up for future finishing.

86 Quail Run Rd, Woodbury
$699,900
3 Beds ⋅ 3 Baths ⋅ 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
$699,900
4 Beds ⋅ 3 Baths ⋅ 24165323 MLS
Watch the parade from your front yard, walk to school, walk to the excellent restaurants in town, walk to the library and to the local park and market! Fabulous location! One of Woodbury's last remaining homes built in the late 1600s. This charming residence offers a unique blend of historic character and modern convenience, ideally situated for those who appreciate easy access to local shops, parks, and restaurants. The interior of the home boasts a rich history with exposed wooden beams, 4 fireplaces, and classic hardwood floors, creating an inviting and warm atmosphere. Outside, a private patio with an open fireplace provides an ideal setting for relaxation or entertaining, surrounded by lush perennial gardens. Adding to the property's versatility is a separate guest house. This additional structure is perfect for an artist's studio, offering a quiet and inspiring space for creative pursuits, or it can serve as a professional office. Woodbury is known for its historical properties, with some homes dating back to the late 17th century. Main Street offers a charming experience with its antique shops, local restaurants, and vibrant Memorial Day parades. Woodbury is known for its picturesque downtown area, featuring beautiful streets and historic houses. Litchfield Hills are home to numerous wineries, forming part of Connecticut's Wine Trail,where you can enjoy tastings and scenic vineyards. The region also boasts farm-to-table restaurants that highlight local produce

339 Main St S, Woodbury
$699,000
3 Beds ⋅ 3 Baths ⋅ 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
$699,000
4 Beds ⋅ 2 Baths ⋅ 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
$675,000
24084159 MLS
Presenting a rare opportunity to acquire a 23-acre parcel that has been held within a family for generations. This expansive property, fronting on a tranquil county road, offers a serene and private setting for your future endeavors. The property is a picturesque combination of woodlands, offering an idyllic setting for those seeking privacy and connection to nature. With approximately 800 feet of road frontage, the property provides ample access and visibility, ideal for a potential for a private residence or nature-inspired retreat. Enriching the value of this land, the Flanders Nature Center/ Land Trust encompasses the northern boundary with about 200 acres and the southern edge with about 28 acres, ensuring the preservation of the natural surroundings and offering a legacy of conservation. This adjacency to protected lands promises enduring tranquility and a haven for local flora and fauna. Conveniently located just minutes from the vibrant Woodbury Center, future owners will enjoy the blend of seclusion with the convenience of nearby amenities, including boutique shopping, fine dining, and cultural experiences. Create something truly special in the heart of Litchfield County.

Cowles Rd, Woodbury
$645,000
3 Beds ⋅ 3 Baths ⋅ 24165212 MLS
QUAIL RUN On the cul de sac - 4 NEW HOMES 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! Construction has begun on 2 homes with anticipated completion in August. #94 is a 3 BR, 2.5 BA FARMHOUSE STYLE SPLIT LEVEL with large front porch, oversized 2 car garage, CATHEDRAL LIVING ROOM and finished lower level with laundry room and half bath.

94 Quail Run Rd, Woodbury

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.