Woodbury CT Homes for Rent
The median home value in Woodbury, CT is $419,500.
This is
higher than
the county median home value of $345,200.
The national median home value is $338,100.
The average price of homes sold in Woodbury, CT is $419,500.
Approximately 71.07% of Woodbury homes are owned,
compared to 20.04% rented, while
8.89% are vacant.
Woodbury real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you see a property you’re interested in, contact a Woodbury real estate agent to arrange a tour today!
$2,100,000
225 Old Sherman Hill Road Woodbury, CT 06798
- Type:
- Single Family
- Sq.Ft.:
- 4,517
- Status:
- Active
- Beds:
- 4
- Lot size:
- 33.98 Acres
- Year built:
- 1969
- Baths:
- 5.00
- MLS#:
- 24072926
- Subdivision:
- N/A
ADDITIONAL INFORMATION
A long winding drive leads you to Four Winds Farm. Perched on the hill, this remarkable 33.98-acre property includes a 4,500 sq ft, 11 room, 4 bedrooms, 4.1 bath residence as well as a home for your horses. The contemporary house has many updates throughout, cathedral ceilings, tall windows, multiple sliders to exterior entertainment areas and spacious deck. There is central air, a security system, central vac, generator, and 4-bay heated garage. The spectacular grounds include the inground gunite saltwater pool, spacious composite deck, mature professional landscaping, and amazing views of distant hills. For the horses there is a two-story 8 stall stable, 14 paddocks with aisle ways, 120' x 200' riding ring with Atwood Equestrian Surface (re-surfaced 4 years ago), 7 run-in sheds, 20' x 20' tractor barn and trail. Woodbury designated as Connecticut's "Most charming small town," by Reader's Digest offers tree-lined Main St, parks, playgrounds, hiking trails and streams to dip your toes in on those hot summer days. Also known as the "Antiques Capital of CT," there's no shortage of shops, boutiques and antiques homes lining the historic district. Woodbury is home to a half dozen fun and diverse restaurants and a brewery with music. Just twenty minutes to the historic Palace Theater for concerts, comedy and much more. Forty minutes to Mohawk Mountain for winter fun. 35 minutes to Brewster Train Station and 90 minutes to NYC. Come see what Litchfield Hills has to offer!
$119,900
Main Street NORTH Woodbury, CT 06798
- Type:
- Land
- Sq.Ft.:
- n/a
- Status:
- Active
- Beds:
- n/a
- Lot size:
- 2.1 Acres
- Baths:
- MLS#:
- 24072843
- Subdivision:
- N/A
ADDITIONAL INFORMATION
Residential lot of record on Main Street North, Woodbury. A private lot with the potential for distant views over the cornfields in the Nonnewaug Valley. An ideal location within a few minutes to Woodbury's historic downtown and 5 to 10 minutes to Bethlehem and Watertown town centers.
$399,900
Main Street NORTH Woodbury, CT 06798
- Type:
- Land
- Sq.Ft.:
- n/a
- Status:
- Active
- Beds:
- n/a
- Lot size:
- 56.29 Acres
- Baths:
- MLS#:
- 24072824
- Subdivision:
- N/A
ADDITIONAL INFORMATION
56 acres in the heart of Woodbury. The perfect spot for a compound or subdivide and create an open space subdivision or a few large parcels. Potential for terrific views over the Nonnewaug Valley. Located a few minutes from downtown and 5 minutes from Nonnewaug High School. Build your dream house and enjoy the views!
- Type:
- Single Family
- Sq.Ft.:
- 2,042
- Status:
- Active
- Beds:
- 4
- Lot size:
- 3.75 Acres
- Year built:
- 2022
- Baths:
- 3.00
- MLS#:
- 24072559
- Subdivision:
- North Woodbury
ADDITIONAL INFORMATION
Nestled in the heart of Woodbury, with easy access to the picturesque towns of Litchfield, Washington, and Roxbury, this newly constructed modern farmhouse-style home offers the perfect blend of comfort, privacy, and New England charm. Built with quality craftsmanship and energy-efficient features, this serene retreat boasts 3 spacious bedrooms, 2.5 bathrooms, plus a versatile 300+/- sq. ft. finished bonus room. The property sits on three acres of beautiful, private land, offering a peaceful sanctuary surrounded by natural beauty. Designed for both relaxation and entertaining, the open-concept kitchen, dining, and living area features a cozy indoor gas fireplace, creating a warm and inviting atmosphere. Step outside onto the back deck, where you can take in expansive, breathtaking views of the meadow and mountains or unwind in the luxurious cedar hot tub. Situated in close proximity to top private schools like Taft and Westover, the home also offers easy access to outdoor recreation, dining, shopping, and local farms, with attractions such as Quassy Amusement Park just a short drive away. Experience the charm and tranquility of Litchfield County living, all while being just two hours from New York City. Now available for sale, a rare opportunity to own a stunning move-in-ready home in one of Connecticut's most desirable areas. The home is currently furnished, and owners are open to selling furnished, partially furnished or unfurnished. Owner is broker/agent.
$899,900
11 Saxony Lane Woodbury, CT 06798
- Type:
- Single Family
- Sq.Ft.:
- 3,124
- Status:
- Active
- Beds:
- 3
- Lot size:
- 4.15 Acres
- Year built:
- 2019
- Baths:
- 4.00
- MLS#:
- 24072388
- Subdivision:
- N/A
ADDITIONAL INFORMATION
Do not miss this beautiful home set back on a private 4.15-acre lot. Main level features a total open floor plan with vaulted ceilings and half bath. Kitchen features Kucht stainless steel appliances, Quartz countertops, with an oversized walk-in pantry. Extra Large dining, kitchen, family room area with built in sound system perfect for entertaining. Upper level adds 2 large bedrooms along with a laundry room and two full bathrooms. Additional to the 2 bedrooms is the Massive Primary suite with fireplace and sitting area, 2 large walk-in closets and a gorgeous full bath with extra-large shower with dual heads. On top of all that a gigantic 1940 square foot 4 bay garage dual deep that can hold up to 7 cars easily with 3/ 9' garage doors and 1/12' door that has a car lift for that person who likes their toys!! Back patio with hot tub. Tesla solar panels with battery backup that are owned outright not a lease that acts as a generator if power goes out! This is a custom built home just waiting for a new owner.
$339,500
54 Mountain Road Woodbury, CT 06798
- Type:
- Single Family
- Sq.Ft.:
- 1,080
- Status:
- Active
- Beds:
- 3
- Lot size:
- 0.49 Acres
- Year built:
- 1849
- Baths:
- 1.00
- MLS#:
- 24062169
- Subdivision:
- N/A
ADDITIONAL INFORMATION
Much of the work on this home has been done by the currant owner and it's gorgeous! Has completed much of downstairs including kitchen and living area but still a work in progress. Downstairs is all open with a loft upstairs. Great value and beautiful surroundings sits on half an acre. Worth a look ! There are no disclosures
- Type:
- Single Family
- Sq.Ft.:
- 4,800
- Status:
- Active
- Beds:
- 3
- Lot size:
- 1.74 Acres
- Year built:
- 1870
- Baths:
- 3.00
- MLS#:
- 24055622
- Subdivision:
- N/A
ADDITIONAL INFORMATION
Your home is your castle! If you've ever dreamed of calling a castle your home, this remarkable 5,000-square-foot stone house is the answer. Known fondly by locals as "The Castle," this property has a fascinating history, with roots tracing back to the 1800s but the all updates including new mechanicals, plumbing, electric, floors, well, septic, roof and more will give you comfort and peace of mind. Originally a stagecoach stop, it stands near a brook that was once a favored path of the legendary Leatherman. In the 1970s, a visionary known as "Cadillac Joe" began expanding the home into a grand stone castle, meticulously crafting every stone by hand. Though his work was left incomplete due to his advancing age, the foundation he laid became the start of a stunning transformation. Enter Mario, whose dedication and years of hard work brought the vision to life, completing this architectural masterpiece with exceptional attention to detail. Today, "The Castle" stands as a beacon of history and craftsmanship, featuring a grand dining room, a massive living room, and a chef's kitchen-perfect for entertaining guests or simply enjoying the beauty of the space. The wraparound balconies offer breathtaking views over the river ravine and treetops, while the stone walkways and tranquil surroundings provide a peaceful retreat from the world. Whether you're captivated by the historic intrigue, the timeless craftsmanship, or the unparalleled setting, this home offers a truly unique living
$1,150,000
27 Middle Quarter Road Woodbury, CT 06798
- Type:
- Single Family
- Sq.Ft.:
- 2,042
- Status:
- Active
- Beds:
- 3
- Lot size:
- 1.48 Acres
- Year built:
- 1825
- Baths:
- 3.00
- MLS#:
- 24049803
- Subdivision:
- Middle Quarter
ADDITIONAL INFORMATION
Discover the charm of this beautifully soon to be restored antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this soon to be renovated vintage gem 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. The exterior is equally impressive, offering room an in-ground gunite pool, 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!
$125,000
103 Mill Road Woodbury, CT 06798
- Type:
- Land
- Sq.Ft.:
- n/a
- Status:
- Active
- Beds:
- n/a
- Lot size:
- 2 Acres
- Baths:
- MLS#:
- 24054677
- Subdivision:
- N/A
ADDITIONAL INFORMATION
This building lot in the pastoral setting of Woodbury, CT, spans 2+/- acres and is approved for a 4 or 5 bedroom house. Preliminary engineering, including surveys, perc tests, and septic plan, is already in place. Situated in a well-established neighborhood, the lot comes with minimal deed restrictions, offering an ideal opportunity to construct either a weekend retreat or a lifelong residence.
- Type:
- Single Family
- Sq.Ft.:
- 2,521
- Status:
- Active
- Beds:
- 4
- Lot size:
- 0.52 Acres
- Year built:
- 1836
- Baths:
- 3.00
- MLS#:
- 24052535
- Subdivision:
- Hotchkissville
ADDITIONAL INFORMATION
Own a piece of history! Enjoy life in historic Hotchkissville of Woodbury in this 1836 Greek Revival home. Just one mile from Woodbury's town center, step back in time while being in close proximity to all major conveniences. Currently functioning as a two family property, this unique home can be easily converted to a four bedroom, three bath, 2500sf single family. Experience the old world charms of exposed beams and wide-board flooring, in this 19th Century structure that was once home to one of Woodbury's most prominent textile families! The main level of the home features one bedroom, galley kitchen, a full bath, and living and dining room options. There is also a loft bedroom with its own private bath. The shop, also on the main level, can be utilized for business purposes again by an occupant or convert this space to a fabulous great room as it connects in two ways to the rest of the main level, open floor plan. On the second level, find two more bedrooms with full bath, finished walk up attic as rec room, or office space as well as a bonus room, currently used as a small kitchenette and laundry room, that can be converted to fit your needs. Property is located within a 1 hour and 30 minute drive from New York City. Lots to see and appreciate at this unique property in Connecticut's Most Charming town according to Reader's Digest Magazine.
- Type:
- Single Family
- Sq.Ft.:
- 3,978
- Status:
- Active
- Beds:
- 5
- Lot size:
- 4.15 Acres
- Year built:
- 2004
- Baths:
- 4.00
- MLS#:
- 24018837
- Subdivision:
- Transylvania
ADDITIONAL INFORMATION
Nestled at the intersection of Route 72 and Route 167 in Woodbury, this exceptional home is the perfect blend of modern amenities and unparalleled convenience. Located in close proximity to both the Center of Woodbury and the Southbury Green you'll be moments away from a diverse selection of shops and restaurants. Enjoy the close by natural beauty of Wood Lake, local parks, walking trails, and make the most of the nearby Southbury Dog Park. With easy access to exits 13, 14, and 15 off of I-84, as well as route 8, commuting will never be easier. This property is directly next to the entrance of Janie Pierce Park and backs up to over 30 acres of serene land conservation, guaranteeing exceptional privacy and tranquility for years to come. Upon entering, you'll be greeted by an open floor plan that seamlessly combines elegance and functionality. The inviting kitchen features granite countertops, a breakfast bar, and a new deck just off the kitchen-ideal for entertaining. The main level is adorned with rich hardwood floors, while the upper bedrooms are enhanced with stylish vinyl plank flooring. The grand living room boasts cathedral ceilings and expansive windows extending to the second floor, creating a dramatic and airy atmosphere. Two staircases provide stylish access to the upper level, where you can overlook the main living area below.
$625,000
5 Washington Road Woodbury, CT 06798
- Type:
- Single Family
- Sq.Ft.:
- 2,515
- Status:
- Active
- Beds:
- 4
- Lot size:
- 0.34 Acres
- Year built:
- 1840
- Baths:
- 4.00
- MLS#:
- 24047043
- Subdivision:
- N/A
ADDITIONAL INFORMATION
Welcome to this beautifully appointed Greek Revival home, nestled in the heart of Woodbury, the antique capital of Connecticut. This stunning property features 4 spacious bedrooms, including a convenient first floor bedroom and full bath which can be used as office space! The open concept design seamlessly connects the living and dining areas, highlighted by a cozy fireplace that sets the perfect ambiance for gatherings. Upstairs, you'll find three additional bedrooms, two of which boast en-suite baths for added privacy and convenience. Set on a sweet little lot, this home offers the ideal blend of tranquillity and accessibility. Enjoy the downtown scene with shops, restaurants, and antique treasures just a short stroll away. This is a rare opportunity to own a piece of history in a charming country community-don't miss out on making this enchanting property your own!
$975,000
148 Flanders Road Woodbury, CT 06798
- Type:
- Single Family
- Sq.Ft.:
- 3,082
- Status:
- Active
- Beds:
- 3
- Lot size:
- 5 Acres
- Year built:
- 1987
- Baths:
- 4.00
- MLS#:
- 24043622
- Subdivision:
- N/A
ADDITIONAL INFORMATION
Come home to a unique 3082 sqft, one of a kind custom built Barn home all set on 5 secluded acres. Featuring an open floor plan, beamed ceilings, oak floors, Plaster Walls, fully applianced Kitchen with breakfast bar, a spacious Family Room with brick fireplace, built-ins, & slider leading to back deck. The Living Room with fireplace is adjacent to a spacious Dining Room area & slider leading to large deck with access to side yard. At the end of the day enjoy the cozy Library with fireplace and built-ins. First floor also has an Office as well as a full Bathroom. As you ascend the stairs to the second floor you will marvel at the unique lighted brick archway. Second floor boasts of lovely Primary Bedroom Suite with brick fireplace & raised hearth, walk-in closets, Full Bath with tub, shower & vanities, and slider leading to balcony. Two other large Bedrooms with skylights, Full hallway Bathroom, and Laundry Room with utility sink. Lower level features an in-law/apartment, Storage Room & Mud Room with storage. This home has easy access to Woodbury's town center, shops, top restaurants, antiquing, and recreation with hiking trails & nearby lake. Enjoy all this property has to offer as well as the area!
- Type:
- Single Family
- Sq.Ft.:
- 2,628
- Status:
- Active
- Beds:
- 3
- Lot size:
- 3.34 Acres
- Year built:
- 1930
- Baths:
- 4.00
- MLS#:
- 24042289
- Subdivision:
- N/A
ADDITIONAL INFORMATION
Welcome to this charming Colonial home, originally built in the 1930s, offering a perfect blend of vintage character and modern upgrades. This unique property features a primary bedroom on the main floor, with glass French doors that flood the space with natural light. The upgraded kitchen is a chef's delight, boasting 2 gas ovens and a subzero refrigerator. With two full baths and two separate laundry areas on the main floor, convenience is key. The home includes a private apartment, ideal for guests or rental income, featuring its own kitchen, private deck, and two separate entrances for added privacy. Upper level with sprawling bath with soaking tub joins two bedrooms. A new garage, built in 2001, connects to a separate room via a breezeway with copper screens. There's an additional 17ft of storage over garage that was used for woodworking projects. The property is rich in history, with various vegetation and the charming nuances of an older estate. Oak floors throughout the first floor and apartment, along with new storm windows and doors for the original windows installed in 2012, New roof 2024. Two garage/storage spaces under main garage. This property is truly a unique opportunity to take in all seasons of country living with all the comforts of home. Endless possibilities for variety of buyers. Whether your looking to bring your extended family, run home based business or generate rental income this property is a rare find.
$1,125,000
16 Gate Post Lane Woodbury, CT 06798
- Type:
- Single Family
- Sq.Ft.:
- 5,781
- Status:
- Active
- Beds:
- 4
- Lot size:
- 2.61 Acres
- Year built:
- 1998
- Baths:
- 4.00
- MLS#:
- 24039243
- Subdivision:
- Flanders
ADDITIONAL INFORMATION
This elegant Colonial in Carriage Hills features approximately 5700 sqft of living space, including a walk-out lower level suitable for an in-law suite. The main level has wood floors, formal living and dining rooms, an eat-in kitchen, bedroom, a full bath, and a family room with a fireplace leading to an oversized deck. Upstairs, there are three bedrooms, a full bath, and a primary suite with a spa-like bath and loft area. The lower level features three finished rooms and a full bath. The private backyard is surrounded by trees and dotted with perennial gardens. Woodbury is one of Connecticut's best small towns filled with charming shops, antiques, coffee shops and restaurants and it's only 90 minutes from NYC
$195,000
14 Roxbury Road Woodbury, CT 06798
- Type:
- Land
- Sq.Ft.:
- n/a
- Status:
- Active
- Beds:
- n/a
- Lot size:
- 9.27 Acres
- Baths:
- MLS#:
- 24018558
- Subdivision:
- Transylvania
ADDITIONAL INFORMATION
In The Hills of Lichfield County! Fantastic Opportunity to Build Your Dream Home w/ Lots of Privacy on this Wooded 9.27 Acres of Nature & Tranquility. Enjoy the Sounds of Transylvania Brook that Flows through this Property. Located in The Overbrook Subdivision of Woodbury. Woodbury named " Most Charming Small Town" by Reader's Digest! Near Roxbury Line and Scenic Route 67 and only 90 Minutes to NYC. Please Do Not Go to Property w/o Confirmed Appointment! Buyer to do their Own Due Diligence!
- Type:
- Single Family
- Sq.Ft.:
- 6,459
- Status:
- Active
- Beds:
- 4
- Lot size:
- 7.06 Acres
- Year built:
- 2013
- Baths:
- 4.00
- MLS#:
- 24019575
- Subdivision:
- N/A
ADDITIONAL INFORMATION
6459sqft Shingle style home with horse barn, paddocks & riding arena, set on 7 acres with a gorgeous westerly view of Roxbury's bucolic rolling hills! Built in 2013, no expense was spared on the construction of this home. Sprawling kitchen w marble countertops, stainless appliances, butler's pantry & breakfast nook opens to a sun-drenched 2-story great room w views. Tastefully done formal living & dining rooms. Dining room w trey ceilings & wood paneling. Charming office w bookshelves & built-ins. Cozy, multi-purpose den w fireplace & french doors. Mudroom & powder room. Upstairs, master suite w bookshelves, built-ins, sitting area, walk-in closet w center island & stunning master bath w heated marble floors, marble countertops, double vanities, stand-up shower & air jetted tub. 3 additional bedrooms all amply sized w walk-in closets & attached baths. Oversized recreation room currently used as a home gym & play area. Additional room on 3rd floor. This property is an equestrian's dream. Horse barn w 5 stalls w waterers. 2nd level in barn loft for additional space. 6 horse paddocks w waterers & electric fence. Perfectly set riding arena w views. This home is set on several cleared acres but is secluded from all neighboring properties and is backed up by 34 acres of open space. The westerly views of rolling hills offer stunning sunsets from bluestone patios. The setting and land are serene and surreal! Plenty of room for a pool. Taxes reflect PA490 tax exemption for 5.22 acres
- Type:
- General Commercial
- Sq.Ft.:
- 2,176
- Status:
- Active
- Beds:
- n/a
- Year built:
- 1987
- Baths:
- 3.00
- MLS#:
- 24006925
- Subdivision:
- Sherman Hill
ADDITIONAL INFORMATION
Investment opportunity with two solid tenants. Cornerstone Professional Office Park. Highly visible and accessible contemporary complex. Four separate buildings, each with abundance of open parking, public / common restroom (each of these office's has their own private bath also) and elevator for ease of access. This condo is a three unit rental, one common entry corridor and unit C has multiple entry/exits. Must be sold as one condo. Broken down as follows: A 552 s/f, reception area, two offices, one bath. $1025/mos. B 841 s/f, reception area, two offices, kitchenette, deep storage closet, one bath. $1325./mos C 672 s/f one office, one very large open room, one bath, remodeled including new windows, separate back entrance, $1100/mos. Lease's include heat/ac/water. $100.00 increase per year HOA$868/mos Eversource $491/mos (2022 figures) Newer heat pump unit and some newer windows.
- Type:
- Land
- Sq.Ft.:
- n/a
- Status:
- Active
- Beds:
- n/a
- Lot size:
- 25.31 Acres
- Baths:
- MLS#:
- 170517471
- Subdivision:
- Nonnewaug
ADDITIONAL INFORMATION
VIEWS: Wonderful views for a home site or farm. Possible two points of entrance. Buyer is responsible for due diligence and approvals. The property runs behind 1053 Main Street North and is contiguous to 867 Main Street North. Approximately 25.31 acres. AVAILABLE IN ATT. DOCS: Dated: 1) Revised lot line survey. 2) Perked results. 3) Soil tests. 4) Elevations
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