Woodbury CT Real Estate & Homes for Sale

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Beds:
2
Baths:
2.00
Sq.Ft.:
1,197
Status:
Active
MLS#:
24185479
Type:
Condo
Subdivision:
Quassapaug
Year built:
1955
Courtesy: Compass Connecticut, LLC 203-290-2477
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ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,360
Status:
Active
MLS#:
24185444
Type:
Single Family
Subdivision:
N/A
Lot size:
1.61 Acres
Year built:
1987
Courtesy: HomeSmart Homes and Estates 845-547-0005
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ADDITIONAL INFORMATION

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

Beds:
4
Baths:
3.00
Sq.Ft.:
2,732
Status:
Active
MLS#:
24184948
Type:
Single Family
Subdivision:
N/A
Lot size:
6.3 Acres
Year built:
1881
Courtesy: Drakeley Real Estate, Inc. 203-263-4336
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,157
Status:
Active
MLS#:
24184647
Type:
Single Family
Subdivision:
N/A
Lot size:
1.38 Acres
Year built:
1976
Courtesy: William Raveis Real Estate 860-354-3906
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ADDITIONAL INFORMATION

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

Beds:
3
Baths:
2.00
Sq.Ft.:
2,448
Status:
Active
MLS#:
24182784
Type:
Single Family
Subdivision:
N/A
Lot size:
5.76 Acres
Year built:
1968
Courtesy: Brown Harris Stevens 203-655-1418
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
2.00
Sq.Ft.:
4,819
Status:
Active
MLS#:
24183601
Type:
Single Family
Subdivision:
North Woodbury
Lot size:
5.91 Acres
Year built:
1854
Courtesy: Coldwell Banker Realty 860-393-0087
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ADDITIONAL INFORMATION

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. Easement for CT DOT to Lewis Atwood Brook at east edge of property; DOT maintains all concrete for brook under road.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,479
Status:
Active
MLS#:
24183597
Type:
Single Family
Subdivision:
N/A
Lot size:
1.34 Acres
Year built:
1987
Courtesy: Klemm Real Estate Inc 203-263-4040
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ADDITIONAL INFORMATION

Charming in-town Gambrel Colonial with views of Orenaug Pond, located just up the road from the South Green. Surrounded by historic landmarks such as King Solomon's Lodge, the Hurd House, the Glebe House, and other notable properties, this home offers three bedrooms, three full baths, and one half bath. It also features a remodeled kitchen with stainless appliances that opens to a family room with vaulted ceilings. Additional highlights include a partially finished walk-out basement, an attached two-car garage, an oversized deck, and private yard. Close to parks, private schools, tennis and swim clubs, shopping and more. Come fall in love with Woodbury.

Beds:
4
Baths:
6.00
Sq.Ft.:
5,316
Status:
Active
MLS#:
24163576
Type:
Single Family
Subdivision:
N/A
Lot size:
18.23 Acres
Year built:
1890
Courtesy: Klemm Real Estate Inc 860-868-7313
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ADDITIONAL INFORMATION

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.

Beds:
5
Baths:
3.00
Sq.Ft.:
4,130
Status:
Active
MLS#:
24181554
Type:
Single Family
Subdivision:
Sherman Hill
Lot size:
1.46 Acres
Year built:
1971
Courtesy: William Pitt Sotheby's Int'l 860-868-6600
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ADDITIONAL INFORMATION

Nestled in the well-established Sherman Hill neighborhood, this five-bedroom home offers a generous footprint to put your personal touches on. Boasting wood flooring and newer windows throughout, the main level features a fluid layout designed for effortless living: a spacious living room, formal dining room, an eat-in kitchen, a cozy family room with a fireplace, a private home office, and a convenient full bath. Upstairs, you'll find five sizable bedrooms, including a primary suite complete with two walk-in closets and a private full 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. Create a game room with the provided pool table and a den area with a second fireplace, or utilize it as a potential in-law suite as light streams through a large picture window with views of the backyard. Outside, a stately 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, this home is ready for you to bring your design ideas and unlock its full potential!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,580
Status:
Active
MLS#:
24179773
Type:
Single Family
Subdivision:
N/A
Lot size:
1.95 Acres
Year built:
1951
Courtesy: Coldwell Banker Realty 203-426-5679
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ADDITIONAL INFORMATION

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

Beds:
4
Baths:
3.00
Sq.Ft.:
3,017
Status:
Active
MLS#:
24181404
Type:
Single Family
Subdivision:
Good Hill
Lot size:
1.47 Acres
Year built:
1995
Courtesy: BHGRE Gaetano Marra Homes 203-758-1300
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ADDITIONAL INFORMATION

Welcome home to this beautifully maintained 4-bedroom, 2.5-bath center hall colonial with quintessential wrap-around front porch, ideally situated on a desirable cul-de-sac just minutes from the charming town centers of Woodbury and Roxbury. Step inside to a gracious foyer flanked by a formal dining room and a versatile living room/den, ideal for a home office, library, or sitting room. The heart of the home is the tastefully remodeled kitchen, featuring granite countertops, stainless steel appliances, gas range and abundant workspace courtesy of the large center island. The kitchen flows seamlessly into the eat-in dining area and spacious family room with cozy wood-burning fireplace. Upstairs, the primary suite serves as a private retreat with a walk-in closet, fireplace and an en-suite bath featuring a soaking tub and separate shower. Three additional bedrooms offer comfortable accommodations with ample natural light. The finished lower level expands the living space with dedicated areas for both work and play, providing endless possibilities for recreation, fitness, media, or office use. Conveniently located off the attached two-car garage with generator hook-up, the mudroom/laundry room with private half bath provides exceptional functionality. Outside, you'll find an oversized shed with loft storage, offering ample room for tools, equipment, and seasonal items. With its attractive features and timeless appeal, this lovely home brings classic New England living to life.

Beds:
4
Baths:
6.00
Sq.Ft.:
4,790
Status:
Active
MLS#:
24181702
Type:
Single Family
Subdivision:
N/A
Lot size:
6.13 Acres
Year built:
1986
Courtesy: Roundtree Realty LLC 475-227-4312
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ADDITIONAL INFORMATION

Escape to your own private retreat in the heart of Woodbury. Nestled on over 6 picturesque acres, this charming property offers the perfect blend of privacy, natural beauty, and country living. Surrounded by mature trees and serene landscapes, the home provides a peaceful getaway while remaining conveniently close to local amenities. The residence itself is full of character and has been well cared for, requiring only minor cosmetic updates to truly make it shine. Inside, you'll find spacious living areas, abundant natural light, and a layout that feels both comfortable and inviting. Outside, the possibilities are endless. Equestrian enthusiasts will appreciate the horse stall already located on the property, while nature lovers will enjoy the expansive grounds, wooded surroundings, and room to explore. Whether you're envisioning a hobby farm, private estate, weekend retreat, or simply a quiet place to call home, this property offers a rare opportunity to create your dream lifestyle. Enjoy the tranquility of country living, breathtaking views in every season, and the privacy that only a property of this size can provide. 77 Hesseky Meadow Rd is more than a home-it's a destination. Private. Peaceful. Full of Potential. Welcome to your Woodbury sanctuary.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,796
Status:
Active
MLS#:
24171961
Type:
Condo
Subdivision:
N/A
Year built:
1985
Courtesy: Drakeley Real Estate, Inc. 203-263-4336
View additional info

ADDITIONAL INFORMATION

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

Beds:
2
Baths:
2.00
Sq.Ft.:
1,182
Status:
Active
MLS#:
24176500
Type:
Condo
Subdivision:
Woodlake
Year built:
1980
Courtesy: Adams & Adams Real Estate 203-592-6062
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ADDITIONAL INFORMATION

A Lovely Renovated End Unit with year round Rhododendron - greenery privacy at the deck. The summer blooms are spectacular! This condo is close to the Woodlake Community Garden, for those wishing to grow your own veggies! Inside you will notice a renovated kitchen with granite countertops, tiled flooring, ceiling fan and stainless steel appliances. The living room and dining room with the enhanced ambiance of hardwood floors. Each spacious Bedroom has hardwood flooring and the Primary is ensuite w/updated vanities and tile. The laundry area (Hookups) are located within the lower level. As an owner, you may finish the lower level with permits as you wish. The fire place is sealed for safety. Woodlake will approve Pellet or Wood burning fireplace stove inserts with permits. The Woodlake Office can help guide you through the easy permit process. Folks love residing in the quintessential Town of Woodbury. Recently voted best small Town in CT., by Readers Digest and The Boston Globe. Main Street has picturesque period homes, 3 "Green" areas: One with Gazebo, the 2nd is a Tribute to our Veterans, the 3rd is a planted area with benches at the corner of Route 6 and Rte 64. Enjoy restaurants galore, boutiques, gift & antique browsing! The commute East or West on 84 is Easy! Fees stated are for F/y 2026-2027! Live the Woodlake "Vacation at Home" life-style. Watch for updates on the Clubhouse Community Room re-opening. Plan your visit soon! Soon!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,673
Status:
Active
MLS#:
24179262
Type:
Condo
Subdivision:
N/A
Year built:
1985
Courtesy: Century 21 Bette Real Estate 203-264-2500
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ADDITIONAL INFORMATION

The finest condo complex in one of Litchfield Counties most charming towns! Woodbury Hill is a lovely community of townhouse style homes in a very attractive setting and features a saltwater pool and tennis/pickleball courts. #17 has seen many upgrades over the past dozen years including new windows, renovated kitchen and baths, upgraded heat pump HVAC and water heater, as well as recent paint inside. This end unit also offers an expanded deck with retractable awning and lovely backyard. Full, unfinished basement, convenient one car attached garage and abundant guest parking too. All this near Woodbury's downtown shops and restaurants!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,182
Status:
Active
MLS#:
24178857
Type:
Condo
Subdivision:
Woodlake
Year built:
1980
Courtesy: BHGRE Gaetano Marra Homes 203-693-1185
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ADDITIONAL INFORMATION

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

Beds:
3
Baths:
2.00
Sq.Ft.:
1,750
Status:
Active
MLS#:
24177873
Type:
Single Family
Subdivision:
N/A
Lot size:
5.51 Acres
Year built:
1970
Courtesy: William Raveis Real Estate 203-264-8180
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ADDITIONAL INFORMATION

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

Beds:
3
Baths:
3.00
Sq.Ft.:
1,708
Status:
Active
MLS#:
24176300
Type:
Condo
Subdivision:
Woodlake
Year built:
1973
Courtesy: RE/MAX RISE 203-714-6479
View additional info

ADDITIONAL INFORMATION

At Woodlake, you're not just buying a home, you're buying a lifestyle. From being FHA Approved condos, to water views at every balcony, trail walks to boat rides to fountains and everything in between, Woodlake truly offers the peaceful, serene setting that we all dream of. This 3 bedroom, 2.5 bath freshly painted end unit has endless possibilities. Need a main level bedroom or office? One can be accommodated. Need a lower level with a separate entry or a workshop? No problem. Want a parking spot right next to your unit? This home has it. Whatever your needs are, 19 Clubhouse drive delivers. Make an appointment to see this diverse unit today! 2 pets allowed per unit.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,704
Status:
Active
MLS#:
24174440
Type:
Single Family
Subdivision:
N/A
Lot size:
0.82 Acres
Year built:
1962
Courtesy: Lotus Realty Group, LLC. 860-274-4772
View additional info

ADDITIONAL INFORMATION

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

Beds:
4
Baths:
4.00
Sq.Ft.:
2,708
Status:
Active
MLS#:
24138386
Type:
Single Family
Subdivision:
N/A
Lot size:
1.41 Acres
Year built:
1728
Courtesy: Klemm Real Estate Inc 203-263-4040
View additional info

ADDITIONAL INFORMATION

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!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,144
Status:
Active
MLS#:
24173270
Type:
Single Family
Subdivision:
N/A
Lot size:
1.43 Acres
Year built:
1964
Courtesy: BHGRE Gaetano Marra Homes 203-693-1185
View additional info

ADDITIONAL INFORMATION

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

Beds:
4
Baths:
3.00
Sq.Ft.:
2,283
Status:
Active
MLS#:
24172742
Type:
Single Family
Subdivision:
N/A
Lot size:
3.19 Acres
Year built:
1850
Courtesy: William Pitt Sotheby's Int'l 860-868-6600
View additional info

ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
5.00
Sq.Ft.:
3,865
Status:
Active
MLS#:
24172449
Type:
Single Family
Subdivision:
N/A
Lot size:
3.12 Acres
Year built:
2007
Courtesy: Drakeley Real Estate, Inc. 203-263-4336
View additional info

ADDITIONAL INFORMATION

Beautiful Colonial set on a private 3+ acre lot in sought-after Curtiss Meadows, ideally located on the southern end of Woodbury abutting the Southbury line. Set back from the cul-de-sac entryway, this well-cared-for home offers a wonderful blend of privacy, comfort, convenience, and thoughtful updates. The level, light-filled driveway provides easy access, while the peaceful setting creates a true sense of retreat just minutes from Woodbury and Southbury town centers, commuting routes, and everyday amenities. Offering 3,865 sq. ft. of finished living space on the main two levels, plus an additional 550 sq. ft. recreation room in the walkout lower level, this spacious home provides plenty of room to live, work, and entertain. The first floor features a gourmet kitchen with granite countertops and a large center island perfect for gathering, a spacious great room with cathedral ceiling, formal living and dining rooms, and a cozy den with fireplace. Upstairs, an open foyer/sitting area leads to a comfortable primary suite and three generously sized bedrooms. The exterior is beautifully maintained and includes a privacy fence, rear patio, and three-car garage. Recent improvements add even more value, including a new HVAC and central air conditioning system installed in March 2026, along with solar panels added by the owners to help curb rising energy costs. The two fireplaces give wonderful comfort and warmth.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,607
Status:
Active
MLS#:
24171620
Type:
Single Family
Subdivision:
N/A
Lot size:
1.01 Acres
Year built:
2000
Courtesy: RE/MAX RISE 203-714-6479
View additional info

ADDITIONAL INFORMATION

Center Hall Colonial with Full In-Law! This majestic brick facing home flaunts its location atop a private lot overlooking sprawling scenic views. Main level features a two-story foyer, formal dining room w/hardwoods & pocket doors leading to a high-end kitchen w/stainless steel appliances including a gas stove. The kitchen delivers with granite tops, upscale cabinetry, breakfast bar, & eat-in area facing French doors opening to a welcoming living room w/hardwood, vaulted ceilings & brick fireplace. The family room/study pulls in the strength of hardwoods, tray ceiling & plenty of natural lighting. The main level bedroom/office & guest bathroom complete this central level. Continuing the journey upstairs & you will be greeted by spectacular views from the transom window aloft the staircase. The path to the primary bedroom suite introduces a tray ceiling, large walk-in closet & full bath w/whirlpool tub, shower stall & skylight. The three additional bedrooms are generous in size while the laundry room, common full bath w/double sink vanity & tub/shower concludes this upper level. The main level full in-law is a desirable focal point showcasing a separate entry, remodeled eat-in kitchen, living room w/vaulted ceiling, gas fireplace, large bedroom, remodeled full bath, laundry closet & staircase to garage w/private basement. Exterior features two new A/C condenser units, custom retaining walls, large deck & three car garage. This sought-after home exceeds all expectations!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,081
Status:
Active
MLS#:
24165212
Type:
Single Family
Subdivision:
Flanders
Lot size:
1.46 Acres
Year built:
2026
Courtesy: Coldwell Banker Realty 203-264-1400
View additional info

ADDITIONAL INFORMATION

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.

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Davis E. Owen, Sr., License REB.0754414, Xome CT LLC, License REB.0790146 , [email protected], 844-400-XOME (9663), 2083 Main Street, Stratford, CT 06615


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Woodbury Real Estate

Woodbury is located in Connecticut. Woodbury, Connecticut has a population of 9,762. Woodbury is less family-centric than the surrounding county with 23.2% of the households containing married families with children. The county average for households married with children is 26.17%.

The median household income in Woodbury, Connecticut is $104,081. The median household income for the surrounding county is $84,797 compared to the national median of $69,021. The median age of people living in Woodbury is 54.7 years.

Woodbury Weather

The average high temperature in July is 84.1 degrees, with an average low temperature in January of 15.8 degrees. The average rainfall is approximately 49.3 inches per year, with 40.2 inches of snow per year.

Woodbury Map

Woodbury Real Estate Market Conditions

  • Median sales price

    $408,250
    13.4%
    change since last quarter
  • # Active listings

    43
    30-day change

Woodbury Schools and Demographics

Education near Woodbury, CT

City County
High School Graduates 97.53 93.89
College Degree - 2 year 6.43 9.19
College Degree - 4 year 50.66 36.19
Graduate Degree 18.8 11.56
Expenditures per Student 26,218 26,218
Students per Teacher 11.5 11.5

Elementary Schools near Woodbury, CT

Grades Students P/T Ratio ZIP
Bethlehem Elementary School KG - 05 264 11.5 06751
Booth Free School KG - 05 78 7.5 06783
Fletcher W. Judson School 03 - 05 294 16.9 06795
Integrated Star Preschool Program PK - PK 51 17 06798
Long Meadow Elementary School PK - 05 521 13.7 06762
Middlebury Elementary School KG - 05 348 13.5 06762
Mitchell Elementary School KG - 05 359 14.2 06798

Middle Schools near Woodbury, CT

Grades Students P/T Ratio ZIP
Memorial Middle School 06 - 08 460 12.6 06762
Woodbury Middle School 06 - 08 364 11.3 06798

High Schools near Woodbury, CT

Grades Students P/T Ratio ZIP
Nonnewaug High School 09 - 12 751 11.2 06798
Watertown High School 09 - 12 861 13.8 06795

Ungraded Schools near Woodbury, CT

Grades Students P/T Ratio ZIP
* Nonnewaug Chiefs Alternative Program 12 - 12 1 06798

Demographics near Woodbury, CT

City County
Neighborhood Type Small town
Population 9,762 185,175
Population Density 268 201
Median Age 54.7 47.6
People per Household 2.2 2.4
Median Household Income 104,081 84,797
Average Income per Capita 63,569 47,811

Real estate near Woodbury