Woodbridge Real Estate

**Discover the Charm of Woodbridge, Connecticut**

Nestled in the picturesque New Haven County, Woodbridge, Connecticut, is a hidden gem that beautifully combines suburban tranquility with a vibrant community spirit. Known for its scenic landscapes and rich history, this charming town offers an idyllic setting for families, professionals, and retirees alike.

Woodbridge boasts a strong sense of community, where neighbors become friends and local businesses thrive. The town is characterized by its lush greenery, featuring sprawling parks and nature reserves that invite residents to explore the great outdoors. Whether you enjoy hiking along the scenic trails of the West Rock Ridge State Park or picnicking in the serene confines of the Woodbridge Town Green, there’s no shortage of ways to connect with nature.

Education is a cornerstone of Woodbridge’s appeal, with top-rated schools that prioritize academic excellence and foster a love for learning. Families are drawn to the area for its commitment to providing a nurturing environment for children, making it an ideal place to raise a family.

Culturally rich, Woodbridge offers a variety of community events throughout the year, from farmers' markets to seasonal festivals, ensuring there’s always something happening. The town’s proximity to New Haven provides residents with easy access to world-class dining, shopping, and entertainment options, while still enjoying the peaceful ambiance of suburban life.

With its blend of natural beauty, strong community ties, and excellent amenities, Woodbridge, CT, is not just a place to live; it’s a place to thrive. Come discover the warmth and charm of this remarkable town, where every day feels like home.

Newest Listings in Woodbridge

$3,200,000

4 Beds ⋅ 4 Baths ⋅ 24194459 MLS

Offered Fully Furnished. Set within nearly three private acres of mature woodland, Winnick Retreat is a reimagined mid-century modern residence where architecture, landscape and everyday life exist in quiet balance. Originally built in 1962 designed by Yale's very own Herbert S. Newman, the home is defined by its low horizontal profile, deep roof planes, clerestory windows and expansive walls of glass. A dramatic two-story central atrium draws natural light through the interior, while nearly every principal room maintains a direct visual connection to the surrounding trees, gardens and changing seasons.Inside, approximately 4,134 square feet of living space offers four bedrooms and three-and-one-half bathrooms. Warm wood, natural stone and glass create interiors that feel composed rather than formal. The renovated primary suite, custom kitchen and carefully updated living spaces respect the home's architectural character while supporting contemporary life. The property's recent transformation extends far beyond the interior. Landscaped grounds now unfold as a sequence of private experiences: a swimming pool with fire and water features, pool cabana, barrel sauna, fire-pit courtyard, outdoor fireplace and Har-Tru tennis court. Terraces, balconies and garden paths connect living spaces to the natural setting. Recreation and restoration become part of the daily rhythm. Mornings begin with a warm drink on the balcony underneath the tree canopy.

17 Pine Ridge Rd, Woodbridge

$629,900

3 Beds ⋅ 2 Baths ⋅ 24191904 MLS

Meticulously maintained by its original owner, this 3 bedroom 1.5 bath ranch style home is nestled on a beautiful, park-like lot on a quiet, tree-lined street. Ideally located close to public schools, walking trails, places of worship, major conveniences, with easy access to Route 15. The thoughtfully designed floor plan offers a spacious eat-in kitchen with direct access to a large deck overlooking the level backyard-perfect for outdoor entertaining and everyday enjoyment. The well-proportioned living room features a pretty casement bay window and a wood-burning fireplace and flows seamlessly into the formal dining room. French doors lead to a cozy family room with walls of windows showcasing picturesque views of the rear yard. The king-sized primary bedroom offers a walk-in closet, while two additional generously sized bedrooms share a remodeled full bath featuring double sinks, a tub, & a separate stall shower. A home office overlooking the front of the property, & a conveniently located laundry area and half bath just off the kitchen complete the main living area. The lower level includes a heated recreation room with a fireplace in addition to plenty of storage space & walkout access to the oversized two-car garage. Additional highlights include multi-zone heating & central air conditioning, an approximately 8-year-old roof, & HVAC systems replaced approx. 10-12 years ago. An exceptional opportunity awaits!

14 Rice Rd, Woodbridge

$750,000

4 Beds ⋅ 3 Baths ⋅ 24169790 MLS

20 Morris... Privacy, Seclusion & Effortless One-Level Living. Tucked away at the end of a long private driveway, this turnkey ranch offers the perfect blend of privacy, comfort & modern farmhouse charm. Pull up to the welcoming covered front porch with classic columns & a two-car attached garage with additional storage space. Step inside to a spacious foyer that opens into an expansive living room filled with natural light, creating a warm & inviting atmosphere. The heart of the home features an open-concept kitchen, dining & sitting area centered around a cozy fireplace-perfect for both everyday living & entertaining. The kitchen boasts granite countertops, a large center island with seating & ample cabinetry. Multiple doors provide seamless access to the outdoor living spaces. Enjoy entertaining on the new Trex deck overlooking the private backyard, or take advantage of the additional side deck that offers convenient access to the other wing. The main level includes 2 generously sized guest bedrooms that share a beautifully renovated full bathroom, along with a primary suite complete with its own private en-suite bath. The finished lower level expands your living space with a family or recreation room featuring a second fireplace, a full bathroom, a 4th bedroom & additional finished flex space ideal for a home office, gym, or playroom. A dedicated storage, laundry & mechanical room provides added convenience.

20 Morris Rd, Woodbridge

$529,900

2 Beds ⋅ 3 Baths ⋅ 24192555 MLS

Welcome to 10 West Street, a beautifully maintained raised ranch offering generous living space, and a private setting in one of Woodbridge's most desirable communities. Filled with natural light, the main level features soaring vaulted ceilings, hardwood floors, and an open-concept layout designed for both everyday living and entertaining. The spacious living room flows into the dining area and well-appointed kitchen, complete with abundant cabinetry, expansive countertops, stainless steel appliances, and a large center island with seating. Oversized windows overlook the peaceful backyard, creating a bright and inviting atmosphere. The primary suite offers a comfortable retreat with ample closet space and an en-suite bath. The additional bedrooms provide flexibility for family, guests, or a home office accompanied by a hallway full bathroom. The finished lower level with half bathroom dramatically expands the home's living space with an oversized recreation room perfect for a media room, playroom, fitness area, or home office, with direct access to the laundry room & attached two-car garage. Outside, enjoy a spacious backyard bordered by mature trees, offering privacy for outdoor entertaining, recreation, or gardening. Located just minutes from Yale University, Downtown New Haven, Route 15, Route 8, shopping, restaurants, hiking trails, and parks, this move-in-ready home combines comfort, convenience, and exceptional value.

10 West St, Woodbridge

$1,259,000

5 Beds ⋅ 5 Baths ⋅ 24191182 MLS

From its lamppost-lined circular drive to its commanding proportions, this luxury residence announces a lifestyle of both serenity & distinction. A soaring 2-story foyer introduces 9' ceilings & marble & parquet floors throughout rooms made for polished occasions & pleasure. Mornings glow in the south-facing breakfast room, while evenings unfold in the west-facing dining room; each thoughtfully oriented to capture its ideal light & both flowing from a kitchen where an island, premium appliances, beverage station, & pantry keep cooking, conversation, & company connected. Fireside rooms frame the main level: a stylish sunken living room & broad family room opening to a 2-tier Azek deck w/ Sunsetter awning & 1.78 private acres. The main-level primary is a serene suite w/ double-sized dressing closet, dual vanities, soaking tub, & marvelous marble steam shower. A dedicated office, laundry room, & secondary staircase complete the free-flowing function of the main level. Upstairs, 4 spacious bedrooms, each w/ a walk-in closet, share 2 full baths plus a balcony sitting area & huge finish-able bonus room over the garage. The refurbished 2,193sf walk-out lower level adds a kitchenette & full bath w/ steam shower; perfect for play or in-law suite potential. Many refined rewards such as a 3-car garage, 4-zone hydro-air, 400-amp underground service, sprinklers, & thoughtful updates bring substance to the scale & offer the freedom to gather generously, retreat peacefully, & live lavishly.

30 Grouse Ln, Woodbridge

$339,000

24191167 MLS

Come build the home you've always dreamed of on this exceptional 7.48 acre parcel in one of Woodbridge's most desirable settings! It's rare to find a lot this size that's also level and oversized - a true builder's or buyer's dream. Best of all, the hard work is already done: this property comes with an approved septic plan and survey in place, saving you time, money, and the headaches that come with the land development process. Location is everything, and this lot delivers - just a short drive to Yale University, downtown New Haven, and easy access to Routes 8 and the Merrit, putting shopping, dining, and commuter routes within easy reach. Enjoy the peace and privacy of a quiet country road while still being close to everything Greater New Haven has to offer.

54 Northrop Rd, Woodbridge

$1,080,000

5 Beds ⋅ 5 Baths ⋅ 24190146 MLS

Set on 2.24 picturesque level acres at the end of a quiet cul-de-sac, this spacious 5-bedroom, 4.5-bath Colonial offers 5,428 sq ft of comfortable living in one of Woodbridge's most desirable neighborhoods. Located in the award-winning Woodbridge and Amity School Districts, just minutes from New Haven and Yale University, the property offers privacy and exceptional convenience. Sun-filled rooms, hardwood floors, generous living spaces, and seamless indoor-outdoor flow make this home ideal for everyday living and entertaining. A welcoming foyer leads to the formal dining room and bright eat-in kitchen with southern exposure and a large picture window. The adjoining family room features a fireplace and sliding doors to the deck. The formal living room offers a second fireplace and French doors to a bluestone patio, while the dramatic great room showcases soaring two-story windows and additional French doors to the patio. A private library connects to a sunlit office with built-ins and access to the spacious primary suite with vaulted ceilings and a rebuilt shower. Laundry on both main and upper levels. Additional highlights include a fully fenced backyard, separate-entry suite with full bath ideal for guests or au pair, plus major improvements including new roof, new HVAC, conversion from oil to propane, fresh interior and exterior paint, and whole-house generator.

11 Highview Dr, Woodbridge

$537,500

3 Beds ⋅ 1 Baths ⋅ 24190950 MLS

This well maintained 3 bedroom, 1 bath Ranch style home sits on an incredible 4.74 Acre lot, ~Equestrian Opportunity includes a 2 story Horse Barn with 4 run in style Stalls, with water & electric, surrounded by several large Pastures & an inground Pool...... The house features Hardwood floors, Stainless appliances, a large living room w/a stone Fireplace & dining area, a beautiful Sunporch, Walk Out basement and an unfinished Walk Up attic w/great expansion potential..... Recent upgrades in 2021 include a brand new Septic system (with 4 bedroom capacity), a new Hot Water heater, and a new well Pump. The refrigerator & dishwasher are less than 1 year old. It has a 6 year old Roof, Trex deck, a Reverse Osmosis water Purification system for drinking water...... ...... ~direct access at end of street to Lake Chamberlain Regional Water Authority trails

14 Apple Tree Ln, Woodbridge

$695,000

4 Beds ⋅ 3 Baths ⋅ 24189188 MLS

Set back on over 1.5 parklike acres in Woodbridge, with a treed border wrapping the property for privacy you don't often find this close to everything. One of the most well laid out ranch homes on the market right now with the open kitchen flowing into a large dining area anchored by a fireplace, and a second fireplace to warm the front living room. Two natural gathering spots, both with real character. The two car garage brings you conveniently into the kitchen area, with the mudroom/laundry room access immediately upon entering. The front side of the home offers three bedrooms, including an en suite with a renovated black-and-white bath that keeps a classic look with all the updates you'd want. A second full bath serves the other two. The back of the home does something most ranches do not - its own living room, a fourth bedroom, walk in closet and full bath, all with direct access out to the yard. Primary suite, in-laws, guests, a home office, whatever you need it to be! Its a great space for entertaining with excellent flow to the deck and yard. Privacy, space, flexibility - this one checks every box!

1140 Johnson Rd, Woodbridge

$975,000

4 Beds ⋅ 5 Baths ⋅ 24188170 MLS

Nestled at the end of a double cul-de-sac on one of Woodbridge's most desirable streets, this privately sited home offers exceptional tranquility, beautiful natural surroundings, and an impressive list of recent upgrades. Completed within the last three months, the stunning new kitchen features elegant granite countertops, custom cabinetry, stylish tile flooring, and premium Cafe stainless steel appliances, creating the perfect space for everyday living and entertaining. Major mechanical improvements provide peace of mind, including a brand-new central air conditioning system, heating system, oil tank, hot water heater, and water filtration system. A newly paved driveway is also scheduled for completion soon, further enhancing the home's curb appeal. Designed with flexibility in mind, the thoughtfully planned layout includes a main-level bedroom with a full bath and its own private deck-ideal for multigenerational living or an au pair suite. Three wood-burning fireplaces add warmth and character throughout the home, while three separate heating and cooling zones provide energy-efficient comfort year-round. Expansive windows fill the home with abundant natural light, creating bright and welcoming living spaces. The finished walk-out lower level offers endless possibilities, whether you're envisioning a recreation room, media room, fitness area, hobby space, or the ultimate entertaining retreat. All of this is located in the highly acclaimed A+ Amity school district.

57 Grouse Ln, Woodbridge

$600,000

3 Beds ⋅ 3 Baths ⋅ 24187646 MLS

Tucked away on a quiet cul-de-sac in Woodbridge, this sprawling High Ranch is set on 1.56 private acres surrounded by nature. Filled with natural light from oversized windows and skylights, this home lives much larger than its square footage suggests. The open-concept living and dining area features a striking two-sided fireplace and flows into a sun-filled three-season room with a cozy wood stove. The kitchen is appointed with maple cabinetry, quartz countertops, and a wine refrigerator. The main level includes three bedrooms, including a primary suite with a full bath, plus an additional full bath. The lower level expands your living space with a welcoming family room, home office, laundry room, third full bath, and a versatile bonus room ready to fit your lifestyle. Step outside to an expansive deck overlooking peaceful wooded surroundings-the perfect setting for entertaining or simply unwinding. A private retreat benefiting from the Amity School System! Just minutes from Yale, downtown New Haven, shopping, and major commuter routes. Owner to leave the gas powered generator to keep things going in case of power outtage.

32 Hallsey Ln, Woodbridge

$1,179,000

4 Beds ⋅ 5 Baths ⋅ 24188100 MLS

This architectural masterpiece, designed and built by Igor Zak, offers over 6,000 sq ft of sophisticated living space nestled in a private 2-acre wooded setting.This unique 4 BR, 4.5 BA home blends luxurious modern design within the natural landscape. A dramatic foyer opens to the grand living room, the centerpiece of this home, showcasing soaring ceilings, an elegant 2-story marble fireplace and expansive windows, filling the interior with natural light and framing gorgeous views of the surrounding property. The modern eat-in kitchen features Corian and granite counters, a new Sub-Zero refrigerator and flows into the formal dining room and adjacent wet bar. The main level also includes 2 sitting areas, attached 2-car garage and private bedroom suite, providing flexibility for guests or multigenerational living. An additional lower-level 1-car garage provides ample parking and storage. Upstairs, an office w built-ins blends into an open gallery with skylights and glass accents. The primary suite features vaulted ceilings, private deck, multiple closets & spa-like bath with dual marble sinks. Two addl. bedrooms & full hall bath complete the 2nd floor. The lower level, with over 1400 sq ft, offers a spacious rec room centered around a large stone fireplace & full bath. Included is an automatic whole-house generator. Outdoor living is impressive with sliders leading to a deck overlooking the heated inground pool with cascading waterfall. Come see this extraordinary home!

25 Milan Rd, Woodbridge

Start Your Search

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.