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$3,200,000

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.

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

$1,089,000

Hidden Gem in Woodbridge - Where Nature, Comfort & Elegance Align Welcome to a private paradise tucked away on a peaceful, tree-lined road in sought-after Woodbridge. Set on 1.6 beautifully landscaped acres, this exceptional home is bursting with character, charm, and over $100,000 in thoughtful updates (see MLS documents for full list). From the long private driveway to the 2-car garage, carport, and oversized deck overlooking your own in-ground pool, every detail has been designed to enhance your lifestyle-indoors and out. Step inside to discover 9 inviting rooms, including 4 spacious bedrooms (some with walk-in closets), and 3 full bathrooms. The main level boasts gleaming new hardwood floors, an updated kitchen, and two sun-soaked great rooms where natural light pours in and picture-perfect views stretch across the backyard oasis. Upstairs, cozy wall-to-wall carpeting makes the bedrooms feel warm and restful, while downstairs, the open flow is perfect for entertaining. Whether you're hosting a sunset dinner on the deck, enjoying morning coffee surrounded by fruit trees and gardens, or cooling off in the pool after a long day-this home makes every day feel like a vacation. features include a refreshing outdoor shower, a carport for extra parking or storage, and a sense of tranquil seclusion that's hard to find-yet just minutes from everything New Haven County has to offer. This is more than just a home-it's a story waiting to be lived. Welcome to your Woodbridge

4 Beds ⋅ 4 Baths ⋅ 24161318 MLS

Hidden Gem in Woodbridge - Where Nature, Comfort & Elegance Align Welcome to a private paradise tucked away on a peaceful, tree-lined road in sought-after Woodbridge. Set on 1.6 beautifully landscaped acres, this exceptional home is bursting with character, charm, and over $100,000 in thoughtful updates (see MLS documents for full list). From the long private driveway to the 2-car garage, carport, and oversized deck overlooking your own in-ground pool, every detail has been designed to enhance your lifestyle-indoors and out. Step inside to discover 9 inviting rooms, including 4 spacious bedrooms (some with walk-in closets), and 3 full bathrooms. The main level boasts gleaming new hardwood floors, an updated kitchen, and two sun-soaked great rooms where natural light pours in and picture-perfect views stretch across the backyard oasis. Upstairs, cozy wall-to-wall carpeting makes the bedrooms feel warm and restful, while downstairs, the open flow is perfect for entertaining. Whether you're hosting a sunset dinner on the deck, enjoying morning coffee surrounded by fruit trees and gardens, or cooling off in the pool after a long day-this home makes every day feel like a vacation. features include a refreshing outdoor shower, a carport for extra parking or storage, and a sense of tranquil seclusion that's hard to find-yet just minutes from everything New Haven County has to offer. This is more than just a home-it's a story waiting to be lived. Welcome to your Woodbridge

11 Ariel Rd, Woodbridge

$950,000

Rarely does a MID-CENTURY MODERN home of this caliber become available. Privately nestled among mature trees in an extraordinary lakefront setting, this architecturally significant residence was thoughtfully designed to capture its natural surroundings, offering exceptional privacy, breathtaking views, and seamless indoor-outdoor living. Walls of glass, expansive sliders, and dramatic contemporary windows flood the home with natural light while framing the landscape from nearly every room. The spectacular Living Room, the centerpiece of the home, features soaring vaulted ceilings, a striking floor-to-ceiling brick wood-burning fireplace, and an office alcove ideal for remote work or creative pursuits. Flowing effortlessly from the Living Room, the Dining Room and Family Room create an expansive open-concept living space centered around a state-of-the-art custom kitchen equipped with premium La Cornue, Wolf, and Sub-Zero appliances. True to its mid-century design, each of the three bedrooms enjoys an en-suite bath and direct access to the private grounds, creating a unique connection to the surrounding landscape. This three-zone central air-conditioned home overlooks the beautifully landscaped saltwater gunite pool, recently resurfaced and updated with new mechanical systems, as well as professionally designed, park-like grounds. Fully owned solar panels provide excess electricity to offset winter months electric use to bare minimum.

3 Beds ⋅ 3 Baths ⋅ 24193957 MLS

Rarely does a MID-CENTURY MODERN home of this caliber become available. Privately nestled among mature trees in an extraordinary lakefront setting, this architecturally significant residence was thoughtfully designed to capture its natural surroundings, offering exceptional privacy, breathtaking views, and seamless indoor-outdoor living. Walls of glass, expansive sliders, and dramatic contemporary windows flood the home with natural light while framing the landscape from nearly every room. The spectacular Living Room, the centerpiece of the home, features soaring vaulted ceilings, a striking floor-to-ceiling brick wood-burning fireplace, and an office alcove ideal for remote work or creative pursuits. Flowing effortlessly from the Living Room, the Dining Room and Family Room create an expansive open-concept living space centered around a state-of-the-art custom kitchen equipped with premium La Cornue, Wolf, and Sub-Zero appliances. True to its mid-century design, each of the three bedrooms enjoys an en-suite bath and direct access to the private grounds, creating a unique connection to the surrounding landscape. This three-zone central air-conditioned home overlooks the beautifully landscaped saltwater gunite pool, recently resurfaced and updated with new mechanical systems, as well as professionally designed, park-like grounds. Fully owned solar panels provide excess electricity to offset winter months electric use to bare minimum.

20 Crestview Incl 24 Crestview Dr Drive, Woodbridge

$874,900

Welcome to 15 Hemlock Hollow Road, a gracious 3-bedroom, 2.5-bath Colonial offering over 3,500 square feet of living space on more than 1.5 beautifully landscaped acres. A circular driveway and inviting covered front porch set the tone for this warm and distinctive home. The dramatic great room features soaring ceilings, oversized windows, a gas fireplace, wet bar, and game area, creating an impressive space for everyday living and entertaining. The spacious kitchen flows seamlessly into the dining and living areas, while a private first-floor office provides an ideal work-from-home setting. Upstairs, the primary suite offers a peaceful retreat with a sitting area, dressing room, walk-in closet, and spa-inspired bath. Outdoors, enjoy your own private oasis featuring a heated saltwater gunite pool, waterfall, spa, pool house, expansive deck, and screened porch. Offering exceptional space, privacy, and resort-style amenities, this remarkable property is a wonderful place to call home.

3 Beds ⋅ 3 Baths ⋅ 24201811 MLS

Welcome to 15 Hemlock Hollow Road, a gracious 3-bedroom, 2.5-bath Colonial offering over 3,500 square feet of living space on more than 1.5 beautifully landscaped acres. A circular driveway and inviting covered front porch set the tone for this warm and distinctive home. The dramatic great room features soaring ceilings, oversized windows, a gas fireplace, wet bar, and game area, creating an impressive space for everyday living and entertaining. The spacious kitchen flows seamlessly into the dining and living areas, while a private first-floor office provides an ideal work-from-home setting. Upstairs, the primary suite offers a peaceful retreat with a sitting area, dressing room, walk-in closet, and spa-inspired bath. Outdoors, enjoy your own private oasis featuring a heated saltwater gunite pool, waterfall, spa, pool house, expansive deck, and screened porch. Offering exceptional space, privacy, and resort-style amenities, this remarkable property is a wonderful place to call home.

15 Hemlock Hollow Rd, Woodbridge

$819,900

Welcome to 16 Burma Road! More than $250,000 in upgrades have been completed over the years, creating a beautifully updated home with high-end finishes and smart-home features throughout. At the heart of the home is a chef's kitchen featuring Viking appliances, a large center island, and plenty of cabinet space. Just off the kitchen, the bright and spacious family room offers vaulted wood ceilings, exposed beams, and walls of windows overlooking the backyard. The primary suite includes heated dolomite flooring and a high-tech talking toilet. With multiple flexible living spaces, the home offers several possibilities for an in-law suite, au pair accommodations, a home office, or guest quarters. Recent improvements include a new furnace and central air conditioning. Outside, enjoy a large deck, private yard, and three-car garage with plenty of parking and storage. Tucked away on a quiet cul-de-sac, this exceptional home is conveniently located near shopping, restaurants, highways, and Woodbridge's award-winning schools.

5 Beds ⋅ 5 Baths ⋅ 24197027 MLS

Welcome to 16 Burma Road! More than $250,000 in upgrades have been completed over the years, creating a beautifully updated home with high-end finishes and smart-home features throughout. At the heart of the home is a chef's kitchen featuring Viking appliances, a large center island, and plenty of cabinet space. Just off the kitchen, the bright and spacious family room offers vaulted wood ceilings, exposed beams, and walls of windows overlooking the backyard. The primary suite includes heated dolomite flooring and a high-tech talking toilet. With multiple flexible living spaces, the home offers several possibilities for an in-law suite, au pair accommodations, a home office, or guest quarters. Recent improvements include a new furnace and central air conditioning. Outside, enjoy a large deck, private yard, and three-car garage with plenty of parking and storage. Tucked away on a quiet cul-de-sac, this exceptional home is conveniently located near shopping, restaurants, highways, and Woodbridge's award-winning schools.

16 Burma Rd, Woodbridge

$795,000

One of the Most Unique & Eclectic Homes in Connecticut! Originally built as a barn in 1750, this expansive and delightfully quirky home is truly one-of-a-kind. From the moment you step inside, you'll be captivated by its whimsical character; starting with the once fully functional cement mixer that has been creatively repurposed as a fireplace with pellet stove. Beyond this conversation piece is a cozy sitting area with fireplace, leading to a serene enclosed porch that overlooks the private in-ground lap pool (8x60) surrounded by lush gardens. The dramatic two-story wood beamed living room is accented by a loft that looks down over the space, adding architectural intrigue. Throughout the home, you'll find an array of alcoves, balconies, lofts, nooks, and crannies-each offering unique charm and functionality. Multiple fireplaces, custom built-in lighting, and intricate architectural details-including stained glass windows-make every corner of this home feel like a discovery. The versatile floorplan includes a private primary suite with steam shower and access to balcony. Adjacent office area leading to a loft with half bath and second stairway. A separate suite of additional bedrooms, each on its own level, sharing a bath and a fireplace in the sitting room. Numerous flexible spaces for bedrooms, offices, studios, or quiet retreats. The peaceful setting enjoys tranquil views over a pond surrounded by mature trees and gardens; offering a true sense of privacy and serenity.

3 Beds ⋅ 3 Baths ⋅ 24182465 MLS

One of the Most Unique & Eclectic Homes in Connecticut! Originally built as a barn in 1750, this expansive and delightfully quirky home is truly one-of-a-kind. From the moment you step inside, you'll be captivated by its whimsical character; starting with the once fully functional cement mixer that has been creatively repurposed as a fireplace with pellet stove. Beyond this conversation piece is a cozy sitting area with fireplace, leading to a serene enclosed porch that overlooks the private in-ground lap pool (8x60) surrounded by lush gardens. The dramatic two-story wood beamed living room is accented by a loft that looks down over the space, adding architectural intrigue. Throughout the home, you'll find an array of alcoves, balconies, lofts, nooks, and crannies-each offering unique charm and functionality. Multiple fireplaces, custom built-in lighting, and intricate architectural details-including stained glass windows-make every corner of this home feel like a discovery. The versatile floorplan includes a private primary suite with steam shower and access to balcony. Adjacent office area leading to a loft with half bath and second stairway. A separate suite of additional bedrooms, each on its own level, sharing a bath and a fireplace in the sitting room. Numerous flexible spaces for bedrooms, offices, studios, or quiet retreats. The peaceful setting enjoys tranquil views over a pond surrounded by mature trees and gardens; offering a true sense of privacy and serenity.

8 Dillon Rd, Woodbridge

$599,900

Experience the Regency at Woodbridge, this 55+ community. The Pierpont Modern Farmhouse: a beautifully designed two-story townhome that blends comfort, style, and ease of living. The main-level primary suite offers convenience and privacy, while upstairs you'll find two additional bedrooms and a versatile loft space, perfect for guests, a home office, or a cozy retreat. Reinvent your lifestyle without compromising on quality. The primary bath features a spacious six-foot seated walk-in shower, creating a spa-like experience at home. The open-concept great room flows seamlessly into the kitchen and dining area; ideal for entertaining or relaxing by the fireplace with a good book. This home is thoughtfully curated with designer-selected finishes, allowing you to move right in with ease. Enjoy quartz countertops, hardwood flooring throughout the first floor, and sleek stainless steel appliances that bring both function and style to your kitchen. The Regency offers a wide array of amenities including a clubhouse, pool, and fitness center. Perfectly positioned with scenic views of West Rock Ridge State Park, this home offers a peaceful backdrop to everyday living. Discover what it feels like to live where every day feels like a getaway. Conveniently located just minutes from New Haven, Yale University, shopping, dining, and major commuting routes.

3 Beds ⋅ 3 Baths ⋅ 24196535 MLS ⋅ Regency At Woodbridge BLDG.

Experience the Regency at Woodbridge, this 55+ community. The Pierpont Modern Farmhouse: a beautifully designed two-story townhome that blends comfort, style, and ease of living. The main-level primary suite offers convenience and privacy, while upstairs you'll find two additional bedrooms and a versatile loft space, perfect for guests, a home office, or a cozy retreat. Reinvent your lifestyle without compromising on quality. The primary bath features a spacious six-foot seated walk-in shower, creating a spa-like experience at home. The open-concept great room flows seamlessly into the kitchen and dining area; ideal for entertaining or relaxing by the fireplace with a good book. This home is thoughtfully curated with designer-selected finishes, allowing you to move right in with ease. Enjoy quartz countertops, hardwood flooring throughout the first floor, and sleek stainless steel appliances that bring both function and style to your kitchen. The Regency offers a wide array of amenities including a clubhouse, pool, and fitness center. Perfectly positioned with scenic views of West Rock Ridge State Park, this home offers a peaceful backdrop to everyday living. Discover what it feels like to live where every day feels like a getaway. Conveniently located just minutes from New Haven, Yale University, shopping, dining, and major commuting routes.

27 Heritage Ln, Woodbridge

Dave Jones Realty llc

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