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$700,000
3 Beds 3 Baths ACTIVE UNDER CONTRACT Status 24204878 MLS
*HIGHEST & BEST OFFERS DUE by 8 PM on Saturday, 9/12* Welcome to this spacious 3 bedroom, 2 1/2 bath home set on a level 1-acre lot in the heart of Orange. The light-filled main level features a front-to-back living room with wood-burning fireplace, while the spacious kitchen offers a cathedral ceiling with skylights, dining area, center island, built-in cabinetry, walk-in pantry, granite countertops, tiled backsplash, and a gas fireplace with stone surround. Sliders open to a large composite deck overlooking the fenced backyard. Three bedrooms are located on the upper levels, including a spacious primary bedroom with ample walk-in closet space. A beautifully remodeled full bath features a combination tub/shower. The split-level design offers versatile living space, including a finished walk-out lower level with a kitchen, half bath, and recreation room; ideal for extended family, guests, a home office, or potential in-law living; providing over 3,000 SF of finished space over 4 levels. The lower level also provides access to an enclosed sunporch and unfinished basement with additional storage. Additional amenities include central A/C, city water, a 2-car garage, and walk-up attic space offering potential for future expansion. Conveniently located near shopping, Yale, Downtown New Haven, Milford, and Fairfield County, with easy access to I-95 and Route 15. A wonderful opportunity to enjoy space, flexibility, and convenience in a desirable Orange location.

361 Miles Rd, Orange

$1,225,000
5 Beds 5 Baths ACTIVE Status 24204758 MLS
Ideal for multigenerational living or in-law suite potential, this luxury residence features a refurbished 2,193 square foot finished walk-out lower level with separate exterior access, kitchenette, full bath and steam shower-an exceptional space for extended family, guests, au pair quarters, recreation or a private home office. Above, a lamppost-lined circular drive introduces 1.78 private acres and commanding proportions. A soaring two-story foyer opens to nine-foot ceilings, marble and parquet floors, a south-facing breakfast room, west-facing dining room and well-appointed kitchen with island, premium appliances, beverage station and pantry. Fireside living and family rooms flow to a two-tier Azek deck with Sunsetter awning. The main-level primary suite offers a double-sized dressing closet, dual vanities, soaking tub and marble steam shower. An office, laundry room and secondary staircase add convenience. Upstairs, four more spacious bedrooms with walk-in closets share 2 full baths, a balcony sitting area and large finish-able bonus room. A three-car garage, four-zone hydro-air, 400-amp underground service, sprinklers and thoughtful updates bring substance to the scale and offer the freedom to gather generously, retreat peacefully, and live lavishly.

30 Grouse Ln, Woodbridge

$565,000
3 Beds 4 Baths ACTIVE Status 24203193 MLS
Imagine coming home to the peacefulness of a quiet cul-de-sac, where the pace feels a little slower and everyday moments become something to savor. Ideally located with easy access to parkways, grocery stores, and charming local markets, this inviting home offers the comfort and ease of one-level living on a beautiful, level lot. Inside, the thoughtfully designed floor plan creates an effortless sense of connection. The eat-in kitchen opens naturally to the dining room and family room, making it easy to gather with family and friends, share a meal, or simply enjoy the rhythm of everyday life. Sliding doors invite you into a bright, window-filled Florida room-a special place to begin your morning with coffee, curl up with a good book, work on a puzzle, enjoy game night, or simply pause and take in the beauty of the backyard. Step outside and let the gentle sound of a small babbling pond create a sense of calm. The beautifully landscaped grounds offer a wonderful backdrop for gardening, outdoor recreation, entertaining, or quiet moments surrounded by nature. There is space here to garden, play, gather, or simply breathe. The living room welcomes you with a picture window overlooking the front yard, while the fireplace adds warmth and charm, creating a cozy setting for relaxing evenings. More than a house, this is a place to enjoy life's simple pleasures, peaceful mornings, gatherings with loved ones, quiet afternoons in the Florida room, and evenings by the fireplace.

10 Vernon Ct, Woodbridge

$1,050,000
5 Beds 7 Baths ACTIVE Status 24202502 MLS
Majestically set on 1.53 private acres, steps to the peaceful Elderslie Preserve is this stunning custom colonial. Over 4,600 square feet of living space on a quiet Woodbridge cul-de-sac the home thoughtfully pairs classic architectural details with a bright, welcoming layout, capturing peaceful seasonal nature views from almost every room. Enjoy the amazing benefits of fully owned solar panels! Inside, quality craftsmanship shows throughout with rich hardwood floors, handsome crown moldings, and coffered ceilings. The main level features a spacious kitchen with granite countertops, island & a breakfast bar that opens right into an inviting family room. Anchored by a stone fireplace with wood stove, this central space boasts cathedral ceiling and a wall of windows that lets in abundant natural light with glass doors out to an expansive deck overlooking a level and serene back yard. A main-floor study is one of many work from home spaces. Living room with a fireplace is perfect for quiet relaxation. Sculptural columns frame the oversized dining room. Also features a main level private guest suite with a full bath. Dual staircases lead up to the second level, where the primary suite includes its own fireplace, 2 walk-in closets and a spa-like bath. There are 3 additional bedrooms each with an en-suite bath and walk in closets. The finished walk-up third floor offers flexible extra space perfect for a media/rec room, guest space or quiet study.

12 Carriage Hill Rd, Woodbridge

$629,000
5 Beds 3 Baths ACTIVE Status 24200234 MLS
Nestled on a quiet cul de sac in Central Woodbridge is this charming raised ranch-style home w/ 5 bedrooms, 3 full bathrooms, & approximately 2800 sq ft of finished living space (including 1188 of living space in the finished walkout lower level). Sited on 1.6 acres, and bordering the Woodbridge Land Trust, this home offers both convenience & privacy. A circular driveway leads to the front entry which, upon entering, steps up to the main living level which features hardwood floors in all rooms (with the exception of the tile floor in the kitchen). The open layout of the main living level flows easily from the large living room w/ a fireplace, to the dining room with a sliding door to the new TREX deck, to the attractive eat-in kitchen with maple cabinetry, corian countertops, stainless steel dishwasher & refrigerator, an electric cooktop, microwave, & a wall oven. The main living level also features the primary bedroom (w/ its own private full bathroom), two additional bedrooms, & a full (hallway) bathroom. The lower level (walkout) living space features two bedrooms, a full bathroom & a large family room w/ a fireplace. The lower level family room also walks out to a gardening/hobby room. The home features hot air heat (using heating oil), central air conditioning, an electric water heater, a 2 car garage, a septic system, well water, and fenced-in backyard. Fantastic access to YALE, UNH, SCSU, RT 63, and RT 15.

14 Watrous Ln, Woodbridge

$874,900
3 Beds 3 Baths ACTIVE Status 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

$599,900
3 Beds 4 Baths ACTIVE Status 24201458 MLS
Welcome to this beautiful expanded ranch, ideally situated on a picturesque Orange street while remaining just minutes from everything you need. This spacious home offers 3 bedrooms, 3 full & 1 half baths, plus an abundance of flexible living space. The inviting living room flows seamlessly into the dining room & kitchen, with a convenient half bath just off the kitchen. Hardwood floors are waiting beneath the main-level carpeting. Three bedrooms & a full bath complete the main level. A sizable bonus room above the attached 2-car garage provides incredible versatility, featuring its own full bath & potential as a primary suite, family room, guest room (with included Murphy Bed) or in-law space for multigenerational living. The partially finished lower level adds even more usable space for a playroom, home office or recreation room, along with plenty of storage. A walk-up attic offers additional storage & exciting potential for future expansion. Outside, enjoy a large rear deck overlooking the level yard-perfect for entertaining while the kids play. Additional highlights include a mudroom, central air, Newer Roof & Septic tank, vinyl siding & tool shed. Conveniently located near shopping, dining, highways & everyday amenities, while enjoying all that Orange has to offer, including the award-winning Racebrook & Amity school districts. Come check this one out Today!

519 Ferry Rd, Orange

$519,000
2 Beds 2 Baths ACTIVE UNDER CONTRACT Status 24201355 MLS
Nothing to do but move in! Impeccably maintained 2 bedroom 1 full 1 half bath home in a sought after commuter-friendly Orange location. Located directly across from Racebrook Tract and adjoining Maltby Lakes which is perfect for outdoor enthusiasts. Convenient to Yale, the Merritt Parkway and I-95. Approximately 5-9 miles from Metro-North/New York City and Amtrak train stations. The entertainment friendly main level has beautiful hardwood flooring and offers a newly renovated kitchen showcasing granite countertops, stainless appliances, and a center island that flows seamlessly into an inviting dining room, a convenient half bath and a sunny home office with a cathedral ceiling, and a substantial living room including a wood burning fireplace, sliders to a custom patio and a beautiful level fenced yard. Two bedrooms on the upper level include a generous front to back primary bedroom with ample closet space including a walk-in attic. A nicely appointed full bath is accented with white and black tile flooring and white bath tile. Potential for future living space in the unfinished lower level which currently houses a newer furnace, hot water tank, oil tank, electrical box, washer/dryer, and hatchway egress. New roof and gutters 2021, new central air 2024, and many recent upgrades. Plentiful storage and an expansive peaceful and private fenced yard and fenced garden area.

888 Racebrook Rd, Orange

$725,000
4 Beds 3 Baths ACTIVE UNDER CONTRACT Status 24198983 MLS
Time to relax and enjoy lakefront living. Welcome to 570 Grassy Hill Road, a sprawling 2,200 sq. ft. ranch beautifully situated on 1.15 acres along Lake Wepawaug. Step right outside your back door and grab a paddleboard, kayak, or fishing pole! This well-maintained home offers 9 rooms, 4 bedrooms, and 2.5 baths with a spacious and versatile layout. The main level features an eat-in kitchen, formal dining room overlooking the lake, and a large living room with a vaulted ceiling, wood-burning fireplace, abundant natural light, and beautiful water views. The primary bedroom suite includes an updated private full bath and walk-in closet. Three additional spacious bedrooms and another updated full bath with laundry are located on the opposite side of the home. The upgraded heated finished walk-out lower level provides even more living space with a large family room with a second wood-burning fireplace, new luxury vinyl floors, and sliders out to the backyard. Additional room is perfect for guest space or a home office, and half bath (plumbed for shower), offering great potential for guests or potential in-law setup. Additional highlights include new HVAC system, new roof, new insulation, and electrical. City water is available in the street. Association fee is $550 annually.The former two-car garage has been finished and is currently utilized as a pet area with a wash station and workshop space, offering flexible options for the next owner (or convert back to a two-car garage

570 Grassy Hill Rd, Orange

$599,000
3 Beds 2 Baths ACTIVE UNDER CONTRACT Status 24193768 MLS
Welcome to this lovely ranch-style home in the heart of Orange, Connecticut! Set on a desirable corner lot, this well-maintained home offers comfortable one-level living in a community known for its award-winning schools, beautiful parks, community events, and convenient location. Enjoy easy access to major highways, downtown New Haven, Yale, and two Metro-North train stations. Inside, you'll find warm hardwood floors, classic six-panel wood doors, built-in shelving, and a charming wood-burning fireplace that creates a welcoming focal point & central air for the hot/humid summer days. The inviting kitchen features granite countertops and a comfortable eat-in area, perfect for casual meals and morning coffee. The spacious primary bedroom offers the convenience of dual closets and a private full bathroom. One of the home's most appealing features is the lovely three-season porch overlooking the private, level rear yard-an ideal spot for relaxing, entertaining, or enjoying the changing seasons. Major recent improvements include brand-new siding and a new roof, both completed in 2025, providing peace of mind for years to come. The fully unfinished lower level offers abundant storage and exciting potential for future expansion, whether you envision additional living space, a recreation area, home office, or hobby space. A wonderful opportunity to enjoy all that Orange has to offer in a convenient and highly sought-after setting!

605 S Greenbrier Dr, Orange

$599,900
4 Beds 3 Baths ACTIVE UNDER CONTRACT Status 24196484 MLS
Opportunity awaits at 556 Forest Road! Ideally positioned at the end of a cul-de-sac, this substantial four-bedroom, two-and-a-half-bath Cape offers exceptional privacy on a spacious 0.72-acre lot. With approximately 2,772 square feet of living space, the home presents an excellent opportunity to renovate and personalize your new home. The generous footprint provides plenty of room for everyday living, entertaining, working from home, and creating spaces that complement your lifestyle. Important recent improvements include a brand-new roof and a hot water heater that is only two years old, giving the next owner a valuable head start. With its classic Cape design, great school system, ample square footage, private setting, and desirable center of Orange location, this property is ready for a fresh vision. Bring your ideas and unlock its full potential. Property is being sold as-is. Subject to probate court approval.

556 Forest Rd, Orange

$549,900
3 Beds 2 Baths ACTIVE UNDER CONTRACT Status 24194959 MLS
Welcome home to this meticulously maintained 3-bedroom ranch, perfectly situated in one of Orange's most sought-after central neighborhoods! Offering timeless charm, a fantastic layout, and endless potential, this home is ready for its next owner to make it their own. Designed with entertaining in mind, the spacious main level features a generously sized Living Room with a cozy wood-burning fireplace, an expandable Dining Room ready to accommodate holiday gatherings and celebrations, and a well-designed eat-in Kitchen complete with appliances. The showstopping four-season Sun Room overlooks the beautifully maintained, expansive level backyard, creating the perfect space to relax year-round while enjoying peaceful views. Hardwood flooring lies beneath the carpeting throughout much of the main level, offering an exciting opportunity to reveal its original beauty. The full lower level already includes a second fireplace and offers outstanding potential for a future Family Room, Game Room, home gym, office, or additional living space. Additional highlights include central air conditioning, propane heat, and a a two-car garage. Ideally located within walking distance of the Orange Community Center and just minutes from shopping, restaurants, parks, schools, and major commuter routes, this home combines convenience with an unbeatable location. Bring your vision and personal updates to transform this home

241 Pine Tree Dr, Orange

$749,900
3 Beds 3 Baths ACTIVE UNDER CONTRACT Status 24194960 MLS
Perfection Has an Address! Impeccably renovated 3-bedroom, 3-bath custom home offers the perfect blend of modern style, exceptional craftsmanship, and thoughtfully designed living spaces. Every detail has been upgraded to create a truly move-in ready home that is sure to impress even the most discerning buyer. A welcoming covered front porch sets the stage for relaxed mornings and quiet evenings. Step inside to discover a bright, open floor plan highlighted by new railings, beautiful wood flooring, and an abundance of natural light. The stunning remodeled kitchen is the heart of the home, featuring quartz countertops, a center island with seating, stainless steel appliances, and a stylish tile backsplash. The expansive living and dining areas are perfect for entertaining, anchored by a sleek state-of-the-art electric fireplace. Just beyond, the inviting sunroom has sliders leading to a spacious deck overlooking the beautifully landscaped level backyard. The main level also features two generously sized bedrooms and a beautifully updated full bath. Escape to the private second-floor primary suite, your own personal retreat complete with a cozy sitting area, desk nook, walk-in closet, and full bath with an oversized 5-foot shower. A walk-in attic provides the opportunity to create additional customized closet space. The finished walk-out lower level has a spacious family room featuring a fireplace, full bath, laundry area,and

868 Bayberry Ln, Orange

$3,200,000
4 Beds 4 Baths ACTIVE Status 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

$574,900
3 Beds 3 Baths ACTIVE Status 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

$319,900
1 Beds 1 Baths ACTIVE UNDER CONTRACT Status 24187530 MLS
Charming 1920s Colonial on a Prime Corner Lot! Step back in time and bring your design vision to life with this classic 1920s Colonial. Perfectly situated on a charming corner lot, this property offers fantastic curb appeal and a wonderful sense of space. Boasting a unique and incredibly generous 7-room layout, provides versatility. From the moment you step inside, you will be greeted by the authentic character of yesteryear, featuring gorgeous hardwood floors throughout that are ready to be buffed to their original shine. The expansive floor plan provides an excellent flow, offering multiple distinct living spaces perfect for a home office, a cozy den, a formal dining area, or creative studio space. Nestled in a desirable neighborhood, this home is a blank canvas just waiting for a little TLC to restore it to its full glory. Whether you are an investor looking for your next project, a contractor, or looking to build sweat equity in a classic property with a great footprint, this is a rare find. Property is situated on a beautiful corner lot and is being sold strictly in as-is condition.

955 Baldwin Rd, Woodbridge

$699,000
6 Beds 4 Baths ACTIVE Status 24183648 MLS
Welcome to 476 Derby Milford Road, a spacious raised ranch set on nearly an acre in desirable Orange, CT. This versatile home offers 6 bedrooms and 4 full baths across the main living areas, plus a fantastic accessory in-law suite - ideal for multi-generational living, or a home office setup. This suite boasts its own entrance, garage, kitchen and bathroom. The lower level includes a recreation room and additional living/storage space, giving this home incredible flexibility. The main level features a bright living room, dining room, primary bedroom, and three additional bedrooms. Enjoy cozy evenings by the fireplace and take advantage of energy savings with the leased solar system. A 3-car attached garage provides ample storage and parking, while the level 0.92-acre lot offers plenty of room to roam. Additional highlights include central air conditioning, and a full walk-out basement. Conveniently located near local amenities and within the Amity school district. Don't miss this rare opportunity to own a home with built-in flexibility for extended family.

476 Derby Milford Rd, Orange

$675,000
5 Beds 4 Baths ACTIVE Status 24178496 MLS
Offering two private suites, generous living space, and thoughtful updates throughout, this exceptional home seamlessly blends comfort, versatility, and convenience in a desirable Orange location. The privately situated main level suite would be ideal as a bedroom, home office, exercise room or even serve a multi-generational need. The eat-in-kitchen, with direct access to a large deck and private backyard, features white cabinetry, granite countertops, a skylight and newer stainless appliances. Conveniently located just off the kitchen are a mudroom, laundry and half bath. Both the living room and family room offer fireplaces, creating warm and inviting spaces for entertaining or relaxing. A generously sized dining room, with hardwood floors, provides a wonderful setting for gatherings large and small. Upstairs, you will find a second primary suite, three additional spacious bedrooms, and two beautifully remodeled full baths. Located in the award-winning Amity school district with easy access to shopping, dining, commuter routes, parks and Yale. Recent updates include a newer septic system (2016), HVAC system (2022), and hot water heater (2021) One year home warranty to be provided at closing.

997 Rainbow Trl, Orange

$735,000
3 Beds 3 Baths ACTIVE Status 24177143 MLS
History feels handsomely at home in the Fairchild House. This 1780 Cape-style sanctuary was relocated c.1930 onto a newly-sited foundation, deeper within the property, then extensively expanded twice in later years. Across 2,800sqft, with 2.5 bathrooms and 4 room options for the 3 bedrooms, the home layers the latest luxuries with late-Colonial craftsmanship such as original millwork mouldings, fireplaces, sconce lighting, and hand-hewn wide-plank floors that glow and tell their story. A circular drive introduces level lawns, bordered by veritable verdure privacy and garden views. Inside, a front-to-back living room offers fireside warmth and wonderful flow, while the formal dining room, with its own wood fireplace, period wall paneling and 2 hutches, elevates candlelit dinners and holiday traditions. The kitchen, updated 10 years ago with maple cabinets, corian counters, and gas cooking, offers a sunny breakfast corner in which to enjoy slow mornings. A soaring family room adds modern scale with cathedral ceiling, exposed beams, walk-in closet, and 9-foot arched window. The latest addition main-level primary suite endows 2 walk-in closets, French doors to the yard, radiant heated floors, and a lavish skylit bathroom. A rustic, wood-paneled office completes the main level. A heated semi-finished rec room downstairs serves as a great fitness or hobby space and a detached 2-car garage and many updates, including mechanicals and an EV charger, round out the full package.

446 Amity Rd, Woodbridge

$650,000
4 Beds 3 Baths ACTIVE Status 24158938 MLS
Great things come to those who wait. Lovingly maintained by its original owners, this well kept Colonial is ideally situated on a coveted cul-de-sac and offers curb appeal, generous living space, and thoughtful updates throughout. This immaculate 4-bedroom, 3-bath home lives comfortably like a ranch, featuring a first-floor bedroom and full bath-perfect for guests or a potential in-law arrangement. Set on a private one-acre property, the home welcomes you with a charming front porch and an entry foyer featuring twin closets, perfect for storing coats, shoes, and everyday essentials. The main level offers excellent flow for entertaining, with a spacious living room with a fireplace, a formal dining room, and an eat-in kitchen that serves as the heart of the home. Just off the kitchen, the first-floor family room includes sliding doors that open to the deck and backyard, creating indoor-outdoor living. A convenient first-floor laundry room. Upstairs, two additional bedrooms share a full bath, while the primary suite overlooks the backyard and features its own private bath. Additional highlights include a freshly painted interior, hardwood floors beneath the carpeting on both levels, and an expansive unfinished basement offering the potential for more than 1,200 square feet of future living space. Ideally located near golf courses, pool clubs, and athletic facilities. Commuters dream with easy access to major highways! Not to be missed if Orange is where you want to be!

11 Williamsburg Dr, Orange

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