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$399,999
3 Beds 4 Baths 24189293 MLS
Welcome to 433 Highland Drive in Waterbury's desirable Town Plot neighborhood! This spacious home offers 3 bedrooms on the main level plus a flexible room perfect as a 4th bedroom, office, or playroom. The main level also features 1.5 baths, including a full bath with a whirlpool tub, a large living room with a wood-burning fireplace, an oversized dining room, and a spacious eat-in kitchen. The fully finished lower level has its own private entrance and offers excellent in-law or multi-generational living potential with a second kitchen, large family room with a wood-burning fireplace, 1.5 baths, and two additional finished rooms-one ideal as a bedroom and the other perfect for a gym, office, or guest room. Enjoy a level backyard with plenty of space for entertaining, gardening, or play. Conveniently located near schools, golf course, shopping, restaurants, and major highways, this versatile home offers space, comfort, and endless possibilities. Sale is subject to Probate Court approval. Listing agent is a co-fiduciary.

433 Highland Dr, Waterbury

$399,900
3 Beds 3 Baths 24205759 MLS
Welcome to 327 Lakeside Blvd W, where thoughtful upgrades meet inviting spaces! A bright kitchen features white cabinetry, stainless steel appliances and a spacious island. The fully finished basement adds room for entertaining, while a bonus room off the kitchen offers flexibility for an office or potential additional bedroom. Updates include a Renewal by Andersen front door (December 2025), Tesla Wall Charger (January 2025), six-unit mini-split system for year-round heating and cooling (January 2026), WiFi enabled Garage Door Opener (December 2024) and attic fan with blown-in cellulose insulation (2024).Solar panels complement the home's energy-conscious features. A second driveway adds convenient parking, while a stone paver walkway connects the back door to a welcoming patio-perfect for gatherings, weekend barbecues or simply relaxing.

327 Lakeside Blvd W, Waterbury

$399,900
9 Beds 4 Baths 24200254 MLS
Fully occupied two-family investment property located in the north end, off Wolcott St, offering a strong unit mix with spacious layouts and excellent income-producing potential. The property features a large 5-bedroom/2-bath unit with approximately 1,800 SF of living space, along with a 4-bedroom/2-bath unit offering approximately 1,340 SF. Both units benefit from separate and tenant-paid utilities (gas heat and hot water + separate electric panels), helping to keep owner expenses minimal. Additional highlights include ample off-street parking and generous bedroom counts that support strong rental demand. Conveniently located with access to shopping, public transportation, major roadways, and area amenities. A solid opportunity to acquire a stabilized, 100% occupied multifamily asset with approximately 3,140 SF of combined living space.

80 Niagara St, Waterbury

$399,900
6 Beds 3 Baths 24197784 MLS
Located in Waterbury's desirable Town Plot neighborhood, this property offers a unique opportunity featuring a renovated single-family home with an in-law apartment plus two additional parcels included in the sale (3 parcels total). The main home has been thoughtfully updated with 3 bedrooms & 2 bath rooms, a newer kitchen and appliances, renovated bathroom, fresh paint, and updated flooring throughout. The in-law apartment provides additional flexibility with 1/2 bedrooms and 1 bathroom, its own full kitchen, newer appliances, updated bathroom, laundry hook-up and fresh paint-ideal for extended family, multigenerational living, rental opportunity or additional private living space. Mechanical updates include newer tankless H&HW COMBI boilers for efficient heat and hot water, with separate utilities. Outside, enjoy a spacious yard, ample off-street parking, and the added benefit of three adjoining parcels offering additional land and future possibilities. Convenient Town Plot location with easy access to shopping, restaurants, highways, and area amenities. A versatile, move-in-ready property with a combination of updated living space, additional land, and flexible occupancy options.

52 Alder St, Waterbury

$399,900
3 Beds 2 Baths 24180116 MLS
Welcome home to this beautifully renovated turn-of-the-century Colonial in Waterbury's desirable Bunker Hill neighborhood. Fresh exterior paint, a detached garage, level lot, and fully fenced backyard create the perfect setting for entertaining, outdoor play, or your furry family members. Inside, gleaming hardwood floors stretch from freshly painted wall to freshly painted wall that showcase the home's blend of classic character and modern updates. The completely remodeled kitchen features brand-new cabinets with soft-close doors, new countertops, a center island, and new appliances. The open-concept design flows seamlessly into the dining room, making holiday gatherings, family dinners, and cozy winter breakfasts a breeze. The inviting living room is anchored by a fireplace, creating the perfect spot to relax and unwind during snowy winter ngihts. Upstairs, you'll find three spacious bedrooms and a an updated bathroom. In addtion to stunning renovations the real beauty is in all your utility costs. Major improvements include brand-new central air and a new fuel-efficient radiant heating system with on-demand hot water heater, providing comfort and efficiency with year-round substantial savings! Storage is abundant with a sealed, bone-dry basement ready for organization and a walk-up attic offering even more space.

88 Coniston Ave, Waterbury

$391,000
2 Beds 2 Baths 24203404 MLS
If you've been waiting for a home where location, space, and lifestyle come together, this Middlebury-border gem is one you won't want to miss! Tucked away on a quiet cul-de-sac this special location offers a peaceful, neighborhood feel while keeping you close to shopping and highways. With over 1900 sqft of living space, this home provides plenty of room to spread out. Upper level has a combination LR/DR with outdoor access to a deck and private backyard. Primary bedroom has a great walk-in closet and the 2nd bedroom has two separate closets. Lower-level space includes family room, half bath and space for guest bedroom, office or private retreat. Property card has it as a 2-bedroom home but the flexible lower-level layout has enabled seller to utilize space as a 3rd bedroom retreat. The possibilities are yours to customize to fit your lifestyle. The private backyard creates a wonderful retreat for relaxing, gardening, or enjoying outdoor gatherings. An oversized 2-car garage provides for abundant room for vehicles, storage, hobbies, or a workshop.

67 Crest St, Waterbury

$390,000
4 Beds 4 Baths 24191952 MLS
Welcome to 26 Trowbridge Street, a beautifully remodeled Cape Cod-style gem in Waterbury's desirable Hillside neighborhood and a fully operational, income-producing Airbnb with documented earnings. This move-in ready home is perfect for a family or an investor, having generated over $45,000 in net rental income across Airbnb and Vrbo in just seven months, with 152 nights booked, making it a rare find for short-term rental investors or anyone entering Airbnb hosting in CT. This spacious 4-bed, 3.5-bath home offers 2,075 sq ft blending classic charm with modern upgrades. The main level features a sunlit living room, formal dining room, a half bath for guests, and an updated kitchen with ample cabinet and counter space. Upstairs, four bedrooms include a primary suite with private full bath plus an additional room ideal as an office, nursery, or walk-in closet, and popular with longer-staying guests. Outside, a detached two-car garage and a low-maintenance yard offer everyday convenience, while a private hot tub has been a guest favorite. Furnishings and hot tub can be discussed to convey. With proven multi-platform earnings, an established 5-star hosting record, and a sought-after location, this is a turnkey home ready for its next owner, whether you're moving in or investing. Schedule your showing today.

26 Trowbridge St, Waterbury

$385,000
4 Beds 2 Baths 24193951 MLS
Beautifully maintained and move-in ready, this spacious 4-bedroom, 2-bath split-level home is ideally situated on a quiet side street in Waterbury's desirable East End, just minutes from the highway for an easy commute. The thoughtfully designed layout offers room for everyone, with three generous bedrooms featuring refinished hardwood floors and oversized closets on the upper level, along with a full bath, linen storage, and convenient access to expansive attic storage. The main level showcases an inviting open-concept design with a stylish kitchen boasting granite countertops, stainless steel appliances, and seamless flow into the dining and living areas. A wood-burning fireplace adds warmth and character, creating the perfect gathering space. The ground level includes a fourth bedroom, a full bath with a walk-in shower, a laundry area with stackable washer and dryer, and direct access to both the attached garage and backyard. The finished lower level provides additional flexible living space ideal for a family room, recreation area, home office, or gym, plus extra storage. Updates include replacement windows, a newer roof, and picture window. Outside, enjoy a beautifully landscaped corner lot with a partially wooded backdrop, a spacious Trex deck for entertaining, a powered storage shed, and a fully fenced backyard with multiple access gates. Conveniently located near schools, walking trails, shopping, and everyday amenities, this home is ready for its next chapter.

35 Wedgewood Dr, Waterbury

$379,900
3 Beds 2 Baths 24193665 MLS
Welcome to 124 Judith Lane! This well-maintained raised ranch offers timeless charm, solid construction, and an exceptional setting on a beautifully landscaped 0.41-acre lot. Featuring 3 bedrooms, 1.5 baths, and 1,421 square feet of comfortable living space, this home has been lovingly cared for and is ready for its next chapter. Step inside to discover a bright and inviting floor plan with spacious living areas, generous bedroom sizes, and an abundance of natural light. The home offers the perfect opportunity for buyers to add their own personal style while appreciating the quality and care that has been invested over the years. Outside, you'll fall in love with the expansive backyard that backs to mature woods, creating a peaceful and private setting rarely found in this price range. Whether you're entertaining, gardening, or simply enjoying a quiet evening outdoors, this property offers plenty of space to relax and unwind. Conveniently located near shopping, dining, parks, schools, and major commuter routes, this home combines comfort, privacy, and everyday convenience. A wonderful opportunity for first-time buyers, downsizers, or anyone looking for a home with great bones and endless potential. Don't miss your chance to make this charming home your own!

124 Judith Ln, Waterbury

$379,000
3 Beds 2 Baths 24199560 MLS
Nestled in a highly desirable Bunker Hill cul-de-sac, this 3-bedroom Cape Cod home has been impeccably maintained and lovingly cared for by the same owners for many years! Their pride of ownership shines through every corner of the property. Step inside to discover a beautifully remodeled kitchen that leads right into the gorgeously updated, standout bathrooms. The main level offers a bright and inviting living area, with an attached 2-car garage providing absolute winter convenience. Head downstairs to find a great, partially finished basement space, perfect for a home office, gym, or recreation room. Outside, enjoy a quiet setting just minutes away from local parks, dining, and daily shopping essentials. A true turn-key gem in a fantastic neighborhood!

18 Kendall Cir, Waterbury

$379,000
3 Beds 1 Baths 24192458 MLS
Enjoy the ease of one-level living in this well-maintained 3-bedroom, 1-bath Ranch-Style home. The bright living room welcomes you with hardwood floors and a large picture window that fills the space with natural light. Just beyond, the spacious eat-in kitchen features ample cabinet space, stainless steel appliances, and a dining area. Down the hall, you'll find three generously sized bedrooms, all with hardwood flooring, along with a full bathroom. The lower level offers a utility area, abundant storage, and interior access to the attached two-car garage. Whether you need extra storage, a workshop, home gym, or future finished living space, the basement provides endless possibilities to suit your needs. Step outside and enjoy the level backyard, offering plenty of room for outdoor dining, gardening, play, or simply relaxing in the shade of the mature trees. The expansive driveway provides ample parking for multiple vehicles. A storage shed offers additional space for lawn equipment, tools, and seasonal items. Conveniently located near the Wolcott town line, this home places you just minutes from Sloping Acres Park, neighborhood playgrounds, shopping centers, grocery stores, restaurants, local dining, and outdoor recreation, all within a short drive. With quick access to route 8 and I-84 , making commuting to surrounding towns and New York City simple and convenient.

85 Bagley Ter, Waterbury

$375,000
2 Beds 2 Baths 24202728 MLS
Welcome to this one-owner ranch style home offering spacious rooms and flexible living options. The main level features two bedrooms, an open living room and dining room, a large eat-in kitchen, and hardwood floors in select rooms. A convenient breezeway connects the kitchen to the garage, providing easy access between the home and garage. A stackable washer and dryer are conveniently located in the main-level bathroom. The expansive finished lower level with approximately another 1,000 square feet adds incredible versatility with a fireplace, wet bar, second kitchen, bathroom with stall shower, another washing machine, and direct access to a screened-in porch and spacious yard-an ideal setup for entertaining, extended family, or a possible in-law arrangement. Additional highlights include central air conditioning and a roof replaced in 2020. With generous living space inside and out, this home offers comfort, flexibility, and plenty of potential.

3430 E Main St, Waterbury

$375,000
7 Beds 3 Baths 24202832 MLS
Welcome to 16 Fairview Street, Waterbury, CT - a solid 3-family property offering an excellent opportunity for investors or owner-occupants looking to build equity while generating rental income. This spacious multi-unit property features three separate apartments, with a desirable layout consisting of 3 bedrooms and 1 full bath on the first floor, and 2 bedrooms and 1 full bath on each of the second and third floors. Each unit offers separate gas and electric utilities. The property offers approximately 3,594 square feet of total living space, providing generous room sizes and versatile living arrangements. Each unit offers hardwood flooring, comfortable living areas, and functional layouts. The first-floor apartment has a renovated kitchen, refinished hardwood flooring, fresh paint, laundry hookups, refrigerator, front porch, and access to the backyard - features that can be attractive to today's tenants. This property offers the potential to increase cash flow through strong tenant demand, thoughtful management, and future rental optimization. The three-unit configuration provides diversification of rental income while giving an owner the opportunity to occupy one unit and rent the others. The location provides convenient access to shopping, restaurants, public transportation, downtown Waterbury, and major routes, making it an attractive location for renters seeking accessibility and convenience.

16 Fairview St, Waterbury

$375,000
4 Beds 2 Baths 24197903 MLS
Nicely renovated 2-family in Waterbury's South End offering a great opportunity for both investors and owner-occupants. Both units feature clean, updated interiors with fresh neutral paint, renovated kitchens with stainless steel appliances, updated bathrooms, and newer flooring throughout. The first-floor unit benefits from approximately 600 additional SF of finished basement space with laundry, providing valuable bonus living space. The property features separate, tenant-paid utilities, including two electrical panels and two efficient tankless COMBI systems for heat and hot water. Exterior improvements include replacement windows and low-maintenance vinyl siding. A private driveway and space in back provides convenient off-street parking. With updated units, efficient mechanicals, separate utilities, and additional finished space, this property is a well-rounded multifamily opportunity with strong appeal for an owner-occupant looking to offset their mortgage or an investor seeking a turnkey rental property.

44 Piedmont St, Waterbury

$375,000
7 Beds 3 Baths 24197390 MLS
Renovated 2-family property with nicely finished 3rd floor attic expansion offering strong owner-occupant or investment potential in Waterbury. The 2nd and 3rd floors have been combined into a spacious upper-level unit featuring modern finishes, refreshed kitchen, 2 full baths, newer flooring, and fresh paint throughout. This unique layout provides additional living space and flexibility, ideal for larger households or enhanced rental income potential. The property offers functional layouts, separate living areas, abundant natural light, and separate, tenant-paid electric utilities (electric H&HW) for added efficiency and reduced owner expenses. Conveniently located near shopping, restaurants, schools, public transportation, and major highways. Excellent opportunity for investors or owner-occupants seeking a move-in ready multifamily property with added space and versatility.

75 Walnut St, Waterbury

$375,000
6 Beds 2 Baths 24182654 MLS
Welcome to this classic Colonial-style home with attached, under home garage located in Waterbury's desirable Boulevard neighborhood. Offering over 2,300 square feet of living space, this spacious residence features 6 bedrooms, 1.5 bathrooms, and timeless architectural charm throughout. The main level boasts a welcoming foyer, a large living room with fireplace, formal dining room, and an updated kitchen with butler's pantry-perfect for entertaining and everyday living. Original character blends seamlessly with modern updates, including replacement windows and ample storage space. Enjoy relaxing on the outdoor decks overlooking the generous lot. Situated on approximately 0.23 acres with convenient access to shopping, schools, parks, and major highways, this home presents an excellent opportunity for buyers seeking space, character, and value. Don't miss your chance to make this distinctive property your next home!

81 Fiske St, Waterbury

$369,900
3 Beds 1 Baths 24202053 MLS
Turnkey One-Level Living with Space, Comfort & Location Looking for a pristine, move-in-ready ranch with the space and convenience you want? This beautifully maintained and thoughtfully updated 3-bedroom ranch in Waterbury's desirable Town Plot neighborhood offers easy one-level living. Set just off Oronoke Road and conveniently located near the Waterbury Country Club, I-84, and Route 8, this bright and welcoming home combines classic midcentury charm with modern updates. The front entry opens to a spacious living room featuring beautiful oak flooring and abundant natural light. The remodeled kitchen is designed for everyday living, with upgraded appliances, extensive cabinetry, generous counter space, and eat-in dining. Three well-appointed bedrooms, each with oak flooring, share an updated full bath, completing the main level. The walk-out lower level features a spacious finished 25' x 16' bonus space for added flexibility-perfect for a media room, playroom, home office, gym, or guest space-along with a partial bath. The property is capped off with a coveted, flat 0.46 acre lot.

421 Como Ave, Waterbury

$369,000
3 Beds 2 Baths 24196701 MLS
Welcome to **82 Midland Road, Waterbury**, where modern updates meet everyday comfort. This beautifully updated home features a **newly renovated kitchen** with contemporary cabinetry, stylish countertops, and modern finishes, creating the perfect space for cooking, entertaining, and daily living. The thoughtfully designed layout offers bright, inviting living spaces filled with natural light and a warm, welcoming atmosphere. Whether you're a first-time homebuyer or simply looking for a move-in-ready home, this property offers both comfort and value. Conveniently located near shopping, restaurants, schools, parks, and major highways, you'll enjoy easy access to everything Waterbury has to offer while coming home to a tastefully updated residence. Don't miss this opportunity to own a beautifully refreshed home with a stunning new kitchen in a convenient location.

82 Midland Rd, Waterbury

$369,000
3 Beds 2 Baths 24175277 MLS
Beautifully maintained 3-5 bedroom opportunity situated on a desirable corner lot offering great yard space and added privacy. Enjoy outdoor entertaining and relaxing on the spacious patio. Inside you will find beautiful hardwood floors throughout the main level and upstairs, adding warmth and character to the home. The updated upstairs bathroom features modern finishes while a convenient half bath is located on the main level. The Second floor also offers 3 generously sized bedrooms. The finished lower level has been converted into an amazing flex space setup featuring 2 additional rooms and a kitchenette providing space for multi-generational living, guests, home office use, or recreation. Conveniently located near shopping, restaurants, schools, and major highways.

167 Fern St, Waterbury

$359,900
3 Beds 2 Baths 24203315 MLS
Immaculately maintained Colonial with wonderful curb appeal and gleaming hardwood floors in the living areas and bedrooms. The main level offers a spacious eat-in kitchen and generously sized family room, providing plenty of room for everyday living and entertaining. A slider off the kitchen leads to a composite deck overlooking the beautifully manicured, fully fenced backyard. The backyard offers an inviting space for relaxing, dining outdoors, or enjoying time with family and friends. Upstairs, the spacious primary bedroom features an oversized walk-in closet. Two additional bedrooms and a full bath complete the second floor. The home also offers central A/C, plenty of storage in the basement, a one-car garage, and additional off-street parking in the driveway. Conveniently located in Waterbury's Town Plot area, this well-cared-for home offers close proximity to schools, restaurants, shopping, and major commuting routes. This turnkey home is ready to enjoy.

124 Russell St, Waterbury

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