531 houses for sale in Toilsome Hill

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Set on an extra-deep, beautifully manicured lot, this refined Cape offers an exceptional blend of craftsmanship, privacy, and rare mechanical amenities. A true standout, the property features a four (4)-bay, fully powered garage with an expansive paved area-ideal for collectors, hobbyists, or those seeking substantial off-street parking and workspace. Inside, the home reveals warm hardwood floors, sunlit rooms, and a thoughtful flow that feels both inviting and elevated. The recently updated kitchen is a highlight, opening gracefully to the dining room and showcasing rich cabinetry, elegant countertops, a center island, stainless steel appliances, a 5-burner gas stove, and a new refrigerator. A charming mini-3-season room offers a serene retreat for morning coffee or evening unwinding. The main level includes an updated full bath and a spacious bedroom, while the upper level continues the hardwood aesthetic with two well-proportioned bedrooms, Full bath and generous storage. The full b

Do not miss your chance to own a immaculately kept 2 family home in the north end. priced to sell fast!

Welcome to 900 Merritt Street, this charming 2 bedroom, 2 baths home located in Bridgeport's desirable North End. Features spacious bedrooms, 2 full bathrooms, and a bright, inviting living area, perfect for relaxing evenings with warm character. The layout offers great flow of everyday living. Garage for convenient parking and extra storage, along with a private outdoor space ideal for entertaining, gardening or simple enjoying the outdoor. Schedule your showing today! Highest and best requested by Saturday, 5/16/2026, at 6:00pm

Welcome to the Brownstones at 3300 Park Avenue. This beautifully maintained townhouse is move-in ready, offering three spacious stories plus a fully finished basement with additional storage. Ideally located directly across from Fairfield, this condo features a charming private front patio as well as a large private back patio

HIGHEST and BEST OFFER DUE BY WEDNESDAY 5/27@6PM EST. Exceptional opportunity for both owner-occupants and savvy investors alike! This well-maintained 2-family property offers strong income potential, valuable updates, and a highly convenient location in a sought-after and growing area. Whether you're looking to offset your monthly living expenses by occupying one unit while collecting rental income from the other, or add a solid cash-flowing asset to your portfolio, this property checks all the boxes. Major recent improvements include new furnaces in both units, new hot water heaters, new appliances throughout, new washer and dryer sets in both units, and a newly fenced-in yard. Unit 68 has been extensively updated with new flooring and a beautifully renovated kitchen, creating a modern and inviting living space. Each unit also enjoys its own private driveway, separate backyard space, and dedicated basement storage area - features tenants and owner-occupants alike will appreciate. Con

A beautifully maintained 3-bedroom, 1-bath single-family home of thoughtfully updated living space in Bridgeport's most desirable North End neighborhood. The updated kitchen flows naturally into a versatile room - ideal as a home office, sunroom, or reading nook - with direct access to a spacious deck and a generous, well-kept backyard perfect for outdoor entertaining. Both the kitchen and bath have been tastefully renovated, and the care put into this home is evident throughout. The attached garage and storage area are crowned by a charming decorative overhang that adds character and curb appeal rarely found at this level. A home that has been loved - and it shows. Potential to add bathroom in basement or at the top of the stairs, dormer roof

North End Bridgeport Multi-Family Opportunity Don't miss this spacious and well-cared-for 2-family property located in the desirable North End of Bridgeport. Whether you're looking to live in one unit while generating rental income from the other, or add a solid asset to your investment portfolio, this property offers outstanding flexibility. Conveniently situated near schools, shopping centers, restaurants, parks, public transportation, and major commuter routes, making it an attractive option for both owners and tenants. A fantastic opportunity to build equity and generate income in a prime location

Sophisticated brownstone living awaits in this beautifully maintained end-unit townhouse offering over 2,700 square feet of thoughtfully designed living space across three finished levels. Featuring three bedrooms plus a spacious flex room that can easily serve as a fourth bedroom, home office, or media room, this exceptional residence combines the spaciousness of a single-family home with the convenience of condominium living. The main level is designed for both everyday living and entertaining, featuring a chef's kitchen with cherry cabinetry, granite countertops, center island, Sub-Zero refrigerator, professional six-burner gas range, and breakfast nook. A formal dining room flows into the sunken living room with a gas fireplace and sliding glass doors leading to a private stone patio. The second level offers the versatile flex room, a spacious primary suite with walk-in closets, a full en-suite bath, and a convenient laundry area. The third level features two generously sized bedro

Colonial house in the North End of Bridgeport, with 3 Bedrooms, Living room, Dining room and extra room that can be used as an office. Kitchen fully equipped with stainless steel appliances, quartz countertops and an island. Dining room leads out to a large deck. Private Backyard with deck great for entertaining, family gatherings or just a quiet place to unwind. Selling as is. New lower price! Schedule your private showing today!

WELCOME TO THIS BEAUTIFULLY UPDATED BRICK RANCH OFFERING THE PERFECT BLEND OF CLASSIC CHARM AND MODERN UPDATES! SITUATED ON A SPACIOUS CORNER LOT, THIS HOME FEATURES 3 GENEROUS BEDROOMS, GLEAMING HARDWOOD FLOORS, FRESH PAINT, RECESSED LIGHTING, AND AN INVITING FLOOR PLAN FILLED WITH NATURAL LIGHT. THE OVERSIZED LIVING ROOM WITH FIREPLACE PROVIDES A WARM AND COMFORTABLE SPACE FOR RELAXING OR ENTERTAINING, WHILE THE WELL-MAINTAINED INTERIOR IS READY FOR ITS NEXT OWNER TO MOVE RIGHT IN. OUTSIDE, ENJOY A LARGE PAVED DRIVEWAY LEADING TO A DETACHED TWO-CAR GARAGE, ATTRACTIVE CURB APPEAL, AND A LEVEL YARD WITH PLENTY OF ROOM FOR OUTDOOR ENJOYMENT. CONVENIENTLY LOCATED NEAR SHOPPING, RESTAURANTS, PARKWAYS, SCHOOLS, AND PUBLIC TRANSPORTATION, THIS HOME OFFERS BOTH COMFORT AND ACCESSIBILITY. THIS IS AN OPPORTUNITY YOU WILL NOT WANT TO MISS!

Well-maintained multifamily property in Bridgeport's desirable North End featuring numerous recent updates. The first-floor apartment has been freshly painted throughout and offers refinished cabinets, skim-coated walls and ceilings, repaired sheetrock and plaster, new light fixtures, hardwood floors, 1 oversized bedroom, 1 full bath, and an in-unit washer and dryer. The second-floor unit has been extensively updated with new flooring, a split A/C and heating system, updated finishes, and a finished attic that provides additional living space, including 2 bedrooms and a half bath. This unit also includes an in-unit washer and dryer. Exterior improvements include updated landscaping, a front deck with new railings, repaired siding, and a roof and gutters replaced approximately three years ago. Front and rear decks, along with a spacious backyard, provide inviting outdoor living areas. Conveniently located near universities, hospitals, shopping, dining, public transportation, and major h

Extensively renovated and move-in ready, this side-by-side two-family property offers an outstanding opportunity for both investors and owner-occupants. The interiors have been beautifully updated with hardwood floors throughout, brand-new kitchens featuring new appliances, and renovated bathrooms. One spacious unit offers 4 bedrooms and 2.5 baths, while the second unit features 2 bedrooms and 1 full bath, providing flexible living arrangements for rental income, multigenerational living, or an in-law setup. The property features updated mechanicals, separate utilities, and a clean unfinished basement ideal for storage. A brand-new roof installed just two months ago adds peace of mind for years to come. Outside, you'll find a private driveway with off-street parking and a level backyard that is perfect for relaxing, entertaining, or enjoying the outdoors. Conveniently located just 7 minutes from Sacred Heart University, with easy access to shopping, restaurants, major highways, public

Expanded Ranch features 4 bedrooms, 2 bathrooms, living room, dining area, open kitchen. The primary bedroom with bathroom. The expanded layout provides more living space than a traditional Ranch, with room to spread out on the main level. The partially finished lower level includes walk-out access to an in-ground pool and covered patio - a seamless indoor-outdoor connection for entertaining and everyday enjoyment. The pool and patio create a private backyard retreat, anchored by the convenience of direct lower-level access. Great investment opportunity, ideal for a primary residence or rental portfolio. - The bones and layout are strong, and the in-ground pool adds immediate value. Located in the Stratfield area of Bridgeport, CT, minutes from Sacred Heart University and close to the Trumbull and Fairfield town lines, local parks, the Merritt Parkway, and I-95

Welcome to a spacious home located on desirable North End! This charming Colonial offers 4 bedrooms and 2 full bathrooms with a spacious, functional layout designed for comfortable everyday living. Hardwood floors add warmth and character throughout, while the enclosed sunrooms provide flexible space for a home office, playroom, or relaxing retreat. The full basement and walk-up attic offer excellent storage and future potential. Step outside to a beautifully maintained, fully fenced backyard featuring a patio and an above-ground pool-perfect for entertaining family and friends all summer long. Conveniently located near Sacred Heart University, shopping, restaurants, parks, public transportation, and major highways, this home combines neighborhood charm with everyday convenience. Whether you're looking for a primary residence or an investment opportunity in a sought-after location, this is a home you won't want to miss. Schedule your private showing today!

Welcome to this beautifully maintained 3-bedroom, 2-bath colonial in Bridgeport's desirable North End. Spanning 1,744 square feet, this move-in-ready home blends classic 1948 character with comfortable, functional living space. Bright, well-proportioned rooms and timeless architectural details give the home warmth and charm throughout. Set on a quiet residential street, you're just minutes from shopping, dining, schools, and major commuter routes - offering the perfect balance of neighborhood calm and everyday convenience. Whether you're a first-time buyer, growing family, or investor seeking a turnkey property in a steady, competitive market, this one checks the boxes. Homes in this neighborhood move quickly - schedule your showing today

Welcome to the Brownstones at 3300 Park Avenue. This beautifully maintained townhouse is move-in ready, offering three spacious stories plus a fully finished basement with additional storage. Ideally located directly across from Fairfield, this condo features a charming private front patio as well as a large private back patio

Welcome to 203 Robin Street! This is a charming ranch in Bridgeport's desirable Brooklawn/St. Vincent's neighborhood! This well-maintained 2-bedroom, 2-full-bath home features a mudroom entranceway, an open concept kitchen, dining, living area, hardwood floors on the main level and a laundry room on the lower level. Gas heat, gas range, private paved driveway, and a manageable, low-maintenance 0.11-acre lot. A brand new in-ground swimming pool was finished days ago. New transferable solar contract turned on Feb 2026. Unbeatable location close to major highways, the train station, the Park Ave bus line, St. Vincent's Medical Center, Trumbull Mall, and Sacred Heart University. Move-in ready - this one won't last. make your appointment today!

Sophisticated brownstone living awaits in this beautifully maintained end-unit townhouse offering over 2,700 square feet of thoughtfully designed living space across three finished levels. Featuring three bedrooms plus a spacious flex room that can easily serve as a fourth bedroom, home office, or media room, this exceptional residence combines the spaciousness of a single-family home with the convenience of condominium living. The main level is designed for both everyday living and entertaining, featuring a chef's kitchen with cherry cabinetry, granite countertops, center island, Sub-Zero refrigerator, professional six-burner gas range, and breakfast nook. A formal dining room flows into the sunken living room with a gas fireplace and sliding glass doors leading to a private stone patio. The second level offers the versatile flex room, a spacious primary suite with walk-in closets, a full en-suite bath, and a convenient laundry area. The third level features two generously sized bedro

Colonial style home in North end offers ten rooms, four bedrooms, two full and one half baths. Living room with fireplace, dining room, eat in kitchen, hardwood flooring, finished basement. partially fenced yard, two car garage, private paved driveway. Located on a corner lot. A must see

Charming Ranch style home with 3 spacious bedrooms and 1 1u002F2 baths. Prime North End, desirable location in Bridgeport. Close to the Fairfield line and Sacred Heart University. Must see to appreciate. Lower level is the full length of the home, for additional space or for an in-law setup. Excellent opportunity for a First Time Buyer to own or for an Investor expansion. Property is being Sold As Is

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank