517 properties for sale in Bridgeport Downtown South Historic District

Great opportunity for investors or owner-occupants! This spacious two-family home offers ample living space and is conveniently located near the Black Rock area. The property features updated kitchens and bathrooms, newer water heaters, and an updated plumbing system, providing added value and peace of mind. A one-car garage and shared driveway offer convenient off-street parking. Whether you're looking to generate rental income or live in one unit while renting the other, this property presents an excellent opportunity with strong potential

Perched on a quiet cul-de-sac, this exceptional home offers breathtaking 220-degree panoramic views of Long Island Sound, Black Rock Harbor, and Fayerweather lighthouse. Designed for effortless main-level living, the residence captures stunning water views from the living room, dining room, and luxurious primary bedroom suite. The remodeled primary bath features elegant marble flooring with radiant heat, creating a spa-like retreat. The dining room is warmed by a charming wood-burning beehive fireplace, while the exceptionally spacious living room boasts vaulted ceilings, a wood-burning fireplace, and sliding doors that open seamlessly to a covered stone deck and in-ground pool- perfect for indoor-outdoor living and entertaining. Enjoy spectacular vistas of the in-ground pool and the Sound from the home's main living spaces. Additional highlights include a laundry on the main level, a rain sensor irrigation system for the gardens and lawn, 3-zone heat/central air, attached two-car gara

First Time on the Market - A Southport Treasure with Endless Possibilities For the first time since 1912, this cherished Southport residence is being offered for sale. Passed down through generations, this classic colonial has been a cornerstone of one family's legacy for over a century - and now it's ready for its next chapter. Set on nearly a half-acre in the heart of Southport, this property offers tranquil water views, timeless charm, and unmatched potential. Originally a four-bedroom single-family home, a thoughtfully designed in-law suite with its own private entrance, separate mechanicals, and utilities was added in 1991 - ideal for multi-generational living, guests, or rental income. While the home is being sold as-is and does require extensive updating, it offers solid bones and architectural character rarely found today. This is a rare opportunity for someone with creativity and passion - to revive, reimagine, and make this beloved home their own. With its premier location, h

Nestled along the water in Milford's highly sought after Rivercliff neighborhood, this exceptional residence offers breathtaking river views and the peace of mind of being located outside a flood zone. Designed for effortless indoor-outdoor living, the home features a serene backyard retreat, beautifully landscaped grounds, and an expansive bluestone patio perfect for entertaining, al fresco dining, or simply enjoying the waterfront setting. Whether kayaking from your backyard or relaxing by the water, every day feels like a getaway. The stunning primary suite serves as a private sanctuary, complete with vaulted ceilings, abundant natural light, and a private balcony overlooking the river. Two additional bedrooms and a dedicated office are located on the second floor, with the office easily convertible into a fourth bedroom, offering flexibility to accommodate changing needs. Inside, thoughtfully designed living spaces are filled with natural light and capture picturesque water views t

Beautifully set on a quiet double cul de sac with winter water views of Lake Mohegan, this comfortable and open home has much to offer. Light and bright Living Room and Dining Room with hardwood floors, Eat in Kitchen, delightful 3-Season Room with beamed vaulted ceiling, three good sized Bedrooms and hall Bathroom with tub complete the main floor. The lower level features a spacious Family Room, refreshed with soft cream color hues and new vinyl tile flooring, warm and inviting, it is the perfect hang out room for family game night and cozy gatherings in front of the wood burning fireplace. Hall storage and laundry area lead to the newly updated bathroom with shower and to the oversized 2 car garage. Outside, the bluestone patio and lush backyard provide a private retreat with ample space for entertaining and play. Exquisite stone retaining wall and meandering walkways gracefully terrace the property and create garden areas with natural beauty and continuous blooms. Additional updates

Great opportunity to buy a Colonial Style Home! Set on a welcoming street in the heart of Stratford, this beautifully updated four-bedroom, one-and-a-half-bath home offers the perfect blend of comfort, style, and convenience. Sunlight pours through generous newer windows, filling every room with warmth and highlighting the freshly painted interior and gleaming, refinished hardwood floors that flow seamlessly throughout the home. Beautiful crown moldings and decorative wall panels add timeless elegance and architectural charm throughout. At the heart of the home, the inviting living room features a charming fireplace-perfect for cozy nights. The modern kitchen is both elegant and functional, featuring granite countertops, stainless steel appliances, and ample space for cooking and gathering in the dinning room. Just beyond, the spacious, updated full bathroom showcases stunning tile work and a clean, contemporary design. Thoughtful upgrades such as central air, a newer roof, updated sid

Brand-NEW construction Home underway in Fairfield's highly sought-after Lake Mohegan neighborhood, crafted by local builders known for exceptional quality and design. There is still time for buyers to personalize select finishes and create the home of their dreams! Offering over 4,000 square feet of thoughtfully designed living space, this stunning residence is situated on a rare, level.89-acre lot with ample room for a future pool and outdoor oasis. Enjoy an unbeatable location just minutes from Lake Mohegan's beach, walking trails, and recreational amenities, while remaining close to Fairfield's beautiful beaches, Metro-North train service to NYC, award-winning schools, shopping, golf courses, and dining. Designed for today's lifestyle, the open-concept floor plan features 5 spacious bedrooms and 4.5 bathrooms including a fabulous Primary suite and spa like bath, and laundry area; providing exceptional flexibility for modern living. The main level includes a spectacular chef's kitche

Welcome to 166 Glengarry Road, a beautifully maintained end-unit townhouse in Fairfield's sought-after Woodfield Village community. Offering 3 bedrooms, 3 full baths, 1 half bath,and a versatile floor plan, this move-in-ready home combines comfort, space, and convenience. Freshly painted throughout and featuring refinished hardwood floors, the home is filled with natural light. The spacious living room showcases vaulted ceilings, oversized windows, and a fireplace, creating an inviting space for everyday living and entertaining. The dining area flows seamlessly into the kitchen, complete with stainless steel appliances and ample storage. The flexible layout offers comfortable living on multiple levels, while the finished lower level provides additional space ideal for a family room, home office, gym, media room, or guest retreat. An unfinished storage area offers excellent room for seasonal items, hobbies, or workshop space. As an end unit, the home enjoys added privacy and beautiful v

Update: Offers are due at 6pm on Saturday, June 20th. Welcome to 73 Fairmount Terrace, a quintessential Connecticut Colonial nestled on one of the most coveted, tree-lined streets in the heart of Stratfield. This home perfectly captures that elusive balance of timeless architectural character and the modern upgrades essential for today's lifestyle. The craftsmanship is evident as elegant crown moldings and custom plantation shutters add a layer of sophistication to every room. The heart of the home is the kitchen, appointed with Carrera marble countertops and a built-in banquette - the ultimate spot for a morning coffee or casual weeknight dinners. Outside, the property is an entertainer's dream. Transition through the newer windows to a private backyard oasis, fully fenced for peace of mind. You'll spend your summers hosting on the expansive slate patio, made even more convenient by an outdoor shower and a lush lawn kept green by a full irrigation system. With natural gas and city wat

Don't miss out on this beautiful, spacious 3-level townhouse featuring 2 bedrooms and 2.5 bathrooms! The main level offers a welcoming open-concept living and dining area with a cozy fireplace, a convenient half bath, and sliding glass doors leading to a private enclosed deck-the perfect spot to enjoy your morning coffee or unwind after a long day. Upstairs, you'll find a spacious primary suite with its own private full bathroom, along with a second generously sized bedroom and an additional full bathroom, providing comfort and convenience for family or guests. The lower level features a partially finished basement with endless possibilities. Create the space you've always wanted-whether it's a family room, home office, gym, recreation area, or additional living space. The laundry area is also located on this level. Additional highlights include 1-Car Garage and 1 Assigned parking space and access to wonderful community amenities Swimming Pool and Clubhouse. This townhouse offers the p

Welcome to Black Rock Gardens Co-Operative and a lovely spot in Fairfield County. You are close enough to walk up to Fairfield Avenue and enjoy all that the terrific restaurants offer! Black Rock is a beautiful neighborhood in Bridgeport and Black Rock Gardens is a co-operative that is owner occupied only. There are no rentals in the complex so, note you must live in your unit in the complex. The purchase and application process is a little different than a condominium.This unit features a living room, dining room/office, bedroom, full bathroom and an eat in kitchen. There is a small sun porch that overlooks the courtyard. There is a back door that leads to the basement where there is storage for this unit. The common charges are 554/month and cover heat, hot water, taxes, water, grounds maintenance, and property management. There are no rentals allowed

Step into the timeless elegance of this gracious 1920s 6-bedroom, 3.5-bath Colonial, nestled on one of Fairfield's most beautiful and coveted streets. Surrounded by neighboring homes with equally exquisite architecture and sweeping lawns, 73 Inwood Road has been a cherished home filled with good cheer and great memories for over 53 years. Special features of this grand dame include gorgeous hardwood floors, multiple French doors, a grand front Entryway and both front and back staircases. The main level offers exceptional flow: Spacious Formal Living and Dining Rooms, a cozy Den with working fireplace, 3-Season Screened Porch, and sun-drenched Breakfast Room. A functional Butler's Pantry enhances the formal spaces. Enjoy seamless indoor-outdoor living with not one but two bluestone terraces - a spacious rear Patio, perfect for outdoor entertaining and a covered front Terrace off the Living Room to watch neighbors and friends passing by. The park-like grounds are dry, level and provide j

Charming 1915 colonial located on a dead end street in the Devon section of Milford! The screened in front porch will greet you and be a perfect spot to enjoy the outside weather! The first floor has wood floors in the living room and dining room. The eat in kitchen with white cabinetry reflects the style of 1915 with an alcove for the kitchen sink and pantry. The second level has 3 nicely sized bedrooms and a full bathroom. This level has a 4th room perfect for an office or den. The third-floor attic has an additional space; great for crafting, home gym, a quiet and/or lots of storage. The full basement has access to the backyard of the home. Come take a look and feel the charm, character and spacious feeling. You will love this home!

Welcome to this highly sought after Dogwood 2 bed, 2 bath condo in Fairfield's Stratfield Village. The interior has been modernized with a spacious combo living/dining area. The compact kitchen is fully renovated with new cabinets, new countertops, a decorative tile backsplash, and upgraded appliances including a dishwasher and microwave. Both full bathrooms are extensively refreshed; one features new floor and shower tiles, a new vanity, and mirrors, while the second offers a new sink, vanity, and modern lighting. The entire interior is finished with a fresh coat of clean white paint for a true turnkey feel. Off the living space, the back patio features a newly raised cement floor for perfect drainage and a replaced closet door. Additional highlights include an in-unit laundry area with a brand-new dryer and exclusive access to a private storage unit located directly underneath the condo. Right outside, enjoy the natural beauty of the condo pool, a serene pond, and a nearby creek. Loc

Classic 4 bedroom 2 bath Stratford Colonial. Living room with fireplace, office / den full bath and formal dining located on the main level. Sliders to the deck from the spacious kitchen. The 4 bedrooms on the upper level feature beautiful hardwood floors. Centrally located near the historic district, Convenient to the Metro North Train Station and just minutes to I-95 ! Stratford Center is just a short walk away. You will enjoy the convenience of a stroll down to the center of town on warm summer nights and have your pick of several fine restaurants. On your way back step into the past to order a classic Hot Fudge Sundae from Goody Bassett's Old Fashioned Ice Cream Shoppe all just a hop skip and a jump from your new home ! The public library, the town senior center, the Academy Hill Green park are but a few of the area amenities within walking distance. Call a Realtor Today !

Coastal living in the heart of Lordship with water views and a true turnkey lifestyle. Just steps from the beach, this move-in ready home offers the ideal blend of modern construction and coastal charm. Spanning three finished levels, this 4-bedroom home features a bright, open layout centered around a stunning chef's kitchen with a 9-foot quartz island, custom cabinetry, and high-end appliances - perfect for everyday living and entertaining. Most furnishings are included, creating an easy and immediate move-in opportunity. The spacious primary suite features its own balcony with water views and a beautifully finished bath with double sinks, soaking tub, and glass-enclosed shower. Additional highlights include hardwood floors throughout, custom millwork, finished third floor flex space, oversized two-car garage, and a fully fenced outdoor area with pergola, hot tub, and enclosed outdoor shower. Priced with intention and offered by a motivated seller, this coastal retreat presents excep

Welcome to the Village at Black Rock! This is a rare opportunity to own a large 1499 square foot corner unit condo on the second floor in the desirable Black Rock neighborhood. A spacious open floor plan, a Primary suite with bathroom, a second bedroom and a second full bathroom. Balcony access from the main living area and the Primary suite- perfect for morning coffee, happy hour drinks and watching the parades on Fairfield Avenue! Home improvements include interior painting, recessed lighting, ceiling fans in the bedrooms, new blinds, new washer/dryer and new refrigerator. Make this your new home and enjoy this vibrant walkable neighborhood with easy access to the scenic Saint Mary's by the Sea waterfront, the Harborview Market, Park City Music Hall and so much more!

Seller ready to move on to their next project! In Milford's coveted Rivercliff neighborhood With serene water views, this stunning home has been masterfully transformed AND EXPANDED from the studs out by Walk Invest, LLC - A premier residential renovation firm with 20+ years of experience and 40+ completed high-end renovations statewide. Their signature is total transformation, and this home is no exception. A reimagined floor plan with almost 1600 sq ft- complete with new staircase and added dormers for expanded square footage - sets the tone for a residence where no detail was overlooked. The sun-drenched new kitchen stuns with new cabinetry, custom pot filler, designer hood, and a handcrafted backsplash. A custom drop zone/mudroom and crown molding throughout add function and elegance in equal measure. A spacious primary suite on the main level with boutique like bath complete with a custom glass shower door. Two other spacious bedrooms upstairs share a well appointed bathroom AND a

Opportunity abounds in this spacious 8-room, 3-bedroom, 2-bath Ranch offering 2,167 sq ft in Fairfield's sought-after Stratfield neighborhood situated on just under a half acre of property. Ready for your personal updates and finishing touches, this home presents an exceptional opportunity to build equity and create the home you've always envisioned. The main level features a bright living room with a fireplace and custom built-ins, a dining area with built-ins, and a white kitchen with Corian countertops and skylights that opens to a vaulted family room, creating an ideal space for everyday living and entertaining. A main-level office offers flexibility for remote work, hobbies, or a quiet retreat. Relax in the screened-in porch, perfect for enjoying the outdoors in comfort. The primary bedroom suite includes a private full bath, while two additional bedrooms share a hall bath. Hardwood floors, abundant storage, cedar closet and a 2-car attached garage add to the home's appeal. The fu

Direct waterfront | cedar beach, milford. Luxury Living on the Shoreline. Enjoy rare waterfront living with panoramic views of Long Island Sound and the Housatonic River from nearly every room. This 2,500+ sq ft home, built in 2004 and extensively upgraded, features 3 ensuite bedrooms, a home office, and 3.5 elegant baths. The open main level boasts a chef's kitchen with Poggenpohl cabinetry, premium appliances, and seamless flow to a waterside deck. Upstairs, the serene primary suite offers a spa-like bath, private balcony, and sunrise views. The lower level includes a private guest/in-law suite with its own entrance, bath, deck, and water views. Additional features: Two-car garage, EV charger, generator, landscaped grounds, paver driveway, rooftop widow's walk with sweeping vistas. Launch kayaks or boats from your backyard! Located in the sought-after Cedar Beach community, steps from the beach and nature trails, and minutes to downtown Milford, marinas, dining, and transit. A perfec

Set on a cul-de-sac in Fairfield's sought-after University area, this custom-built 5-bedroom, 6-bath residence was originally designed as the developer's own home, with a focus on natural light, architectural detail, and elevated everyday living. The primary suite features soaring 18-foot cathedral ceilings, a custom white oak ceiling treatment, an 11-foot picture window, and a spa-inspired bath. A 300-square-foot covered balcony with 18-foot ceilings extends the living experience outdoors and serves as one of the home's defining spaces. Designed for both entertaining and everyday living, the home includes a gourmet kitchen with Sub-Zero refrigeration, quartzite countertops, custom cabinetry, an oversized island, and a fully outfitted butler's pantry with additional refrigeration, wine storage, a dishwasher, and prep space. Three additional bedrooms offer en-suite baths, while the finished third level provides flexible space for a home office, recreation room, guest suite, or studio. T

Welcome to 44 Washington Parkway, a beautifully appointed home in Stratford's sought-after Lordship neighborhood, where spectacular views of Long Island Sound, the beach access and the 'Seawall' enhance everyday living. This 4-bedroom, 3-bath home has been thoughtfully designed to capture the beauty of its surroundings while offering comfortable spaces for both everyday living and entertaining. The open-concept main living area seamlessly connects the bright and airy living room, dining area, and kitchen with expansive windows that frame panoramic views of the Sound The sparkling updated kitchen boasts quartz countertops, a breakfast bar, stainless steel appliances with a slider to a spacious deck overlooking the shoreline and private backyard. Also on the main level is a bedroom, a full bath and convenient laundry area. The upper level showcases 3 bedrooms, 2 full baths and hardwood flooring throughout. The 1st bedroom has a private balcony with water views, while the 2nd bedroom has

TWO incredible waterside opportunities await! That's right, not one, but TWO fantastic beach area homes are offered! With their direct waterfront locations (1235. Beachfrontu002FLI Sound; 1236. Canal side), both homes have amazing water views, beach access and a convenient, fantastic location all in one! Both homes also offer excellent investmentu002Frental opportunities. 1235 is rented for the 2025-'26 &'26-'27 college academic calendar years (1236 is presently rented month-to-month). The home can be your beachside escape for the summer months. Or rent it out monthly for additional income! When it's time for you to reside in the homes, create your own compound with a bright and airy house on each side of the water! 1235 has newer bathrooms, kitchen and tankless water heater. All newer windows on the beach-facing side of the home. Newer roof & skylights (2021). Recently painted exterior. Enjoy the incredible views of the Sound from the primary bedroom balcony! Take a dip in the sound a

Seller ready to move on to their next project! In Milford's coveted Rivercliff neighborhood With serene water views, this stunning home has been masterfully transformed AND EXPANDED from the studs out by Walk Invest, LLC. A premier residential renovation firm with 20+ years of experience and 40+ completed high-end renovations statewide. Their signature is total transformation, and this home is no exception. A reimagined floor plan with almost 1600 sq ft. Complete with new staircase and added dormers for expanded square footage. Sets the tone for a residence where no detail was overlooked. The sun-drenched new kitchen stuns with new cabinetry, custom pot filler, designer hood, and a handcrafted backsplash. A custom drop zoneu002Fmudroom and crown molding throughout add function and elegance in equal measure. A spacious primary suite on the main level with boutique like bath complete with a custom glass shower door. Two other spacious bedrooms upstairs share a well appointed bathroom AND

Direct waterfront. CEDAR BEACH, MILFORD Welcome to an exceptional opportunity to live by the water in comfort, style, and tranquility. Built in 2004 and impeccably maintained with numerous upgrades, this 2,500+ sq ft coastal residence offers sweeping views of Long Island Sound and the Housatonic River from nearly every room. The flexible floor plan features three spacious bedrooms, each with a full bath, plus a dedicated home office and 3.5 bathrooms finished with marble and natural stone. Designed for both elegance and ease of living, the main level showcases unobstructed water views from the kitchen with imported Poggenpohl cabinetry and high-end appliances. The light-filled dining area and a living room with waterside deck is perfect for entertaining or quiet evenings overlooking the water. Upstairs, the primary suite is a private retreat with generous closets, a luxurious spa bath, a private waterside deck, and breathtaking water views. The lower level offers a private waterside su