Stratford Downtown, CT Homes for Sale under $500,000

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  /26

  $379,900

  • 1 Bed
  • 1.5 Baths
  • 1,080 Sq Ft

  53 Ferry Ct, Stratford, CT 06615

  Beautifully renovated potential 2BR townhouse in Stratford's hidden waterfront community, Village Square. Modern kitchen with white shaker cabinets, quartz counters, tiled backsplash, stainless steel appliances, and 5burner gas cooktop. Luxury vinyl plank flooring, smooth ceilings, and updated baths create a clean, move-in ready interior. Enjoy afternoon sunshine from your private deck.

  

  Elizabeth Heatter

  YellowBrick Real Estate LLC

  53 Ferry Ct, Stratford, CT 06615
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  /38

  $399,900

  • 3 Beds
  • 1.5 Baths
  • 1,634 Sq Ft

  64 Glendale Ave, Bridgeport, CT 06606

  A Rare North End Treasure, Ready for Its Next Chapter. Available for the first time ever, this cherished North End Colonial presents a rare opportunity to own a home rich in history and potential. Solidly built and lovingly maintained through generations, the home features a remodeled kitchen, newer windows, updated mechanicals, and hardwood floors in the living and dining rooms. Upstairs offers

  

  Victoria Stillings

  Coldwell Banker Realty

  64 Glendale Ave, Bridgeport, CT 06606
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  /38

  $485,000

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  292 Naugatuck Ave, Milford, CT 06460

  Step out of the ordinary and into this amazing Mediterranean-style Ranch, featuring a bright, sunny open floor plan with gleaming hardwood floors and a cozy fireplace. The remodeled eat-in kitchen offers granite counters, stainless steel appliances including a top of the line, Wolf gas stove and Thermador dishwasher, the sliders lead to a covered backyard patio-perfect for relaxing or

  

  Pam Famiglietti

  William Raveis Real Estate

  292 Naugatuck Ave, Milford, CT 06460
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  /40

  $499,900

  $30K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,562 Sq Ft

  2 Chatham Terrace, Bridgeport, CT 06606

  Rarely does an opportunity come along to live on one of the North End's most desirable cul-de-sacs just off beautiful Lake Forest-a place where neighbors move in and never want to leave. With peaceful water views overlooking the Lake Forest Association park, this well-maintained home offers the perfect blend of comfort, lifestyle, and location. The optional association provides access to a

  

  Alan Stewart Jr.

  ASJ Realty Partners

  2 Chatham Terrace, Bridgeport, CT 06606
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  /28

  $435,000

  • 3 Beds
  • 1.5 Baths
  • 1,106 Sq Ft

  146 Wood Ave, Stratford, CT 06614

  3-bedroom, 1.5-bath Colonial featuring original 1930s wood finishes, beautiful arched doorways, and 9-foot ceilings that give the home an airy, spacious feel. Enter through the welcoming sunroom and sip your morning coffee as the breeze comes in through the adjustable glass panel walls. Natural light streams into the window-lined, open-concept sitting room and adjacent living room with a tiled,

  

  Todd Auslander

  Keller Williams Prestige Prop.

  146 Wood Ave, Stratford, CT 06614
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  /31

  $450,000

  • 4 Beds
  • 2 Baths
  • 2,167 Sq Ft

  55 High Park Ave, Stratford, CT 06615

  BEST & FINAL OFFERS DUE 8/15-7PM - A lot rare opportunity to own a well-loved two-family home with an incredible 80-year family history! Built and owned by the same family for generations, 55 High Park Avenue offers a solid foundation, generous space and exciting potential for an owner-occupant, investor or multi-generational household. Each unit features 2 bedrooms and 1 full bath, along with

  

  Wendy Barry

  Coldwell Banker Realty

  55 High Park Ave, Stratford, CT 06615
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  /30

  $419,000

  • 2 Beds
  • 1.5 Baths
  • 1,784 Sq Ft

  62 Winter St, Stratford, CT 06614

  Welcome to this charming 2-bedroom, 1.5-bath Colonial offering approximately 1,784 square feet of living space and a spacious lot. The classic two-story layout provides comfortable living areas and timeless Colonial character, while the full basement offers valuable additional space for storage, hobbies, a workshop, or future possibilities. A fireplace adds warmth and character to the home, while

  

  Eric Bergers

  William Raveis Real Estate

  62 Winter St, Stratford, CT 06614
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  /19

  $375,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  25 Beechwood Ave, Milford, CT 06460

  Just a short stroll from Walnut Beach, this charming Milford home delivers the relaxed coastal lifestyle you've been looking for. Set on an unusually spacious .17-acre lot for the neighborhood, it blends outdoor living with the warmth and character of a classic coastal home. Inside, you'll find hardwood floors and a nice living room anchored by a large wood-burning fireplace-perfect for cozy

  

  Laura Danforth

  William Raveis Real Estate

  25 Beechwood Ave, Milford, CT 06460
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  /32

  $474,900

  Open Sat 1PM - 3PM

  • 3 Beds
  • 1.5 Baths
  • 1,578 Sq Ft

  704 W Taft Ave, Bridgeport, CT 06604

  Welcome to this inviting 3-bedroom, 1.5-bath Colonial located in Bridgeport's desirable Brooklawn area! Offering plenty of space inside and out, this home features a comfortable traditional layout along with a finished lower level providing additional living, recreation or flex space. With potential for future expansion and customization, there's plenty of opportunity to make this home your own.

  

  Khaliq Brown

  CLMA Realty

  704 W Taft Ave, Bridgeport, CT 06604
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  /32

  $439,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  41 Quince St, Bridgeport, CT 06606

  Updated and move-in ready, this well-maintained home offers a refreshed kitchen, fresh interior paint, and a versatile floor plan. The finished lower level includes an additional bedroom, second kitchen, full bath, and separate living space, providing excellent flexibility for extended household living or a potential in-law setup (buyer to perform their own due diligence regarding permitted use).

  

  Rudy Pierre

  YellowBrick Real Estate LLC

  41 Quince St, Bridgeport, CT 06606
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  /27

  $250,000

  • 1 Bed
  • 1 Bath
  • 702 Sq Ft

  661 West Ave Unit 15, Milford, CT 06461

  Cute, updated, and close to everything Milford has to offer! This 1-bedroom, 1-bath condo is tucked into a charming complex and makes low-maintenance living easy. Inside, you'll find a bright, comfortable layout with tasteful updates throughout, making it truly move-in ready. Enjoy being just minutes from vibrant Downtown Milford, the Metro-North train station, major highways, shopping, dining,

  

  Kelly Hill-Mihalyak

  Coldwell Banker Realty

  661 West Ave Unit 15, Milford, CT 06461
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  /25

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,001 Sq Ft

  332 Palisade Ave, Bridgeport, CT 06610

  Opportunity Alert at 332 Palisade! ... If you've been waiting for a home you can truly make your own, THIS is the one. Bring your ideas, bring your style - this place is ready for a full glow-up! Inside, you'll find three bedrooms (one on the main level and two upstairs), plus a full bathroom and laundry hookups conveniently located on the main floor. There's a very large living room and a bright

  

  Lisa Nussbaum

  Top Tier Realty Group, LLC

  332 Palisade Ave, Bridgeport, CT 06610
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  /9

  $235,000

  • 1 Bed
  • 1 Bath
  • 707 Sq Ft

  115 Short Beach Rd Unit 104, Stratford, CT 06615

  Welcome to 115 Short Beach Road #104, a beautifully maintained 1-bedroom, 1-bath condominium offering comfortable, low-maintenance living in a convenient Stratford location. This bright and inviting unit features a spacious open layout, generous natural light, and a well-appointed kitchen that flows seamlessly into the living and dining areas, creating an ideal space for both everyday living and

  

  Javyn Roundtree

  Roundtree Realty LLC

  115 Short Beach Rd Unit 104, Stratford, CT 06615
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  /36

  $440,000

  • 4 Beds
  • 1.5 Baths
  • 1,957 Sq Ft

  157 Fairview Ave, Bridgeport, CT 06606

  Welcome Home! This massive colonial with a whopping 1,957 SQFT 4 Bedrooms and 2 Full bathrooms.Welcome Home! This massive colonial with a whopping 1,957 SQFT 4 Bedrooms and 2 Full bathrooms. The Location on this home could not be more perfect not only with the hospital within walking distance but also the Trumbull Mall being 5 mins away. All of your needs are within shouting distance. This

  Angel Torres Century 21 Scala Group

  157 Fairview Ave, Bridgeport, CT 06606
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  /39

  $469,000

  $11K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,548 Sq Ft

  110 Ruby Ln, Stratford, CT 06614

  Welcome to 110 Ruby Lane, a spacious and inviting 3-bedroom, 1.5-bath home nestled in a desirable Stratford neighborhood. Thoughtfully designed for comfortable living, this home offers generous living spaces, a finished lower level perfect for a family room, home office, gym, or playroom, and an attached two-car garage. One of the home's standout features is the versatile covered breezeway

  Daniel Villacis Modern Day Real Estate

  110 Ruby Ln, Stratford, CT 06614
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  /40

  $364,900

  • 2 Beds
  • 2 Baths
  • 1,686 Sq Ft

  3200 Park Ave Unit 5C2, Bridgeport, CT 06604

  Spacious and inviting 2-bedroom, 2-bath condo featuring a large private balcony with stunning views of Long Island Sound. This well-appointed unit offers high ceilings, beautiful hardwood flooring, and generously sized rooms throughout. The eat-in kitchen provides ample space for dining, with a convenient laundry just off the kitchen. The primary suite boasts abundant closet space and a full

  Belinda Memoli Memoli&Memoli Real Estate,LLC

  3200 Park Ave Unit 5C2, Bridgeport, CT 06604
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  /32

  $424,900

  • 2 Beds
  • 1 Bath
  • 1,350 Sq Ft

  90 Elliott St, Stratford, CT 06614

  Welcome to 90 Elliott Street! Charming, versatile, and well-maintained, this 2-3 bedroom ranch is move-in ready. Step inside to a spacious living room featuring a cozy fireplace that seamlessly flows into the formal dining room. The bright eat-in kitchen offers abundant cabinet storage, complemented by generous bedrooms with flexible layout options. Outside, enjoy a fenced-in backyard ideal for

  Maureen McLarin Century 21 AllPoints Realty

  90 Elliott St, Stratford, CT 06614
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  /18

  $480,000

  • 3 Beds
  • 1 Bath
  • 1,416 Sq Ft

  10 Bell Terrace, Stratford, CT 06614

  Welcome to 10 Bell Terrace, a charming 3-bedroom home located in a well-established Stratford neighborhood where homes are not often available for sale. The main level offers a comfortable living room, dining area, and kitchen, with hardwood floors throughout much of the home. The interior has been freshly painted, offering a bright and inviting feel. Enjoy being just moments from Longbrook Park,

  Sonia Zumba eRealty Advisors, Inc.

  10 Bell Terrace, Stratford, CT 06614
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  /2

  $399,900

  • Land
  • 3.5 Acres
  • $114,257 per Acre

  364 Orange Ave, Milford, CT 06461

  Former apple orchard. Pesticides were found. The parcel is partially in a R-30 zone and partially in a R-A zone. A three lot subdivision was approved at one time. A subdivision is needed from the existing home that is there. The home and barn are not included. A survey has been done. This is a beautiful property with possibilities. Buyer will need to do due diligence. Call for details.

  Walter Nichols Property World

  364 Orange Ave, Milford, CT 06461
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  /13

  $240,000

  • 1 Bed
  • 1 Bath
  • 836 Sq Ft

  155 Short Beach Rd Unit 102, Stratford, CT 06615

  LOCATION, LOCATION, LOCATION!!! Welcome to Lordship!! This coastal community is perfect for anyone looking to live near the beach, have ocean views, and bonus: live steps to a golf course!!! This 1-bedroom, 1-bath condo with open floor plan, car port and washer/dryer on premises, offers the perfect blend of coastal living and everyday convenience. Situated just moments from Short Beach and

  Lisa Nuzzo RE/MAX Heritage

  155 Short Beach Rd Unit 102, Stratford, CT 06615
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  /30

  $430,000

  • 4 Beds
  • 1 Bath
  • 1,152 Sq Ft

  500 Woodlawn Avenue Extension, Bridgeport, CT 06606

  Welcome to this beautiful fully renovated Cape Cod-style single-family home, offering four spacious bedrooms and one full bathroom. this move-in ready property features a completely renovated kitchen and bathroom, fresh interior paint, new hardwood flooring, updated lighting, and new electrical throughout. The home also offers a generous private yard, a spacious deck ideal for outdoor

  Angel Mora eXp Realty

  500 Woodlawn Avenue Extension, Bridgeport, CT 06606
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  /35

  $294,500

  $31K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,128 Sq Ft

  2625 Park Ave Unit 11P, Bridgeport, CT 06604

  PRICED TO SELL!. Rarely available, south facing 11th floor end unit. This two-bedroom, two bath home offers 1128 sf of living space plus a 13x6 balcony with unobstructed spectacular views to Long Island Sound and beyond. This light filled unit is best described as part mid-century, part traditional. Seller's pride of ownership is obvious in all recent remodeling. The kitchen offers Maple

  Richard Henrietta William Raveis Real Estate

  2625 Park Ave Unit 11P, Bridgeport, CT 06604
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  /16

  $445,000

  $45K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,030 Sq Ft

  26 Marsdale Ave, Bridgeport, CT 06606

  This beautiful colonial offers timeless charm with comfortable living spaces. Inside you will find a spacious living room a formal dining room and an eat in kitchen. Three generously sized bedrooms with hardwood floors, natural light and warmth throughout. Schedule your showing today.

  Colette Daye-Hall Century 21 AllPoints Realty

  26 Marsdale Ave, Bridgeport, CT 06606
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  /28

  $430,000

  • 3 Beds
  • 1 Bath
  • 1,210 Sq Ft

  45 Kasper Cir, Stratford, CT 06614

  This very well maintained ranch sits on a very quiet street with beautifully landscaped lawn, bushes and trees. The first thing you notice is the America Flag blowing in the wind on the flag pole in the front yard. Walk into the living room with wall to wall carpeting. The dining area is attached to the kitchen where there is ample space to sit at the counter or have a formal dinner. The bedrooms

  Mike Robinson Century 21 AllPoints Realty

  45 Kasper Cir, Stratford, CT 06614
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  /38

  $475,000

  $45K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,205 Sq Ft

  44 Wood Ave, Milford, CT 06460

  Coastal cottage charm with NO FLOOD INSURANCE awaits it's new steward! Welcome to this sweet beachy bungalow, nestled in one of Milford's most sought after coastal communities - Walnut & Windermere Beach. Enter through the open living & dining area, accented with custom built-in dry bar. This flows to the sunny kitchen with granite countertops, the most perfect breakfast nook, and full tile

  Melanie Gunn Coldwell Banker Realty

  44 Wood Ave, Milford, CT 06460
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  /30

  $310,000

  $39K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,620 Sq Ft

  134 Ogden St, Bridgeport, CT 06608

  Welcome to 134 Ogden Street, a charming Colonial-style home located in Bridgeport's East End. This property features spacious living across multiple levels, a bright living room, hardwood flooring, recessed lighting, an eat-in kitchen, and a functional layout with comfortable bedroom space and multiple bathrooms. Conveniently located near local shops, restaurants, public transportation, I-95,

  Oswaldo Torres Las Americas Real Estate

  134 Ogden St, Bridgeport, CT 06608
• 

  

  /22

  $330,000

  • 3 Beds
  • 1 Bath
  • 1,338 Sq Ft

  59 Harvey St, Bridgeport, CT 06610

  We have multiple offers. Seller is looking for Highest and Best by 5;00 Pm Friday 09/18/2026. Remodeled Cap-Cod. Newer kitchen cabinets. New gas tankless heat and hot water. new gas stove. Finished basement. Move-in condition. One car garage and a private back yard. Large patio. Convenient to public transportation, Railroad and I 95.

  Val Baptista RE/MAX Right Choice

  59 Harvey St, Bridgeport, CT 06610
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  /11

  $255,000

  • 2 Beds
  • 1 Bath
  • 1,260 Sq Ft

  75 Wheeler Ave Unit 205, Bridgeport, CT 06606

  Good condition unit with remodeled kitchen. Features 4 spacious rooms, 2 bedrooms and 1 full bath, with 1260 square feet of living space. Located on the second floor. There is an elevator. One reserved parking space. North End location.

  Domingos Dias RE/MAX Right Choice

  75 Wheeler Ave Unit 205, Bridgeport, CT 06606
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  /27

  $339,900

  • 2 Beds
  • 2 Baths
  • 1,686 Sq Ft

  3200 Park Ave Unit 4C1, Bridgeport, CT 06604

  Welcome to Inwood South! This spacious two-bedroom, two-full-bath apartment offers comfortable single-level living with a bright, open layout and generously sized rooms throughout. The eat-in kitchen provides plenty of space for casual dining, while the sprawling living area opens to a large private balcony-perfect for relaxing and enjoying the outdoors. Both bedrooms are nicely sized, including

  Kyle Neumann Houlihan Lawrence

  3200 Park Ave Unit 4C1, Bridgeport, CT 06604
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  /24

  $495,000

  Open Sun 11AM - 2PM $4K PRICE DROP

  • 6 Beds
  • 2 Baths
  • 3,108 Sq Ft

  185 Grandview Ave, Bridgeport, CT 06606

  Welcome home to this spacious and beautifully maintained single-family colonial located in the North End of Bridgeport. This home features six bedrooms and two full bathrooms with an updated Kitchen newer stainless steal appliance's and tons of storage. With its expansive layout, this property offers endless possibilities to make it your own. You'll find a detached two-car garage providing

  Carolyn Colon-Ortega Century 21 Scala Group

  185 Grandview Ave, Bridgeport, CT 06606
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  /33

  $449,900

  Open Sun 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,236 Sq Ft

  914 Longbrook Ave, Stratford, CT 06614

  Highest & Best Due by 12:00 Tuesday 09/22. Welcome to a beautifully updated home where soaring ceilings, warm hardwood floors, and thoughtfully designed living spaces create an inviting first impression. The main living area is highlighted by dramatic 14+ foot cathedral ceilings with decorative beams, a gas fireplace, and a large bay window overlooking the park. At the heart of the home, the

  Stephanie Devaney Coldwell Banker Realty

  914 Longbrook Ave, Stratford, CT 06614
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  /39

  $410,000

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 760 Sq Ft

  103 Orland St, Milford, CT 06460

  Welcome to this charming, exceptionally well-kept beach cottage in Milford's sought-after Bay View Beach Association. Bay View Beach is a private neighborhood beach available to homeowners within the association boundaries, offering a relaxed shoreline setting, seasonal lifeguard coverage, boat-rack availability, and an active community calendar of summer gatherings and activities. The town lists

  Lisa Andrade Ellison Homes Real Estate

  103 Orland St, Milford, CT 06460
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  /12

  $375,000

  • Land
  • 12,632 Sq Ft
  • $1,293,103 per Acre

  37 Eighth Ave, Milford, CT 06460

  True opportunity in a very sought after beach community in town. Enjoy a true slice of paradise with a potential second and third floor ocean view. You get the best of both worlds, an elevated tranquil lot with breathtaking wilderness and a quick walk to a privately gated beach. You will be amazed how peaceful and secluded the neighborhood is all the while being very close to the highway to make

  Mitchell Delancy LAER Realty Partners

  37 Eighth Ave, Milford, CT 06460
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  /40

  $399,000

  • 2 Beds
  • 2 Baths
  • 1,128 Sq Ft

  2625 Park Ave Unit 11N, Bridgeport, CT 06604

  A true home connoisseur's dream! This newly renovated modern hi-rise masterpiece seamlessly blends luxury highend living w/calming nature views. The corner large terrace provides a tranquil exterior escape. This bespoke residence presents a chef's kitchen, highend S/S appliances, includ concealed his & hers separate refrigerators, self cleaning convection wall oven, 36-inch induction cooktop &

  Tina Angelos Berkshire Hathaway NE Prop.

  2625 Park Ave Unit 11N, Bridgeport, CT 06604
• 

  

  /22

  $449,000

  $16K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft

  18 Drake St, Stratford, CT 06614

  Wonderful Neighborhood a block from Nichols Ave. 3 bedroom cape fully refurbished with many new features. New condenser for central air conditioning. Newly renovated full bath on main level. Newly renovated full bath on upper level. New paint and finishes throughout. Covered patio straight off the kitchen leading to a small yard with both a very small sledding hill and a level grassy area to kick

  Heide Moeller Coldwell Banker Realty

  18 Drake St, Stratford, CT 06614
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  /33

  $480,000

  • 4 Beds
  • 2 Baths
  • 1,377 Sq Ft

  54 Agnes St, Bridgeport, CT 06606

  Welcome to 54 Agnes Street, a rare North End cul-de-sac opportunity in Bridgeport. Offered As Is at $480,000, this property invites you to bring your designer, architect, or builder and curate the home you've always wanted. The tree-lined, level lot sits within the Lomax Residential Development, with covenants, restrictions, and planned City water and sewer designed to support a cohesive

  Elizabeth Anderson Realty ONE Group Connect

  54 Agnes St, Bridgeport, CT 06606
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  /35

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,645 Sq Ft

  1412 Windward Rd Unit 1412, Milford, CT 06461

  Welcome to 1412 Windward Road in Caswell Cove, one of Milford's hidden gems for waterfront living along the Housatonic River. This spacious 1,645 sq. ft. garden-level ranch offers 2 bedrooms, 2 updated full baths, a detached garage and the ease of one-level living, all complemented by beautiful water views and spectacular sunsets. The generous floor plan features a spacious living room with

  Amie Belile William Raveis Real Estate

  1412 Windward Rd Unit 1412, Milford, CT 06461
• 

  

  /40

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,375 Sq Ft

  21 Meadow St, Milford, CT 06460

  Welcome to this beautifully renovated 3-bedroom, 2-full-bath Cape in Milford, where modern updates meet classic charm. Every major improvement has already been completed, including a brand-new kitchen, updated bathrooms, updated throughout, new appliances, new hot water heater, new central air, updated electrical, new roof, new siding and all new plumbing creating a truly move-in-ready home. The

  Michael Debiase Keller Williams Realty

  21 Meadow St, Milford, CT 06460
• 

  

  /22

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,838 Sq Ft

  431 Jane St, Bridgeport, CT 06608

  This 3-bedroom, 2-full-bath colonial offers a solid opportunity for buyers looking for a home with character and upside. The house features original details throughout, including a wood staircase with turned balusters and hardwood floors, along with a new appliances and cabinets in kitchen and comfortable living spaces on the main level. Recent updates include a new roof and new windows, both

  Rebeca Urbina Century 21 Scala Group

  431 Jane St, Bridgeport, CT 06608
• 

  

  /30

  $499,900

  • 3 Beds
  • 2 Baths
  • 1,996 Sq Ft

  380 Rockwell Ave, Stratford, CT 06615

  Bright and spacious oversized colonial. The first level features a large living room with a fireplace, filled with natural light from its many windows, a dining room, and a kitchen with white shaker cabinets, marble countertops, and stainless-steel appliances. There's also a full bath and a convenient home office/den on this floor. Hardwood floors run throughout. Upstairs, you'll find three roomy

  Isabel Leonard BHGRE Gaetano Marra Homes

  380 Rockwell Ave, Stratford, CT 06615

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