Stratford Homes under $500,000

Welcome to Stratford, Connecticut – a charming town nestled in the heart of Fairfield County, where picturesque landscapes meet vibrant community life. Known for its rich history and scenic waterfront, Stratford offers a perfect blend of suburban tranquility and urban convenience. With its beautiful parks, bustling downtown, and proximity to the Long Island Sound, residents enjoy a lifestyle that emphasizes both relaxation and recreation.

Stratford is not just a place to live; it’s a community where neighbors become friends and families flourish. The town boasts excellent schools, a variety of local shops, and an array of dining options that cater to every palate. Outdoor enthusiasts will appreciate the numerous parks and recreational facilities, including the scenic Stratford Point and the expansive Short Beach, perfect for picnics, walking trails, and enjoying the beauty of nature.

For those seeking an affordable entry into the Stratford real estate market, there are numerous homes available under $500,000. These properties offer a diverse selection of styles and sizes, catering to first-time homebuyers, growing families, and anyone looking to invest in a vibrant community. From cozy single-family homes to charming townhouses, these options provide a wonderful opportunity to experience the Stratford lifestyle without breaking the bank.

Whether you’re drawn by the allure of the waterfront, the sense of community, or the affordability of housing, Stratford is a hidden gem waiting to be discovered. Come explore your new home in this delightful Connecticut town, where every day feels like a retreat!

Newest Stratford Homes under $500,000

$379,000

3 Beds ⋅ 1 Baths ⋅ 24210775 MLS

A one-level opportunity near Wooster Park: renovate, reimagine, make it yours. Bring your vision to this well-located Stratford home and unlock its potential. Situated on a corner lot adjacent to Wooster Park, this 3-bedroom, 1-bath home offers a practical single level floor plan, oversized 1-car garage, driveway parking, central air conditioning and gas baseboard heat. At approximately 1044 square feet, the home provides a manageable footprint with plenty of opportunity for renovation and personalization. This property conveys AS IS

20 Karen Ave, Stratford

$435,000

4 Beds ⋅ 2 Baths ⋅ 24210509 MLS

Welcome home to this well-maintained Cape offering a flexible floor plan, hardwood floors and thoughtful updates throughout. The main level features a comfortable living room with hardwood flooring and an updated kitchen with granite countertops, center island, dishwasher, microwave and refrigerator. A spacious dining room with hardwood floors, ceiling fan and closet is currently used for entertaining but can easily be converted back to a main-level bedroom. The primary bedroom offers hardwood floors, ceiling fan and a private full bath. An additional hall bath features tile flooring, a Bath Fitter tub, new vanity and linen closet. Convenient laundry options are available on either the main level or in the basement. Upstairs you'll find two additional bedrooms, both with hardwood floors and ceiling fans, including an oversized bedroom offering plenty of space and versatility. The basement provides additional storage and features a block foundation, sump pump and radon mitigation system. Additional highlights include oil-fired hot water baseboard heat, a pressure-treated deck, low-maintenance vinyl siding and a roof replaced in 2021. A classic Cape with a versatile layout, important updates and plenty of opportunity to make it your own!

96 Van St, Stratford

$449,000

4 Beds ⋅ 2 Baths ⋅ 24211003 MLS

Welcome to 10 Prospect Drive, a charming Stratford home offering character, flexibility, and a convenient location. Set in an established neighborhood, this home features a versatile layout with comfortable living spaces and plenty of opportunity to make it your own. A standout feature is the flexible first-floor room, previously used by the seller as a primary bedroom and by past owners as a formal dining room. Whether you need a main-level bedroom, dining room, home office, or additional living space, this room can easily adapt to your needs. Adding to the home's character is its connection to Stratford's local history. Per the seller, homes in the neighborhood were originally built for GE workers who traveled by train to the nearby GE factory, giving the area an interesting tie to Stratford's industrial past. Conveniently located near shopping, dining, major commuting routes, train access, and area amenities, 10 Prospect Drive is a great opportunity for buyers looking for charm, versatility, and potential in a well-established Stratford neighborhood.

10 Prospect Dr, Stratford

$500,000

4 Beds ⋅ 2 Baths ⋅ 24211139 MLS

Set in Stratford's sought-after North End, this 4-bedroom Colonial offers a warm, functional layout with an open flow designed for everyday living and entertaining. The heart of the home is the spacious kitchen with granite countertops, stainless steel appliances, abundant cabinetry and hardwood floors, opening seamlessly to the dining area and inviting living room with a wood-burning fireplace. Step through the back door onto the deck overlooking a flat, usable yard-perfect for outdoor dining, entertaining or simply enjoying the space. At the front of the home, a separate room offers flexibility as a home office, den or sitting room, while a convenient mudroom adds everyday function. A first-floor half bath is already plumbed for a corner shower, offering future potential. Upstairs are four well-proportioned bedrooms and a beautifully renovated full bath with modern finishes. Additional highlights include hardwood flooring throughout much of the home, a detached one-car garage, natural gas heat, 200-amp electrical service and public water and sewer. Enjoy a convenient North End location near Paradise Green, local shops and restaurants, parks and recreation, Metro-North and major commuter routes, with Stratford's shoreline, beaches and waterfront amenities just a short drive away. A wonderful opportunity to enjoy space, character and convenience in one of Stratford's most sought-after areas.

162 Anson St, Stratford

1700 Broadbridge Ave Unit C48, Stratford

$245,000

2 Beds ⋅ 2 Baths ⋅ 24211389 MLS ⋅ Stratford Manor BLDG.

Welcome to 1700 Broadbridge Ave, Unit C48! This updated end unit features 2 bedrooms, 2 full bathrooms, and is vacant and ready for immediate occupancy. Perfect for commuters, the Stratford Metro North Train Station is just minutes away, with convenient service to Grand Central. Enjoy easy access to major highways, shopping, dining, and Stratford's beautiful beaches. Whether you're a first time buyer, downsizing, or looking for a move in ready home, this unit is ready for its next owner. Come take a look!

1700 Broadbridge Ave Unit C48, Stratford

$469,000

3 Beds ⋅ 2 Baths ⋅ 24211165 MLS

Step inside 110 Ruby Lane, a spacious and inviting 3 bedroom, 1.5 bath home nestled in a desirable Stratford neighborhood. Designed with comfortable living in mind, the home offers generous living areas, a finished lower level that can be used as a family room, home office, gym, or playroom, and an attached two car garage. The covered breezeway connecting the main living area to the garage adds a versatile space filled with natural light. Whether used as a sunroom, reading nook, sitting room, hobby space, or relaxing retreat, this unique area also overlooks the backyard. Outside, the beautifully private backyard offers plenty of room for entertaining, gardening, or unwinding in a peaceful outdoor setting. With parks, schools, shopping, restaurants, and major commuter routes nearby, this home offers the space, comfort, and convenience you're looking for. Don't miss the opportunity to make 110 Ruby Lane your next home!

110 Ruby Ln, Stratford

$356,000

1 Beds ⋅ 2 Baths ⋅ 24208274 MLS ⋅ Oronoque Village BLDG.

This lovely Emerson model ranch features a sun-drenched, open layout boasting 1,175 square feet of main-level living space. Step inside to find a welcoming living area anchored by a cozy fireplace, perfectly transitioning into the dining and kitchen spaces for effortless entertaining. The primary suite offers a peaceful retreat complemented by 1.5 baths. Enjoy additional flex space with the partially finished lower level-perfect for a home office, den, or guest area. A convenient basement garage provides easy parking and extra storage. Step outside to your private deck to enjoy the peaceful, tree-lined surroundings that make this neighborhood so special. As an Oronoque Village resident, you'll gain access to world-class amenities including renovated clubhouses, three swimming pools, tennis and pickleball courts, and social membership access to the golf course. SELLER TO PAY SPECIAL ASSESSMENT FOR NEW ROOF.

88 S Tril Unit A, Stratford

$389,000

1 Beds ⋅ 2 Baths ⋅ 24210848 MLS ⋅ Oronoque Village BLDG.

Welcome to Oronoque Village, one of Fairfield County's premier 55+ communities, nestled among the scenic fairways of Blackhawk Country Club. This beautifully maintained townhouse offers the perfect balance of comfort, convenience, and an exceptional lifestyle. Filled with natural light, the spacious floor plan features dramatic 20-foot vaulted ceilings, hardwood floors, and an open living and dining area designed for both everyday living and effortless entertaining. A versatile bonus room with French doors offers the flexibility of a guest bedroom, home office, or den, while the generously sized primary suite provides a peaceful retreat with ample closet space and an en-suite bath. Enjoy the convenience of a private garage, in-unit laundry, abundant storage, and a secluded outdoor space perfect for morning coffee or relaxing evenings. A spacious private landing at the top of the staircase creates a gracious entry to the home while offering a rare bonus flex space-ideal for a cozy sitting area, reading nook, hobby space, home office, or beautifully displayed seasonal decor.

13 Algonquin Ln Unit B, Stratford

$300,000

4 Beds ⋅ 2 Baths ⋅ 24206655 MLS

Bring your vision and ideas to 303 Bruce Street! This Stratford property is priced to sell and offers an excellent opportunity for buyers looking to renovate, customize, and create a home that truly reflects their style. The house needs work and is being offered in its current condition, providing the perfect canvas for those with a vision. Conveniently located near shopping, dining, transportation, parks, and Stratford's shoreline, this property is ready for its next owner to unlock its potential. Don't miss this opportunity to transform this property into something special! Inspection for informational purposes only. 2 hours notice needed prior to showing.

303 Bruce Ave, Stratford

$450,000

3 Beds ⋅ 2 Baths ⋅ 24210581 MLS

Charming and inviting, this classic Cape Cod home located in the Stratford's desirable North End offers the perfect blend of comfort, space and convenience. Featuring 3 bedrooms, 2 full bathrooms, enclosed front porch, wood floors through out. The Yard is fenced in and spacious with plenty of room for your future imagination. This home is only missing the next family to begin a whole new chapter.

421 Wakelee Ave, Stratford

$367,000

3 Beds ⋅ 1 Baths ⋅ 24205833 MLS

Opportunity awaits! Ideally located in the heart of Stratford, this 3-bedroom, 1-bathroom Cape offers over 1,200 square feet of living space and is ready for its next chapter. The home features a functional floor plan with a spacious living room, formal dining room, hardwood floors, and an oversized driveway. Situated on a level corner lot close to shopping, restaurants, parks, major highways, and key public transport corridors, this property presents an exceptional opportunity for investors, flippers, or contractors. Key capital infrastructure updates are already in place, including a complete main sewer line replacement ($20k capital expense cleared) and a brand-new hot water heater (Jan 2026). Bring your vision and unlock the massive equity potential this home has to offer! Terms of Sale: Sold strictly 100% AS-IS with tenant in place through November. Cash or Hard Money preferred. DO NOT DISTURB TENANT.

11 Cardinal Pl, Stratford

$479,000

3 Beds ⋅ 2 Baths ⋅ 24210369 MLS

Classic North Stratford Colonial on Quiet Cul-de-Sac | Renovated Kitchen & Bath | Large Level Lot.Welcome to this impeccably maintained 3 Bedroom, 1.5 Bath Center Hall Colonial, perfectly situated on a quiet, tree-lined cul-de-sac in North Stratford. Offering 1,857 square feet of comfortable living space, this classic home combines timeless charm with thoughtful updates and endless potential. The inviting main level features a spacious front-to-back Living Room accented by a fireplace and glass doors leading to a sunny Sunroom/Home Office. A perfectly proportioned Dining Room is ready to host holidays and special occasions, while the beautifully renovated Kitchen showcases granite countertops, stainless steel appliances, custom built-ins, and abundant workspace for everyday living and entertaining. Completing the first floor are a convenient Pantry/Laundry Room, Powder Room, and direct access to the new maintenance-free composite deck overlooking the expansive level backyard. Upstairs, you'll find three generously sized Bedrooms, including a spacious Primary Bedroom, along with a tastefully renovated Full Bath. Beautiful hardwood flooring enhances much of the home. The unfinished lower level offers excellent storage and exciting possibilities for future living space. Newer roof and a large detached two-car garage. A short walk to the shops and restaurants of Paradise Green and a short ride to Metro-North/New York City train. Customize and create your dream home!

50 Vine St, Stratford

Start Your Search

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.