Upper Stepney Real Estate

Welcome to Upper Stepney, a charming neighborhood nestled in the picturesque town of Monroe, Connecticut, located in the heart of Fairfield County. Known for its serene atmosphere and close-knit community, Upper Stepney offers a delightful blend of suburban tranquility and convenient access to urban amenities.

As you stroll through the tree-lined streets, you’ll discover beautifully maintained homes that reflect a variety of architectural styles, from classic colonials to modern designs. The neighborhood is characterized by its spacious lots and lush greenery, providing residents with a peaceful retreat from the hustle and bustle of city life. Families will appreciate the excellent schools in the Monroe public school system, which are renowned for their commitment to academic excellence and community involvement.

Upper Stepney boasts a wealth of recreational opportunities. The nearby parks and nature reserves, such as the scenic Great Hollow Lake and the expansive Wolfe Park, offer residents a chance to enjoy outdoor activities, from hiking and biking to fishing and picnicking. The community is also home to several local shops, restaurants, and cafes, where you can savor a delicious meal or grab a quick coffee with friends.

With its friendly atmosphere, beautiful surroundings, and strong sense of community, Upper Stepney is not just a place to live; it’s a place to thrive. Whether you’re looking for a family-friendly environment or a peaceful retreat, this neighborhood has something for everyone. Come and experience the charm of Upper Stepney—your new home awaits!

Newest Listings in Upper Stepney

$285,000

1 Beds ⋅ 1 Baths ⋅ 24193446 MLS ⋅ The Hills Of Monroe BLDG.

Welcome to Monroe CT living and an easy, convenient lifestyle for sure! The Hills of Monroe is a private, secluded condominium complex that is set back off of Route 25. So you've got peacefulness and a serene park-like setting with wooded views, yet the convenience and ease of access to stores, restaurants, shopping and commuting at the same time. This one bedroom, second floor unit features a large living room with built ins, a fireplace and access to your own personal and private balcony for a glass of something cold to quiet the soul and worries or a beautiful cup of coffee to start the day enjoying a natural setting! Both are soul-filling ideas. The living room features wall to wall carpeting as floor covering. The dining room has a ceiling fan and parquet flooring and is large enough to host a dinner party for 8! The eat in kitchen has built-ins and features stainless appliances...oven, dishwasher and fridge. The flooring in the kitchen is tile. The laundry is in a hall closet and the machines are full sized. The primary bedroom features a walk in closet and wall to wall carpeting. There is plenty of space, closets, and a storage area additionally, in a different building. You've got a one car garage that is attached to the building for easy access during inclement weather! The pool and tennis court are fun and a short walk away! The common charges cover everything except gas, electricity and water. Life and living in the Hills of Monroe is just perfect all around!

215 Windgat Cir Unit E, Monroe

$999,900

4 Beds ⋅ 4 Baths ⋅ 24190320 MLS

COMPLETED AND READY TO MOVE IN! Luxury new construction set on a scenic 3.25-acre homesite. This 4BR, 3.5BA home offers 3,674 sq ft of beautifully finished living space including a walkout lower level. The exterior features board-and-batten siding and a covered front porch with composite decking. Inside, a bright open floor plan with hardwood floors throughout the main level includes a dedicated office, formal dining room, and a stunning kitchen with stone countertops, high-end stainless appliances including a double oven, a large island with sink, and a spacious walk-in pantry with custom shelving. The kitchen flows seamlessly into the family room with a gas fireplace & shiplap feature wall. A mudroom area just off the garage adds everyday convenience. Upstairs, the primary suite offers a walk-in closet and spa-like bath with double vanity, tiled shower, and heated marble floors. Three additional bedrooms provide generous space, including one with a large adjoining bonus room ideal for storage/future finished flex space such as a playroom or hangout area. A convenient second-floor laundry room adds practicality. The finished walkout lower level includes a full bath and flexible space for a gym, media room, or possible in-law setup. Composite rear deck w/ hose spigot overlooks the natural landscape. Oversized 24x34 garage offers room for a workshop, or even a golf simulator. Spray-foam insulated envelope along w/ Ring doorbell & two security cameras. Don't miss this ONE!

1427 Monroe Tpke, Monroe

$549,000

3 Beds ⋅ 1 Baths ⋅ 24187034 MLS

A move-in ready ranch offering comfortable living in a convenient Monroe location. This 3-bedroom, 1-bath home features a bright living room with a fireplace, an updated kitchen with stainless steel appliances, and a dining area ideal for everyday living and entertaining. Hardwood floors and central air add to the home's appeal. The partially finished lower level provides additional flexible living space perfect for a home office, recreation room, or gym. An attached two-car garage offers added convenience and storage. Situated on a level 0.46-acre lot with a deck overlooking the backyard, this property provides plenty of outdoor space for relaxing, gardening, or entertaining. Conveniently located near shopping, restaurants, parks, schools, and major commuter routes, this home offers the perfect combination of comfort and accessibility. Recent Updates Include: Central AC unit 2025, Refrigerator, Dishwasher, Oven, Microwave all new 2025, Water softener, Water heater, pH system, Well tank 2026, Well brought up to code 2026, Septic pumped May 2026, Kitchen sink & piping 2026, Shower faucet/showerhead replaced 2026, Pipes replaced from house to septic 2024. Schedule your showing today!

104 Bart Rd, Monroe

$100,000

24137670 MLS

Corner of Rte 25 (Main St) and Rte 59 prime Upper Stepney location. Classic ice cream shop business for sale. 20000 cars/ day. High traffic, great visibility, plenty of parking, and red light to get in/out of parking lot providing great ease for customers. 50+ years as ice cream shop. Owner retiring. Lease renewable Oct 2026. Busy all day. Great profits here. Shared parking lot. Fixtures/inventory all convey. Be open 7.5-8 months per year - go to FL all winter! No need to advertise: people know it - strong, loyal, local customer base. No lockbox. Potential buyers/realtors visiting: Be discreet. Do not ask questions or talk about this sale in front of customers. Visit 12.30-2.30 Monday - Friday ONLY. Owner is the only employee. No financials will be disclosed without NDA, POF and LOI; no exceptions, so don't ask the owner over the counter.

444 Main St, Monroe

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