Stepney Real Estate

Welcome to Stepney, a picturesque neighborhood nestled in the charming town of Monroe, Connecticut. Known for its serene landscapes and tight-knit community, Stepney offers a delightful blend of suburban tranquility and convenient access to urban amenities.

Stepney is characterized by its beautiful tree-lined streets, spacious yards, and a variety of well-maintained homes that reflect the area’s rich history and modern charm. Residents here enjoy a peaceful lifestyle, with plenty of opportunities for outdoor activities, including hiking and biking along the scenic trails of nearby parks. The neighborhood is also home to several playgrounds and recreational facilities, making it an ideal place for families and active individuals alike.

One of the standout features of Stepney is its strong sense of community. Neighbors often come together for local events, seasonal festivals, and farmers' markets, fostering connections that turn acquaintances into lifelong friends. The local schools are highly regarded, providing quality education and a supportive environment for children to thrive.

Conveniently located just a short drive from major highways, Stepney offers easy access to shopping, dining, and entertainment options in nearby towns. Whether you’re exploring the quaint boutiques in Monroe or enjoying a meal at one of the local eateries, there’s always something to discover.

In Stepney, you’ll find not just a home, but a vibrant community where you can create lasting memories. Experience the charm and warmth of this lovely neighborhood—your perfect retreat awaits!

Newest Listings in Stepney

$559,000

4 Beds ⋅ 3 Baths ⋅ 24195196 MLS

Welcome to 87 Jockey Hollow Road, a wonderful opportunity to own a charming home in one of Monroe's most desirable neighborhoods. Lovingly cared for over the years, this home reflects true pride of ownership and offers the perfect canvas for its next owner to make it their own. While some cosmetic updates and TLC will enhance its full potential, the home features a functional layout, generous living spaces, and a warm, welcoming atmosphere that has been enjoyed for years. Set on a beautiful property with plenty of outdoor space, the yard offers endless possibilities for gardening, entertaining, or simply relaxing in a peaceful setting. As a member of the sought-after Lake Estate Association, you'll enjoy access to the lake and the unique lifestyle it offers, including swimming, kayaking, fishing, and enjoying the natural beauty of the community. Located in the award-winning Monroe school district and just minutes from shopping, restaurants, parks, and major commuter routes, this home combines everyday convenience with the tranquility of suburban living. Whether you're looking to personalize your forever home or invest in a property with tremendous potential, this is an exceptional opportunity to build equity in a highly desirable location. Don't miss your chance to bring your vision and make this special property your own. Property SOLD AS-IS. Professional photos coming soon!

87 Jockey Hollow Rd, Monroe

$369,900

1 Beds ⋅ 2 Baths ⋅ 24192680 MLS ⋅ Northbrook Of Monroe BLDG.

Welcome to Northbrook, one of Monroe's most sought-after condominium communities. This ranch-style unit offers comfortable one-level living with a spacious primary bedroom, a versatile den/office, 1.5 bathrooms, and an attached garage. The open living and dining areas overlook a peaceful pond, providing a tranquil setting to enjoy year-round. A private patio offers the perfect spot to relax and take in the scenic surroundings. While the home is ready for its next owner, it also presents an excellent opportunity to update and personalize to your own style. With solid bones, a desirable floor plan, and an exceptional location within the community, this unit offers tremendous potential. Residents of Northbrook enjoy beautifully maintained grounds, walking trails, ponds, two swimming pools, tennis courts, and a clubhouse, all conveniently located near shopping, restaurants, parks, and major commuter routes.

21 Sprucebrook Trail Unit 21, Monroe

$624,900

3 Beds ⋅ 1 Baths ⋅ 24191984 MLS

Welcome to this charming and surprisingly spacious split-level home, ideally located in one of Monroe's most desirable neighborhoods. This well-maintained home features an open-concept layout with beautiful hardwood floors, recessed lighting, and a welcoming living room with a cozy fireplace. The dining room flows seamlessly into a well-designed kitchen with access to a deck, making it perfect for everyday living and entertaining. The upper level offers three comfortable bedrooms and a full bathroom. On the lower level, you'll find a spacious family room, along with a dry bar that's ideal for hosting family gatherings and special occasions. The finished basement provides even more versatile living space, including bonus rooms, a guest bedroom with a private bathroom, a gym, and a combined laundry and mechanical room. The home has been lovingly cared for and updated throughout the years. Outside, enjoy beautifully landscaped grounds featuring a bluestone patio, gazebo, hot tub, and a lovely backyard designed for entertaining, relaxing, and play. A swimming pool adds the perfect touch for summer enjoyment. Recent improvements include a new furnace and central air conditioning, offering added comfort and peace of mind. This home truly has everything you could need, combining space, comfort, and exceptional outdoor amenities in a sought-after Monroe location. Property is being sold as-is.

38 Pastors Walk, Monroe

$869,000

4 Beds ⋅ 4 Baths ⋅ 24114367 MLS

This Private 7.9-acre Monroe Colonial offers the Perfect Blend of Seclusion and Convenience, just Minutes from Town. Featuring 4-5 Bedrooms, 2 Full and 2 Half baths, and a Spacious Finished Lower Level. This Open Floor Plan Home Boasts a Beautiful Inground Pool and Stunning Setting. The Main Level Includes a Living Room with Vaulted Wood Beam Ceiling, Floor-to-Ceiling Stone Fireplace with Gas Insert, Dining Area with Balcony Views of the Grounds, and French Doors leading to a Light, Bright Family Room with Walls of Windows Overlooking the Pool. HW Floors. The Kitchen features Granite Counters, Stainless Steel Appliances, Island, and a Cute Garden Window, while the Laundry/Mud Room offers Abundant Cabinetry for Storage or Pantry use. The Main-Level has the No Stairs Primary En Suite Bedroom with Walk-in Closet and a Beautifully Tiled Bathroom w/Full Shower & Whirlpool Tub. Upstairs, there's a Second Primary Bedroom with Walk-in Closet, 2 Additional Large Bedrooms, and a Full bath. The Expansive Lower Level (approx. 1100 sq ft) is Ideal for Guests, Extended family, or Entertaining, with a Living area, Kitchen Space, Billiard Room, Cedar Closet, and a Glass Three-Season Room Opening to the Oversized 18x36 Inground Pool Surrounded by Stone Paths, Gardens, and Nearly Eight Acres of Privacy. Two-car Garage, Generator-Ready. Perfect Home for Family Living! Even Enough Land to Have that Pony you Always Wanted! Enjoy Wolfe Park, Excellent Schools, and Everything Monroe has to Offer

137 Guinea Rd, Monroe

$389,000

2 Beds ⋅ 2 Baths ⋅ 24189630 MLS ⋅ The Hills Of Monroe BLDG.

A beautifully maintained 2-bedroom, 2-bath nestled in The Hills of Monroe - a quiet, wooded cul-de-sac community that delivers the feel of a private retreat while keeping you connected to everything Monroe has to offer. A fireplace in the living room, and sliders leading out to a private patio with stunning wooded views define the main living space. The spacious eat-in kitchen features updated stainless steel appliances, with a bow window framing beautiful natural views. Generous bedrooms with walk-in closets, in-unit washer/dryer on the main floor, and central air complete this move-in ready package. Low-maintenance living at its finest - in one of Fairfield County's most sought-after condo communities. Brand new windows installed last month!

301 Fairmount R Unit D, Monroe

$675,000

3 Beds ⋅ 3 Baths ⋅ 24186272 MLS

Welcome home to Great Oak Farm! This immaculate classic colonial is sited perfectly in a quiet area overlooking a small Green. Within the past 5 years, the owners have had a new roof and hardwood floors installed. The washer/dryer and hot water heater are 2 years old. Painting and carpeting have been done recently. Enjoy this low maintenance home in a neighborhood known for it's friendly atmosphere. Participate as much or as little as you desire in the many events in the GOF community. Monroe is proud of it's award-winning schools, fabulous library, weekly farmer's market, great commuter location and easy access to stores and restaurants. In addition, you'll love the access to Rails to Trails biking and hiking paths, the gorgeous Great Hollow Lake and Wolfe Park. Yes, you can make Great Oak Farm your home! A dream come true!

105 Secret Hollow Rd, Monroe

$649,900

4 Beds ⋅ 3 Baths ⋅ 24185267 MLS

Welcome to 37 Country Ridge Drive, one of the best neighborhoods in Monroe. Located on a private one acre lot, this home features 4 bedrooms and 2.5 baths and over 2300 sq feet of living space. The main level has a welcoming layout with ample room for entertaining and a cozy feel with a pellet stove in the family room and a gas stove in the kitchen. The upstairs you'll find the four bedrooms including a primary suite with private bathroom. The home also offers central air, an attached garage and a partially finished lower level that can be converted to either a home office, gym or playroom. This property is conveniently located near Monroe's award winning schools, parks, shopping, restaurants and commuter routes. This home is located in a great neighborhood but also has the convenience for your everday life. Don't miss this opportunity to make this house your home! *Rarely loses power during storms*

37 Country Ridge Dr, Monroe

$610,000

3 Beds ⋅ 2 Baths ⋅ 24186406 MLS

1.5 story house. 1939 Cape with 1,649 s.f. of living area. 2.14 AC lot. Wooded. Large level backyard. County: Fairfield Neighborhood: Stepney Wood frame construction Foundation: Stone Asphalt shingle roof. Replaced about 2017. Oak floors Heat fuel: Oil. New burner about 2017 Heat type: Steam radiators Hot Water: Supplied by furnace to Storage Tank Electrical Service: 200A Insulated windows Kitchen: All new 2017 Central A/C: No. Window units Bedrooms: 3 Living Room with fireplace & stove Dining Room Bathrooms: All new 2017. 2 full-(1) up (1) down Basement: 1/2 basement Washer/Dryer: Yes. Entire interior painted March 2026 Rear: Terrace with roof Garage: Heated (2) car, detached, w/full attic above w/separate entrance Storage shed next to garage Driveway: Asphalt (repaved about 2017) Water: Private well. New well being dug June 2026 Septic: Private. New tank installed June 2026. Flow test performed April 2026-passed. Sewer line video inspection April 2026-passed R.E. Taxes: $8,484 As of July 2025 Book & Page: 1906 / 0111 Map-Lot: 046-037-00 Zoned RF2 Property abuts forest lands Price: $620,000. Appraised in June/2026 for $591K before improvements. * All information herein has been obtained from Town Assessor records and other sources. Complete accuracy of all of the information in this Listing is not guaranteed. * Property sold as-is.

113 Pepper St, Monroe

$474,900

3 Beds ⋅ 2 Baths ⋅ 24185884 MLS

A rare opportunity to own a ranch-style home that combines comfortable one-level living with versatile finished lower-level space. This 3-bedroom, 1.5-bath home features a bright and inviting living room with a cozy pellet stove that flows seamlessly into the dining area, creating an ideal setting for both everyday living and entertaining. The main level is completed by three bedrooms, a full bathroom, and a convenient half bathroom. The kitchen offers convenient access to the attached 2-car garage. The lower level provides an additional finished room that can serve as an extra bedroom or many other possibilities and a finished walk out area that adds valuable living space. The large patio sits in an open space with the backyard including a large wooden shed that provides ample storage for tools, lawn equipment, and outdoor gear. Don't miss this opportunity and schedule your showing today!

293 Guinea Rd, Monroe

$699,900

4 Beds ⋅ 3 Baths ⋅ 24182920 MLS

Welcome home to 79 Old Colony Road! This charming property is located in the highly desirable Great Oak Farm community of Monroe. This home offers an unbeatable lifestyle with exceptional convenience, situated within easy walking distance to the scenic Rails-to-Trails hiking and biking paths, beautiful Great Hollow Lake, and the endless recreational activities at Wolfe Park. The main level features a comfortable open layout perfect for daily living and entertaining. A recently updated roof, a newer central air conditioning system, and a newer hot water heater provide excellent mechanical integrity and long-term peace of mind. Bring your personal design ideas to customize and update the interior spaces exactly to your taste, allowing you to build effortless equity over time. Outside, situated on a private cul-de-sac & private backyard the neighborhood shines with its welcoming atmosphere and picturesque surroundings. Neighborhood parties and events galore you can participate as much or as little as you'd like! Residents enjoy access to Monroe's award-winning school system and a prime location that balances peaceful suburban living with quick access to local shopping, dining, and major commuting routes. Do not miss this fantastic opportunity to move right into a sought-after neighborhood and make this home your own.

79 Old Colony Road Unit 79, Monroe

$679,900

3 Beds ⋅ 3 Baths ⋅ 24185446 MLS

Nestled on a peaceful cul-de-sac in one of Monroe's desirable neighborhoods, this beautifully maintained 3 bedroom, 2.5 bath Colonial offers the perfect combination of space, comfort, and modern updates. Sunlight pours through the home's abundant windows, filling every room with natural light and creating a bright, welcoming atmosphere throughout. The thoughtful floor plan features spacious living and entertaining areas, including a warm and inviting family room, elegant formal living and dining rooms, and comfortable everyday living spaces designed for today's lifestyle. Recent improvements make this home truly move-in ready. Major upgrades include a brand new dual-zone central air system with two condensers, two air handlers, and Ecobee smart thermostats, new flooring throughout the entire second floor and family room, refinished hardwood floors in the living and dining rooms, complete interior painting, a new dishwasher, and a new electric heating system in the basement. The living room is pre-wired for a music system with speakers that will remain for the new owners. Outside, enjoy the privacy and tranquility of the professionally refreshed property. The driveway has been completely redone, the deck has been freshly stained and painted, and the yard has been expanded through brush clearing and reseeding to create additional usable outdoor space. Fresh landscaping, new shrubs, mulch, and meticulous maintenance add to the home's impressive curb appeal. See it today!

21 Harmony Ln, Monroe

$329,000

1 Beds ⋅ 2 Baths ⋅ 24184761 MLS ⋅ The Hills Of Monroe BLDG.

Welcome to The Hills of Monroe! This spacious and versatile one-level ranch-style condo offers the ease of low-maintenance living in one of Monroe's most desirable condominium communities. Featuring 1 bedroom plus a potential second bedroom, home office, or den, and 2 full bathrooms, this home provides flexibility to fit your lifestyle. The inviting living room is the heart of the home, complete with a cozy fireplace and plenty of space for relaxing or entertaining. The adjoining dining room flows seamlessly into the eat-in kitchen, creating a comfortable and functional layout. The generous primary bedroom features a large walk-in closet and easy access to a full bath, while the additional room is ideal for guests, a home office, or a second bedroom. Enjoy the convenience of in-unit laundry, a one-car garage, and additional basement storage for all your seasonal and household needs. Step outside to your private covered balcony overlooking a peaceful wooded setting, offering the perfect spot to enjoy your morning coffee or unwind at the end of the day. Residents of The Hills of Monroe enjoy beautifully maintained grounds, a clubhouse, pool, tennis/pickleball courts, and a convenient location close to shopping, dining, and major commuting routes. This rare one-level living opportunity combines comfort, privacy, and convenience in a sought-after community. Perfect for downsizers, first-time buyers, or anyone seeking maintenance-free living in a tranquil Monroe setting.

211 Windgate Cir Unit B, Monroe

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