Stepney Real Estate

Welcome to Stepney, a charming neighborhood nestled in the heart of Monroe, Connecticut. Known for its picturesque landscapes and tight-knit community, Stepney offers a unique blend of suburban tranquility and easy access to urban amenities. This delightful enclave is characterized by its tree-lined streets, historic homes, and a welcoming atmosphere that makes it a perfect place for families, young professionals, and retirees alike.

Stepney is steeped in history, with many homes showcasing beautiful architectural styles that reflect the area’s rich heritage. Residents enjoy the peaceful surroundings, with ample green spaces and parks, perfect for weekend picnics or leisurely strolls. The nearby Great Hollow Lake offers opportunities for fishing and kayaking, while the surrounding nature trails invite outdoor enthusiasts to explore the stunning Connecticut scenery.

Education is a priority in Stepney, with highly-rated schools that foster a nurturing environment for children. Families can take advantage of Monroe’s community programs, sports leagues, and cultural events that bring neighbors together and enrich the local lifestyle.

Conveniently located, Stepney provides easy access to major highways, making commutes to nearby cities like Bridgeport and New Haven a breeze. Residents also enjoy a variety of shopping, dining, and entertainment options just a short drive away, ensuring that everything you need is within reach.

In Stepney, you’ll find not just a place to live, but a community to call home. Experience the warmth and charm of this delightful neighborhood, where every day feels like a breath of fresh air. Welcome to Stepney, where your dream home awaits!

Newest Listings in Stepney

$292,609

1 Beds ⋅ 1 Baths ⋅ 24198986 MLS ⋅ The Hills Of Monroe BLDG.

"This Condo's Got It All (Yes, Even a Jacuzzi Shower) - Come See!" Move-in ready and full of charm - this first-floor ranch-style condo is the kind of place that makes you want to kick off your shoes and stay awhile. One-level living means no stairs, no hassle, just easy, breezy comfort from day one. Freshly painted from top to bottom, the whole place feels bright, clean, and ready for you to make it your own. The crisp white kitchen is a total charmer, with stainless steel appliances and just the right amount of space to whip up breakfast or pour a glass of wine while dinner's on the stove. Cozy up by the fireplace under a gorgeous new chandelier, with peaceful nature views right outside your window setting the mood for quiet nights in. Grab your coffee (or your favorite cozy blanket) and head out to your own private deck - the perfect little escape as summer eases into fall. And that bathroom? Pure spa vibes. Think brand-new walk-in Jacuzzi shower, sleek black fixtures, a fresh vanity, and new flooring - basically a permanent staycation. Your own private garage and extra storage make everyday life easier, and the resort-style perks don't stop there - think pool days, pickleball matches, and tennis court rallies right outside your door. Furry friends welcome too, per HOA rules! Freshly painted, move-in ready, and bursting with cozy charm - this one's ready when you are. Come see it for yourself!

302 Firmount Dr Unit A, Monroe

$419,000

1 Beds ⋅ 2 Baths ⋅ 24187929 MLS ⋅ Northbrook Of Monroe BLDG.

This impeccably stunning townhouse offers a combination of modern, convenience and exceptional comfort. Experience the ease of move-in ready living in this beautiful home, situated on the highly desirable and peaceful park-like complex of Northbrook, which meets super tranquility. The house is freshly painted w/new dishwasher, C/A, 4yr old furnace and hot water heater. This three-story residence is thoughtfully designed to deliver spacious living areas, everyday functionality, timeless marvelous views. The main floor features a beautifully designed open-concept layout, highlighted by an eat in kitchen with granite countertops and abundant cabinetry. The adjacent dining area flows seamlessly into a generously sized living room, enhanced by the sliders opening to a spacious wood deck and level backyard. The upper floor features a spacious primary bedroom, complete with double walk-in closets plus a large Jack and Jill bathroom with double vanities, a tub with shower. An additional generous size room completed the floor. The ground level offers a spacious flexible space with carpet floor which is ideal for a home office, playroom or a personal home gym plus an attached one-car garage. Residence in Northbrook enjoy exceptional amenities: club house, 2 in-ground pools, tennis and pickleball court, scenic trails, ponds with water fountains, a meticulous gazebo and charming little bridges. Minutes away from major highways, shopping, restaurants, cafes and all the vibrant activities.

23 Eagle Rock Cir Unit 23, Monroe

$585,000

4 Beds ⋅ 3 Baths ⋅ 24196379 MLS

Don't let the exterior fool you, this home offers much more space than meets the eye! Welcome to this versatile 4-bedroom, 3-bath single-family home with over 3,100 sq. ft. of living space on 1.33 private acres. Featuring 2 kitchens and 2 spacious living rooms, the flexible layout is ideal for multigenerational living, a potential private in-law suite, or the potential for rental income. Recent updates include beautifully renovated kitchens and bathrooms with modern cabinetry and stainless steel appliances, a new roof (2025), and AireForce heat pump systems (2021 & 2025). Move right in and enjoy the comfort, space, and flexibility this home has to offer. Outside, you'll find an expansive lot with abundant parking for multiple vehicles, RVs, boats, trailers, or work equipment. The property also backs up to the Pequonnock Valley Trail, providing direct access to miles of scenic hiking and biking. As a legal non-conforming single-family residence located in Monroe's I-2 Industrial Zone, this property offers a rare combination of home, lifestyle, and opportunity! Whether you're dreaming of a home-based business, need space for commercial vehicles or equipment, or simply want the flexibility that few properties can offer, this home delivers. Opportunities like this are hard to find, don't miss your chance to own a truly one-of-a-kind property with endless possibilities!

556 Pepper St, Monroe

$460,000

2 Beds ⋅ 3 Baths ⋅ 24195198 MLS ⋅ Northbrook Of Monroe BLDG.

Welcome to Northbrook, one of Monroe's most desirable condominium communities. This exceptionally well-maintained, move-in ready townhouse offers a spacious open floor plan with vaulted ceilings, beautiful hardwood floors, and an updated kitchen. The inviting living room features a cozy fireplace and nearly floor-to-ceiling windows that showcase peaceful views of the pond and stream beyond. The adjacent screened porch provides another comfortable space to relax while enjoying the same scenic setting. The main-level primary bedroom suite offers convenience and privacy with a full bath, while the upper level features a second bedroom suite with its own full bathroom, making it ideal for guests or additional living space. The partially finished lower level provides flexible space for recreation, a home office, fitness area, or hobbies, along with a spacious storage room, utility room, and an attached one-car garage. Northbrook offers a park-like setting with beautifully maintained grounds, walking paths, gazebos, two in-ground swimming pools, tennis courts, and a clubhouse. Conveniently located near shopping, restaurants, parks, and major commuting routes, this home also benefits from Monroe's highly regarded public school system. A wonderful opportunity to enjoy low-maintenance living in a scenic community.

12 Wrabel Cir Unit 12, Monroe

$529,000

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. Owner is deeded member of the lake 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.

87 Jockey Hollow Rd, 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

$759,000

4 Beds ⋅ 4 Baths ⋅ 24114367 MLS

** REDUCED 8/17**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.

137 Guinea Rd, Monroe

$619,900

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

$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

$650,000

4 Beds ⋅ 2 Baths ⋅ 24183917 MLS

Not your average split-level! This beautifully renovated contemporary home offers 4 bedrooms, 2 full baths, and a flexible layout designed for today's lifestyle, all set on a quiet cul de sac in Monroe's desirable Stepney neighborhood. Step inside to a bright, open concept interior filled with natural light and warm hardwood floors throughout. The updated kitchen flows seamlessly into the spacious living area, creating an inviting setting for everyday living and entertaining. Sliding glass doors open to an expansive deck overlooking the beautifully landscaped yard, extending the living space outdoors. Upstairs, you'll find three generously sized bedrooms and a beautifully renovated spa-inspired bath featuring a tiled walk-in shower and soaking tub. The primary bedroom offers a truly distinctive feature, a walk down closet accessed by a spiral staircase, providing exceptional storage and a unique architectural detail rarely found in homes of this style. The lower level adds even more versatility with a comfortable family room featuring a wood-burning stove, a fourth bedroom, and a full bath. Whether used for guests, a home office, gym, media room, or additional living space, this level easily adapts to your needs. Outside, enjoy multiple spaces for relaxing and entertaining, including a spacious deck and a beautiful stone patio with a built-in fire pit.

110 Bart Rd, Monroe

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