N/A Homes with Jockey Hollow Middle school

Welcome to Monroe, Connecticut, where charming suburban living meets the comforts of a close-knit community. Nestled in Fairfield County, this picturesque town is known for its beautiful landscapes, excellent schools, and family-friendly atmosphere, making it an ideal place for both first-time homebuyers and those looking to settle down.

One of the standout features of Monroe is its commitment to education, particularly with the highly regarded Jockey Hollow Middle School located nearby. Families will appreciate the strong emphasis on academic excellence and extracurricular activities that prepare students for future success. The school’s dedicated staff and engaging programs foster a nurturing environment where children can thrive.

As you explore the homes in Monroe, you'll find a diverse range of architectural styles, from charming colonials to modern builds, all set against a backdrop of scenic parks and well-maintained neighborhoods. The community is rich with amenities, including local shops, dining options, and recreational facilities that cater to all ages. Whether you enjoy hiking the trails of the nearby parks or participating in community events, there’s always something happening in this vibrant town.

With its blend of natural beauty, top-notch education, and a strong sense of community, Monroe is more than just a place to live—it's a place to call home. Discover your perfect property today in this delightful corner of Connecticut, where your family can grow, learn, and create lasting memories.

Newest N/A Homes with Jockey Hollow Middle school

$1,295,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24206103 MLS

Once-in-a-lifetime opportunity to own an iconic modern farmhouse. A dramatic two-story foyer welcomes you, highlighted by a stunning glass modern staircase that sets the tone for the home's sleek yet timeless design. The double doors welcome you into a sun-drenched interior filled with natural light, recessed lighting, & 5-inch white oak hardwood flooring. The heart of the home is the custom kitchen featuring White Thasos quartz countertops, a 9-foot waterfall island, a cooktop, double ovens, a microwave drawer, & a large custom pantry. The living space is elevated by a honed marble fireplace surround, creating a sophisticated yet inviting focal point. Formal Dining room. Thoughtful details continue throughout, including a mudroom with custom cubbies. Second-floor laundry room with floating custom cabinetry. Large primary suite with his-and-hers closets. The primary bathroom features a porcelain tile shower, double sinks, a soaking tub, & a spa-like feel. A private ensuite bedroom offers a beautifully appointed full bath with porcelain tile and a tub/shower combination-perfect for guests or multigenerational living. 2 additional large bedrooms share a Jack-and-Jill bath with double sinks. Exterior features a blue stone walkway & patio. Hardee Plank Cement Board Siding. Buried 500-gallon propane tank. City Water. Truly a stunning home with high-end finishes, custom details, & modern farmhouse design throughout.

361 Spring Hill Rd, Monroe

$425,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204090 MLS

CREATIVE VISIONARIES, NATURE & HISTORY LOVERS, TAKE NOTE! This Colonial farmhouse, just a half mile north of the historic town center, is set on a surprisingly private, deep, and level pie wedge of land. With its 11 rooms, including two distinct 2nd floors, it's chock full of flexible living space. Large Eat in Kitchen flows into a delightful Sun Room which opens to the patio w/hot tub, overlooking the level, fenced backyard, anchored by an exquisite Spruce tree. Also off the kitchen is a full bathroom/laundry room, a hallway leading to huge pantry, & staircase up to a Studio/Office/Guest Room. The Living Room leads to a cozy Office and via French Doors, to a Den w/half bath. The Den leads to Bedroom 1, which is also accessible from the large front 'office' which was walled off by a past owner. Upstairs is a full Bathroom, and 3 more Bedrooms, two of which are contiguous. Basement is accessed via the outside. 2-car detached garage and a generous driveway offer lots of space for parking. This property has much to love, for those willing to do some work.

840 Monroe Tpke, Monroe

$1,199,900

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24203959 MLS

This is the house you have been waiting for! This stunning classic Colonial offers an incredible layout with 2 primary suites, 2 additional bedrooms with a hallway bath, plus a main-level bedroom with a full bath - perfect for large families or multi-generational living. Designed with both comfort & entertaining in mind, the home features 2 staircases, custom built ins, a spacious Great Room with surround sound theater speakers, a propane fireplace, & access to an oversized deck. A beautiful main-level office is ideal for working from home. The oversized family room offers a cozy pellet stove, beautiful wood beams, a half bath, & pantry closet. A large formal dining room with a wood-burning fireplace provides the perfect setting for gatherings. The gourmet chefs eat-in kitchen is truly impressive, featuring 2 paneled dishwashers, a Sub-Zero refrigerator, a Sub-Zero freezer, a six-burner cooktop, double ovens, & granite countertops. The finished lower level includes a home gym and game room, offering even more space for entertaining. 2nd level laundry room & additional laundry hook-up on main level. Exterior highlights include a heated in-ground pool, a pool house with electricity & audio speakers, a fenced side yard with invisible fence perfect for pet owners, a whole-house generator, a new driveway and 4-car garage. This location is perfect, with schools, shopping & highways minutes away. This home has been designed for every season & is just waiting for its new owners!

7 Hannah Ln, Monroe

$799,900

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24202895 MLS

Set behind classic stone walls on 2 acres in Monroe's Hammertown District, this beautifully sited Colonial offers 5 bedrooms and 3 full baths. Inside, nearly 3,600 square feet unfold over three finished levels, with re-sanded & freshly stained hardwood floors, traditional millwork & a beautiful floor Plan. Two wood-burning fireplaces set the tone - one anchoring the family room for cool fall & winter nights, the other warming the spacious walk-out lower-level family room. The eat-in kitchen serves up granite counters, a center island, breakfast bar, pantry and sliders to the expansive deck overlooking a private yard bordering conservation land - the natural hub for holiday hosting. A rare, town-approved main-floor in-law apartment is a home within the home: a private entrance opens to a beautiful eat-in kitchen (remodeled in 2021), a large bedroom w/2 closets, a full bath & an office/den w/access to a large deck - ideal for extended family or guests. Upstairs, the primary bedroom includes a full bath, hardwood floors & 3 closets. The upper floor is completed by 3 additional bedrooms & a full bath. Central air, thermopane windows, mudroom, 2-car under-house garage & full walk-out finished basement with abundant storage. Spend spring, summer & fall afternoons on your large expansive deck listening to nature (the hummingbirds are regulars) as your perennial gardens bloom. Minutes to Monroe's town center, parks, pool, library, & schools

132 Hammertown Rd, Monroe

$404,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24202883 MLS

Original owner ranch home with a nice private treed yard. Located right on the Monroe/Trumbull town line. A cozy living room has hardwood floors under the carpeting along with a fieldstone fireplace. Eat-in kitchen has a vinyl floor. Enclosed breezeway sunporch also has access to a one car garage with storage. All bedrooms have hardwood Floors. Many Recent 2025 updates include: A Total bathroom remodel with walk-in shower. New refrigerator, light fixture & ceiling fan in kitchen. New septic tank. New water tank. Electrical panel updated along with all outlets. Interior freshly painted. Brand new Epoxy garage floor in 2026. New Roof in 2014. (30 year roof). Laundry hook up in basement. Pretty garden & plantings. Home is nearby to Wolfe Park for outdoor recreation including pool, tennis, playground, hiking & biking trails. This home is an Estate. The property is to be sold in As-Is Condition. Some updates and TLC are needed. Commuter friendly & easily accessible to all major thruways -Merritt Parkway and I 95 highway connectors. All conveniences-shops & restaurants are just minutes from home.

257 Spring Hill Rd, Monroe

$400,000

1 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24203158 MLS ⋅ Northbrook Of Monroe BLDG.

Welcome to Northbrook Condominiums, where easy living, flexible space, and a peaceful wooded setting come together in the heart of Monroe. This beautifully maintained, move-in-ready home offers a thoughtful layout with plenty of room to live, work, and unwind. The main level features an inviting eat-in kitchen with stainless steel appliances. The living room is the true heart of the home, with a dramatic vaulted ceiling, two skylights with remote-control shades, a ceiling fan, and a brick gas fireplace that creates a warm and welcoming focal point. Sliding doors lead to the deck overlooking a private, wooded backyard-the perfect setting for morning coffee, outdoor dining, or relaxing at the end of the day. The primary bedroom offers a walk-in closet and private full bath with convenient linen storage. Just outside, a versatile loft adds valuable bonus space and can easily adapt as a home office, nursery, reading nook, or additional guest sleeping area. The finished lower level provides even more room to spread out, along with additional storage and direct access to the heated one-car garage. With a hot water heater replaced in 2018 and high-efficiency furnace in 2019, this home has been carefully maintained and is ready to enjoy from day one. Offering privacy, versatility, and the ease of condominium living, this Northbrook home is one you'll want to see.

6 Juniper Cir Unit 6, Monroe

$740,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24202605 MLS

Welcome to this beautifully updated four-bedroom Colonial, set well back from the road on 2.21 picturesque acres, offering a wonderful combination of privacy, space and modern updates. A welcoming front porch sets the tone before stepping inside, where a classic, comfortable layout has been enhanced by thoughtful improvements. The beautifully renovated kitchen serves as the heart of the home, featuring soft gray cabinetry, stone countertops, stainless steel appliances and a center island. The kitchen flows naturally into the formal dining room, while lots of new flooring and custom millwork add character throughout. The inviting family room is centered around the fireplace, and a convenient main-level laundry room adds everyday functionality. Upstairs, the spacious primary suite features a vaulted ceiling, private full bath and generous walk-in closet with a custom closet system, accompanied by three additional bedrooms. Outside, the setting truly shines. The home sits privately back from the road surrounded by beautiful grounds, mature landscaping and plenty of usable outdoor space. An expansive rear deck provides a great place to relax, entertain and take in the property, while the enclosed garden area adds another special feature to the 2.21-acre setting. Additional highlights include vinyl siding, public water, C/A, solar panels, EV charger, a walk-out lower level and 2-car garage. Beautifully updated, impeccably maintained and truly move-in ready-welcome home!

1344 Monroe Tpke, Monroe

$675,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24196510 MLS

Set on just over 2 acres, 341 Old Zoar Road offers a comfortable Colonial layout with generous living space, thoughtful updates and plenty of flexibility. With approximately 2,400 square feet, four bedrooms and two and a half baths, the home blends traditional spaces with an oversized family room that serves as a natural gathering point on the main level. Vaulted ceilings, hardwood floors and a fireplace give the room character, while direct access to the deck creates an easy connection to the outdoor space. The updated kitchen and bathrooms add meaningful improvements while still leaving room for a new owner to make the home their own. The first floor offers flexible space that can be used as a dining room, home office or additional living area depending on your needs. Upstairs, four generously sized bedrooms provide comfortable separation from the main living areas. The walkout basement adds another layer of potential, with the opportunity to create additional finished living space in the future. Outside, the just over 2 acre setting provides plenty of room and privacy. Additional features include a two car under garage, solar panels and a Tesla battery backup system. A well cared for Monroe home with updated living spaces, a flexible layout and room to grow into over time

341 Old Zoar Rd, Monroe

$985,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24202684 MLS

Welcome to this 1990 built Colonial home, tucked back from the road, allowing for ultimate privacy. Offering 3300+ square feet of living space. Set on a level lot of 5+ acres. Stunning yard with a custom built Trellis, large custom built patio (New in 2023), professional landscaping and plantings throughout, stately gardens, bocci court - fabulous for your outdoor entertaining. The main floor offers a Formal Living Room, Formal Dining Room/with additional sitting area, large Family Room with vaulted ceilings, wood burning fireplace, wet bar, built ins with convenient access to the adjacent Sun Room. Main floor Laundry Room. Updated Kitchen features Quartz counters, SS appliances and large center island. Note - TWO Dishwashers. Upper Level offers a spacious Spacious Primary Bedroom Suite offering a Full Bath, Banquette window seat, multiple closets including a spacious custom built Walk-In-Closet. The Primary Full Bath (new 2013) features: radiant heated marble floor, heated towel rack, double marble vanities, marble shower, with several shower heads. THREE well appointed bedrooms and Hall Full Bath. Large, unfinished basement. Two car attached garage. Gunite Salt water heated pool with Jacuzzi Tub. Pool Updates include: pool heater (2021), pump (2022), new plaster. Three Zones-Central air (2017)/Oil Heat. New Oil Tank (2023). Newer boiler (2017). New roof (2025). City water / Septic. Whole house generator (2021). Impeccably maintained and shows beautifully throughout!

490 Cutlers Farm Rd, Monroe

$1,125,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24199494 MLS

Located in the "Wedgewood Estates" subdivision, this spacious 4-bedroom, 3 full and 2 half-bath center hall colonial features a legal accessory apartment with a private lower-level entrance. A covered front porch welcomes you into the dramatic two-story foyer, flanked by formal living and dining rooms. The main level features hardwood floors throughout, with new neutral carpeting in the family room. The expansive country kitchen offers granite countertops, new stainless steel appliances, abundant cabinetry, and a casual dining area. Just off the kitchen, the family room features a wood-burning fireplace and sliders to the rear deck overlooking the in-ground pool. A home office area, powder room, and laundry closet complete the main level. Upstairs, the primary suite includes a private bath and walk-in closet, plus three additional bedrooms and a full hall bath. A third-floor bonus room offers flexible living space. The lower level provides direct access to the two-car garage and features a legal accessory apartment with private entrance, full kitchen, open living/dining/sleeping area, 1.5 baths, two walk-in closets, and separate laundry. Additional highlights include a new roof and skylights, an expansive deck, an in-ground pool, a large driveway (just sealed) with plenty of parking, and a corner lot in a beautiful subdivision. A great place to call home!

151 Meadows End Rd, Monroe

$629,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24197156 MLS

Welcome to 73 Gay Bower Road, a beautifully renovated home set on over an acre in a desirable Monroe neighborhood. Thoughtfully updated throughout, this property blends quality finishes, modern design, and generous living and entertaining space. Inside, stained oak hardwood floors are complemented by crown molding, upgraded trim, built-in closet systems, and ambient recessed lighting with indirect options. The open-concept kitchen features stainless steel appliances, a gas range, black quartz countertops, and an easy flow into the surrounding living areas. An expansive family/sunroom addition off the rear provides a standout space for entertaining and everyday living, while the finished lower level offers additional flexibility for a recreation room, office, gym, or guest space. Outside, enjoy a beautiful, flat and level lot of over one acre with a partially wooded rear for added privacy and plenty of room for play and outdoor entertaining. Complete with a one-car garage, recent renovations, and quality upgrades throughout, 73 Gay Bower Road offers a move-in-ready opportunity in a sought-after Monroe setting.

73 Gay Bower Rd, Monroe

$468,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24197171 MLS ⋅ Northbrook Of Monroe BLDG.

Welcome to 11 Sprucebrook Trail in the desirable Northbrook Condominium Complex. This beautifully maintained Barclay end-unit sits at the end of a quiet cul-de-sac, offering privacy, comfort, and low-maintenance living. The main level features gleaming hardwood floors, a spacious sun-lit kitchen with Stainless Steel appliances and Corian countertops, plus a bright three-season room with skylights and a ceiling fan. The private deck is perfect for relaxing or outdoor dining. Upstairs, two oversized bedrooms feature new LVT flooring, en-suite full baths, and ample closet space. The primary bedroom includes custom built-ins, while convenient second-floor laundry features a newer GE washer and dryer. The finished lower level offers flexible space for a family room, home office, or recreation area, with tile flooring, recessed lighting, and custom built-ins, plus an attached oversized one-car garage with a newer garage door opener. Enjoy easy access to the main pool and clubhouse, additional pool, tennis courts, gazebo, and scenic ponds. Conveniently located near shopping, restaurants, parks, and major commuter routes, this move-in ready home offers style, comfort, and convenience. Just unpack and move right in!

11 Sprucebrook Trail Unit 11, Monroe

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