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

$924,900

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24191881 MLS

Welcome to this custom-built Colonial located on three acres of land. This sought-after neighborhood offers plenty of space with 5 bedrooms and 3.5 bathrooms. The home features a first-floor full in-law suite, ideal for generating rental income or providing additional space for parents, nannies, or grown children, offering exceptional flexibility. The main house includes a spacious kitchen with granite counter tops, large center island, stainless steel appliances, and double ovens. The family room offers French doors with beautiful wood burning stone fireplace that was harvested from the yard when the home was built. Harwood floors throughout the main floor. The master bedroom offers a tray ceiling, large en-suite, and a walk-in closet. This home offers endless possibilities for the new owners to put their touch on it. Roof 2019, Cooling system main house 2016, heating & cooling for in-law 2019.

64 Grist Mill Rd, Monroe

$599,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24189609 MLS

Beautifully renovated from top to bottom, this inviting Cape offers the perfect combination of modern finishes and peaceful surroundings. Featuring four generously sized bedrooms and two updated full baths, the home is designed for both comfort and functionality. The stylish eat-in kitchen showcases a center island, new appliances, and an open layout that flows seamlessly into the sun-filled living room, highlighted by a contemporary electric fireplace. The finished lower level provides valuable additional living space, a dedicated laundry area, and convenient walk-out access to the backyard. Step outside to your own private retreat, where a picturesque pond and mature landscaping create a tranquil setting to relax or entertain. Extensive renovations include a new kitchen, bathrooms, windows, roof, siding, electrical system, driveway, and more, offering true move-in-ready convenience. Ideally situated just 10 minutes from I-84 and only minutes from shopping, dining, parks, and schools, this exceptional home delivers the perfect balance of everyday convenience and natural beauty. Simply unpack and start enjoying everything this stunning property has to offer.

602 Fan Hill Rd, Monroe

$1,295,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24189729 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. 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.

355 Spring Hill Rd, Monroe

$569,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24187093 MLS

HIGHEST AND BEST BY THURSDAY, 7/2, BY 12:00! Experience single-level comfort in this tastefully updated, meticulously cared-for 3BD/2BTH Ranch on a tranquil, level 2-acre lot with sparkling in-ground pool! Perfectly located in Monroe's heart, minutes from all conveniences, this move-in-ready home invites you to simply unpack and relax. Inside, enjoy gleaming H/W floors, fresh paint, crown molding, new stone entry steps, front porch/deck, and a new ductless C/A system. A spacious heated/cooled sunroom with vaulted ceiling and tile floor overlooks the heated I/G pool, patio, 2-story pool shed, and serene backyard-ideal for gatherings! The sunroom flows into a remodeled EIK with SS appliances, granite counters, tile backsplash, and soft-close drawers. A bright, generous LR sits just off the kitchen. Three roomy BDs with ceiling fans and a remodeled BTH complete the main level. The newly carpeted LL adds 612 sqft with a large FR, plus a versatile room for office/gym/guest space, and a stunning new full BTH with radiant tile heat. Ample storage in the unfin LL with workbench, pull-down insulated attic, and extra shed. A peaceful pond graces the rear of the property. Circular driveway offers abundant parking. Vinyl siding, city water, septic, generator wiring. Survey/architectural plans included - great expansion potential! Top-rated Monroe schools. Minutes to shopping, highways, dining, parks, and nearby golf. Don't wait!

17 Gray St, Monroe

$939,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24182661 MLS

Room to grow, space to gather, & a neighborhood made for lasting memories--Welcome to 49 Georges Ln. Where your next chapter can unfold w/ the perfect balance of space, community, & everyday comfort. Nestled within a charming neighborhood, this spacious 4 BR, 2.5 BA home offers the perfect blend of comfort, flexibility, & endless possibilities. The main level is thoughtfully designed for both everyday living & entertaining, featuring a large LR, DR, eat-in kitchen, family rm, & sun porch that invites relaxed mornings, casual gatherings, & year-round enjoyment. Whether hosting holidays, game nights, or summer get-togethers, this home was made to bring people together. Upstairs, the primary suite offers a private retreat w/ vaulted ceilings, beams, WIC, & full updated bathroom w/ skylight. 3 additional BRs & a full BA provide plenty of space for family, guests, home offices, or changing lifestyle needs. The LL includes a large Rec Rm featuring a built-in bar, gym, pantry, & cedar closet, creating endless possibilities for entertaining, fitness, or movie nights. Above the 2-car garage, a spacious Bonus Rm currently used as a game rm adds even more flexibility for today's lifestyles. Outside, the property truly shines. The yard offers space to play, entertain, & unwind, w/ a large side yard that has hosted countless football games, gatherings, & outdoor memories over the years. Quiet suburban living with easy access to Fairfield County parks, dining & shopping.

49 Georges Ln, Monroe

$1,199,900

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24179158 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

$765,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24177924 MLS

Price Improved! Discover one of Monroe's most versatile properties, offering a rare opportunity to own a spacious single-family home with a fully permitted accessory apartment-all under one roof and eligible for conventional single-family financing. The heart of the main home is a stunning open-concept living space featuring a show-stopping kitchen with a large center island, vaulted ceilings with exposed beams, skylights, and seamless access to the two-tier deck and heated pool-perfect for entertaining year-round. The fully permitted accessory apartment offers exceptional flexibility. Designed with stair-free, one-level living, it features a private entrance, separate mailing address, spacious bedroom suite, luxury bath with low-profile shower, granite kitchen with pantry, full-size appliances, guest half bath, and direct access to a private patio and backyard. Interior access to the main home allows the property to adapt to a wide variety of living arrangements and changing needs over time. Recent improvements include a whole-house Generac generator (2026), LeafGuard gutters (2025), electric pet fence (2026), upper deck flooring, stairs, and exterior paint (2026), pool heater (2025), and oil tank (2026). The heated pool includes a robotic cleaner and solar-powered skimmer. Major appliances in both kitchens convey. Set on a beautifully maintained property in one of Fairfield County's most desirable communities, this move-in ready home is a must see.

148 Osborn Ln, Monroe

$775,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24157651 MLS

If you're looking for a wonderful home with space for everyone, in an incredible area of town, search no further! 3 levels of expanded living offers beautiful details, lots of natural light and spacious rooms. Over 3,400 sq ft with 4 bedrooms and 3 full baths on 1.24 acres. The cook's kitchen is huge with plentiful counter space, 2 wall ovens, an oversized island with seating and room for a causal dining table. Enjoy beautiful formal Living and Dining Rooms, plus an inviting Family Room with vaulted ceiling and wood burning fireplace. Through a set of french doors is the quiet Sunroom - an added plus. On the upper level are 4 bedrooms with lots of storage space and all with hardwood flooring. The Primary Bedroom has a huge WIC and a renovated full bathroom. The walk-out lower level is perfect with the light and bright Rec Room, including a slider that opens to the backyard. There's also a private office if working from home is a necessity. Natural gas, Central AC and public water for the systems. Amazing backyard with plenty of space for everyone to enjoy, and so convenient to schools, shopping and major highways. This home has been lovingly maintained and improved over the years, and ready for the next owner to make it their own.

78 Benedict Rd, Monroe

$665,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24171474 MLS

Charming Colonial set on a private 1.2acre lot in the heart of Monroe. Step inside and immediately appreciate the spacious living room featuring vaulted ceilings, exposed wood beams, and gleaming hardwood floors. The kitchen offers newer stainless steel appliances and a peninsula with seating for two, seamlessly opening to the dining room, ideal for entertaining. Double doors off the kitchen lead to a large Trex deck overlooking the patio and private backyard. The main level also includes two additional generously sized rooms, perfect for use as an office, playroom or media room. Upstairs, you'll find three bedrooms with engineered wood flooring throughout and a full bathroom with convenient laundry. The spacious primary bedroom features board and batten wall trim, a walk-in closet, and an additional secondary closet. Outside, the spacious backyard with endless possibilities. Lush garden spaces create the perfect backdrop for outdoor entertaining-whether hosting gatherings on the patio, enjoying the shaded picnic area, relaxing by the custom brick fire pit, or on the deck sipping your morning coffee while listening to the birds. Additional highlights include ample parking in the expansive driveway and an oversized workshop with loft/attic space, ideal for tools, hobbies, and gardening equipment. Conveniently located close to Wolfe Park, Great Hollow Lake, shopping in Monroe Center, plus easy access to route 111 and 25

148 Cross Hill Rd, Monroe

$969,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24153850 MLS

Welcome to this stunning new construction modern Colonial offering approx. 2,800 sq ft of thoughtfully designed living space. Set on a private 2+ acre lot bordered by protected open space, this home delivers privacy, comfort, and contemporary style. The open floor plan is ideal for today's lifestyle and features hardwood floors throughout, central air, and abundant natural light. The main level includes a dedicated home office, perfect for remote work or flex use, along with generous living and dining areas ideal for entertaining. Upstairs, the spacious primary suite offers a spa-like bath and a large walk-in closet. Three additional bedrooms, well-appointed baths, and a convenient walk-up attic provide excellent storage and future expansion potential. The walkout basement adds flexibility for future finished space. Enjoy award-winning schools, outstanding recreational facilities, and easy access to shopping, dining, and major commuting routes. Built by a reputable local builder-quality craftsmanship and modern living at its best.

261 Moose Hill Rd, Monroe

$779,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24127389 MLS

This custom-built Colonial offers 4 bedrooms and 4 bathrooms, nestled on 3 serene, private acres with stunning pond views. The spacious layout features a primary bedroom with an en-suite bathroom and walk-in closet, plus a potential 5th bedroom on the main level, conveniently located steps from a full bathroom. The expansive family/great room is perfect for relaxation equipped with a beautiful wood burning fireplace, while the large eat-in kitchen provides access to a deck ideal for outdoor entertaining. Formal living and dining rooms showcase elegant hardwood floors. The walkout lower level offers additional living space, including another family room, a home office, a full bathroom, and direct access to the three-car garage. With meticulously maintained grounds, this home embodies pride of ownership and offers the perfect private retreat for peace and tranquility.

491 Hammertown Rd, Monroe

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