N/A Homes with Jockey Hollow Middle school

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

86 Purdy Hill Rd, Monroe
$619,900
3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24211163 MLS
Welcome to 86 Purdy Hill Road-a beautifully maintained home situated on a picturesque, level 1.03-acre corner lot. Offering 3 bedrooms and exceptional versatility, this property seamlessly blends classic comfort with modern updates. The main level features a bright, open-concept living space anchored by a renovated kitchen equipped with stainless steel appliances, granite countertops, and an oversized center island perfect for entertaining. Step through sliding glass doors directly onto your private rear deck-the perfect spot to relax while taking in views of the expansive, level backyard. Upstairs, the generous primary suite serves as a true retreat, complete with three closets and an en-suite full bath. Two additional guest bedrooms, a second full bath, and a dedicated home office complete this level. The lower level provides tremendous flexible living space with its own private entrance, featuring a cozy family room with a grand gas fireplace, a half bath, and a large laundry room. The converted 2-car garage currently functions as ideal bonus office/storage space but can easily be restored to a full 2 car garage to suit your needs. This home offers central A/C, propane heating, public water and septic. The HVAC system and roof are all just 10 years young. Great location minutes from Monroe's top shopping, dining, parks, and major commuter highways. Turn-key and ready for its next owner-welcome home!

86 Purdy Hill Rd, Monroe
3 Rockview Cir Unit 3, Monroe
$439,999
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24210007 MLS ⋅ Northbrook Of Monroe BLDG.
Discover move-in ready perfection in this beautifully-maintained Barclay model in the highly sought-after Northbrook community of Monroe. As a coveted end-unit, this home is bathed in natural light, offering a bright and airy atmosphere throughout the spacious main level. Start your day on the cozy screened-in porch-the perfect retreat for your morning coffee. Upstairs, the home features plush, brand-new carpeting (installed August) across the staircase and both generously sized bedrooms. Each bedroom includes a private full bathroom, and the convenient laundry room is located right between them. Need extra space? The fully finished lower level is ideal for a dedicated home office, gym, or recreation room. The oversized garage features a unique "bump-out" extension and heating, creating the ultimate workshop or hobby space. One of the few units with a front yard and very few steps to enter. This is a rare find with endless potential-schedule your showing today!

3 Rockview Cir Unit 3, Monroe
30 E Maiden Ln, Monroe
$659,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24213966 MLS
Welcome home to easy, single-level living in this beautifully renovated, 4 bedroom, 2 full bath ranch style home. An ideal option for a first time home-buyer or those looking to downsize. Step inside to freshly finished hardwood floors and a thoughtfully designed kitchen featuring white cabinetry, quartz countertops, stainless steel appliances and crown molding. The kitchen flows nicely into an inviting living room with wood burning fireplace. Three generously sized bedrooms share a spacious, updated full bathroom. Also on the same floor, the large primary suite offers a comfortable sense of privacy, feauturing a vaulted ceiling, walk-in closet, tastefully updated full bathroom with a stall shower and its own exterior entrance. First-floor laundry and an attached two-car garage add everyday convenience, while the full, dry basement offers potential for future finished space. Extensive improvements include new heating and air-conditioning systems, new windows, new plumbing, new electrical, new septic system, new well and new roof! Close to highways, restaurants, shopping, Farmer's Market and Whitney Farms Golf Course. Take advantage of all the town of Monroe has to offer, including award-winning schools, Great Hollow Lake and Wolfe Park, where you can enjoy, swimming, hiking/biking trails, playgrounds, picnic tables, athletic fields and more. Don't miss this opportunity to make this home your own and create lifelong memories in a wonderful community

30 E Maiden Ln, Monroe
148 Cross Hill Rd, Monroe
$599,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24211507 MLS
Room to grow, space to entertain, and exceptional flexibility-this Colonial in the heart of Monroe offers a 5-bedroom setup on 1.2 acres of level, partially fenced land. With five rooms currently used as bedrooms, the home provides options for guests, work, and hobbies, adding substantial appeal at this price point. Town tax records designate the home as three bedrooms. Inside, the spacious living room features soaring cathedral ceilings, exposed wood beams, and beautiful hardwood floors. The kitchen offers stainless steel appliances and a peninsula with seating, opening to the dining area for easy everyday living and entertaining. Double doors lead to a large Trex deck overlooking the private backyard. The versatile layout includes several rooms on the main level, with 3 bedrooms and a full bath upstairs. An oversized detached garage, privately tucked behind the home and just steps from the back door, adds another layer of possibility. Though listed as a one-car garage, its generous footprint offers space for motorcycles, storage, or a workshop. With its own electricity, it also presents potential for a studio or home office, subject to required approvals. Outside, the expansive backyard offers room for pets, gardening, entertaining, and recreation. Relax on the deck or patio, gather around the custom brick fire pit, and enjoy the space and privacy that make this property such a compelling opportunity.

148 Cross Hill Rd, Monroe
308 Shelton Rd, Monroe
$559,990
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24210997 MLS
Beautiful, spacious Ranch set on a landscaped acre with an in-ground pool, patio and deck! The large Living Room features a fireplace and flows into the formal Dining Room. Center-island Kitchen with quartz countertops and pantry opens to the deck. Cathedral-ceiling Family Room features a marble fireplace and wet bar and opens to the patio overlooking the pool. The Primary Bedroom offers a beautifully remodeled private Bath, plus two additional Bedrooms and a remodeled hall Bath. Hardwood floors, Thermopane windows, Nest thermostat and solar panels add comfort and efficiency. Major updates include a newer 3-zone boiler and oil tank, roof replaced in 2020 and water heater in 2022. The lower level offers a laundry room, playroom and workshop. An oversized 2-car garage, retaining wall, driveway and drainage improvements complete this well-maintained home. Move right in and enjoy spacious one-level living, an impressive list of updates and a fantastic backyard built for entertaining! Pool was last opened in 2025. Pool heater is not operational and is being sold as-is.

308 Shelton Rd, Monroe
131 Hillside Ln, Monroe
$660,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24210524 MLS
Multiple Offers - Please present high/best offers by Wednesday 10/7 at 12 noon. See agent only remarks for more info. Welcome to 131 Hillside Lane, a beautifully appointed 3-bedroom, 2.5-bath Colonial in Monroe's desirable Whitney Farms Golf Course community. Set on a .51-acre lot with approximately 1,906 square feet, this inviting home blends classic Colonial charm with tasteful updates and numerous improvements. The main level offers a comfortable flow for everyday living and entertaining, while three well-proportioned bedrooms upstairs include a spacious primary suite with private full bath. An additional full bath and convenient main-level half bath provide flexibility for family and guests. Bathrooms were tastefully updated in 2022 and 2025, and the kitchen features stainless steel appliances, including a newer refrigerator/freezer and microwave. Major improvements include Harvey windows, updated siding, a rebuilt chimney completed in 2026, and a refreshed deck with a new surface and select supports replaced in 2025. The roof is backed by a 50-year transferable warranty, offering added peace of mind. The home also features gas heat, a tankless gas water heater, and full-size laundry. Enjoy the peaceful residential setting of Whitney Farms, with the golf course just minutes away and convenient access to Monroe's schools, shopping, dining, parks, and everyday amenities. The spacious .51-acre property offers plenty of room to relax, garden, play, or entertain.

131 Hillside Ln, Monroe
195 Webb Cir, Monroe
$920,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24208554 MLS
Once in a blue moon does a home like this become available! Nestled in the Webb Mountain region of Monroe, this 7.5-acre property features a 4 BD, 2.5 BTH Cape-style home with all the comforts and updates for today's living, while preserving the peaceful, serene charm of yesteryear. Step back in time & enjoy bucolic open fields, a gardener's paradise with raspberry bushes & homegrown vegetables of every kind & plenty of land where pets can roam freely! A lovely custom cabana, fully fenced I/G pool & patio create the perfect setting for entertaining. With 3,074 SQFT plus a finished LL with a second FPL, this spacious home boasts numerous upgrades & improvements within the last 2 years. Features include spacious BDS, gleaming refinished H/W floors, C/A, elegant built-ins, remodeled BTH, recessed lighting, fresh interior paint, walkin closets, cedar closet, mudroom with pantry, and all new: boiler, oil tank, hot water heater, interior French drain system, gutters, updated electrical, flooring, pool pump/filter, washer/dryer & so much more (see attached list)! Work from home in the remodeled, heated/cooled home office above the garage while overlooking naturally beautiful conservation land. An addl 3rd garage, outbuildings/sheds, walkin attic & full basement offer even more storage. Hiking trails from the property, Webb Mtn Discovery Zone nearby, minutes to everything! From the moment you enter this lovingly maintained home with a true homestead feel, life just seems to simplify!

195 Webb Cir, Monroe
83 Pepper St, Monroe
$649,900
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24209460 MLS
Welcome to 83 Pepper Street, a charming Farmhouse/Cape-style home built in 1850 and set on 6.39 beautiful acres. Blending historic character with thoughtful updates, this 3-bedroom, 3-bath home offers warmth, flexibility, and plenty of space to enjoy the privacy of the property. Hardwood flooring and two active fireplaces with wood stoves create inviting spaces throughout the home. An in-law apartment provides additional living space, guest accommodations, or potential rental income.Recent improvements include new Pella windows installed in 2023, a new well pump, and an automatic generator for added peace of mind. Outside, an oversized mahogany deck is perfect for entertaining, complemented by a beautiful bluestone patio, raised garden beds, fenced dog-pen area, cedar garden shed, and mature landscaping and plantings throughout the property.The expansive grounds offer endless possibilities for gardening, recreation, entertaining, or simply enjoying the tranquility of your own private retreat. With approximately 6 acres, this property provides exceptional privacy and the potential opportunity for subdivision of the land. A rare combination of character, acreage, flexibility, and opportunity. Make your appointment today!

83 Pepper St, Monroe
59 Hannah Ln, Monroe
$700,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24208131 MLS
As soon drive into the circular driveway you notice the tranquil setting on a cul de sac. This 1985 custom ranch home has 3 bedrooms and 3.5 baths with almost 2500 sq ft with additional 700 sq ft finished in lower level with a full bath(great for multigenerational use). Great room has fireplace flanked with built-ins and soaring ceilings with skylights. Primary bedroom with2 walk in closets and a verylarge ensuite addition with valted ceilings making the bath the spa like feel overlooking gardens. Laundry room and an additional half bath. The huge deck is private and has a storage closet. The property backs up to openspace. Beautiful perennial gardens and babbling brook on side of property. property goes into the wooded area.

59 Hannah Ln, Monroe
361 Spring Hill Rd, Monroe
$1,295,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE UNDER CONTRACT 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-& -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 & 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, and custom details.

361 Spring Hill Rd, Monroe
7 Hannah Ln, Monroe
$1,149,900
5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24203959 MLS
This is the home you've been waiting for! Offering over 5,000 sq ft of living space on 2 acres, this stunning Colonial features an incredibly versatile layout with 2 primary suites, 2 additional bedrooms with a hall bath, plus a main-level bedroom with full bath-ideal for 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 wa

7 Hannah Ln, Monroe
132 Hammertown Rd, Monroe
$780,000
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
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