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$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
$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
$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
$669,000
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
$699,900
3 Beds ⋅ 3 Baths ⋅ 24182918 MLS
Welcome to this beautifully updated, turn-key Colonial nestled in Monroe's highly desirable Great Oak Farm neighborhood. Packed with high-value upgrades and freshly painted throughout, this pristine property offers the perfect blend of modern comfort and classic charm. The main level boasts a completely updated kitchen, a tastefully renovated half bath, and an inviting living space anchored by a cozy wood-burning fireplace. Unwind in the sun-drenched sunroom or head down to the expansive, finished walk-out basement, which features brand-new carpeting and generous extra storage space. Structural and mechanical integrity shine with a two-year-old roof, seven new Andersen windows, a new skylight, and a full-house generator for total peace of mind. Outside, the fully fenced-in backyard provides a private oasis for outdoor enjoyment and relaxation. Enjoy all the local features of Great Oak Farm like summer movie nights and holiday parties, walks to local Rails to Trails hiking and biking as well as everything the wonderful town of Monroe has to offer, including award winning schools, parks, local shopping, and convenient commuter routes. This move-in-ready gem is waiting for you!

85 Old Colony Road Unit 85, Monroe
$349,000
2 Beds ⋅ 1 Baths ⋅ 24182222 MLS
Set on 1.58 acres in a desirable Monroe location, this charming two-bedroom, one-bath home offers a unique opportunity to enjoy today while planning for tomorrow. Surrounded by newer, high-value homes, the property presents exceptional potential for expansion, making it an ideal choice for buyers looking to create additional living space and build long-term equity. Inside, the home features a beautifully updated kitchen with granite countertops, modern finishes, and a functional layout that maximizes every square foot. Natural light fills the living spaces, creating a warm and inviting atmosphere throughout. The expansive lot provides ample room for an addition, outdoor entertaining areas or future enhancements to suit your lifestyle. Whether you're a first-time buyer, builder, or someone looking for a property with room to grow, this is a rare opportunity to secure acreage, location, and future potential in one package.

277 Spring Hill Rd, Monroe
$719,000
3 Beds ⋅ 3 Baths ⋅ 24178264 MLS
Welcome to 20 Pequot Court! These original owners have beautifully maintained this home, nestled in the highly desirable Great Oak Farm community of Monroe. Situated on a peaceful cul-de-sac, this inviting residence offers 3 bedrooms, 2.5 baths, and a thoughtfully designed floor plan that combines comfort, functionality, and modern convenience. Step inside to a light-filled foyer that opens to spacious living areas ideal for both everyday living and entertaining. The main level features primary bedroom suite, comfortable gathering spaces, a warm and welcoming atmosphere, and seamless flow throughout the home. Upstairs, complemented by two additional bedrooms and well-appointed bath, and an office space for private living. The finished lower level offers valuable additional living space and is perfect for a media room, home gym, playroom, home office, or guest area. Recent improvements and meticulous care make this home truly move-in ready. Outside, enjoy the privacy of the cul-de-sac setting while being just minutes from local parks, shopping, dining, and major commuter routes. This property offers the perfect balance of convenience, community, and lifestyle. Whether you're entertaining guests or enjoying a quiet evening at home, 20 Pequot Court provides everything you need to enjoy comfortable living in one of Monroe's most beautiful neighborhoods. Welcome home!

20 Pequot Court Unit 20, Monroe
$574,900
3 Beds ⋅ 3 Baths ⋅ 24178863 MLS
Step into the beauty of an open concept living. Gorgeous new kitchen with quartz counters and an island effortlessly flows into the dining and living area. Two bedrooms with Jack & Jill bath, and another powder room with laundry hook up complete the first floor. Second floor offers astonishing master suite with his and hers walk-in closets. Rinse off all of your daily worries in expansive master bath with stand up shower, stand alone tub and double vanity. All of the systems are new, including propane gas, central air, septic and more. Catch a sunset on your new stone patio, surrounded by generous flat yard and peaceful nature views. Convenient location for commuting, close to schools, highways and numerous shopping options. This home really checks all of the boxes - come see for yourself!

57 Lovers Ln, Monroe
$949,000
4 Beds ⋅ 4 Baths ⋅ 24175102 MLS
Thoughtfully maintained and move-in ready, this 4-bedroom Colonial features newly refinished hardwood floors, fresh interior paint, and over 3,200 square feet of living space designed for both comfortable daily living and entertaining. The sun-filled interior includes an eat-in kitchen, formal dining room, private den, spacious family room with fireplace, and flexible upper-level bonus/media space. Outside, the property feels like a private retreat. Mature landscaping, expansive lawn space, and a swimming pool create an ideal setting for summer entertaining, quiet mornings, or evenings spent outdoors. Located just minutes from Wolfe Park, Great Hollow Lake, Monroe's Rail Trail system, shopping, dining, and commuter routes, the home offers rare access to both nature and convenience. Enjoy nearby hiking trails, pickleball, kayaking, biking, and some of Monroe's most loved outdoor recreation amenities-all while coming home to privacy and space. A rare opportunity to enjoy move-in ready living in one of Fairfield County's most nature-connected communities.

104 Cutlers Farm Rd, Monroe

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