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$740,000
4 Beds 3 Baths 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

$739,900
3 Beds 4 Baths 24178122 MLS Castlewood BLDG.
**REDUCED** Beautifully maintained Colonial in the desirable Castlewood complex offering 3 bedrooms with potential for a 4th bedroom. This spacious home features formal living and dining rooms, along with a gracious oversized family room with fireplace just off the kitchen, creating the perfect flow for everyday living and entertaining. Sliders lead to an expansive deck overlooking the large private backyard and peaceful scenic views. The updated kitchen boasts newer cabinetry and appliances, while the freshly painted interior and gleaming hardwood floors create a bright, inviting atmosphere enhanced by abundant natural light throughout. The impressive primary suite offers two walk-in closets and a beautifully appointed spacious bath. The second floor also includes a large family room or optional 4th bedroom, two additional bedrooms, full bath, convenient laundry room, and pull-down access to a very large attic for additional storage. The fully finished walk out basement provides even more living space with an additional room, half bath, and utility room. Completing the home is a 2-car garage and an exceptional location at the end of a quiet cul-de-sac with gorgeous views and a truly serene setting.

30 Castlewood Dr Unit 30, Monroe

$699,900
3 Beds 3 Baths 24205890 MLS
Set on a quiet cul-de-sac in Monroe's Great Oak Farm community, 5 Pequot Ct offers the space of a traditional Colonial with even more room to spread out in the finished lower level. The two-story foyer makes a welcoming first impression and opens to a comfortable main level designed for everyday living. The eat-in kitchen connects easily to the attached two-car garage, while the nearby dining area opens directly to the deck and fully fenced backyard. A spacious living room provides another place to gather and unwind. Upstairs are three bedrooms, including a generous primary suite with a vaulted ceiling and two closets, one of which is a walk-in. The private primary bath includes double sinks, a soaking tub and a separate walk-in shower. The huge finished lower level adds valuable space for a family room, home office, gym, playroom or any combination that works for you. Additional highlights include a generator, new driveway and new central air condenser installed in 2025. All of this is close to Wolfe Park, the Pequonnock River Trail, Monroe schools, shopping and convenient commuter routes.

5 Pequot Ct Unit 5, Monroe

$699,900
4 Beds 3 Baths 24185763 MLS
Welcome to Monroe, Connecticut, as you ascend the paved, picturesque treed and private paved driveway, you will observe stone walls and additional parking. Upon reaching the front of the house via the paver walkway, you will notice the recently updated front porch, ideal for morning coffee and relaxation. As you enter the home, you will find the formal dining room to your left and the Den/Office to your right. As you traverse the hallway, you will discover the sliders leading to the rear patio and the spacious island in the newly renovated kitchen. The kitchen underwent a comprehensive update and remodel in 2021, incorporating ample storage and counter space, making it a true chef's kitchen. The great room, situated adjacent to the kitchen and dining room, boasts high vaulted ceilings adorned with beams and a corner fireplace with a propane insert, complemented by abundant natural light, creating an inviting atmosphere for entertaining. The upper level comprises three bedrooms, a hall-full bathroom, and the Masterbedroom suite, which features a walk-in closet and an updated bathroom. The lower level encompasses over 1,000 square feet, offering a family room with numerous storage closets, and a utility room. The patio and fire pit adjacent to the kitchen provide an excellent setting for entertaining and family gatherings. If you are seeking one of the finest school systems in the state, complemented by a plethora of outdoor activities and youth sports this home is for you.

242 Turkey Roost Rd, Monroe

$699,000
5 Beds 2 Baths 24190335 MLS
Welcome to this spacious 3,150+-square-foot raised ranch nestled in one of the most desirable neighborhoods in Monroe. This well-maintained home offers the perfect blend of comfort, functionality, versatility and a sun room that you will fall in love with. The main living area boasts generous room sizes, abundant natural light, and an inviting floor plan designed for both everyday living and entertaining. The expansive kitchen opens to comfortable living and dining spaces, with a bonus 4 season sun room. The generously sized primary bedroom offers a jack and Jill bath, ample closet space and a beautiful view of the grounds. The remaining main level bedrooms all boast hardwood floors, some being preserved with carpets, and large closets. The legal in-law suite offers privacy and independence with its own living space, and entrance making it a rare and valuable feature. Whether you're seeking a multigenerational living arrangement or additional income potential, this flexible setup adds tremendous value. Situated on a beautifully maintained property in a highly sought-after neighborhood, this home enjoys a peaceful setting while remaining conveniently close to schools, shopping, dining, parks, and major commuting routes. This is a rare opportunity to own a spacious home with a legal in-law apartment in an exceptional location. Updates include: roof (10 years), Furnace (7 years), in law carpet (4 months) and many more.

69 Forest Rd, Monroe

$694,000
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

$689,900
3 Beds 3 Baths 24200594 MLS
Custom-built by its current owner, a professional builder, and meticulously maintained since 1988, this exceptional ranch reflects a level of craftsmanship and structural integrity rarely found today. Substantial construction, thoughtful proportions, and enduring materials speak to a home designed with longevity in mind. Framed by beautiful stone walls and impeccably maintained landscaping, the property is bordered by two town trails, creating a remarkable sense of privacy and tranquility. Inside, the open floor plan features vaulted ceilings, refinished hardwood floors, new windows, and a dramatic floor-to-ceiling stone fireplace that serves as the centerpiece of the living space. Abundant natural light fills the home, while a tiled front room offers a peaceful escape for reading, or relaxing. Three generously sized bedrooms offer ample closet space, including a primary bedroom w/ double sinks and a tiled stall shower. A sprawling new deck wraps along the back and side of the home, overlooking the spectacular property that provide privacy, and color throughout the seasons. The heated, walk-out lower level is already plumbed for a kitchen and offers excellent potential for an in-law suite or expanded living space. Built with intention and maintained with exceptional care, this distinctive residence offers timeless craftsmanship, flexible living, and an extraordinarily private setting.The home feels tucked away yet close to Monroe parks, schools and Route 25 conveniences.

65 Cottage St, Monroe

$675,000
4 Beds 3 Baths 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

$669,000
5 Beds 3 Baths 24196662 MLS
Some renovations are cosmetic. This one is the real deal. Welcome to 24 Old Fawn Hill Road, a completely transformed 5-bedroom, 3-bathroom Colonial set on 2.3 private acres in one of Monroe's most desirable neighborhoods. Thoughtfully renovated throughout, kitchen, baths, flooring, and more, the bones of this home are solid and the updates are all already done, leaving the next owner a fantastic canvas to make their own. The kitchen is a standout, featuring white shaker cabinets, subway tile backsplash, a large center island, and stainless steel appliances, open, bright, and built for the way people actually live. The main level also offers a full bath and bedroom. A fireplace anchors the living area, and natural light pours in throughout. Upstairs, four generously sized bedrooms include a primary suite with walk-in closet and a spa-like bath featuring a tiled walk-in shower, and double vanity. A conveniently located second floor laundry rounds out the upper level. Set on 2.3 acres with lush, private surroundings, this is a fantastic opportunity to own a renovated Colonial in Monroe at a great value. Come see it for yourself.

24 Old Fawn Hill Rd, Monroe

$649,900
3 Beds 2 Baths 24187944 MLS
Welcome to your own private retreat in the heart of Monroe! Set on a picturesque 1.4-acre lot, this 2,139-square-foot home offers the perfect combination of comfort, charm, and exceptional outdoor living. Featuring three bedrooms, two on the main level, one and a half baths, gleaming hardwood floors, and a spacious family room, there's plenty of room for everyday living and entertaining. Relax in the beautiful screened-in porch with its stunning flagstone floor. Step out onto the rear trex deck overlooking the private backyard. Spend summer days enjoying the in-ground Gunite, pool, all surrounded by a peaceful, private setting. The three-car garage with a loft/studio above provides great space for vehicles, storage, hobbies, or a workshop. While the home will benefit from some updating, it has been well cared for and offers an exceptional opportunity to add your personal touches and build instant equity. Situated on 1.4 acres in one of Monroe's most desirable locations, this property combines privacy with convenience to award-winning schools, shopping, parks, and commuter routes. Move in in time for the school year! Being sold as is! It has a whole house generator and 2 gas fireplaces. Don't miss the chance to make this wonderful property your own! Builders take note!

692 Elm St, Monroe

$649,900
3 Beds 3 Baths 24179281 MLS
Welcome Home to 106 Greenwood Lane! This home boasts an extra 0utdoor heated with electrical woodworking building which can be used for a multitude of uses & has extra parking spaces... This spacious 3 BR, 2 Full Bath 1 partial single-family home is beautifully situated on a gorgeous 1.08-acre lot in Monroe! Relax at home in the light & bright sunroom or on the expansive back deck with cabanas and an above ground pool. Enjoy your hobbies in the heated out-building space currently used as a workshop or turn it into a pool house or whatever suits your needs. Offering 2,379 sq. ft. of versatile living space, this 1971 classic features a large light-filled living room with a feature fireplace. Great layout with generous bedroom sizes, a 2 car attached garage, and plenty of storage space. Extra outdoor storage is available in the two sheds. The 806 sq. ft finished lower level boasts a playroom with a bar & a second fire place, office and laundry room/ 1/2 bath. Enjoy the peace and quiet of a sprawling, tree-lined lot on a cul-de-sac while remaining just moments from local shopping, dining, and award-winning schools. A fantastic value with endless potential-move right in or bring your custom design updates to make it your own!

106 Greenwood Ln, Monroe

$629,900
3 Beds 2 Baths 24199707 MLS
There's much more to this charming & distinctive home than first meets the eye! Originally built in 1927 & thoughtfully expanded in 2007, it blends timeless character, modern updates & an unexpectedly spacious floor plan. Set on .86 level acres framed by mature trees & perennial gardens, the home feels warm & inviting from the moment you arrive. Hardwood floors flow throughout the light-filled main level. The recently updated kitchen features white cabinetry w/crown molding, quartz counters, stainless appliances, gas range, new refrigerator & breakfast bar, opening to both the living & dining rooms for an easy, everyday living & entertaining. French doors from the dining room lead to deck & side yard. A private office, full bath & mudroom/laundry complete this level. Upstairs are 3 generously sized bedrooms, including a spacious primary w/nook & double closets, plus an updated full bath. The partially finished walk-out lower level offers flexible living space & storage. Outside, enjoy an expansive level lawn, perennial gardens, large paver patio & plenty of room to play, garden, entertain or simply relax. Oversized 2 car garage w/rear double-door access adds exceptional functionality. Central air, propane heat, newer main-level furnace, gutters & Azek decking on all 3 porches. Convenient to award winning schools, parks, trails, shopping, dining & commuter routes. Thoughtfully updated, beautifully maintained & filled with character-you'll want to experience in person!

595 Wheeler 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

$589,900
3 Beds 3 Baths 24203686 MLS
Welcome to this well-maintained home, ideally situated near the end of a peaceful cul-de-sac in a highly desirable neighborhood. Enjoy exceptional privacy while remaining conveniently close to major commuting routes, shopping, and local amenities. Inside, the oversized living, dining, and kitchen areas provide plenty of space for everyday living and entertaining. Generously sized bedrooms offer comfort and flexibility, while the inviting family room features a cozy fireplace, perfect for relaxing at the end of the day. Additional highlights include a two-car garage with ample parking and storage, plus city water availability. Offering space, privacy, and a wonderful neighborhood setting, this is a rare opportunity you will not want to miss. Schedule your private showing today!

59 Countryside Dr, Monroe

$589,900
4 Beds 3 Baths 24194477 MLS
Welcome to this wonderful 4 bedroom, 2.5 bath split level home nestled in one of Monroe's most desirable neighborhoods. Offering the perfect blend of comfort and functionality, this home features gleaming hardwood flooring throughout and an inviting layout designed for everyday living and entertaining. The heart of the home is the spectacular great room, highlighted by a soaring cathedral ceiling, stunning fireplace, and walls of windows that fill the space with an abundance of natural light. Sliding glass doors provide seamless access to the spacious deck, creating the perfect indoor-outdoor flow for gatherings or quiet evenings overlooking the level backyard. The well-designed floor plan offers generous living spaces, comfortable bedrooms, and plenty of room for today's lifestyle. Outside, the flat yard provides endless possibilities for recreation, gardening, or simply enjoying the outdoors. Conveniently located near Monroe's top-rated schools, parks, shopping, and commuter routes, this move-in ready home combines timeless charm with an exceptional setting. Don't miss the opportunity to make this bright, welcoming home your own.

19 Crestwood Rd, Monroe

$575,000
3 Beds 2 Baths 24186176 MLS
Buyer Failed to Secure Financing!! Tucked into one of Monroe's established, tree-lined neighborhoods, 3-bedroom, 1.5 bathrooms approximately 1,696 square feet of comfortable living space on a spacious lot. Built in 1967 and lovingly maintained, it blends timeless New England character with room to make it your own. Inside, you'll find a sun-filled living room, an eat-in kitchen, and comfortable spaces throughout. The bedrooms offer generous closet space, and both full baths retain classic charm. Step outside to a private yard - ideal for entertaining, gardening, or simply enjoying the outdoors. Beyond the home itself, the location is a standout. Monroe offers a top-rated public school system, abundant outdoor recreation at Wolfe Park, Webb Mountain, and miles of nearby trails, plus convenient access to Bridgeport, Danbury, and New Haven, with New York City within reach. Don't miss the opportunity to own in this sought-after community. Schedule your private showing today. Property is being sold AS IS

98 Osborn Ln, Monroe

$575,000
3 Beds 1 Baths 24151805 MLS
Bring your vision to this unique property nestled on almost 4 picturesque acres in desirable Monroe, CT. Set back from the road and surrounded by nature, this home offers a rare chance to create something truly special in a location that's increasingly hard to find. The existing house needs renovation but provides a solid footprint and endless potential whether you're looking to restore, expand, or reimagine entirely. The real star of the property is the land: rolling acreage, mature trees, and a serene private pond that creates a peaceful, storybook setting perfect for outdoor living, gardening, or simply enjoying the quiet beauty of the surroundings. With plenty of space for a dream home, workshop, or additional outdoor amenities, this property is ideal for contractors, investors, or buyers ready to customize a home to their exact taste. Enjoy the best of both worlds-privacy and nature, yet convenient access to Monroe's schools, town amenities, and commuter routes. Property selling as is and some items might be left behind after sale. Come book your appointment today!!!

360 Garder Rd, Monroe

$550,000
3 Beds 1 Baths 24204003 MLS
Easy one-level living awaits in this completely remodeled and freshly painted three-bedroom ranch in desirable Monroe. The updated kitchen features quartz countertops, a stylish backsplash, and premium smart stainless-steel appliances, flowing seamlessly into the dining area. The spacious primary bedroom offers a vaulted ceiling with recessed lighting, hardwood floors, two ample closets, and sliding glass doors leading to a private patio. Two additional generously sized bedrooms with hardwood floors are located on the opposite side of the home. The beautifully renovated full bath features a glass shower enclosure, modern vanity, and contemporary mirror. A bright and sunny sunroom provides flexible additional living or dining space and opens to a stone patio-perfect for entertaining or relaxing outdoors. Additional updates include a newer above-ground oil tank, crown molding, recessed lighting, and energy-efficient LED fixtures. An expansive driveway provides ample off-street parking and leads to an oversized detached two-car garage offering abundant storage and workspace. Schedule your private showing before it's gone!

178 Church 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

$425,000
4 Beds 3 Baths 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

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