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$319,900

Yesteryear and today all rolled into one! This older two-story home brings some charm, character and recent updates. (Furnace, oil tank 2023; hot water heater 2025; roof 2017) Second floor remodeled aprox. 12 yrs. ago, with 1/2 bath included! Full bath on first floor boasts striking stained glass window. House sold "as is" for informational purposes. Owner must find suitable housing. Another full bath located in walk-out unfinished basement ideal for possible in-law setup (or framed room first floor possible.) Framed room , with fireplace, (approx. 18x16) adjacent to kitchen ready for your imagination. Bring your plans and envision a bonus room (or in-law) on the main level! Some remodeling on first floor.

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24193191 MLS

Yesteryear and today all rolled into one! This older two-story home brings some charm, character and recent updates. (Furnace, oil tank 2023; hot water heater 2025; roof 2017) Second floor remodeled aprox. 12 yrs. ago, with 1/2 bath included! Full bath on first floor boasts striking stained glass window. House sold "as is" for informational purposes. Owner must find suitable housing. Another full bath located in walk-out unfinished basement ideal for possible in-law setup (or framed room first floor possible.) Framed room , with fireplace, (approx. 18x16) adjacent to kitchen ready for your imagination. Bring your plans and envision a bonus room (or in-law) on the main level! Some remodeling on first floor.

1 Second Ave, Seymour

$314,900

Move-in ready with more space than you would expect, this well-maintained home offers a flexible layout and convenient location. Inside, you'll find a large eat-in kitchen with access to the flat backyard and shed, giving you plenty of room for everyday living, entertaining, and extra storage. The main level features two well-sized bedrooms, a full bath, a spacious living room, and a formal dining room. A bright sunroom/breezeway at the front of the home adds even more usable space and is perfect for relaxing, a home office nook, or plant lovers. Upstairs offers an additional well-sized bedroom along with walk-in attic storage, providing extra flexibility and room to grow. The full basement adds even more value with additional storage space, a full bath, and a one-car garage bay. With public water, public sewer, and easy access to Route 8 and Route 67, this home offers a practical layout with the space and features to fit a variety of needs. HIGHEST AND BEST WEDNESDAY 7/22 12:00 PM

3 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24190592 MLS

Move-in ready with more space than you would expect, this well-maintained home offers a flexible layout and convenient location. Inside, you'll find a large eat-in kitchen with access to the flat backyard and shed, giving you plenty of room for everyday living, entertaining, and extra storage. The main level features two well-sized bedrooms, a full bath, a spacious living room, and a formal dining room. A bright sunroom/breezeway at the front of the home adds even more usable space and is perfect for relaxing, a home office nook, or plant lovers. Upstairs offers an additional well-sized bedroom along with walk-in attic storage, providing extra flexibility and room to grow. The full basement adds even more value with additional storage space, a full bath, and a one-car garage bay. With public water, public sewer, and easy access to Route 8 and Route 67, this home offers a practical layout with the space and features to fit a variety of needs. HIGHEST AND BEST WEDNESDAY 7/22 12:00 PM

172 Cedar St, Seymour

$650,000

Opportunity knocks! Been looking for a terrific house with an ideal in-law setup? This one checks all the boxes! Fabulous neighborhood, and huge, gorgeous 2.53 acre yard that extends far beyond the stone wall onto the woods for endless exploration and adventures! Plenty of space for everyone here, too. Choice of two home offices, one on the main level and another in the walk out lower level. Open concept living and dining area with double bay windows and gas fireplace in the living room. Walk in pantry in the eat in kitchen.Head on upstairs to your spacious primary bedroom with walk in closet and gorgeous remodeled full bath. Three more bedrooms up here share the full bath for a total of 4 bedrooms in the main house. Separate laundry room on 2nd floor keeps that chore simple! Head downstairs to the enormous walk out lower level where you will find a front to back family room with that second office. Sliders lead to your gorgeous yard complete with double patios and a wonderful above ground pool for loads of summer fun! Two story inlaw apartment with beautiful remodeled kitchen, also open floor plan with combination living room/dining area. Full bath with full size washer and dryer complete the main level. Head downstairs to your super sized bedroom with half bath and triple closets for plenty of storage. Walk out to your own patio. Two car attached garage plus huge 3 car detached garage for all your cars and toys! Solar on home and garage save you money on your electric bill!

5 Beds ⋅ 5 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24185373 MLS

Opportunity knocks! Been looking for a terrific house with an ideal in-law setup? This one checks all the boxes! Fabulous neighborhood, and huge, gorgeous 2.53 acre yard that extends far beyond the stone wall onto the woods for endless exploration and adventures! Plenty of space for everyone here, too. Choice of two home offices, one on the main level and another in the walk out lower level. Open concept living and dining area with double bay windows and gas fireplace in the living room. Walk in pantry in the eat in kitchen.Head on upstairs to your spacious primary bedroom with walk in closet and gorgeous remodeled full bath. Three more bedrooms up here share the full bath for a total of 4 bedrooms in the main house. Separate laundry room on 2nd floor keeps that chore simple! Head downstairs to the enormous walk out lower level where you will find a front to back family room with that second office. Sliders lead to your gorgeous yard complete with double patios and a wonderful above ground pool for loads of summer fun! Two story inlaw apartment with beautiful remodeled kitchen, also open floor plan with combination living room/dining area. Full bath with full size washer and dryer complete the main level. Head downstairs to your super sized bedroom with half bath and triple closets for plenty of storage. Walk out to your own patio. Two car attached garage plus huge 3 car detached garage for all your cars and toys! Solar on home and garage save you money on your electric bill!

29 Evergreen Ter, Seymour

$649,900

Bring the whole family-and the extended family too! This completely remodeled grand Colonial sits on sprawling, park-like grounds and offers the perfect blend of charm and modern new conveniences. The property features a detached three-car plus garage with storage room and work area, a large in-ground pool surrounded by a new paver patio, expansive lawn space for recreation, and a covered outdoor entertaining area with a cozy exterior fireplace. Renovated from top to bottom, the home boasts all new mechanicals, a new driveway, and new garage doors. Inside, spacious rooms abound, beginning with a stunning chef's kitchen featuring new cabinetry, quartz countertops, tiled backsplash, updated lighting, and new appliances. The classic dining room with a bay window flows seamlessly into the oversized living room highlighted by abundant windows and recessed lighting. A bright study overlooking the pool provides an ideal home office or reading retreat. Upstairs, you'll find three generously sized guest bedrooms along with an enormous primary suite complete with a fireplace, walk-in closet, and private full bath. All three full bathrooms have been beautifully remodeled. Gorgeous views from a wrap around second level porch accent the architecture. Please see Agent-to-Agent remarks prior to submitting an offer.

4 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24175013 MLS

Bring the whole family-and the extended family too! This completely remodeled grand Colonial sits on sprawling, park-like grounds and offers the perfect blend of charm and modern new conveniences. The property features a detached three-car plus garage with storage room and work area, a large in-ground pool surrounded by a new paver patio, expansive lawn space for recreation, and a covered outdoor entertaining area with a cozy exterior fireplace. Renovated from top to bottom, the home boasts all new mechanicals, a new driveway, and new garage doors. Inside, spacious rooms abound, beginning with a stunning chef's kitchen featuring new cabinetry, quartz countertops, tiled backsplash, updated lighting, and new appliances. The classic dining room with a bay window flows seamlessly into the oversized living room highlighted by abundant windows and recessed lighting. A bright study overlooking the pool provides an ideal home office or reading retreat. Upstairs, you'll find three generously sized guest bedrooms along with an enormous primary suite complete with a fireplace, walk-in closet, and private full bath. All three full bathrooms have been beautifully remodeled. Gorgeous views from a wrap around second level porch accent the architecture. Please see Agent-to-Agent remarks prior to submitting an offer.

40 Church St, Seymour

$330,000

Welcome home to this charming Cape Cod, with a fabulous front porch to rock away your cares. Also, where timeless character meets thoughtful updates. Renovated over the years while preserving its classic appeal, this warm and inviting home truly "feels like home" from the moment you arrive. Start your mornings or unwind in the evenings on the spacious front porch, perfectly suited for rocking chairs and relaxed conversation. Inside, you'll find comfortable living spaces with a natural flow, ideal for everyday living and entertaining alike. The dining room slider opens to a covered patio, creating a seamless indoor-outdoor connection-perfect for summer gatherings or quiet evenings outside. Featuring low-maintenance vinyl siding and replacement windows, many of the important updates have already been taken care of, offering both efficiency and peace of mind. If you're looking for a home with character, comfort, and a welcoming feel, this Cape is not to be missed.

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24172664 MLS

Welcome home to this charming Cape Cod, with a fabulous front porch to rock away your cares. Also, where timeless character meets thoughtful updates. Renovated over the years while preserving its classic appeal, this warm and inviting home truly "feels like home" from the moment you arrive. Start your mornings or unwind in the evenings on the spacious front porch, perfectly suited for rocking chairs and relaxed conversation. Inside, you'll find comfortable living spaces with a natural flow, ideal for everyday living and entertaining alike. The dining room slider opens to a covered patio, creating a seamless indoor-outdoor connection-perfect for summer gatherings or quiet evenings outside. Featuring low-maintenance vinyl siding and replacement windows, many of the important updates have already been taken care of, offering both efficiency and peace of mind. If you're looking for a home with character, comfort, and a welcoming feel, this Cape is not to be missed.

74 Maple St, Seymour

$585,000

Experience waterfront living at its finest in this exceptional DIRECT WATERFRONT home on the beautiful Housatonic River. Offering a rare combination of a private sandy beach, two floating docks with room for up to four boats, and breathtaking water views, this property is perfect for boating, kayaking, fishing, or simply relaxing by the river. The outdoor space is designed for entertaining with expansive Trex decking, floating walkways, a hot tub overlooking the water, gazebo, raised garden beds, and a beautifully landscaped yard. An oversized detached garage, additional one-car garage, lean-to, and pull-through driveway provide exceptional storage and parking for vehicles, boats, and recreational equipment. Inside, the bright and inviting 2-bedroom, 1.5-bath home features an open-concept layout filled with natural light, recessed lighting, tinted windows, and custom blinds. The kitchen flows seamlessly into the living area, creating an ideal space for everyday living and entertaining. Recent updates include a metal roof, siding and mini-split heating and cooling systems (2017), and a Blaze King wood stove (2023). The finished lower level offers additional living space with a propane stove, electric heat, and plenty of storage. Whether you're looking for a year-round residence or a weekend retreat, this one-of-a-kind waterfront property offers the perfect blend of comfort, recreation, and unforgettable riverfront views.

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24173848 MLS

Experience waterfront living at its finest in this exceptional DIRECT WATERFRONT home on the beautiful Housatonic River. Offering a rare combination of a private sandy beach, two floating docks with room for up to four boats, and breathtaking water views, this property is perfect for boating, kayaking, fishing, or simply relaxing by the river. The outdoor space is designed for entertaining with expansive Trex decking, floating walkways, a hot tub overlooking the water, gazebo, raised garden beds, and a beautifully landscaped yard. An oversized detached garage, additional one-car garage, lean-to, and pull-through driveway provide exceptional storage and parking for vehicles, boats, and recreational equipment. Inside, the bright and inviting 2-bedroom, 1.5-bath home features an open-concept layout filled with natural light, recessed lighting, tinted windows, and custom blinds. The kitchen flows seamlessly into the living area, creating an ideal space for everyday living and entertaining. Recent updates include a metal roof, siding and mini-split heating and cooling systems (2017), and a Blaze King wood stove (2023). The finished lower level offers additional living space with a propane stove, electric heat, and plenty of storage. Whether you're looking for a year-round residence or a weekend retreat, this one-of-a-kind waterfront property offers the perfect blend of comfort, recreation, and unforgettable riverfront views.

3 Roosevelt Dr, Seymour

$334,900

Beautifully maintained and full of charm, 3-bedroom, 1.5-bath Cape-style single-family home with garage in Seymour offers comfort, functionality, and timeless appeal. Featuring gleaming hardwood floors throughout much of the home and newer windows that provide abundant natural light and improved energy efficiency, this inviting property is ready for its next owner. A spacious layout offers comfortable living areas perfect for everyday living and entertaining alike. Step outside to enjoy the deck, ideal for relaxing evenings, outdoor dining, or hosting guests. A mostly finished basement provides valuable extra living space with endless possibilities for a family room, home office, gym, or recreation area, while the separate private laundry area adds practicality and organization. Conveniently located near local shopping, restaurants, parks, and commuter routes, this charming home combines classic New England character with modern updates in a desirable location. Don't miss the opportunity to make this wonderful property your next home!

3 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24173618 MLS

Beautifully maintained and full of charm, 3-bedroom, 1.5-bath Cape-style single-family home with garage in Seymour offers comfort, functionality, and timeless appeal. Featuring gleaming hardwood floors throughout much of the home and newer windows that provide abundant natural light and improved energy efficiency, this inviting property is ready for its next owner. A spacious layout offers comfortable living areas perfect for everyday living and entertaining alike. Step outside to enjoy the deck, ideal for relaxing evenings, outdoor dining, or hosting guests. A mostly finished basement provides valuable extra living space with endless possibilities for a family room, home office, gym, or recreation area, while the separate private laundry area adds practicality and organization. Conveniently located near local shopping, restaurants, parks, and commuter routes, this charming home combines classic New England character with modern updates in a desirable location. Don't miss the opportunity to make this wonderful property your next home!

205 S Main St, Seymour