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110 Sport Hill Rd, Redding
$1,650,000
5 Beds ⋅ 6 Baths ⋅ 24165654 MLS
A rare blend of scale, privacy and value, this beautifully maintained Redding retreat offers over 6,000 square feet of flexible living space. From the gracious front entry, the home unfolds with purpose and ease. To the right, a private library/home office creates a quiet place to work. Straight ahead, the living room frames peaceful views of the pool and grounds, while the formal dining room leads toward the heart of the home: a large eat-in gourmet kitchen open to an impressive family room with soaring ceilings, walls of windows, and abundant natural light overlooking the property. The traditional second floor offers a spacious primary suite with walk-in closets and serene backyard views, along with three additional bedrooms. The finished lower level adds tremendous versatility, featuring a large suite and lounge area ideal for guests, au pair, or in-law living, with direct access to the mudroom, garages and a separate exterior entrance. A second exterior entrance leads to a fully private studio or workshop. Outdoor living is a standout, with an expansive deck surrounding the pool and generous space for entertaining, relaxing and enjoying the private setting. The detached pool house/guest house adds incredible flexibility with a living area, kitchenette, bedroom and loft space. With exceptional square footage, privacy, lifestyle amenities and tremendous value compared with pricing being achieved in surrounding Fairfield County towns, this is a must see property.

110 Sport Hill Rd, Redding
15 Silversmith Ln, Redding
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 24167129 MLS
Artisan Craftsmanship Meets Modern Autonomy - Your Private Oasis Awaits! Nestled on 4 idyllic, professionally landscaped acres at the end of a quiet cul-de-sac, this spectacular 2002 post-and-beam is a perfect blend of artisan craftsmanship and modern design. Built to exacting standards, this "one-of-a-kind" residence presents a dramatic, flexible open floor plan bathed in natural light through walls of windows highlighting exposed beams, soaring ceilings, and rich hardwoods. The chef's kitchen gleams with cherry cabinetry, upscale appliances, and quartz and limestone finishes. The home features a much-desired bedroom suite on the main floor as well as a primary suite upstairs, two additional bedrooms and a sleeping loft! Outdoor living is unrivaled: a heated Gunite salt-water pool, an expansive stone patio and fireplace, a wrap-around porch with panoramic views of the lush landscape, gardens, and a private stream-fed pond with a fountain. Beyond the beauty lies incredible efficiency. This home boasts high-efficiency mechanicals, seamed metal and arch shingle roofing (2021), a whole-house generator, on-demand hot water system, propane/HW system, pond-fed irrigation system, electric car charger, and a 1000-gallon propane tank for up to two weeks of off-grid autonomy. Sophisticated, secure, loaded with character, immaculate and artfully designed. This is the dream lifestyle realized - a mini-resort in the Summer, a wonderland in the Winter and very, very special.

15 Silversmith Ln, Redding
128 Black Rock Tpke, Redding
$1,600,000
4 Beds ⋅ 4 Baths ⋅ 24168509 MLS
Set in the heart of charming Redding, Connecticut, this meticulously maintained home offers the perfect blend of New England character, modern efficiency, and everyday convenience. Known for its award-winning schools, scenic walking trails, and peaceful, serene surroundings, Redding provides an exceptional lifestyle-and this property places you right in the center of it all, just minutes to the high school, hiking trails, and major commuting routes (59 miles to Midtown). Privately set back from the road, the home is surrounded by beautiful, thoughtfully designed, low-maintenance landscaping, including mature hydrangeas that frame the outdoor spaces. Outdoor entertaining is enjoyed with the spacious bluestone patio, separate firepit area and outdoor audio system. Ample room for a future pool if desired. Inside, pride of ownership is evident throughout the expansive 4,000 square feet of living space. With custom Cedar entry doors, custom details throughout, and 10-foot ceilings on the main level, every detail is thoughtfully executed. The gourmet eat-in kitchen features an expansive limestone counter, Sub-Zero, Viking, and Bosch appliances, a coffered ceiling, and a wood-burning fireplace. Upstairs, four bedrooms include a spacious primary suite with a drop-dead gorgeous walk-in fitted closet and spa bathroom. The layout could also support an in-law suite

128 Black Rock Tpke, Redding
15 Tunxis Trl, Redding
$1,170,000
4 Beds ⋅ 3 Baths ⋅ 24133358 MLS
Highest and best is due Monday, Nov. 10th at noon. No escalation clauses. Please call me with questions.Thank you This magical 4,000 square-foot English Tudor with its loft library overlooking the 35' great room featuring a soaring stone fireplace is perfect for weekend escapes from the big city, or for gracious full-time family enjoyment. Sited on 2.65 dog-fenced acres, this home -- once featured in The New York Times -- has a rich history. Custom-designed, it 's been home to musicians and writers. Features include the great room flooded with light, soaring stone fireplace, and stairs to the bookcase-lined loft. The bright, eat-in kitchen with all new appliances features a banquette overlooking the flagstone terrace and rear property bordered by protected land. The coffered ceiling dining room is an entertainers' delight. Closeby is a cozy den with a raised hearth fireplace, and powder room. The center entry hall has two closets and full-length mirrors. The 2nd level includes the master suite with dressing room, clawfoot tub and steam shower. There are three other bedrooms with generous closets, and a full bath with double sinks. The finished lower level includes a family room, gym, imported English pub, and laundry room. This extraordinary property with recent exterior renovations is just 15 minutes to the Merritt, 20 minutes to Westport, and an hour to Grand Central.

15 Tunxis Trl, Redding
5 Dry River Ct, Redding
$1,135,000
4 Beds ⋅ 5 Baths ⋅ 24195753 MLS
Commanding a private 2-acre setting in a coveted Redding CUL-DE-SAC, this CUSTOM-BUILT residence blends timeless architecture, exceptional craftsmanship & METICULOUS care. A Belgian block-lined stone drive leads to DOUBLE-DOORS & a 2-story foyer w/CURVED STAIRCASE. The sun-filled OPEN LAYOUT includes a gourmet EIK w/center island, built-in desk & bluestone PATIO access, plus a FORMAL DINING RM with floor-to-ceiling windows. The family room features a massive floor-to-ceiling FIELDSTONE FIREPLACE, soaring ceiling, skylights, wall of windows, built-ins, WET BAR and patio access; an upper gallery connects it visually to the foyer. The living room adds another wood-burning FIREPLACE and patio access, while the OFFICE/DEN has matching built-ins. The primary suite offers a 3rd wood-burning FIREPLACE, WIC, PRIVATE BALCONY & skylit bath with DUAL VANITIES, jetted tub & separate shower. A freshly painted 2nd EN-SUITE offers guest, in-law, rec or office flexibility. Two more bedrooms complete the upper level; one has direct bath access & a Juliet BALCONY, & both have ceiling fans. The MUDROOM connects the BACK STAIRCASE, laundry room with utility sink and oversized 3-CAR GARAGE. The lower level includes a SAUNA, adjacent full bath & gym/yoga room. With 4 bedrooms, 4 full & 2 half baths, HDWD FLRS throughout & newer mechanicals, this home is ready to enjoy from day one. EXCEPTIONAL PRIVACY, easy access to amenities & Metro-North, & a Redding setting deliver both lifestyle lasting value.

5 Dry River Ct, Redding
44 High Ridge Rd, Redding
$1,127,000
4 Beds ⋅ 3 Baths ⋅ 24173871 MLS
Serenity awaits in this classic colonial nestled on two level acres in a walker-friendly cul de sac neighborhood. This turn-key home has perfect flow for entertaining. French double doors off the spacious, quartz countered kitchen open up to the sun-soaked four season room with the light and bright great room attached featuring skylights, cathedral ceilings, a fireplace, and a bar area. The bonus room over the garage is ideal for casual gatherings while the living room and dining room with crown molding ceilings and hardwood floors exude elegance for more formal entertaining. An additional room off the kitchen is perfect for guests or as a home office. The upper-level features four generously sized bedrooms with hardwood floors throughout. The primary bedroom suite includes a large walk-in closet and a separate vanity area with a sink outside of the bathroom. Bathrooms are all updated and include high-end fixtures. Hosting will be a breeze in this quintessential New England charmer featuring a long circular driveway. This exceptional property feels like an oasis for quiet, cozy nights in too. Social or secluded, you can have both when you call this home.

44 High Ridge Rd, Redding
16 Black Rock Tpke, Redding
$1,080,000
4 Beds ⋅ 5 Baths ⋅ 24097511 MLS
A long and winding drive leads to this exceptional colonial sited under a grand old oak tree. Upon entering there is an impressive double staircase in foyer with a palladium window and display shelf above door. Perfect for entertaining this open floor plan includes DR, LR w/fpl sunroom with walls of glass, library with fpl and French doors. There is a cook's kitchen, pass thru to large FR. French doors lead to brick patio. Primary BR has tray ceiling, full bath w/vaulted ceiling, skylight, whirlpool tub & shower. Property abuts nature preserve

16 Black Rock Tpke, Redding
81 Pinetree Rd, Redding
$905,000
4 Beds ⋅ 3 Baths ⋅ 24174134 MLS
A rare opportunity to own a thoughtfully updated antique home with a separate guest cottage, set on 1.66 picturesque acres in Redding, blending timeless character with modern livability in a way that is increasingly hard to find. A welcoming foyer with a vaulted ceiling sets the tone, leading into a sunlit living room anchored by a gas fireplace, custom built-ins, and a large picture window. The space flows easily into the dining area and an updated kitchen, creating a natural layout for both everyday living and entertaining. Just beyond, a light-filled family room with Saltillo tile floors and oversized windows opens through French doors to a crushed stone patio, where a fire pit and mature hydrangeas create an ideal setting for outdoor gatherings and quiet evenings alike. The main level also features the primary bedroom, offering ease and flexibility, while upstairs includes two additional bedrooms, a full bath with laundry, and a separate bonus space well-suited for a home office or reading nook. Adding to the property's appeal is a separate one-bedroom cottage with a full bath, living room, kitchenette, and its own heating system, an exceptional option for guests, work-from-home needs, or creative use. Set amid established landscaping with a sense of privacy and calm, this storybook home lives beautifully day to day, with the added flexibility and character that make it truly stand apart. OFFER DEADLINE MON 5/18 @ 5pm.

81 Pinetree Rd, Redding
29 Meeker Hill Rd, Redding
$812,500
4 Beds ⋅ 3 Baths ⋅ 24123993 MLS
Welcome to 29 Meeker Hill Road, a warm and inviting 4-bedroom, 2.5-bath home nestled on 2 acres of level, cleared land in beautiful Redding. With nearly 1,900 sq. ft. of living space, this multi-level home is filled with natural light and offers the perfect blend of comfort, charm, and practicality. The property's standout feature is the incredible barn-ideal as a workshop, studio, or creative space. Surrounded by open, usable land, you'll have plenty of room to garden, entertain, or simply enjoy the peace and quiet of country living. This is a rare opportunity to own a home with character, space, and potential in a sought-after community with excellent schools. Don't miss your chance-schedule a showing today and see why 29 Meeker Hill Road is the cozy retreat you've been waiting for. HIGHEST AND BEST BY MONDAY AT 5PM...

29 Meeker Hill Rd, Redding
1 Long Wall Rd, Redding
$800,000
5 Beds ⋅ 3 Baths ⋅ 24118336 MLS
First time on the market in forty-two years, welcome to 1 Long Wall Road! Situated in the center of Redding, minutes from Redding's schools, on a quiet Cul de sac, where neighbors stroll, walk dogs and families safely ride bikes. Nearby, Georgetown, Bethel and the Redding Market to shop. A multi-generational home on 2.76 acres, mature landscaping and babbling brook, access to Redding's hiking trails. The main house consists of 3 beds and 2 full baths, a breathtaking two-story cathedral ceilinged Great Room with roughhewn timbers and stone fireplace. A large, central kitchen adjoins the great room, den, loft space, dining area, and the large, screened porch looking out over a flat, expansive and bucolic backyard. A second story, primary bedroom suite with large ensuite bath and balcony that leads down to a multi-level, wraparound back deck connecting to the screened porch provides for an ideal entertaining area for family barbeques, festivities or simply serene afternoon siestas! Beautiful slate accents, kitchen counters and bathroom floors, lovingly repurposed by the owners from the roof tiles of their 19th century Vermont farmhouse. The lower level, finished living space converted from a two-car garage includes two separate rooms housing mechanicals with large areas for storage. Integrated into the main house is a spacious 2-bed, 1-bath, legal apartment with kitchen, livingroom w/stone fireplace, dining room. Ideal accessory apartment, access from main house. A must see gem!

1 Long Wall Rd, Redding
5 South Ln, Redding
$740,000
3 Beds ⋅ 2 Baths ⋅ 24160906 MLS
Perched at the crest of Redding Ridge on a lane shared by only five homes, this beautifully restored Cape occupies a truly commanding position. The property encompasses an entire side of South Lane, framed by original stone walls and mature trees that provide a sense of established privacy. In a region known for its rolling terrain, this home offers the rare luxury of an entirely usable, "pancake-flat" lot, providing the perfect vantage point for unobstructed views of both the sunrise and the sunset. The interior of the residence preserves its classic New England charm while embracing a modern, open-concept flow. Original wood-beamed ceilings and hardwood floors run throughout, lending an air of historic authenticity. The heart of the home is a sweeping living room anchored by a large central fireplace, flanked by thoughtful built-ins. For those who love to host, the formal dining room and renovated spaces make this house a true entertainer's delight, with practical upgrades like central air and main-floor laundry. The living space extends gracefully outdoors through an enclosed three-season porch, which serves as a bright transition to the backyard. This porch leads directly to a raised flagstone deck which offers peaceful views of the level grounds. With three generous bedrooms, two fully renovated baths, and a separate two-car garage, this home offers a timeless ridge-top lifestyle that is as functional as it is picturesque.

5 South Ln, Redding
159 Cross Hwy, Redding
$730,000
3 Beds ⋅ 2 Baths ⋅ 24165406 MLS
Charming turn-of-the-century Craftsman farmhouse on one of Redding's most picturesque Scenic Roads - a rare find for those seeking space, character, and a genuine sense of place within reach of the city, but worlds away from it. Featuring authentic period details including crown molding, a bay window, beautiful hardwood floors, and soaring 9-foot ceilings, this three-bedroom, two-bath home balances historic charm with thoughtful modern updates. A newly expanded primary suite and a brand-new full bath on the second floor - complete with new HVAC - make the home as comfortable as it is characterful. Once the original switchboard for Redding Ridge, the property sits on a large, level lot with mature landscaping, spectacular perennial gardens that bloom spring through fall, a deck, brick terrace, and storage shed. The new roof and all-new windows mean the big work is done - just move in. Beyond the property itself, Redding delivers the lifestyle that's increasingly hard to find closer to the city: miles of open space, hiking trails, and beloved local institutions like the Mark Twain Library, New Pond Farm, Huntington State Park, and Putnam Park. It's a town with a strong sense of community, where weekends mean farmers markets and trail walks, not traffic. Additional highlights include an EV charger, generator, and 25 years of careful stewardship. History, updates, and room to grow - all in one of Connecticut's most desired small towns

159 Cross Hwy, Redding
5 Iris Ln, Redding
$710,000
3 Beds ⋅ 2 Baths ⋅ 24165744 MLS
Set on a quiet cul-de-sac within a true neighborhood setting, this 3 bedroom, 2 bath ranch offers easy, one-level living on a beautifully flat .78-acre property, a rare find in Redding. Charming details throughout, including built-ins, multiple window seats, picture windows, and a wood-burning fireplace, create a warm and inviting atmosphere filled with natural light. The kitchen features a Sub-Zero refrigerator and direct access to the deck, making outdoor dining especially convenient. The primary bedroom includes an ensuite bath, while 2 additional bedrooms share the second full bath, providing comfortable space for guests, a home office, or hobbies. A partially finished lower level offers additional usable space, ideal for a gym, media room, or playroom. Central air, a classic ranch layout, and a two-car garage add everyday convenience, while the level yard offers outdoor enjoyment without the maintenance of a larger property. A wonderful alternative to condo living, this home combines charm, space, and the ease of single-level living. Welcome Home! OFFER DEADLINE TUESDAY 4/14 at 12pm.

5 Iris Ln, Redding
101 Sport Hill Rd, Redding
$705,000
2 Beds ⋅ 2 Baths ⋅ 24162857 MLS
Set behind a classic New England stone wall in highly desirable West Redding, this move-in ready home offers space, flexibility, and charm across 2,294 sq ft on the main level plus 952 sq ft in the finished lower level. Thoughtfully laid out and currently utilized as a 3-bedroom, the home includes a versatile additional room ideal for a bedroom, office, or guest space. Bright, open layout with hardwood floors and abundant natural light throughout. The main living areas feature two fireplaces and a wood stove, adding warmth and character, while multiple access points lead to the expansive back deck for seamless indoor-outdoor living. The oversized primary suite offers vaulted ceilings, ceiling fans, and direct deck access, creating a private, retreat-like feel. The finished lower level adds 952 sq ft of valuable additional space, including a recreation room with fireplace, along with a dedicated workshop, laundry area, and ample storage-ideal for recreation, hobbies, or a home gym. Step outside to a large deck with pergola overlooking a peaceful, wooded setting, offering privacy and space for entertaining or everyday enjoyment. Additional highlights include central air conditioning and a layout designed for comfort and functionality. Located in a town known for its top-rated schools, with convenient access to nearby train stations and major routes, making commuting to NYC and surrounding areas both practical and accessible.

101 Sport Hill Rd, Redding
18 Great Meadow Rd, Redding
$650,000
3 Beds ⋅ 2 Baths ⋅ 24099619 MLS
Welcome to 18 Great Meadow Road, a newly renovated home with a completely flat 2.5 acre lot on a quiet, cul-de-sac street. This house is the perfect combination of country side living but in a state of the art, almost new construction house. Although quiet and scenic, you are only 2 miles from the highly rated Joel Barlow high school and essentially in "central" Fairfield County close to all great neighboring towns. A completely new roof structure including new rafters, plywood and shingles creates the 14-foot cathedral ceiling resulting in a large bright and airy feel very similar to a brand new center hall colonial mansion. Right off the living room is a 4-season sunroom with baseboard heat and two brand new skylights providing year-round light and relaxation. Walk directly out the sunroom to the second level deck which overlooks the backyard, driveway and basketball hoop. The brand new kitchen from start to finish boasts high end, soft close, all wood cabinetry with ample storage including an 8ft pantry cupboard. The countertops are high end Quartz with an extra large center island that comfortably fits 4 or 5 large stools making it a complete eat in kitchen or the perfect spot for entertaining. All new appliances including a Frigidaire Gallery collection, smudge proof, stainless steel French door refrigerator as well as an ultra quiet third rack dishwasher and newly vented 3 speed hood range.

18 Great Meadow Rd, Redding
280 Newtown Tpke, Redding
$408,000
2 Beds ⋅ 1 Baths ⋅ 24126777 MLS
estate, sold as is, cash only ,proof of funds, contents of house to be left.

280 Newtown Tpke, Redding

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