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240 Umpawaug Rd, Redding
$3,975,000
6 Beds ⋅ 6 Baths ⋅ 24181754 MLS
Steeped in history and natural beauty, the Charles Ives House (ca. 1913) is a masterfully restored 18-acre West Redding summer retreat where the famed modernist composer lived and created his signature works. Designed and built by Ives himself, this iconic Arts and Crafts estate seamlessly pairs vintage authenticity with ultra-luxury modern updates. Inside, original architectural integrity shines. The spectacular great room features a double-height wood-beamed ceiling, a stunning original paned picture window, and custom staircase balusters subtly crafted to resemble musical staff notes. A country-chic chef's kitchen boasts elite appliances (La Cornue, Miele, Bosch), a cozy built-in banquette, and a fireplace inset with original vintage tile. The second-level primary suite offers panoramic views of the lush, pastoral grounds, a luxurious marble bath, and an expansive walk-in closet. Retain your own inspiration in the original music studio/office where Ives composed, complete with untouched original hardwood floors. The extraordinary 18-acre grounds double as a private resort, featuring a charming 1BR guest cottage (ca. 1900), a heated Gunite infinity-edge pool and spa, a tennis court, and a classic century-old timber frame barn with a new foundation and roof. Effortlessly sophisticated, enchantingly rustic, a rare opportunity and an absolute masterpiece of living history.

240 Umpawaug Rd, Redding

24 Mark Twain Ln, Redding
$1,800,000
4 Beds ⋅ 5 Baths ⋅ 24193453 MLS
A once-in-a-generation offering. Once part of the Redding's historic Samuel Clemens (Mark Twain) estate, this extraordinary 5.41 acre property was later home to renowned American Abstract Expressionist painter Robert Natkin, whose creativity inspired its remarkable evolution. Set beside the 161-acre Stormfield Preserve, this secluded private compound offers miles of hiking trails just beyond your doorstep. The understated approach gives way to an unforgettable interior where architecture masterfully employs "compression and release". Step through the glass entry and the home unfolds to a spectacular designer-renovated chef's kitchen with Wolf range/double ovens, Sub-Zero refrigerator, quartz waterfall island, wet bar and a full wall of glass that opens creating seamless indoor-outdoor living to the screened porch, heated saltwater pool and sweeping grounds, ideal for entertaining on any scale. Every principal room captures views of the surrounding landscape, creating a seamless connection to its setting. A climate-controlled studio with 9' glass garage doors opening to the landscape-equally suited as an art studio or fitness space. Designed for multi-generational living with first and second-floor primary suites, three ensuite bedrooms, guest/in-law/au pair apartment, workshop, entry gallery and temperature controlled pole barn for collectors, equestrians, car enthusiasts or hobbyists. R-2 zoning on 5.41 acres offers possible subdivision potential with due diligence.

24 Mark Twain Ln, Redding

42 Topstone Rd, Redding
$1,700,000
4 Beds ⋅ 4 Baths ⋅ 24157966 MLS
Nestled on three private acres in highly sought-after Redding, Connecticut, with a private backyard gate entering directly into Topstone Park, this exceptional property offers a lifestyle defined by tranquility, privacy, and space. Surrounded by mature trees and drenched in natural light, the home embodies the timeless charm that has earned Redding its reputation as the 'Vermont of Connecticut". Designed with entertaining in mind, the resort-style backyard is a true retreat featuring a heated in-ground pool with spa, an inviting outdoor fireplace, and expansive, fully fenced grounds perfect for year-round enjoyment. A newly paved driveway adds to the home's impressive curb appeal and arrival experience. Inside, thoughtful modern upgrades ensure both comfort and efficiency, including energy-efficient electric heat pumps with central air conditioning, updated garage doors, and a whole-house generator that also services the finished barn. The kitchen is equipped with premium Thermador appliances, including a high-end oven, cooktop, and dishwasher, ideal for both everyday living and hosting. Providing incredible versatility, the 400 sq ft finished barn serves as a premier home office, fitness studio, or creative retreat, further extending the home's expansive living and entertaining potential. Move-in ready and meticulously maintained, this property offers a rare combination of privacy, functionality, and upscale living in a peaceful, natural setting all just minu

42 Topstone Rd, Redding

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

36-40 Fox Run Rd, Redding
$1,585,000
4 Beds ⋅ 4 Baths ⋅ 24155674 MLS
CT Country Estate on 5.46 acres (#36) + Separate 2.17 acre building lot (#40) - Highest attention to detail in this quintessential New England colonial featuring attached garage plus detached cheery red carriage barn w/storage loft on total 7.63 pastoral acres in top West Redding location adjacent to Redding's cherished, 161 acre, Stormfield Preserve. It's hard to believe that this classic CT country estate has its roots in a circa 1938 Bauhaus home. In 1989, with the help of renowned Westport architect John Wagner, the owners completed a down to the studs renovation plus extensive 3 story addition resulting in a seamless transformation - new entrance foyer, open concept living & dining rooms, expanded primary suite, bath & dressing room, plus new walk-out lower level. Everything was built w/the highest attention to detail including custom cabinetry, built-ins & 4 distinct fireplace mantles; 12-over-12 true divided light windows; plus fully new interior/exterior including electric, plumbing, cedar siding, septic & extensive landscape/hardscape including rebuilding the original native fieldstone patio w/curved railing. The only other element that was kept was the prized Helo Finnish Sauna off of the family room/studio wing. Total 4,548 sf, 3/1 baths, recently remodeled top of the line kitchen, powder room & luxe primary suite bath, plus expansive lower level w/multiple workshop/storage areas. Separate approved bldg. lot plus potential to subdivide further. Spectacular setting!

36-40 Fox Run Rd, Redding

74 George Hull Hill Rd, Redding
$1,560,000
4 Beds ⋅ 5 Baths ⋅ 24157566 MLS
Nestled on three picturesque acres and surrounded by open space, this beautiful country retreat offers privacy, comfort, and exceptional outdoor living. The expansive patio is perfect for entertaining, featuring a full outdoor kitchen, fireplace, TV, and integrated audio system. A large level yard provides plenty of space for recreation and the potential for a pool. Inside, the home showcases high-end finishes and a thoughtful layout. The spacious eat-in kitchen features custom cabinetry, granite countertops, and premium appliances from Thermador, Wolf, and Sub-Zero. The family room is highlighted by dramatic picture windows and a stunning floor-to-ceiling stone fireplace. The main level also includes a welcoming two-story foyer, formal living and dining rooms, a private home office, two powder rooms, and a mudroom with access to the three-car garage. Upstairs, the primary suite offers a luxury bath and dual walk-in closets. Two bedrooms share a Jack-and-Jill bath, while a fourth has its own ensuite. A laundry room and large bonus room complete the upper level. Additional features include radiant heated floors in the kitchen and baths, a home sound system, Generac whole-house generator, security system, irrigation, and unfinished basement. Ideally located in West Redding close to the train, hiking trails, Routes 7 & 84, shopping, and dining.

74 George Hull Hill Rd, Redding

7 Long Meadow Ln, Redding
$1,550,000
4 Beds ⋅ 5 Baths ⋅ 24149592 MLS
Sweeping meadow views, privacy & sunsets from an elevated setting 7 Long Meadow Lane is a distinctive property defined by its scale, setting, and versatile layout, offering generous proportions and an architectural presence that supports a wide range of lifestyles. Sited on an elevated, scenic 4.39 acres with exceptional privacy and open meadow outlooks, the home enjoys a peaceful setting surrounded by natural beauty and expansive skies. The interior features light-filled spaces with wide hallways, oversized rooms, and a layout that emphasizes flow and functionality. Multiple living and gathering areas provide flexibility for entertaining, everyday living, and extended stays with family and guests. Large windows throughout capture abundant natural light and tranquil views, with sweeping sunrises and sunsets unfolding across the landscape and changing with the seasons. The home's scale and configuration allow the spaces to adapt naturally over time. Outdoor living is a standout feature, highlighted by an in-ground pool with an expanded patio surround, thoughtfully positioned to maximize privacy and open views. The generous patio provides ample space for dining, lounging, and entertaining, creating a true extension of the home and a resort-like setting for relaxed summer living. Located within reach of NYC yet feeling distinctly removed, the property offers an appealing sense of retreat-ideal as a weekend escape, multi-generational residence, or long-term family compound.

7 Long Meadow Ln, Redding

15 Dayton Rd, Redding
$1,475,000
3 Beds ⋅ 4 Baths ⋅ 24166623 MLS
Impeccable shingle style country cape on park-like 2.76 acres adj. Redding Land Trust conservation property, connecting directly to Devil's Den, the largest preserve in CT w/1,800+ acres. Exceptional attention to detail inside & out, w/extensive recent improvements & designer finishing. Impressive circular drive w/Belgian block apron & center inlay, lush lawn, flowering trees & Wisteria covered pergola. Drenched in natural light, the modern open floor plan features a state of the art chef's kitchen w/Wolf 6 burner gas range, island w/bar seating, pantry, & fireside dining area, wide open to the expansive FR w/cstm built-in entertainment center, new SONOS surround sound, & French doors to the extensive deck for outdoor enjoyment. High tech w/Nest thermostats; fiber internet; Ring alarm system/sensor array; & custom Hunter Douglas motorized blinds. Total 4,943sf w/3-4 BRs, 3/1 updated baths, & primarily one level living. The main floor also boasts the sophisticated LR w/wall of windows & French doors to the deck & yard; elegant primary BR suite with luxe bath featuring soaking tub/separate shower & marble double vanity; plus 2 more sizable BRs w/shared bath. Walk-up to the soaring beamed & vltd bonus room, plus expansive walk-out lower level rec room w/4th BR option, full bath & direct access to the oversized 2 car garage. Idyllic home in sought after West Redding, minutes to restaurants/shopping in nearby Georgetown, Ridgefield, Wilton & Bethel, plus just 58 miles to Midtown.

15 Dayton Rd, Redding

313 Umpawaug Rd, Redding
$1,450,000
4 Beds ⋅ 3 Baths ⋅ 24166799 MLS
Nestled on a picturesque country road in the heart of Redding, this National Register of Historic Places landmark offers a rare blend of 18th-century soul and modern New England estate living. The home's historic integrity is preserved through twin stone chimneys, original wide-plank flooring, and exquisite period woodwork. Sun-filled living spaces flow seamlessly from the warm central hall to a spacious kitchen and inviting dining areas-ideal for both everyday comfort and sophisticated entertaining. The layout provides exceptional flexibility, featuring generous bedrooms and additional rooms perfectly suited for a home office, den, or guest wing. Set on two serene acres of curated gardens and mature trees, the exterior offers a peaceful retreat for outdoor gatherings or quiet mornings in nature. While seemingly worlds away in its rural tranquility, 313 Umpawaug Road in prestigious West Redding is located just minutes from top-rated schools, hiking trails, and the charming town center. Once the residence of Continental Army soldier Aaron Barlow, this 1723 Georgian gem served as a strategic hub for General Israel Putnam and a literary sanctuary where the famed Joel Barlow penned The Vision of Columbus in 1787. A rare opportunity to own a living piece of history, meticulously maintained for the modern steward.

313 Umpawaug Rd, Redding

8 Windy Hill Rd, Redding
$1,400,000
4 Beds ⋅ 4 Baths ⋅ 24171032 MLS
Set on over 2 private acres in a coveted neighborhood in SW Redding, this sun-filled 4 BR Colonial blends timeless style, scale and effortless living. Designed for both entertaining and daily life, the main level centers around a spacious EIK w/center island, all-new appliances and seamless flow to the adjoining family room w/gas fireplace. Sliders open to the deck and grounds beyond, creating an easy indoor-outdoor flow. A formal dining room is ideal for gatherings, while a second living room w/fireplace provides an inviting retreat. A dedicated home office with a wall of custom built-ins & a powder room complete the main floor. Upstairs, the expansive primary suite is a sanctuary, featuring dual walk-in closets and a large bath w/soaking tub. 3 additional bedrooms share an updated hall bath, while 2nd floor laundry adds convenience. The finished lower level adds versatility with a spacious recreation/media room, dedicated gym & half bath. Outside, the property truly shines. A level, usable yard is anchored by a heated gunite saltwater pool w/travertine surrounds, creating a private resort-like setting for summer entertaining and quiet afternoons. The charming barn has outstanding potential to become a pool house or studio. Minutes from Route 7, downtown Ridgefield, MetroNorth, and Topstone Park, this home delivers the rare combination of neighborhood living, privacy and convenience, just in time for summer.

8 Windy Hill Rd, Redding

10 Chapman Pl, Redding
$1,310,000
4 Beds ⋅ 5 Baths ⋅ 24172519 MLS
Private Luxury Meets Modern Sophistication in Redding! Discover the perfect blend of classic New England charm and cutting-edge convenience. This pristine 4,414 SF Colonial is situated on 2.67 acres at the end of a peaceful cul-de-sac. Inside, you are welcomed through a stately foyer with marble flooring, a sweeping staircase, and soaring ceilings. Gleaming hardwood floors guide you through a spacious layout featuring four bedrooms, three full and two half baths, and a seamless flow between formal entertaining areas and casual gathering spaces. The heart of the home is the cozy family room, anchored by a stately fireplace and bathed in natural light. Adjoining this room is the expansive chef's kitchen with Sub-Zero and other high-end appliances, plus lots of storage. The exterior is a gardener's dream, boasting professional plantings and ample room for a pool, all maintained by an integrated irrigation system. Technologically unmatched, the residence is equipped with commercial-grade Wi-Fi, an advanced security system, and a whole-house surge protector. Complete with a three-car garage and a meticulously maintained interior, this home is truly "turn-key." Located just minutes from the West Redding train station and world-class shopping, dining, and cultural events, this is a rare opportunity for a lifestyle of quiet elegance.

10 Chapman Pl, Redding

7 Jeremiah Sanford Rd, Redding
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 24171692 MLS
Exceptional custom designed and built 4 bedroom Colonial, bathed in natural sunlight, is nestled perfectly on 2 lush level manicured acres at the end of a small quiet cul-de-sac in a coveted area of town, a perfect tranquil oasis. The open floor plan provides timeless functionality and effortless living with dramatic high ceilings and extensive walls of glass. The special landscaped entrance porch opens into the welcoming 2-story foyer which leads into the gracious living room flowing into the banquet sized dining room. The spacious chef's kitchen with center island enjoys new stainless-steel appliances, granite counters, and an adjacent dining area which steps out onto a large deck, patio and extensive lawn; ideal for everyday peaceful enjoyment, activities, entertaining as well as ample room for a pool. Directly next to the kitchen is the comfortable family room with fireplace and access to the big deck. Upstairs is the primary suite with generous bath providing a comfortable retreat, 3 family bedrooms and a hall bathroom. Come to Redding, the "Vermont of Fairfield County", and enjoy the peaceful privacy yet convenience to Topstone Park's hiking and swimming, activities at New Pond Farm, NY Metro train, commuting roads and shopping. Move-in, just in time for Summer! AGENTS PLEASE SEE SIGNIFICANT PUBLIC ADDENDUM REMARKS

7 Jeremiah Sanford Rd, Redding

98 Hopewell Woods Rd, Redding
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 24158436 MLS
Custom-built in 2004 and meticulously maintained, this 2.18-acre home offers a true escape from the everyday. Surrounded by perennial gardens, stone walls, and specimen trees, the grounds are anchored by a stunning stone patio-your own private sanctuary for quiet mornings or lively entertaining. Inside, discover 3,669 square feet of sun-drenched living space featuring 11 rooms, 4 bedrooms, and 2.5 baths. The first floor boasts an effortless layout, including a private library/office, formal living and dining rooms, and a gourmet kitchen with new appliances. The kitchen's center island and breakfast area transition seamlessly into the family room, where a gas fireplace creates a cozy focal point. And did we mention the four-season sunroom, with views of the expansive lawn and patio? The second level is home to a luxurious primary suite featuring a spa-like bath with a soaking tub, oversized glass shower, and double walk-in closets. Three additional spacious bedrooms provide plenty of room for family or guests. Notably, the property features a 5-bedroom septic system, offering potential for future expansion. Added features include a 3-car garage, 9-foot ceilings, custom millwork, cooper roof overhangs, expansive unfinished basement (imagine the potential), and an irrigation system. Located across the street from Huntington State Park, you have access to over 1,000 acres of trails and scenic ponds. The home is also centrally located to NYC (car or train) and down county.

98 Hopewell Woods Rd, Redding

40 Deer Hill Rd, Redding
$1,225,000
4 Beds ⋅ 4 Baths ⋅ 24169044 MLS
Tucked away on a quiet, tree-lined street in the center of town, 40 Deer Hill Road offers the rare balance of privacy, comfort, and everyday convenience. The moment you step inside, you are greeted by cascading natural light from a dramatic wall of windows. At the heart of the home is the main living area, an inviting space anchored by a fireplace, soaring cathedral ceilings, and windows that frame the changing seasons and bring the outdoors in. Just beyond, the deck serves as a private retreat, perfect for morning coffee or summer dinners overlooking the serene property. The updated eat-in kitchen is designed for both everyday living and entertaining, featuring a center island, double ovens, and generous space to gather. With comfort and flexibility in mind, the home also features a first-floor primary suite with a fireplace, private deck, dual walk in closets and a spacious primary bath w/oversized shower and soaking tub, creating a true retreat. The main level is rounded out with a second bedroom, 2 additional baths, dining room, & an office. Upstairs are 2 large bedrooms sharing a full bath. A bonus room above the garage offers versatility, ideal as a second office, playroom, media room, or guest space. With extensive improvements, peaceful surroundings, and a location that offers convenient access to town, schools, commuter routes & dining, this is a home that effortlessly combines everyday ease with the space to relax, gather, & truly enjoy.OFFER DEADLINE TUES 4/28 12PM

40 Deer Hill Rd, Redding

5 Musket Ln, Redding
$1,200,000
4 Beds ⋅ 4 Baths ⋅ 24166384 MLS
Nestled on a tranquil cul-de-sac in bucolic Redding, this expansive 3,650 SqFt, 4 bedroom, 3.5 bath classic Colonial has been completely re-imagined and renovated, both inside and out. This 11 room home offers 5 fireplaces; a new eat-in kitchen with oversized island and large dining area with a wood burning fireplace; step-down living room with fireplace; formal dining room with custom millwork. The expansive family room boasts a cathedral ceiling, wood beams, floor-to-ceiling brick fireplace, built-ins and flows seamlessly into a four-season sunporch with skylights and scenic views of the deck, outdoor eating area, gardens and charming side yard brook. Upstairs, the private retreat primary bedroom has a gas fireplace, updated radiant heated floor bath, double walk-in closets. Two additional bedrooms share an updated bath. The 4th bedroom has been smartly converted into a convenient office/laundry room. The versatility of the home is further enhanced by an oversized finished LL activity room. This flexible space, which includes a fireplace, cedar closet, and a full heated floor bath, can easily serve as a generous fourth bedroom alternative or a dedicated recreation space. Located just 58 miles from Midtown Manhattan, convenient to award winning schools, parks, hiking trails, Mark Twain Library, New Pond Farm, shopping, and public transportation. This is more than a home...it is the ultimate destination where you can experience the perfect Connecticut country lifestyle.

5 Musket Ln, Redding

19 Mine Hill Rd, Redding
$1,195,000
5 Beds ⋅ 4 Baths ⋅ 24157688 MLS
Welcome to this pristine, sun-drenched, sophisticated contemporary colonial home in sought-after Southwest Redding. Designed with an open floor plan and walls of windows throughout, the home is filled with natural light and offers seamless spaces for both everyday living and entertaining -- The dramatic living room features soaring cathedral ceilings and a stunning floor-to-ceiling wood-burning fireplace as its centerpiece, flowing effortlessly into the dining room with striking floor-to-ceiling windows. The chef's kitchen showcases high-end finishes and a sleek modern design, including cherry cabinetry, quartz countertops, a gas cooktop, and a cozy eat-in area -- The main-level primary suite overlooks the private backyard and features a beautiful spa-like bath with double sinks, a soaking tub, and an oversized tiled shower. The open and spacious second level offers three additional light-filled bedrooms and a renovated hallway bath -- The remodeled walk-out lower level provides exceptional additional living space, including a playroom, exercise room, laundry area, cedar closet, abundant storage, plus a fifth bedroom and full bath, ideal for guests or an in-law setup -- Sliding doors lead out to the deck and hot tub. Relax on the spacious deck with modern cable railings while overlooking the serene and private two-acre property, professionally landscaped with mature plantings. Conservation land directly behind the home provides access to scenic hiking trails.

19 Mine Hill Rd, 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

127 Limekiln Rd, Redding
$1,125,000
5 Beds ⋅ 4 Baths ⋅ 24179911 MLS
Tucked behind a historic New England stone wall on 2.5 park-like acres, 127 Limekiln Road is a stunning 5-bedroom, 3.5-bath home commanding a magnificent presence. The exterior features a sweeping gravel driveway, detached 2-car garage, fieldstone chimney, copper gutters, a new cedar shingle roof, and a deep front porch. Inside, the bright and flexible floor plan is highlighted by a coveted main-level primary bedroom suite. Designed for both effortless daily living and grand-scale entertaining, the main floor boasts a seamless flow between the sophisticated formal dining room and a gourmet kitchen that opens to a bright breakfast nook. A stylishly appointed half bath adds ultimate convenience to this level. The home's architectural heritage takes center stage in the spectacular family room, where original hand-hewn ceiling beams contrast beautifully with white-washed brick accent walls and a massive wood-burning fireplace. The upper level includes incredibly spacious secondary bedrooms with classic deep-set dormer window alcoves, generous closet space, and two immaculate full baths. The outdoor living space features an expansive, level bluestone patio overlooking a vast, private lawn framed by mature trees. A masterclass in timeless Connecticut heritage, modern luxury, and lifestyle flexibility.

127 Limekiln Rd, Redding

6 Winding Brook Ct, Redding
$1,050,000
5 Beds ⋅ 3 Baths ⋅ 24173873 MLS
**Final offers due by Monday 5/18 at 5pm** Tucked at the end of a cul-de-sac down a long private driveway, 6 Winding Brook Ct offers the rare balance of quiet living and everyday convenience. Surrounded by mature landscaping and nature, this classic 5-bedroom Colonial captures the warmth and character so many buyers are searching for, while still being just minutes to Georgetown's restaurants and cafes and Redding schools. Built in 1971 and thoughtfully designed for both gathering and retreat, the home features beautifully scaled living spaces filled with warmth and charm. The inviting living room centers around a traditional wood-burning fireplace, while the spacious family room-with its dramatic fieldstone fireplace-serves as the heart of the home. Just beyond, a screened-in porch offers the perfect setting for morning coffee, al fresco dining, or quiet evenings listening to the sounds of nature. The eat-in kitchen offers a layout that comfortably supports modern living, flowing naturally into the home's gathering spaces. A dedicated office/library lined with built-ins creates an ideal work-from-home or reading retreat, while the dining room strikes the perfect balance between classic and comfortable.

6 Winding Brook Ct, Redding

25 Starrs Ridge Rd, Redding
$1,000,000
6 Beds ⋅ 5 Baths ⋅ 24181802 MLS
Nestled amidst a serene setting, this exceptional property offers the perfect blend of privacy, space and natural beauty. With 6 bedrooms, 4-1/2 bathrooms, and 4,955 sq. ft. of living space, this residence provides ample room for everyday living and entertaining. Situated on 5.15 acres of lush grounds, this home provides breathtaking views of a picturesque pond and enjoys a secluded setting. The main living area features 9 ft. ceilings, Brazilian cherry flooring, a gas fireplace, sliders to the rear patio & architectural details of crown molding, built-ins, recessed lighting and tray ceilings. At the heart of the home is a custom-designed chef's kitchen, seamlessly integrated into the open floor plan, creating an ideal gathering space and maintaining a natural connection to the family room. Additionally, the main level offers a spacious living room, elegant dining room, pantry, laundry room, half bath & access to the oversized 3 car garage. The upper level showcases an impressive primary suite with a vaulted ceiling, dressing room/walk-in closest, spa-inspired bath with steam shower, and stunning views of the pond. The finished 3rd floor with a 6th bedroom is ideal for an au pair, extended family, media room, playroom, or guest accommodations. The expansive unfinished walk-out lower level offers endless potential to create additional living space. Conveniently located near Rt 7, Danbury and Ridgefield, this home combines peaceful country living with easy commuter access.

25 Starrs Ridge Rd, Redding

149 Old Redding Rd, Redding
$990,000
3 Beds ⋅ 4 Baths ⋅ 24203939 MLS
You'll love this true nature lover's retreat, just 60 miles from NYC! Bordering 280 acre Topstone Park, this rare gem is a special place to call home. It underwent a total rebuild in 2003, resulting in a home that feels both timeless & entirely current. The professionally landscaped grounds burst with color creating a seamless connection between the indoors & the gorgeous natural landscape.At the heart of the home a chef's kitchen serves as the ultimate gathering spot, flowing into the dining/liv. areas. Here, soaring cathedral ceilings & large windows invite the light in.The charm of this home lies in its "not a cookie-cutter" personality. You'll find delightful nods to its heritage, like original oversized planked floors, exposed brick, paired with the rustic warmth of hand-hewed beams and hardwood floors that run throughout most of the home. With 3-4 beds and 2 fpls, the layout is as functional as it is beautiful. The primary suite on main level with walk-in closet & full bath is ideal. The lower level is a revelation, with high ceilings, a massive fireplace, bath & private entrance offering incredible potential. As a model of modern efficiency, a new roof was installed with a cutting-edge solar power system in 2023 with a prepaid 25-year assumable lease:this system currently generates more energy than the home consumes, providing a massive financial benefit. Having a nature sanctuary bordering your prop. with a beach, trails & boating is the ideal place to call home.

149 Old Redding Rd, Redding

86 Seventy Acre Rd, Redding
$985,000
4 Beds ⋅ 3 Baths ⋅ 24169087 MLS
Set on a level 2-acre property, bordered by over 200 acres of protected nature preserve with scenic trails, this exceptional home offers a rare blend of privacy, convenience, and outdoor beauty. The grounds are meticulously landscaped with exquisite stonework, creating stunning garden spaces, while an oversized backyard deck with a firepit provides the perfect setting for entertaining or relaxing in a peaceful, wooded backdrop. Inside, this split-level home features 4 bedrooms and 2.5 bathrooms, enhanced by skylights that fill the space with natural light. The updated kitchen features new cabinet doors and drawer fronts, stainless steel appliances, granite countertops, heated floors, and a skylight. It flows seamlessly into the dining area, where sliding doors lead directly to the expansive deck overlooking the private backyard. The living room offers both elegance and comfort with French doors, additional skylights, and a slider to the front yard, creating an inviting and airy atmosphere. The primary bedroom is complete with its own slider to the deck and serene backyard views, along with a beautifully updated primary bathroom. The lower level continues to impress, featuring a cozy fireplace and sliding doors that open to the backyard-ideal for additional living or recreation space. Completing the home is a two-car garage and an oversized driveway. This is a unique opportunity to enjoy refined living surrounded by nature, all while being in a prime West Redding location.

86 Seventy Acre Rd, Redding

45 Great Pasture Rd, Redding
$975,000
4 Beds ⋅ 3 Baths ⋅ 24071709 MLS
Antique lovers, prepare to fall in love! The historic Deacon Samuel Read house, a Federal style colonial, built in 1745 by the founding family of Redding, CT. Enter the stunning 11 X 24 entry hall with exquisite millwork, a gracious sweeping staircase and original wide plank oak floors that run throughout the house. 9+ foot ceilings on the first floor enhance the elegant formal living room and dining rooms, each with a wood burning fireplace to warm your guests. The spacious Sun room with stone floors looks out on the beautifully landscaped, sloping property. A "new" addition built in 1857 includes a cozy family room with a 3rd wood burning fireplace and access to a charming porch where you will sit in the warm weather and enjoy the designated scenic road in front of the homestead. An office/bedroom sits between the family room and the large country kitchen. The dining area in the kitchen opens to a stone patio that leads to the heated in-ground pool. There is a powder room area with a separate shower also on the main level. At the top of the staircase is a large landing area where you will find three generous sized bedrooms and 2 full baths. There are two attic areas that offer expansion possibilities. This property must be seen to fully appreciate the unique character and exudes from every corner. Redding CT is considered "a slice of Vermont" within 60 miles of New York. Come be awed by the area and this magnificent home!

45 Great Pasture Rd, Redding

Redding
$970,000
4 Beds ⋅ 4 Baths ⋅ 24138909 MLS
Stunningly renovated Vintage Antique. Up-to-date and yet still very authentic with beams and wide board floors. Set on over 2 level Acres ringed by trees for privacy; includes a lofted barn with possible potential to convert to a 1 BR guest ctg. The kitchen with new stainless appliances, granite and wood floors steps down to the cozy family rm warmed with a wood burning stove, built-in window seat, and sliders leading out to a large stone patio with sunset views. The formal dining rm has a built-in vintage corner cabinet and wide board flrs. The formal living rm also features wide board pegged flrs and is centered with an original stone fireplace updated with rustic gas logs. There is a main flr primary bedroom and ensuite bathrm w blt-ins and a large walk-in closet. Also on the main level in a quiet corner is an inviting library plus a den presently serving as an art studio. The upper level features two bedrooms with wide board floors, beams and antique doors; an updated full bath and a third bedroom presently a home office. In the past, this home served as a two-family so there is a second kitchen with a cork floor on the second flr which opens to a balcony/deck with steps to the private back lawn. The third flr highlights a guest/ in-law space that includes a full bath, bedrm and cozy TV rm. The property explodes with color in the spring and summer with perennials like peonies and hydrangeas and a large fenced garden. Metro North Train to NYC is just around the corner.

Redding

380 Black Rock Tpke, Redding
$955,000
4 Beds ⋅ 4 Baths ⋅ 24190805 MLS
Privately set back from the road on 2.94 wooded acres, this spacious Redding Colonial offers versatile living space, treetop views, and a layout designed for both everyday comfort and entertaining. The light-filled main level features an inviting family room with a gas fireplace, built-ins, and French doors opening to a private deck and backyard. At the heart of the home, the eat-in kitchen includes a center island, butler's pantry, and casual dining area, while separate formal living and dining rooms provide additional space for gatherings. Upstairs, the primary bedroom includes a walk-in closet and a freshly renovated en suite bathroom. Three additional bedrooms and an expansive recreation room offer flexible space for a home office, playroom, or a media room. The finished walkout lower level provides even more living space, with a full bathroom, ample storage, a workshop area, and a separate room well suited for an office, gym, or hobby space. A large backyard deck and pergola ideal for entertaining complete the property. The home is located in a sought after location with close proximity to Huntington and Putnam Memorial State Parks.

380 Black Rock Tpke, Redding

86 Fire Hill Rd, Redding
$950,000
4 Beds ⋅ 3 Baths ⋅ 24175213 MLS
Nestled on a peaceful cul-de-sac at the highest point in Redding, this meticulously cared-for 4-bedroom, 2.5-bath home offers the perfect blend of privacy, space, and charm on 2+ gorgeous acres. Surrounded by mature trees and natural beauty, the property provides a serene retreat while remaining conveniently close to local amenities, schools, and commuter route. Inside, spacious living areas are filled with natural light and designed for both comfortable everyday living and effortless entertaining. The home features a welcoming living room, a formal dining room, and a dedicated home office, providing flexible space for work, relaxation, and gatherings. The inviting family room offers a cozy fireplace, perfect for relaxing evenings with family and friends. The eat-in kitchen is well-positioned for convenience and flow, making entertaining a breeze. A powder room and large deck complete this main level. Hardwood floors under the existing carpet offer exciting potential to customize and enhance the home's timeless appeal. Head upstairs to find the Primary Bedroom Suite along with three additional bedrooms and a full bathroom. Hardwood floors under the existing carpet offer exciting potential to customize and enhance the home's timeless appeal. A large unfinished walk-out basement is already prepped for future expansion, complete with plumbing in place for an additional bathroom-offering endless possibilities for added living space, a guest suite, home gym, or recreation area.

86 Fire Hill Rd, Redding

2 Brick School Dr, Redding
$925,000
4 Beds ⋅ 3 Baths ⋅ 24137543 MLS
Set on a beautiful 2-acre property just off prestigious Umpawaug Road in West Redding, this classic 4-bedroom, 2 full and 1 half bath Gambrel Colonial offers timeless New England character with a charming farmhouse feel. Freshly painted with gleaming refinished hardwood floors, the home is filled with warmth and natural light. The main level includes a spacious living room with a wood-burning fireplace, a formal dining room, and a bright kitchen with ample cabinetry and counter space. Just off the kitchen is a large, finished family room-perfect for everyday living and entertaining-overlooking both the front and back yards, each with mature trees and natural landscaping. Upstairs are three generously sized bedrooms and a full bath. A flexible in-law suite with a separate entrance on the first floor can be reconfigured back into a main-level primary suite, subject to your preference. The basement offers additional potential, providing great space for a future workout room, TV room, or hobby area. While the home is in move-in condition, it is best suited for buyers seeking a fixer-an opportunity to update systems, improve efficiency, and personalize the home over time. With its classic Gambrel Colonial architecture, farmhouse charm, and desirable location near Ridgefield and Bethel, this property presents a compelling opportunity for buyers looking to create a home tailored to their vision-all within minutes to schools, parks, and convenient commuting routes.

2 Brick School Dr, Redding

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