Refine Search
Map
Sort by
$419,900
1 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24194246 MLS ⋅ Georgetown Place BLDG.
Welcome home to this charming, light-filled condo in the heart of Georgetown! Featuring an open floor plan with soaring vaulted ceilings and a ceiling fan, this inviting home is filled with natural sunlight and offers a bright, airy feel throughout. The thoughtfully updated interior includes beautiful laminate flooring (2020), a new dishwasher (2022), washer and dryer (2022), range and microwave (2023), and major mechanical updates completed in 2025, including a new heating system, electric heat pump, and hot water heater, providing comfort and peace of mind for years to come. A newer smoke detector with a 10-year battery adds another valuable update. The versatile loft offers endless possibilities as a home office, fitness area, guest room, or creative space. The spacious primary bedroom features a walk-in closet, and the home also includes a very large storage unit for all your extra belongings. The exterior of the building was freshly painted in 2024, enhancing the property's curb appeal. With its blend of modern updates, flexible living space, and convenient Georgetown location, this move-in-ready condo is one you won't want to miss!

56 Portland Ave Unit 3, Redding
$1,800,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 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
$999,500
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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
$1,329,000
5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24191583 MLS
The Rebecca Denison Homestead, established in 1708 with the present Greek Revival residence built in 1824, is a rare historic offering that beautifully combines architectural significance with modern-day living. Listed with the Connecticut State Historical Commission, this exceptional property is privately situated on 2.37 park-like acres and showcases timeless craftsmanship, meticulous maintenance, and thoughtful updates throughout. Offering more than 4,100 square feet of living space, this distinguished 12 room residence features 5 bedrooms, 4 updated full baths, and an updated half bath. Details include the original historic front door, exposed beams, paned windows, hardwood floors, five fireplaces (one gas fireplace in the family room and four wood-burning fireplaces), and abundant natural light throughout. Designed for both elegant entertaining and comfortable everyday living, the home offers gracious living and dining spaces with exceptional versatility, including a private entrance to a potential home office, study, or guest suite with Jotul cast iron gas stove. The chef's kitchen serves as the heart of the home, featuring high-end appliances, modern finishes, a large center island, generous pantry with prep sink, additional refrigerator, and abundant workspace. The kitchen flows seamlessly to the expansive deck, creating a wonderful indoor-outdoor living experience.

286 Black Rock Tpke, Redding
$899,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24189050 MLS
Expansive colonial home on 2.62 private acres in top West Redding location with mature trees & flowers, stone walls, large deck for outdoor enjoyment, & 3 car garage. This light-filled home offers a grand foyer with two story staircase, open to the adjoining living room & dining room for ease of entertaining. The elegant living room features custom millwork including the impressive coffered ceiling & custom fireplace surround. Gather family & friends in the lovely oversized dining room with graceful arched opening & hardwood floor. The heart of this spacious home is the 29' kitchen with center island & sunny dining area with walls of windows & French door to the deck. The kitchen opens directly to the soaring vaulted family room with dramatic floor to ceiling stone fireplace, skylights, built-in display shelving, hardwood floor, & double set of French doors to the inviting deck and sprawling level side yard. There's room to spread out on the second floor too - the stylish primary suite offers a vaulted ceiling, third fireplace, more custom built-ins, huge walk-in-closet, plus marble bath with double vanity, jetted tub, & separate shower. There are three additional spacious bedrooms, all with hardwood floors, including one with a private half bath, plus the shared hall bath, convenient laundry room, and back stairway. Don't miss the huge lower level & attic with tons of storage. Idyllic natural setting, yet moments to shops, restaurants, train, & just 60 miles to Midtown.

123a Peaceable St, Redding
$910,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24189421 MLS
Nestled on a quiet residential loop in one of Redding's desirable neighborhoods, this beautifully maintained 4-bedroom, 3 full and 1 half bath center hall Colonial offers timeless design, generous living space, and a secluded setting surrounded by mature landscaping. The gracious floor plan begins with a large living room that flows seamlessly into the formal dining room, where dramatic floor-to-ceiling windows fill the space with natural light and provide beautiful views of the yard. The kitchen combines warmth and function with rich wood cabinetry, soapstone countertops, stainless steel appliances, a large eat-in area, and generous workspace for everyday living. A butler's pantry between the kitchen and dining room provides additional storage, a prep sink, a desk/work area. The inviting family room features a classic fireplace, an oversized picture window, and hardwood floors. A screened porch and expansive deck overlook the backyard, offering an ideal setting for outdoor dining, relaxing, or entertaining. A highlight - the bonus suite above the garage, featuring a full bath and walk-in closet. Ideal as an in-law or au pair suite, guest quarters, home office, or recreation room. Upstairs, the primary suite is complemented by three additional bedrooms, including one with a charming loft that creates a unique retreat for reading, play, or additional sleeping space. This exceptional Colonial offers flexible living spaces, comfort, and a peaceful setting.

28 Winding Brook Ln, Redding
$869,900
3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24150713 MLS
Welcome to 119 Peaceable Street! Set on over 5 private acres in one of Redding's most picturesque settings, this lovingly maintained 3-bedroom, 3-bath home is being offered for the first time by its original owners. Thoughtfully cared for throughout the years, the home reflects pride of ownership at every turn. Large windows throughout the home flood the interior with natural light, creating bright, inviting living spaces while framing beautiful views of the surrounding property. Freshly painted inside and out and featuring a new water heater, this move-in-ready home offers the perfect balance of comfort and peace of mind. Step outside to your own private retreat, where an in-ground pool is surrounded by mature landscaping and serene natural beauty. Whether entertaining guests, enjoying a quiet morning coffee, or unwinding poolside, the setting offers exceptional privacy and tranquility. Rarely does a property combine this level of seclusion, natural beauty, and meticulous care. A unique opportunity to own a cherished home with over 5 acres of land in the heart of Redding.

119 Peaceable St, Redding
$65,000
ACTIVE UNDER CONTRACT Status ⋅ 24188701 MLS
Nestled in a peaceful setting, this lightly wooded property offers an ideal blend of privacy, natural beauty, and everyday convenience. With approximately 150 feet of road frontage and R-2 zoning, this property presents a wonderful opportunity to bring your vision to life. Enjoy the serenity of country living while remaining just minutes from shopping, dining, parks, schools, and commuter routes. Private well and septic required. Buyers to verify all information independently.

14 W Woodland Dr, Redding
$975,000
ACTIVE Status ⋅ 24188749 MLS
Listing is for 2 previously approved building lots, 4.09 acres and 3.479 acres. Lots have been rough graded, 2 septic's installed, build your dream house, build 2 homes, horse property? property tax is combined amounts of both lots. More photos to come

26 & Rd, Redding
$625,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24187187 MLS
Discover the quintessential Redding lifestyle in this charming circa 1898 home, perfectly positioned to enjoy the town's excellent schools, open space, and recreational opportunities like hiking, fishing, and kayaking. This 2/3 bedroom (3rd bedroom being used as a study) residence features a 3-bedroom septic system, central air and 2 full bathrooms, offering versatile living options. Step inside to discover timeless character with original hardwood floors and high ceilings. The living areas and 2 bedrooms are highlighted by four fireplaces-three decorative and one fully functional with a heater insert - adding warmth. The dining room boasts exposed beams, original leaded glass windows while newer windows throughout the remainder of the house ensure modern efficiency. Relax and unwind on the inviting covered and screened front porch. Need flexible space? The partially heated basement has been used as a home office, and a newer, spacious shed on the property offers endless potential as a workshop or a creative studio. Additionally, existing expansion plans-drawn up by previous owners-are available to help you visualize future possibilities (not submitted for town approval). Ideally located for an easy commute, you are just moments from Joel Barlow High School and the convenient shopping hubs of Bethel and Georgetown. A rare opportunity to embrace the peace of Redding living while staying connected to it all.

78 Black Rock Tpke, Redding
$435,000
1 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24181361 MLS ⋅ Georgetown Place BLDG.
Nestled in the charming village of Georgetown, this sun-filled first-floor end unit offers over 1,700 square feet of thoughtfully designed living space and a rare opportunity for convenient single-level living. The main level features a spacious one-bedroom primary suite with abundant windows that fill the home with natural light. The bright and inviting kitchen flows seamlessly into the dining area, creating an ideal space for everyday living and entertaining. A generously sized living room offers comfortable gathering space, while updated flooring throughout adds a fresh, modern touch. The finished lower level expands the living space with a large family room featuring a cozy fireplace, an additional bedroom or flexible office space, a full bathroom, laundry room, and ample storage. Move right into this light-filled home and enjoy all that Georgetown has to offer, including local dining, nearby train stations for easy commuting, and the convenience of Caraluzzi's just moments away.

56 Portland Ave Unit 9, Redding
$1,150,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24186160 MLS
Turn Key completely Renovated down to the studs! This 4-bed, 3.5-bath Cape Cod farm style home has 3400 SqFT.. New Roof, electrical, plumbing, HVAC & more! Entering notice a beautiful open floor plan w/ expansive natural light, w/ new hardwd floors through out. Main attraction.. the beautiful Kitchen! The white quartz countertops, waterfall island w/ plenty of seating, 2 tone color cabinets, VIKING appliances incl. oven/range-gas cooktop, hood, dishwasher & Refrigerator. Custom tile backsplash, under-cabinet lights, pot filler & abundant cabinetry... a chefs dream! Vaulted ceiling great/ dining room combo showcases exposed wood beams, recessed lighting & a floor to ceiling whitewashed brick fireplace. A huge flr plan where entertaining awaits! W/ 2 primary suites, including a mid-level grand suite w/ exterior access & potential in law! W/ a walk-in closet, private patio, freestanding soaking tub, custom tile waterfall shower w/ glass enclosure, high end faucets, mirrors and Kohler toilets. 2nd primary offers hardwd floors w/ a beautiful full bath w/ a tiled shower. Enjoy a covered trex deck overlooking yard. Upstairs bedroom has a private balcony overlooking the yard & pool, while 2nd bedroom shares a renovated full bath. The finished lower level provides additional living space, media/ Rec room w/ a pellet stove & ample storage. Amazing yard for hosting! Brand new white stone priv. driveway. Peace of mind living, quality craftsmanship w/ extensive updates! Don't miss out!

33 Old Stagecoach Rd, Redding
$305,000
ACTIVE Status ⋅ 24176562 MLS
A wonderful opportunity in the Putnam Park neighborhood of bucolic Redding Connecticut. Bring your dream home to life on 3.69 acres of raw undeveloped land. Potentially build to suit or buy direct. Previously an approved building lot for a 4 Bedroom home with a pool. Approximately one acre partially cleared and has a deeded right of way for access to a beautiful wooded rear lot. This is your chance to own a private slice of Redding paradise convenient to Georgetown, Easton, Rt 7. Showings strictly by appointment only, do not walk lot unaccompanied.

162 Lonetown Rd, Redding
$634,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24184928 MLS
Welcome to your dream home, ideally located just steps from Devil's Den Park Trail. Set on nearly an acre of beautifully private land, this fully updated property offers the perfect blend of comfort, space, and modern style surrounded by nature. From the moment you arrive, you'll notice the brand-new roof, new siding, freshly painted interior, and rich hardwood floors that flow throughout the home. New light fixtures add a bright, contemporary feel to every space, enhancing the home's clean and updated look. The kitchen has been completely transformed with high-quality Wren Kitchens cabinetry, brand new appliances, and elegant quartz countertops, creating a space that is both stylish and highly functional for everyday living and entertaining. The living room features an updated fireplace that brings warmth and character, making it a cozy focal point for relaxing evenings. Just off the dining area, step out onto an oversized patio complete with a fire pit, perfect for hosting gatherings or enjoying peaceful nights outdoors. Each bedroom and bathroom has been remodeled with attention to detail, offering comfort and a fresh modern finish throughout. The fully finished basement expands your living space with a bedroom and full bathroom, along with a convenient walkout entrance that adds flexibility for guests or multi-use living. An attached one car garage and oversized driveway provide plenty of parking and everyday convenience.

70 Dayton Rd, Redding
$1,075,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24182650 MLS
Imagine a home where the air is fresh & the pace of life slows. This is a true nature lover's retreat, just 60 miles from NYC. This gem underwent a total rebuild in 2003, resulting in a home that feels both timeless & entirely current. The professionally landscaped grounds burst with color and texture, 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 for in-laws. 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. 280 acre Topstone Park borders this beauty with a beach, trails & boating. The ideal place to call home!

149 Old Redding Rd, Redding
$699,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24182601 MLS
Welcome to this stunning 4-bedroom ranch home, nestled on 1.57 secluded acres while still being conveniently close to Georgetown Center, U.S. Route 7, and the train station. The main level features a cozy living room with a fireplace, a spacious kitchen with a dining area, and sliders that open to a large deck-perfect for outdoor entertaining. Enjoy the family room adorned with vaulted ceilings and skylights, along with three generous bedrooms, including a primary suite with a full bath. The lower level offers ample storage, a laundry area, and a versatile studio or in-law apartment complete with its own kitchen and laundry. Don't miss the detached 2-car garage, large parking area, potting shed, full house generator and garden to complete this beautiful property.

Redding
$899,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24181978 MLS
Experience modern luxury in this beautifully renovated Colonial. Newly seeded lawn! A grand double-door entry opens to a bright foyer. The all-new gourmet chef's kitchen boasts a massive waterfall quartz island, high-end appliances, and pot filler. The open-concept main level flows into a spacious living room with brick fireplace, while a secondary family room features a dramatic floor-to-ceiling stone fireplace and custom built-ins. Upstairs, the expansive primary suite serves as a true private retreat, featuring a generous walk-in closet and a stunning spa-like bathroom complete with a deep soaking tub and a double sink. Two additional bedrooms on this level provide ample space for family or guests. The newly finished, versatile attic showcases beautiful cathedral ceilings and currently serves as a family room and gym, offering endless possibilities for your lifestyle needs. The main level features a first-floor bedroom, ideal for guests or home office, plus a mud room with laundry area. The finished walk-out basement is an entertainer's dream with wet bar, movie theater with built-in speakers, and contemporary powder room. Outside, enjoy a private backyard with spacious deck. Two-car attached garage and semi-circular driveway accommodate multiple vehicles. Perfectly positioned in desirable Georgetown neighborhood, offering peaceful wooded surroundings with convenient access to shopping, dining, and major routes.

299 Redding Rd, Redding
$1,200,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24178497 MLS
Classic New England charm meets modern luxury in this beautifully updated 1921 Colonial. Perfectly situated just minutes from the quaint Georgetown boutique shops , restaurants, and Route 7. Set on nearly half an acre lot, this home offers effortless living and entertaining inside and out. The heart of the home features a renovated eat-in kitchen with timeless marble countertops, a 4 seated island, and newer stainless-steel appliances. Entertain with ease in the formal dining room, unwind by the gas fireplace in the living room, or settle into the versatile sunroom - equally suited as a home office. Upstairs, the primary suite is a true sanctuary, complete with gas fireplace, a spacious walk-in closet and renovated spa-inspired bathroom with soaking tub. Two additional bedrooms and a well-appointed hall bath round out the second floor. The third level offers a wonderfully flexible carpeted family room - ideal as a playroom, media space, or guest retreat. Step outside to a stunning country backyard oasis with a fresh 1,200 square foot bluestone patio equipped with a built in DCS grill and cozy fire pit nook. With its flat, usable property, timeless architectural character, and every major update already done, this home is a rare find in one of Redding's most convenient locations.

207 Redding Rd, Redding
$1,245,000
4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24158172 MLS
Private Cul-de-Sac Colonial on 2.95 Acres in Redding! Desirable custom-built Center Hall Colonial privately set at the end of a cul-de-sac abutting protected Green Acres land for exceptional privacy and natural beauty. Professionally landscaped with classic stone walls and mature trees, picturesque views of neighboring horse property and ample space for a pool and tennis court. A dramatic two-story foyer with custom crown molding sets the tone for the home's refined yet inviting interior. The formal living room boasts a wood-burning fireplace with marble surround. The formal dining room is enhanced by custom millwork, perfect for entertaining. The open floor plan flows effortlessly into the spacious kitchen and 2 family rooms, each with wood-burning fireplaces. The walk-out finished lower level provides additional living space ideal for a media room, home office, gym, or guest suite. Located in the sought-after town of Redding, known for preserving the tranquility and beauty of traditional New England countryside, this home offers both privacy and convenience. Redding boasts an award-winning school system and has twice been ranked the #1 small town by Connecticut Magazine. With easy access to I-95, I-84, the Merritt Parkway, Metro-North rail service to New York City, and major airports. 11 Long Meadow Lane is ideally positioned for both commuting and weekend living. The NY Times aptly describes Redding as "an upscale town with upcountry style.

11 Long Meadow Ln, Redding
$999,000
6 Beds ⋅ 5 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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
$1,275,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24176717 MLS
Known as the Aaron Davis House, ca. 1848, this exceptional historic Georgetown residence blends authenticity, artistic craftsmanship, and modern versatility in one of Redding's most cherished neighborhoods. Set on a beautifully landscaped property, it offers a rare opportunity to own a significant piece of local history while enjoying spaces thoughtfully adapted for contemporary living. Original historic glass windows, period architectural details, and carefully preserved character reflect the home's rich heritage, while custom renovations showcase an extraordinary level of artistry throughout. Hand-applied decorative finishes, bespoke design elements, & thoughtfully curated materials create interiors that are both timeless & distinctive. Light-filled living spaces, inviting gathering areas, & a seamless connection to the spacious deck & surrounding gardens lend the home warmth, texture, and sophistication. A truly remarkable feature of the property is the detached carriage house, rebuilt on the site of the original barn and extensively updated. Offering 2 extended garage bays below w/48amp car charger & approximately 1,067 SF of finished space above, the structure serves as a private studio. Features include a private office, loft-style workspace with skylights, kitchenette, full bath, and a deck overlooking the grounds. Whether used for remote work, creative pursuits, a guest space, or simply as a place to escape and recharge, it is an exceptional extension of the property

18 Church St, Redding
$799,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24178600 MLS
Beautifully professionally landscaped, level 2-acre lot on the peaceful end of Newtown Turnpike, this charming 3-bedroom, 2.5-bath. Cape combines classic character with modern living. The home has been meticulously maintained and upgraded, offering a perfect retreat in the heart of Redding. Step into the heart of the home: a brand-new custom kitchen featured in the recently added expansion. Designed with both style and functionality in mind, the kitchen boasts white shaker cabinets, quartz countertops, a spacious center island with built-in microwave and beverage fridge, and high-end stainless steel appliances, including a gas cooktop and double-door refrigerator. Two large gold pendant lights and recessed lighting highlight the vaulted ceilings, creating a bright and luxurious atmosphere ideal for cooking and entertaining.

471 Newtown Tpke, Redding
$1,395,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24178330 MLS
This unique property offers the perfect blend of living, working and investing in a picturesque and convenient setting. For 15 years, the current owner has enjoyed a seamless "work from home" lifestyle, with a spacious upstairs apartment above the main building and store. The property also includes a separate retail cottage, ideal for generating rental income or expanding your business operations. With two commercial retail lots sold as one parcel, the property offers endless possibilities. The main building and retail cottage are perfect for businesses such as a shop, restaurant, pub, gourmet market, coffee shop, brewery, garden center, florist, wellness center, therapist office, physical training studio, ice cream shop, or even an AirBnb rental. The versatility of this property makes it a rare find. Located in a prime transit-oriented district, the property is directly across from the Redding Train Station and within walking distance of the Post Office and a shopping center featuring a pizza parlor, liquor store, hair salon and more. A feasibility study is available for CT 8-30g Affordable Housing with potential for 7-15 apartment units or up to 25 units with a clubhouse, making it an excellent investment opportunity. Impeccably maintained, the property features multiple patios, lush gardens, and ample parking. The current business, Fleur De Lis Antiques and Design, is available for purchase. This one of a kind property is ready to bring your vision to life.

4 Long Ridge Rd, Redding
$1,149,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24176689 MLS
Ideal setting and location! This spacious 12 room split level home tucked away on a country lane in the heart of Redding, offers the perfect blend of privacy, charm, and versatility. Set on 3.64 acres, this unique property features a spacious main residence with an open floor plan providing easy living, hardwood floors, an expansive primary suite, in-ground concrete pool, Ironwood deck, and peaceful wooded surroundings, creating an ideal setting for relaxing or entertaining. There are three levels of living with an additional finished area in the walk out basement. A detached two-car garage with space above provides excellent potential for guests, extended family, or a home office. This special property delivers the quintessential Redding lifestyle with easy access to commuting routes and nearby amenities.

16 Shady Ln, Redding
$1,745,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24177771 MLS
***Rare turn-key opportunity at an unbeatable price point*** For buyers seeking exceptional craftmanship, serenity, a strong sense of community, award winning schools and uncompromised value. 2 Longwood Drive is a rare opportunity to purchase a 6,200+ square foot luxury home in southern Redding below recent comparable sales. Experience the exceptional lifestyle that has made Redding one of Fairfield County's most desirable towns for discerning buyers. Known for its scenic landscapes, extensive open space, award-winning parks, the Redding Country Club, and highly regarded public schools, Redding offers an unmatched quality of life just over an hour from Manhattan. With convenient access to Metro-North stations in Westport, Wilton, and West Redding, commuting and weekend travel are effortless. This 6,259 square foot custom built and meticulously maintained colonial is a must see, perfectly positioned on 2.72 professionally landscaped acres in one of Redding's most sought-after neighborhoods. Surrounded by mature trees, rolling lawns, and classic New England charm, the property provides a peaceful retreat while remaining just minutes from Redding schools, hiking trails, top-rated restaurants, shopping, cultural attractions, and the neighboring towns of Ridgefield, Westport, and Wilton.

2 Longwood Dr, Redding
$7,725,000
7 Beds ⋅ 13 Baths ⋅ ACTIVE Status ⋅ 24164249 MLS
Exquisite Nantucket-style country estate magnificently sited on seven sprawling acres in Redding, CT's coveted Umpawaug neighborhood. Comprised of three extraordinary residences, this masterfully crafted 2008 HOBI award-winning compound offers 13,904 sf of carefully constructed living space with meticulous architectural details, effortlessly balancing timeless elegance with modern function. The main residence greets with a sweeping two story entry bathed in natural light, flanked by gracious formal living & dining rooms with fireplaces. The heart of the home, a chef's kitchen with custom cabinetry, high-end appliances, butler's pantry & French doors to an expansive terrace, seamlessly integrated with spectacular grounds. Additional main-level highlights include great room & study with fireplaces, steps from a serene covered porch; mudroom, full bath, & attached three-car garage. Upstairs, a primary suite sanctuary with fireplace, sitting room with wet bar, dressing room with custom cabinetry & spa-like bath with soaking tub & steam shower. Completing the 2nd floor, four additional bedrooms featuring en-suite baths & walk-in closets, family room and laundry. On the 3rd level, 2nd office, gym, half bath & ample storage. Elevator to wine cellar, home theater, billiards room & walkout au pair suite; commercial grade utilities & generator. Award-winning pool house, carriage house with in-law suite, heated gunite pool, spa & manicured grounds complete a remarkable legacy property.

206 Umpawaug Rd, Redding
$1,325,000
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24175555 MLS
You will take a deep breath as soon as you drive through the beautiful and tranquil landscape of this part of Redding. As you approach the driveway you are greeted by a large antique barn for storing Animals/Cars/Toys. driving down the driveway you see the large colonial farmhouse with expansive front porch 5 bedroom and 4 full baths. The flexible open floor allows for easy daily life as well as being great for entertaining. Kitchen has a huge pantry and large island overlooking a stone fireplace in Living room and dining area. 1st floor ensuite with entrance to front porch(Could be great for in-law, nanny or office.) A Large mudroom leads to an oversized 3 car garage. There is a huge playroom over the 3 car garage. The large patio is a great spot to sun or watch nature. Miles of hiking trails are steps from the front door. The house has a large walk up attic for storage in addition to the 2000 unfinished sq ft in basement with walkout utility garage door.

28 Goodridge Rd, Redding
$995,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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
$499,000
ACTIVE Status ⋅ 24172380 MLS
Glorious interior lot in pine setting on scenic Umpawaug Rd. Owner architect/builder can design and build to suit. See listing #170511696 Owner/agent

65 Umpawaug Rd, Redding
$900,000
ACTIVE Status ⋅ 24172383 MLS
Exceptional land on scenic Umpawaug Rd. House site overlooks spectacular quartz quarry to the rear with panoramic views to the front. Perfect for breathtaking hideaway in the country. Owner/architect can design and build to suit. Additional land available. Owner/agent

67 Umpawaug Rd, Redding

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.