Refine Search
Sort by
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

28 Winding Brook Ln, Redding
$900,000
4 Beds ⋅ 4 Baths ⋅ 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

33 Topledge Rd, Redding
$900,000
3 Beds ⋅ 3 Baths ⋅ 24168459 MLS
Welcome to this well maintained 3-bedroom, 3-bath Colonial ideally situated on a quiet cul-de-sac with stunning front yard views and a peaceful setting. This spacious home offers an inviting layout designed for both comfortable living and entertaining. The sun-filled living room flows seamlessly into the formal dining room featuring a bay window overlooking the picturesque front yard. The custom kitchen is equipped w/ stainless steel appliances, granite countertops, a center island, and an abundance of cabinet space. Adjacent to the kitchen is the large family room featuring a vaulted ceiling and fireplace, offering the perfect space for gathering with family and friends. A dedicated first-floor office includes custom built-in desks and cabinetry, creating the ideal work-from-home space. A convenient full bath completes the main level. Upstairs, the expansive primary suite offers generous closet space and a luxurious en-suite bath with a soaking tub and oversized separate shower. Two add'l spacious bedrooms and another full bath complete the second floor. The finished walk-out LL provides exceptional living space including an additional office area and recreation room, ideal for playroom, gym, media room, or guest space. Outdoor living is just as impressive with a screened-in porch featuring a ceiling fan, a spacious deck. Enjoy direct access to Topstone Park, a 280-acre facility that offers hiking trails beautiful sand beach and guarded swimming area w/kayaks and canoes.

33 Topledge Rd, Redding

19 Marchant Rd, Redding
$900,000
3 Beds ⋅ 3 Baths ⋅ 24163881 MLS
Set on over six private, lightly wooded acres, this expansive single-level home offers more than 3,500 square feet of living space in a highly desirable Redding location, just 3 minutes to the West Redding train station with direct access to Grand Central. Hardwood and tile flooring run through the main living areas, with carpeted bedrooms for comfort. The home features a sunken living room with fireplace and vaulted ceiling, a family room with its own fireplace and vaulted ceiling, and abundant windows providing exceptional natural light. A large custom cabinet with stone countertop adds both function and style. The living room, dining room, and kitchen all open to patios, creating seamless indoor-outdoor living. The primary suite includes a large walk-in closet and oversized bath with tub and separate shower. A second bedroom offers an ensuite bath with separate tub and shower. Additional features include a two-car garage under the home, brick facade, whole-house generator, fenced gardens, and landscaped grounds. Property offers "first cut" subdivision potential and is bordered by a scout camp for added privacy. A rare opportunity to enjoy spacious, single-level living on significant acreage with both privacy and future potential in a prime Redding setting.

19 Marchant Rd, Redding

76 Pocahontas Rd, Redding
$885,000
4 Beds ⋅ 3 Baths ⋅ 24178050 MLS
This distinct 4-bedroom Colonial offers a rare blend of charm and modern luxury. Originally built as a ranch in 1962, the home was completely transformed in 2000 with a full second-floor addition, resulting in a unique, airy open floor plan. A stunning 2-sided brick fireplace serves as the heart of the home, artfully dividing the living spaces while maintaining a seamless flow. The chef's kitchen is a standout, featuring a restaurant inspired American 5 burner gas range, a large center island with new quartz countertops and a wide picture window that frames the lush yard. Flooded with natural light through oversized windows, the home feels vibrant and inviting throughout. The second floor hosts an expansive primary ensuite retreat, accompanied by three additional bedrooms. A versatile den or office on the first floor provides perfect space for remote work. Situated on a flat, park-like property, the home is surrounded by mature trees and shrubs for complete privacy yet close enough to meet your neighbors. Ideally located, you can walk to the scenic trails of Putnam Park and Huntington State Park for hiking, biking horseback riding, kayaking and fishing. Enjoy the close proximity to shopping and dining in Bethel, Georgetown and Ridgefield, plus access to Redding's highly rated schools. Redding, dubbed the Vermont of Fairfield County, offers a serene, community focused lifestyle that is truly a special. A wonderful place to call home.

76 Pocahontas Rd, Redding

11 Fire Hill Ln, Redding
$860,000
4 Beds ⋅ 3 Baths ⋅ 24194618 MLS
Designed by acclaimed architect George Van Geldern, this exceptional mid-century modern residence is a rare opportunity to own an architecturally significant home that blends timeless design with its natural surroundings. Tucked away on a quiet cul-de-sac in one of Redding's most picturesque locations, 11 Fire Hill Lane is set on two private, park-like acres, offering the perfect balance of privacy, tranquility, and modern living. Just a 9-minute drive to the Redding Metro-North station, the home provides convenient access for commuters while maintaining the serenity of its secluded setting. Rich wood finishes, exposed beams, clean architectural lines, and expansive windows fill the home with natural light while framing the surrounding landscape. The thoughtfully designed floor plan creates a seamless connection between the indoors and nature. A striking Kiva-style fireplace and a cozy wood-burning stove serve as distinctive focal points, adding warmth, character, and authentic mid-century charm. The residence features four spacious bedrooms with optimal storage, two full bathrooms, one half bath, and a two-car garage, offering a layout suited everyday living and entertaining. The desirable first-floor primary suite includes a private en-suite bathroom, providing the convenience of one-level living. Outside, the spectacular two-acre property provides privacy surrounded by mature trees, two large sheds and room for a pool, presenting the opportunity to create your own oasis

11 Fire Hill Ln, Redding

123-A Peaceable St, Redding
$850,000
4 Beds ⋅ 4 Baths ⋅ 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.

123-A Peaceable St, Redding

39 Seventy Acre Rd, Redding
$850,000
3 Beds ⋅ 2 Baths ⋅ 24173176 MLS
Idyllic & sprawling country ranch on 1.38 private acres with fenced in backyard in top West Redding location. Charming yet sophisticated with extensive designer updates throughout. Total 1,753 sf of light, bright & open living space, plus additional 963 sf of nearly finished space in the expansive walk-out lower level with wood grained tiled floor & flexible space for fitness, game room, or home office. Convenient one level living at its finest including great room featuring inviting fireplace with wood stove insert & wall of custom built-in display shelves, open to the bright dining room with triple windows & adjoining newly remodeled kitchen. The kitchen is a chef's dream with stunning white quartz countertops, custom recessed panel cabinetry, floor to ceiling steel blue tiled backsplash/walls, slate floor, & high-end Bosch appliances, perfect for preparing gourmet meals & entertaining guests. Total 3 bedrooms/2 full baths including the elegant primary suite with luxe remodeled bath featuring quartz topped vanity, custom tiled shower, & generous walk-in closet with laundry. Two additional generous bedrooms with updated hall bath featuring subway tiled walls & pedestal sink. Don't miss the walk-up attic, perfect for storage or future expansion potential. Scenic level property featuring inviting bluestone patio with stone seating walls & lush level private backyard. Additional: two car garage; automatic generator; most convenient Redding location; & just 69 miles to Midtown!

39 Seventy Acre Rd, Redding

119 Peaceable St, Redding
$840,000
3 Beds ⋅ 3 Baths ⋅ 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

37 Lamppost Dr, Redding
$840,000
4 Beds ⋅ 3 Baths ⋅ 24175748 MLS
Highest and best due 6/1/@ 4PM Nestled on a quiet cul-de-sac in desirable West Redding, this inviting 4 bedroom, 2.5 bath home offers the perfect blend of comfort, space, sustainability, and commuter convenience. Located in a town affectionately known as the "Vermont of Connecticut," Redding is cherished for its scenic wooded landscapes, top ranked schools, and peaceful atmosphere. Inside, a thoughtfully designed floor plan provides both functionality and warmth. The spacious front to back living room features a classic wood burning fireplace, creating the perfect gathering space for relaxing or entertaining. A formal dining room with beautiful built in banquet cabinets, while a private home office offers flexibility for today's work from home lifestyle. A standout feature is the expansive bonus room, currently used as an art studio, offering endless possibilities as a playroom, media room, gym, or creative space. Upstairs, four generously sized bedrooms and two full baths provide comfortable accommodations for family and guests alike. Outdoor living is equally inviting. The large screened in porch is the ideal place to enjoy a quiet morning coffee or unwind with an afternoon cocktail while taking in the peaceful surroundings. Just beyond, the paver patio creates the perfect setting for roasting marshmallows, entertaining guests, or simply enjoying the idyllic scenery that makes Redding so special.

37 Lamppost Dr, Redding

35 Deer Spring Rd, Redding
$810,000
4 Beds ⋅ 4 Baths ⋅ 24177343 MLS
Classic New England colonial with 3 car garage and 2.05 sprawling level acres with in-ground pool. This home has been lovingly cared for by the same owners for over 30 years. Traditional center hall layout with welcoming entry foyer that leads to the formal living room with hardwood floor, fireplace, and sliders to the rear terrace flanked by floor to ceiling built-in bookshelves; plus elegant dining room with crown and chair rail moldings. Expansive kitchen with center island, sunlit breakfast nook with bay window, skylights, plus adjoining patio overlooking the pool and gardens. The impressive 24' x 22' level great room with full bath makes a wonderful family room, main level primary or guest bedroom, and features walls of windows and sliders to the picturesque backyard. The second floor offers the spacious primary suite with adjoining sitting room, hardwood floors, and private bath; plus two additional cheery bedrooms with shared hall bath. Of note: central air; garden shed; pull down attic with storage; plus expansive, partially finished lower level featuring abundant storage space, workshop, and rec room. Idyllic setting and desirable location, convenient to the West Redding train station and just 69 miles to Midtown. Note: the pool has not been opened in some time and is being sold as-is. It has a vinyl liner which may need to be replaced. Amazing opportunity and unlimited potential in this stately home!

35 Deer Spring Rd, Redding

148 Old Redding Rd, Redding
$800,000
4 Beds ⋅ 3 Baths ⋅ 24169820 MLS
HIGHEST and BEST By TUESDAY MAY 5TH. Tucked away, off the beaten path and down a quiet country lane, this charming 4-bedroom, 2.5-bath Cape Cod home offers a peaceful retreat surrounded by nature. With more than 2,300 square feet of living space, this well-loved home combines warmth, character, and endless potential. The main level features two bedrooms, a full bath, and a flexible layout that includes a kitchen, dining room and living room with a fireplace. A beautiful sun-room overlooking the woods provides a special retreat to unwind from the day. An office/library area with built-in shelves and access to the deck provides the perfect space for working or relaxing. An additional roughed-in bath offers an opportunity for future customization. Upstairs, you'll find two bedrooms and another full bath. A walk-in attic with an adjacent walk-in closet leads to an additional attic space above the garage, presenting excellent storage or expansion possibilities. The partially finished walk-out lower level adds valuable living space, complete with an updated family room with fireplace, laundry area, half bath, updated lighting, and durable LVT flooring-ideal for extended living, guests, or a potential in-law setup.

148 Old Redding Rd, Redding

429 Rock House Rd, Redding
$800,000
4 Beds ⋅ 3 Baths ⋅ 24155279 MLS
Privately set on a serene back lot, this spacious 4-Bedroom, 2.5-Bath Colonial offers the perfect blend of classic charm and everyday comfort. Gleaming Hardwood Floors run throughout the home - excluding the Kitchen and Baths - adding warmth and continuity to the well designed layout. The Main Level features a gracious Formal Living Room with stately FP and Slider access to the expansive, well-maintained wood deck-ideal for relaxing or entertaining while enjoying the changing seasons. The Formal Dining Room is accented by a bright bay window-in fact-there is an abundance of windows throughout the home that allows for plenty of natural light. All Four Bedrooms are located on the Upper Level, offering privacy and a quiet retreat. Mechanical updates include a new furnace and hot water heater installed in 2021. The property features lovely level grounds bordered by light tree cover, creating a peaceful and usable outdoor space. A wonderful opportunity to own a spacious home in a desirable Redding location-Privacy, Comfort, and Natural Beauty all in One! Sale subject to probate approval.

429 Rock House Rd, Redding

471 Newtown Tpke, Redding
$799,000
3 Beds ⋅ 3 Baths ⋅ 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

18 Ledgewood Rd, Redding
$797,500
4 Beds ⋅ 3 Baths ⋅ 24169652 MLS
*Best & Final Offers by Monday (5/4) at 2pm* Welcome to 18 Ledgewood, a beautiful Contemporary home offering 2,900 square feet of well-proportioned living space in a desirable Redding, Connecticut setting. This 4-bedroom, 3 full bath home features a flexible layout with a potential main-level 5th bedroom and full bath, ideal for guests, extended family, or a private home office. The home offers generously sized living and dining areas with great natural light, providing a strong foundation for both everyday living and entertaining. The kitchen with breakfast bar features deck access to allow for easy indoor and outdoor entertaining. Upstairs, the additional bedrooms are spacious and well laid out, including a primary suite with ample closet space. Key improvements include a brand new roof and newer mechanicals, offering peace of mind on major components. A finished lower level walk-out to the backyard which is highlighted by an in-ground pool, creates the perfect setting for outdoor enjoyment and summer entertaining. With its exceptional layout, substantial square footage, and prime Redding location, this home presents a fantastic opportunity in a highly desirable area.

18 Ledgewood Rd, Redding

6 Great Pond Ln, Redding
$775,000
3 Beds ⋅ 1 Baths ⋅ 24191966 MLS
Discover a private Mid-Century Modern sanctuary tucked at the end of a cul-de-sac, approached by a quiet wooded lane and set on 2.68 private, rolling acres. Designed to embrace its natural setting, the upper-level living spaces were completely renovated in 2022, with soaring wood ceilings, oak hardwood floors, walls of glass, custom mahogany windows, a massive fireplace, and 2 sets of Andersen sliders opening to a huge deck overlooking lush perennial gardens and an in-ground pool. The show-stopping chef's kitchen features a Wolf induction range, undercounter oven, Bosch refrigerator, Electrolux dishwasher, custom granite countertops with bar seating and waterfall edge, and a 140-bottle wine refrigerator. Three spacious bedrooms with gorgeous wood ceilings are located on the garden level, including a primary bedroom with a beautiful built-in bookcase and sliders to a private outdoor garden area. A full bath and laundry area complete this level. The spectacular backyard features a gunite pool, lush landscaping, newly refinished expansive deck, and partially fenced grounds. Recent improvements include new lower-level flooring, ductless HVAC (2023), and a whole-house generator. Near the Ridgefield border in West Redding, with easy access to Route 7 and I-84, this exceptional property offers the perfect balance of privacy, natural beauty, and convenience. A truly remarkable home made for both entertaining and unwinding. Come experience it for yourself.

6 Great Pond Ln, Redding

172 Gallows Hill Rd, Redding
$760,000
2 Beds ⋅ 2 Baths ⋅ 24161711 MLS
Casually elegant stone & clapboard ranch on stunning property in most desirable West Redding. Park-like setting w/extensive flowering gardens, specimen trees, stone walls, stone patios, & inviting covered pergola seating area. This sophisticated home beckons w/glass breezeway between the 2 car garage w/cheery cupola & the main home w/fieldstone foundation, chimney, & cladding. Generous proportions & open flow including 1,373 sf on the main level plus 735 sf in the walk-out lower level w/total 2-3 BRs & 2 full baths. The heart of this home is the large living room w/custom built-ins & stone fireplace w/wood burning stove insert. The DR, open from the LR for ease of entertaining, features wide board floors & custom built-in shelving/lower cabinets flanking a large picture window. The main floor also features the bright white kitchen w/open shelves, S/S appliances, pantry & views to the stone patio/gardens. The bedroom wing offers one large BR w/multiple closets; 2nd BR w/built-in shelving, currently used as a den; plus the hall bath w/updated vanity & tub/shower. The walk-out lower level has been completely updated to create flexible living space including a family room w/2nd fieldstone fireplace; optional primary suite or guest bedroom w/French door to the stone patio; & full bath featuring glass basin sink & deep soaking tub. Many updates including exterior repainted & brand new roof (2025). Top location in sought after Redding, the "VT of CT," yet just 61 miles to Midtown.

172 Gallows Hill Rd, Redding

27 Apple Ln, Redding
$750,000
3 Beds ⋅ 2 Baths ⋅ 24181066 MLS
Idyllic country ranch in park like setting on 1.1 park like acres on desirable West Redding cul de sac with detached 2 car garage. This elegant home offers mature trees, flowering perennial gardens, deck, pea gravel patio w/stacked stone outdoor fireplace, & expansive rolling lawn. The sprawling main level is light, bright & open with newly refinished bleached hardwood floors & freshly painted interior. Ideal for gracious living & entertaining - enjoy the spacious living room w/brick fireplace flanked by built-in display shelves, plus the large family room/dining room featuring a built-in wet bar, sliders to the balcony/deck, more built-in shelving, plus open to the sunny kitchen showcasing brand new S/S appliances, breakfast nook, & adjoining deck. Step down from the kitchen to the dramatic vaulted sunroom, drenched in natural light, w/skylight, ceiling fan, wood burning stove, & double set of sliders to the deck for outdoor enjoyment. Total 2,265 sf on main & lower levels w/3 bedrooms, one full & one half bath. The primary bedroom offers a full wall of closets w/custom closet systems. All of the bedrooms offer hardwood floors & share the newly refreshed main floor bath with tub/shower enclosure, new fixtures & plantation shutters. Total 420 sf in the walk-out lower level rec room/den with new luxury vinyl plank flooring & newly remodeled powder room. Many additional updates (see Public Remarks Addendum). Top location, convenient to shops/train, & just 57 miles to Midtown.

27 Apple Ln, 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

29 Lonetown Rd, Redding
$725,000
3 Beds ⋅ 3 Baths ⋅ 24195147 MLS
Welcome to 29 Lonetown Road, a timeless 1915 Colonial, where historic character, thoughtful updates and an extraordinary setting come together. Set on 1.5 picturesque acres, this lovingly maintained home has been cherished by the same family for more than 36 years and is ready for its next chapter. Inside, original hardwood floors, built-ins and beautiful period details create warmth and character throughout. The main level offers a gracious living room anchored by a stone fireplace, a formal dining room, and a stunning four-season sunroom filled with natural light. The large kitchen blends vintage charm with a commercial-inspired feel, featuring a 6-burner Garland range, center island, generous prep space, pantry with French doors, and easy access to both the bluestone patio and rear deck for indoor-outdoor entertaining. A convenient powder room completes the first floor. Upstairs, the spacious primary suite offers a light-filled retreat with an oversized bath featuring skylights, large walk in shower and dressing area, while 2 additional bedrooms share a full hall bath. Outside, enjoy spectacular sunsets, a peaceful brook winding through the property, enclosed vegetable garden and a detached 2-car garage. Across the street, the Lonetown Marsh Wildlife Sanctuary offers scenic walking trails, protected open space and year-round opportunities to enjoy nature just steps away. A rare opportunity to own a beautifully preserved piece of Redding history in an idyllic setting.

29 Lonetown Rd, Redding

Redding
$715,000
4 Beds ⋅ 3 Baths ⋅ 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

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

9 Deacon Abbott Ln S, Redding
$695,000
4 Beds ⋅ 3 Baths ⋅ 24205858 MLS
There are multiple offers-all bids are to be submitted by Tuesday 9/15 at noon with their highest & best terms. Welcome to this lovely, well-maintained home cherished by its long-term owner. Situated on a highly sought-after, level cul-de-sac lot, this property offers 4 bedrooms, 2.5 baths, and a perfect blend of comfort and potential. Inside, you are greeted by spacious, light-filled rooms. The living room features large Anderson windows and a stunning stone fireplace with a raised hearth. The heart of the home is the country kitchen, complete with a cozy breakfast nook and sliding glass doors that lead to a sprawling deck. Just off the kitchen, step down into the inviting family room, which opens to a wonderful screened-in porch overlooking the park-like backyard. The main level also features a renovated powder room and a convenient laundry area. Upstairs, you'll find four generously sized bedrooms and two full baths. The walkout lower level offers excellent potential for future finished space. Outside, the home boasts a rustic stone wall, attractive landscaping, a paved driveway, and a newer roof. Located just moments from the quaint Redding town center-home to summer concerts, parks, and schools. This home has been lovingly maintained and is ready for your personal updates. A truly great value in an unbeatable location!

9 Deacon Abbott Ln S, Redding

78 Black Rock Tpke, Redding
$635,000
2 Beds ⋅ 2 Baths ⋅ 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 home (3rd bedroom being used as a study) also features and 2 full bathrooms, offering versatile living options, a 3-bedroom septic system, central air, updated electical system, thermo pride boiler with lifetime transferable warranty on the heat exchanger and a new shed in the yard. 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. Being sold "as is".

78 Black Rock Tpke, Redding

15 Old Mailcoach Rd, Redding
$610,000
2 Beds ⋅ 2 Baths ⋅ 24174036 MLS
THANK YOU FOR YOUR INTEREST. PLEASE SUBMIT HIGHEST AND BEST OFFERS BY TUESDAY MAY 26, 5:00PM. Discover a storybook sanctuary nestled in the heart of Redding, CT. This charming, vintage Cotswold inspired cottage provides a magical retreat that feels worlds away, yet remains perfectly connected. Situated on a lushly landscaped 2.3 acre property, the grounds are a gardener's dream featuring a tapestry of vibrant perennials with mature flowering shrubs and trees. Grow your own produce in the fenced-in vegetable garden or enjoy the serene sounds of nature by your own private pond with babbling brook and charming footbridges. The lovely stone patio is your front row seat to the beauty of the grounds, making it the perfect setting for quiet reflection or dining al fresco. The 1,481 sq. ft. interior features 2 bedrooms and 2 baths plus a large living room with expansive views of the property. Ceiling beams and a fieldstone fireplace add to the charm. There is a large eat-in kitchen with lots of room to customize. While this home does need some updating, recent improvements provide peace of mind, including a new roof and gutters, new windows and a new septic system. This home provides a captivating opportunity whether you are looking for a weekend escape or a permanent residence. This is an estate so there are no disclosures. Sale is not subject to probate approval. SOLD STRICTLY AS IS.

15 Old Mailcoach Rd, Redding

9 Apple Ln, Redding
$579,350
3 Beds ⋅ 2 Baths ⋅ 24173981 MLS
SUBMIT HIGHEST & BEST OFFER BY NO LATER THAN TUESDAY 5/26 AM. ATTORNEY INSISTS ON PLAIN LANGUAGE OFFER. SEE DOCUMENTS: OTHER (1st document) Perched proudly on a mature level 1.3 acres, boasting flowering dogwoods, giant red maples and towering pines is this well cared for 3-bedroom 2-bath Ranch on a quiet cul-de-sac yet so convenient to Georgetown shopping, restaurants, Metro train and commuting roads. Sunny living room with fireplace is open to the dining room, both with large window walls, and next to the eat-in kitchen. Three bedrooms and tub bath complete this level. The basement adds 912 sq ft per the Vision Appraisal field card (see other in documents) It includes a family room with gas log fireplace, office/den, washer & dryer room and basement combination entry & entertainment area with wet bar and shower bath, which accesses the enclosed porch breezeway which leads to the attached 2 car garage as well as to the front and back yards. There is a storage attic area over the garage best accessed from the back. Bring your creative decorating and remodeling ideas and make this gem shine. Revel in the gorgeous land, perfect for gardening and numerous activities with room for a pool. PLEASE NOTE: This property is in an estate and there is no property condition report. However, the mechanicals appear to be newer and well cared for which you can easily see in the basement. NOTE: This property is being sold "AS IS".

9 Apple Ln, Redding

64 Portland Ave, Redding
$549,000
2 Beds ⋅ 2 Baths ⋅ 24143998 MLS
Welcome to this two-bedroom, two-bathroom home offering comfort, convenience, and versatility. Step inside to find an open, functional layout with generously sized rooms and laundry all located on the main living level. Standout features of this property include the oversized primary suite as well as the heated basement, which has exciting potential to be finished - perfect for a home office, guest suite, studio, or recreational space. With its own separate entrance and high ceilings, the lower-level offers added flexibility and future possibilities. Outside, appreciate the manageable yard and home's ideal setting, close to dining, shopping and commuter routes. Move-in ready with room to grow, this property is a wonderful opportunity for a first-time buyer, downsizers, or anyone looking for a well-maintained home with bonus potential.

64 Portland Ave, Redding

34 Dorethy Rd, Redding
$500,000
3 Beds ⋅ 3 Baths ⋅ 24168666 MLS
Charming 3-bedroom, 2.5-bathroom Raised Ranch with mid-century modern character, tucked into a lightly wooded setting that offers privacy without isolation. The open floor plan provides wonderful flexibility for a variety of uses. The kitchen features chef-grade stainless steel appliances with generous counter and cabinet space. Vaulted ceilings in the family and dining rooms create an airy, light-filled atmosphere throughout the day. The primary suite offers a peaceful retreat with a full bath, while two additional generously sized bedrooms share a well-appointed full bath. The finished lower level with half bath is ideal as a den, home office, or additional sleeping quarters. A well-priced opportunity - don't miss it.

34 Dorethy 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.

How much is your home worth?

Get instant property value now!