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260 Umpawaug Rd, Redding
$1,450,000
3 Beds ⋅ 3 Baths ⋅ 24211675 MLS
Rare West Redding Opportunity: Massive Upside, Privacy & Unmatched Potential. An exceptional property nestled in one of West Redding's most prestigious estate areas. Spanning over 5,000 sq ft of partially finished space across 3 levels, this distinctive custom-built Contemporary Colonial sits on 12.04 private, park-like acres in a secluded woodland setting. 3 bedrooms include a main level Primary suite, 3 full baths, and 3 half baths. The main living areas are bathed in natural light through walls of windows, with multiple decks taking in the spectacular, tree-lined views. The expansive walk-out lower level adds versatility and flexible living space-ready to make it your own. Adding incredible value and utility is a separate, working two-bay barn-ideal for a contractor, landscape equipment, large vehicle storage, or a workshop. While the residence requires a full interior and exterior renovation, the structure, grounds, and premier location make this a rare value-add investment and an outstanding treasure. Bring your inspiration, passion, and ingenuity to restore and preserve the deep-rooted spirit and enduring legacy of this remarkable residence. Enjoy a sought-after Redding location convenient to the train, top-rated schools, local shopping, and commuter routes-all just 65 miles to the Upper West Side of Manhattan. A real diamond-in-the-rough to be sold "as is"- Price reflects condition.

260 Umpawaug Rd, Redding
85 Lonetown Rd, Redding
$539,000
2 Beds ⋅ 2 Baths ⋅ 24216380 MLS
Welcome to 85 Lonetown Road! This charming New England home offers a wonderful blend of character, comfortable living, and beautiful outdoor space. This 2 bedroom 2 bathroom home features a beautifully updated kitchen with granite countertops and stainless steel appliances, and a cozy brick fireplace. Additional living space on the upper level provides flexibility for a variety of needs. Outside, enjoy the open lawn, mature trees, and picturesque natural scenery that abuts a beautiful golf course. A spacious stone patio and covered porch make it ideal for entertaining or unwinding. The property also features an attached garage with washer and dryer included and a detached storage shed for added convenience. This home is a wonderful opportunity to enjoy classic Connecticut charm. (Property to be sold as is) *Also included is water softener system, outdoor security system, and Invisible Fence*

85 Lonetown Rd, Redding
Black Rock Tpke, Redding
$599,999
24215777 MLS
Unlock Premier Development Potential in Redding Ridge, Redding, CT! Imagine crafting a stunning Luxury subdivision on this expansive 15+ acre parcel of vacant land in prestigious Redding, Connecticut. The property may be sub-dividable (subject to approvals), offering flexibility and opportunity for a discerning developer to bring custom designs to life. This exceptional land is not located in a flood zone, adding peace of mind to your plans. Enjoy unparalleled convenience with nearby shopping, renowned golf courses, and abundant recreational activities. Commuting is easy with the Danbury Fair Mall and I-84 just a 20-minute drive away. Located within the highly rated Redding school district, this is the ideal setting to create an exceptional residential enclave.

Black Rock Tpke, Redding
126 Picketts Ridge Rd, Redding
$925,000
4 Beds ⋅ 3 Baths ⋅ 24215752 MLS
Idyllic and historic 4 bedroom Colonial, built in 1805 by Revolutionary War Loyalist John Pickett, formerly the Burr Sanford Dairy Farm, and lovingly cared for and updated over the past two centuries. Set on two park-like, level acres and surrounded by estates and farmland, this special property has mature trees and gardens and a sweeping grassy lawn leading to the detached barn/garage, making it ideal as a potential equestrian property. Inside you're greeted by formal dining and living rooms with hardwood flooring, plus multiple fireplaces and charming built-in nooks throughout. The cozy Family Room features a large stone fireplace and exposed beams and the generously sized kitchen leads to a versatile sitting room with bay window and wood stove. On this level there is also a convenient powder room, laundry room/pantry and a bright sunroom leading to the back gardens. The second floor features gorgeous wide plank flooring and original wood working, with four spacious bedrooms and two full baths, including a primary suite with walk-in closet and full bathroom. Finished third level attic with cathedral ceiling and original wood beams adds 899 sqft. The lower level offers plenty of room for storage and the detached barn garage has a loft above. Take in the picturesque views of the property from your side porch or private stone patio. Situated just minutes to the West Redding train station, Route 7 and 90 minutes to NYC making this an ideal spot for year-round or vacation living

126 Picketts Ridge Rd, Redding
34 Dorethy Rd, Redding
$825,000
3 Beds ⋅ 3 Baths ⋅ 24215319 MLS
Completely renovated and move in ready on two private, wooded acres in beautiful Redding! Blending architectural character with modern comfort, this stunning home features soaring cathedral ceilings, exposed beams, expansive windows, and a fireplace. The beautifully updated kitchen showcases marble countertops, skylights, a Wolf gas range, and Sub-Zero refrigerator. Enjoy peace of mind with extensive renovations, including a brand new roof, septic system, high-efficiency heating & cooling systems, and beautifully updated interiors, with warranties on applicable improvements. Unwind on the private wraparound deck overlooking tranquil woods, perfect for birdwatching and morning coffee. Once lovingly tended by a gardening enthusiast, the grounds offer wonderful potential to bring the gardens back to life. Conveniently located near Georgetown's shops and restaurants, Route 7, Metro-North, and scenic trails. All the character, none of the renovation headaches. Simply move in and enjoy!

34 Dorethy Rd, Redding
76 Peaceable St, Redding
$1,400,000
3 Beds ⋅ 4 Baths ⋅ 24215045 MLS
Welcome to "Stone Fences"-a historic 10-acre country estate tucked away in the quiet forests of Redding, Connecticut, just 90 minutes from Manhattan. Custom-built in 1938 by architect Richard Rowe for his wife, the home was awarded House Beautiful's top design honor in 1941. An MIT and Ecole des Beaux-Arts graduate who refined his craft alongside NYC architect Aymar Embury II, Rowe achieved an exceptional balance: an intimate, cozy atmosphere paired with an expansive living room built for grand entertaining. The architecture features a captivating fusion of English, Early American, French Provincial, and subtle Modern elements. Anchored by a Cotswold-style main cottage with two bedrooms and 3.5 bathrooms under an authentic slate roof, the residence opens onto grounds that unfold like a private sanctuary with manicured gardens, a gentle waterfall, a 14-foot-deep stone "bathing pool" pond, and a dramatic bridge spanning Gilbert Bennett Brook. A separate guest cottage, heated three-car garage, and custom chicken coop complete the estate, while comprehensive modern upgrades-including high-efficiency HVAC, updated windows, insulation, a full-house generator, a newer septic tank, roof, driveway, and bridge-ensure timeless beauty meets complete contemporary comfort.

76 Peaceable St, Redding
82 Simpaug Tpke, Redding
$749,000
3 Beds ⋅ 2 Baths ⋅ 24215005 MLS
Set along the Redding/Ridgefield line in scenic West Redding, 82 Simpaug Turnpike offers timeless character, thoughtful modern updates, and beautiful views of Umpawaug Pond. Cherished by one family for over 50 years, the home is rich in history, with an expansive living room anchored by a striking stone fireplace handcrafted from materials gathered on the property. A beautifully refreshed kitchen features a center island topped with soapstone, while three bedrooms, including a primary suite, two fully renovated baths, and a second wood-burning fireplace offer comfort and character throughout. Extensively updated since 2023, improvements include a new roof, HVAC, whole-house generator, electrical upgrades, and refinished hardwood floors. Outside, a fully fenced backyard creates a private retreat, complete with a low-maintenance Trex deck and a new paver patio. A two-car finished attached garage with new doors and epoxy flooring adds everyday convenience. Less than 10 minutes from Ridgefield's vibrant Main Street, with easy access to Route 7, shopping, dining, and nearby Topstone Park, this exceptional location offers the best of country living with everything close at hand.

82 Simpaug Tpke, Redding
131 Peaceable St, Redding
$985,000
4 Beds ⋅ 4 Baths ⋅ 24207344 MLS
Discover a striking contemporary retreat nestled on nearly three private acres of lush, wooded Redding privacy. Featuring a picturesque brook, tranquil pond, and private waterfall, this property blends modern design with natural splendor. At the heart of the home, a magnificent double-sided fieldstone fireplace anchors the sun-filled living and dining rooms. Expansive windows and sliding glass doors frame serene views, opening to an oversized wraparound deck designed for effortless indoor-outdoor living, entertaining, or peaceful mornings. The meticulously renovated kitchen showcases custom-cut marble countertops imported specifically for the home, complemented by updated baths featuring custom tile. The spacious main-level primary suite serves as a true sanctuary with vaulted ceilings, a large distinctive open loft overlooking the bedroom, an updated ensuite bath, and a private balcony. Three additional bedrooms, updated bathrooms, and flexible living spaces offer exceptional comfort and versatility. The finished walkout lower level adds spacious recreation room, wet bar, half bath, and abundant storage. Ideally located close to New Pond Farm, Top Stone park, scenic hiking trails, nature preserves, local shops, and dining. Enjoy seamless commuting with convenient access to Metro-North train lines and NYC, plus close proximity to neighboring Ridgefield, Weston, and Wilton. A private country escape with convenience to everything.

131 Peaceable St, Redding
81 Sport Hill Rd, Redding
$350,000
24214406 MLS
Create your own private retreat in the heart of Redding Ridge. Set back from the road, this 7.22-acre parcel offers a private setting and the opportunity to bring your vision for a home to life in one of Connecticut's most scenic communities. Raw and undeveloped, the land is zoned for a single building site, offering space to thoughtfully shape a home and landscape around the way you want to live. The property backs to nearly 14 acres of Connecticut DEP-owned land, 48 acres of Aquarion-owned land, and the Aspetuck River. This expansive backdrop offers a meaningful buffer from neighboring homes and enhances the property's exceptional sense of privacy. Whether you envision a timeless country home or a contemporary retreat, this is an exceptional opportunity to own a private piece of Redding and create something distinctly your own. Showings are strictly by appointment only. Do not enter or walk the property unaccompanied.

81 Sport Hill Rd, Redding
85 Cross Hwy, Redding
$975,000
4 Beds ⋅ 4 Baths ⋅ 24212649 MLS
True pride of ownership in this exceptional colonial home with extensive recent improvements, set back on 3 picturesque acres surrounded by nature & protected watershed forest with access to the Little River trail system & its 100 acre land preserve. This sophisticated home offers 3,350sf of living space with 4 BRs, 3 full/1 half updated baths, 3 fireplaces, crown moldings, built-ins, hdwd floors & open floor plan. The main level offers the generous LR with elegant brick fireplace & custom wood mantle/surround with French door access to the private office featuring a wall of custom bookshelves with lower cabinetry. The 1st floor also features the inviting kitchen with white cabinetry, contrasting black granite counters, & direct access to the stunning new screened porch, dining room, plus adjoining FR w/floor to ceiling brick fireplace & sliders to the Trex deck for outdoor enjoyment. Upstairs is equally impressive with elegant primary suite featuring a large custom WIC & luxe bath with mosaic stone floor, marble topped double vanities, plus oversized shower with elegant arched opening. There are 3 additional BRs, all with hdwd floors, one with vltd ceiling & 3rd fireplace, plus convenient laundry room. The lower level features a spacious rec/game room plus mudroom access to the attached 2 car garage. Recent improvements: new roof/gutters & chimney rebuilt; exterior repainted; Bluestone walkway; new windows; deck rebuilt & part converted to screened porch; new C/A; plus more!

85 Cross Hwy, Redding
128 Gallows Hill Rd, Redding
$995,000
3 Beds ⋅ 3 Baths ⋅ 24211132 MLS
Sunlit architectural modern residence set back deeply on 4.03 private acres surrounded by woodlands, wildflowers, picturesque stream fed pond, & adjoining the 72 acre Gallows Hill Nature Preserve, featuring historic Revolutionary War camp sites & peaceful trails. This Zen sanctuary is a rare find - tucked fully into its natural surroundings yet expansive open floor plan that blurs the lines between indoor & out with soaring 2 story windows, skylights, extensive glass walls/sliders, plus wrap around Ipe deck for panoramic views. Significant improvements by the current owners including: new Hardie plank batten board siding; new windows, exterior doors & skylights; new HVAC; roof (2016); portable generator; new main floor office converted from laundry; & other designer enhancements. Total 2,740 sf of inviting living space including 3 BRs; 2 full/1 half baths; & lower level studio/fitness room, plus laundry & mudroom leading directly to the 2 car garage. Clean lines & modern flow from the sun drenched, two story entry foyer to the wide open great room including striking Brazilian cherry floors, vaulted living room with sliders to the deck, open dining room with double sliders to the deck, plus sleek, state of the art kitchen featuring Carrera marble counters, center island with bar overhand, S/S appliances & custom glass front stainless pantry system. Enjoy luxe main floor primary suite with spa like bath & custom closet, plus top West Redding location, just 56 miles to Midtown.

128 Gallows Hill Rd, Redding
87 Giles Hill Rd, Redding
$747,500
3 Beds ⋅ 2 Baths ⋅ 24208310 MLS
Set in a peaceful Redding setting, 87 Giles Hill Road is a charming Cape with a thoughtful and inviting floor plan and exceptional outdoor spaces designed for both relaxation and entertaining. The home has a warm and welcoming feel, with hardwood floors throughout the main living areas, generous natural light, and a comfortable flow from room to room. Two bedrooms located upstairs offer private retreats separate from the main living spaces. Outside, the property truly shines. A custom heated Gunite pool with spa and waterfall creates a private backyard retreat, while the custom outdoor fireplace provides another inviting gathering space for entertaining or relaxing outdoors. The lower deck grilling area is also conveniently equipped with a direct propane connection. With propane heat, classic Cape character, versatile living spaces, and exceptional outdoor amenities, 87 Giles Hill Road offers a wonderful opportunity to enjoy the privacy, natural beauty, and relaxed lifestyle that make Redding such a special place to call home.

87 Giles Hill Rd, Redding
23 Lee Ln, Redding
$935,999
3 Beds ⋅ 3 Baths ⋅ 24211235 MLS
Set along scenic Redding Road across from the Mark Twain Stormfield estate, just minutes from the Wilton/Weston town line, this 3/4 bedroom home is the perfect blend of privacy and convenience in one of Redding's most desired settings. Set on a peaceful, picturesque, designated scenic road, the home features an open floor with vaulted ceilings, abundant natural light and a great flow for everyday living and entertaining. The first floor primary suite provides a sought-after single level living option. The second floor has two additional bedrooms and an office/bonus room with a full bathroom. Freshly painted, the home is move-in ready with modern conveniences throughout, including fiber-optic wiring, ethernet, and a whole-house generator. The expansive lower level offers exceptional versatility and ample room for a playroom, home gym, media/rec room. This is a rare opportunity to enjoy tranquility and natural beauty of Redding while remaining close to shopping, dining, schools and commuter routes. 1500+ sq ft of finished basement not included in the square footage

23 Lee Ln, Redding
115 Limekiln Rd, Redding
$2,495,000
4 Beds ⋅ 7 Baths ⋅ 24185787 MLS
Architecturally Masterful design, inspired by famed architect HR Richardson's classic exteriors is married with a sophisticated, modern interior plan. This unique Redding estate home offers a scenic, private gated 9.54 acres and over 7200SF of modern living. The grand and gracious living room and dining rooms, formerly owned by a classical pianist, were utilized for elegant gatherings and concerts in the area & large enough for a concert grand. Warmed by a mantled fireplace with built-ins, the living area opens to a formal dining area to seat 12 special guests. The elegant foyer greets you with an expertly crafted, freestanding curved stair that leads to the upper floor. Adjacent to the dining room is a stark white kitchen with new quartz counters, an unusual contrast to the warm woods of the white oak floors and family room with stone,raised hearth fireplace. An adjacent Pecan wood study with walls of bookshelves and file drawers; an idea home office. A main level primary suite offers a series of custom closet built-ins & marble bath with shower, double sinks and even a bidet; a private owner retreat. Also, on this level is an excercise room w/whirlpool tub, sauna & full bath. Head up the back stair to the 2nd level w/2 bedroom suites, one serving as an ideal studio, with sink and an additional bedroom with large marble bath. A third bedroom & another full bath. The lower level offers a game room w/wood stove, office & den/ library wall. Inground gunite pool, 3 car garage

115 Limekiln Rd, Redding
83 Sherman Tpke, Redding
$805,000
4 Beds ⋅ 2 Baths ⋅ 24208230 MLS
Tucked back from a designated scenic road, 83 Sherman Turnpike offers the ease of one-level living in a peaceful and private Redding setting. Set on two acres bordered by town-protected open space, this classic ranch is surrounded by mature trees and established landscaping, creating a wonderful sense of privacy while still feeling connected to the community. Inside, hardwood floors run throughout the main level, where comfortable living spaces are centered around a wood stove and an easy, functional floor plan. A deck extends the living outdoors and provides a natural place to relax, dine, and enjoy the surrounding landscape. The finished lower level adds valuable additional living space and flexibility for a family room, home office, recreation space, or guest accommodations. Lovingly maintained by its current owners, the home has been thoughtfully cared for. Improvements over the years include a refurbished deck, an expanded back lawn, and a new stone parking area. Adding significant value for the next owner, a brand-new septic system is being installed. Comfortable and welcoming as it stands today, the home also offers an opportunity for its next owner to personalize the interiors and make thoughtful updates over time. The sellers are also offering flexible closing terms, providing buyers with additional options to structure a timeline that works for their needs. Located in the desirable Deer Hill neighborhood, the home

83 Sherman Tpke, Redding
207 Redding Rd, Redding
$1,099,000
4 Beds ⋅ 2 Baths ⋅ 24209017 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
Redding
$275,000
24209052 MLS
Turn-key RESTAURANT BUSINESS/ASSET FOR SALE opportunity featuring a substantial existing buildout and attractive lease structure. Sale includes furniture, fixtures, and equipment (FF&E), commercial kitchen infrastructure, dining and bar areas, allowing a new operator to step into an established restaurant environment without the significant time and expense associated with a new buildout. Well-positioned for a chef-owner, restaurant group, or experienced operator looking to introduce their own concept. Sale is for business assets and leasehold interest only; real estate is not included. Reach out to Listing Broker for additional information regarding the Business For Sale Opportunity.

Redding
248 Simpaug Tpke, Redding
$724,900
4 Beds ⋅ 2 Baths ⋅ 24206309 MLS
Classic New England Charm in West Redding Center! This charming home offers far more than meets the eye. Hardwood floors flow throughout, beginning in the spacious living room, where a beautiful stone fireplace adds warmth, character, and timeless appeal. -------- The thoughtfully renovated kitchen features granite countertops, a center island, and stainless-steel appliances, all new in 2024, including an induction range. Just off the kitchen is a flexible den or dining room, along with a convenient mudroom/laundry room offering abundant storage and access to a three-quarter bath. The light-filled sunroom overlooks the private backyard, creating a bright and inviting place to relax. An additional room adjacent to the kitchen and dining area is perfect for a bar, playroom, or casual entertainment space. ----- Upstairs, you will find three bedrooms, an updated full bath, and a separate office. The walk-up attic is an unexpected bonus, offering excellent storage and exciting possibilities for a hobby space, studio, or whatever your imagination can create. ----- The property truly shines outdoors. Three separate patios provide multiple places to relax, entertain, or enjoy your favorite beverage. Established perennial gardens add beautiful seasonal color, while the property's location alongside the 170-acre Boy Scout Reservation provides exceptional privacy, with no neighbors directly behind the home or on one side.

248 Simpaug Tpke, Redding
85 Mountain Rd, Redding
$668,000
5 Beds ⋅ 3 Baths ⋅ 24202631 MLS
Welcome Home to this inviting five-bedroom, three-full-bath Colonial set on 2.15 peaceful, lush acres in sought-after Southwest Redding. Hardwood floors throughout the main level and abundant natural light complement a flexible floor plan. The spacious living and dining area is a standout, with a vaulted ceiling, skylights, and brick wood-burning fireplace creating an open and airy gathering space. The updated kitchen offers extensive cabinetry, granite counters, stainless steel appliances, and casual dining. A comfortable family room opens to the outdoors. The main-level primary bedroom features its own private full bath, while a second full bath serves this level. Upstairs are four additional bedrooms and a full hall bath. Enjoy the beautiful setting from the screened porch and adjoining brick patio, surrounded by mature trees, gardens, stonework, and natural rock outcroppings. Central air, an unfinished lower level, and two-car garage complete the home. Ideally located with access to the Lincoln Selleck Trail just across the street, connecting to more than 200 acres of preserved open space and miles of walking trails, plus convenient access to Branchville, Georgetown, and the vibrant town centers of Ridgefield and Wilton. Welcome Home!

85 Mountain Rd, Redding
121 Picketts Ridge Rd, Redding
$1,150,000
5 Beds ⋅ 4 Baths ⋅ 24204798 MLS
seller offers price adjustment to 1,150,000 due to the higher mortgage rates in the market. This is a lovingly lived-in sprawling custom build 4,614sf ranch with 5 bedrooms and 3 and 1 half baths with an oversized 3 car garage on a lush bucolic private 2.38 lot . You have such a generous amount of space with this home as 3,600sf plus is on the main first floor, making living easy step in and enjoy the whole homes expanse. Indeed the primary suite is on the main level as are the 4 bedrooms. This homes notable features include an expansive interior upper balcony leading into the huge 1,000sf plus hardwood floor finished upper story over the expanded 3 car garage, also included on the upper level second floor is an unfinished 2,400plus attic, with lots of potential and a great deal of storage. The home also boasts a raised 2,000sf plus walk out basement with extra large over head access for all garden and outdoor equipment, also a generous amount of space and storage. Making this your family's home offers an incredible opportunity for an abundance of wonderful space and privacy. Excellent Commute only 2 miles to the west Redding metro north train station. Excellent schools, easy shopping up and down route 7 & 53 Come and See , owner selling as is, if you like space and easy 1st floor living you'll love this home with all it's added potential.

121 Picketts Ridge Rd, Redding
22 Great Pasture Rd, Redding
$699,999
3 Beds ⋅ 2 Baths ⋅ 24202113 MLS
Lovely 3-bedroom, 2-bath home nestled on 2.44 private acres in desirable Redding. Offering a wonderful blend of character, space, and potential, this property is ready for your finishing touches and personal vision. The inviting living space features a fireplace, while the circular driveway provides convenient access and plenty of parking. Adding to the appeal is a separate cottage located on the property, offering exciting possibilities as an artist's retreat, private studio, workshop, home office, or creative space. Surrounded by mature trees and a peaceful natural setting, the property provides privacy while still offering convenient access to everything the area has to offer. A unique opportunity to create something truly special in one of Fairfield County's most charming communities. Bring your ideas and discover the possibilities at 22 Great Pasture Road. A must-see!

22 Great Pasture Rd, Redding
15 Fire Hill Ln, Redding
$849,000
4 Beds ⋅ 3 Baths ⋅ 24199054 MLS
Welcome to this beautifully maintained 4-bedroom, 2.5-bath home nestled on a peaceful cul-de-sac in desirable West Redding. Set on 2.05 gorgeous acres surrounded by mature trees, this property offers a wonderful combination of privacy, space, and natural beauty. Offering timeless Colonial charm with stylish updates and comfortable modern living, this exceptional property is truly move-in ready. The home boasts hardwood floors throughout creating a warm and elegant flow from room to room. Spacious living areas are perfect for both everyday living and entertaining, with a beautiful fireplace providing a warm and welcoming focal point. The updated kitchen offers a fresh, modern feel, while the updated bathrooms add style and convenience. A wonderful three-season room extends the living space and provides the perfect spot to relax, enjoy morning coffee, or take in the peaceful surroundings. Step outside onto the large deck, ideal for summer entertaining, outdoor dining, or simply enjoying the tranquil setting. Upstairs, four spacious bedrooms provide plenty of room for family, guests, or a home office. The primary bedroom offers a comfortable private retreat, while the additional bedrooms provide flexibility for a variety of needs. Set in the scenic and sought-after town of Redding, this beautiful home combines classic Colonial character with thoughtful updates and exceptional indoor-outdoor living.

15 Fire Hill Ln, Redding
123 Cross Hwy, Redding
$995,000
4 Beds ⋅ 4 Baths ⋅ 24198160 MLS
Beautiful and serene, this special property has been lovingly maintained by the same family for the past 37 years. Set on 6.18 picturesque acres in a desirable neighborhood surrounded by other expansive properties, the 4 bedroom, 3.5 bath home offers privacy, space, and a wonderful sense of tranquility. Well maintained throughout, the home features thoughtful updates, including a roof that is just 3 years old. With generous living spaces, a beautiful natural setting, and plenty of room to enjoy the outdoors, this property presents a wonderful opportunity to create your own lasting memories in a truly special setting.

123 Cross Hwy, Redding
19 Olmstead Rd, Redding
$499,900
2 Beds ⋅ 2 Baths ⋅ 24197883 MLS
If you want to enjoy all that Redding has to offer without the upkeep of a large home and expansive yard, this charming home may be just what you're looking for. Located in a quiet West Redding neighborhood, this home sits on an inviting corner lot and offers classic New England character throughout. As you enter through the enclosed front porch, you're welcomed by a wonderful sense of charm. The front door opens into the kitchen, which flows into a sun-filled, open-concept living and dining area featuring a fireplace and access to the rear deck overlooking the neighborhood. The first floor also includes a comfortable den and full bath. Upstairs, you'll find a primary bedroom with its own full bath, a second bedroom, and ample storage tucked into the eaves off the hallway. The lower level provides laundry, generous storage space, and a one-car garage. Whether you're looking to move right in or renovate and make the home your own, this property offers an appealing alternative to condominium living, with the privacy and character of a single-family home and far less maintenance than a larger Redding property. A great opportunity to enjoy Redding without taking on a large house and yard. Click on the link for the virtual tour.

19 Olmstead Rd, Redding
12 Werf Dr, Redding
$1,395,000
6 Beds ⋅ 5 Baths ⋅ 24197397 MLS
Extraordinary, beautifully updated six-bedroom Colonial, where timeless architecture meets modern luxury. Set on an impressive 2.42-acre estate, this property offers a rare blend of privacy, scale, and refined presence creating a true retreat just moments from everyday conveniences. A sweeping wraparound driveway delivers a grand and memorable arrival, complementing the home's stately facade while providing ample parking in addition to the attached two-car garage perfectly suited for hosting guests and effortless daily living. Step inside to a gracious foyer adorned with refinished hardwood flooring that flows seamlessly throughout the main level, setting a warm yet sophisticated tone. The foyer opens into an elegant living room, where a classic fireplace anchors the space, offering both ambiance and timeless character. The home's thoughtfully designed open-concept layout effortlessly balances traditional charm with contemporary living, creating an inviting setting for both intimate moments and large-scale entertaining. At the heart of the home lies a stunning, fully updated kitchen designed to impress. Featuring sleek quartz countertops, stainless steel appliances, and beautifully refreshed cabinetry, this space delivers both style and functionality. The expansive eat-in area provides ample room for casual dining and transitions seamlessly to a large rear deck an ideal extension of the living space. Here, you can take in the beautiful scenic views.

12 Werf Dr, Redding
56 Portland Ave Unit 3, Redding
$384,900
1 Beds ⋅ 2 Baths ⋅ 24194246 MLS ⋅ Georgetown Place BLDG.
NEW PRICE - $384,900! OWNER WILL CONSIDER RENTING! Enjoy the best of both worlds in this charming, sun-filled condo in Georgetown, Redding- offering a peaceful setting with easy access to neighboring Fairfield County towns. Walk to the center of Georgetown, 5 miles from Ridgefield Center and 6 miles from Wilton Center, this location puts shopping, dining, and charming downtown destinations within easy reach. Inside you'll find an inviting floor plan, soaring vaulted ceilings, natural light, and a generously sized loft with endless possibilities for a gym, office, or a dedicated sleeping area with added separation for greater privacy. Thoughtful updates include newer flooring, appliances, heating system,electric heat pump, and hot water heater-making the move in ready with peace of mind. There is plenty of space to design this cozy unit around your needs. Don't overlook this Georgetown gem!

56 Portland Ave Unit 3, Redding
286 Black Rock Tpke, Redding
$1,329,000
5 Beds ⋅ 5 Baths ⋅ 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
44 Portland Ave, Redding
$1,850,000
2 Baths ⋅ 24191067 MLS
Church campus located in the Georgetown section of Redding, consisting of a one story frame bi-level religious facility and a single family dwelling. The campus also includes a separate residential building lot containing +/- 0.76 acres known as 36 Portland Ave. The church and house are well maintained and have parking for more than 50 cars. With a total land area of +/- 2.2 acres, the property lends itself to a wide variety of development or expansion options.

44 Portland Ave, Redding
14 W Woodland Dr, Redding
$50,000
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
26 & Rd, Redding
$975,000
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

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