Moving to Redding CT | real estate for sale in Redding Connecticut | Property Statistics of living in Redding

Redding is known for its rural character, extensive open space, and upscale residential properties situated on large lots. The housing market consists primarily of custom homes, country estates, and owner-occupied residences. Property values are supported by privacy, natural beauty, and limited development opportunities. Buyers often seek Redding for its tranquil environment and proximity to lower Fairfield County employment centers.

Current Real Estate Statistics for Homes in Redding CT as of Tuesday, July 14, 2026
53 Active Homes Listed
54 Avg. DOM
$105 Avg. $ / Sq.Ft.
$399000 Med. List Price
7/12/2026 1:45:53 AM
Under Contract CTS
119 Peaceable Street Redding CT
119 Peaceable Street

Redding, Connecticut 06896

$869,900 | Under Contract - Continue

3 Beds | 3 Baths | 2182 Sqft | 5.27 Acres | 5 Days on Market

Property Type: Single Family For Sale

Welcome to 119 Peaceable Street! Set on over 5 private acres in one of Reddings 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 pr...

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7/10/2026 1:48:29 PM
Under Contract CTS
74 George Hull Hill Road Redding CT
74 George Hull Hill Road

Redding, Connecticut 06896

$1,595,000 | Under Contract - Continue

4 Beds | 5 Baths | 4786 Sqft | 2.94 Acres | 75 Days on Market

Property Type: Single Family For Sale

Nestled on three picturesque acres and surrounded by open space, this beautiful country retreat offers privacy, comfort, and exceptional outdoor living. The expansive patio is perfect for entertaining, featuring a full outdoor kitchen, fireplace, TV, and integrated audio system. ...

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7/10/2026 1:16:31 AM
Active
12 Werf Drive Redding CT
12 Werf Drive

Redding, Connecticut 06896

$1,495,000 | Active

6 Beds | 5 Baths | 4033 Sqft | 2.42 Acres | 187 Days on Market

Property Type: Single Family For Sale

Welcome to this expansive and beautifully updated six-bedroom Colonial, offering three full and two half baths and thoughtfully positioned on a sprawling 2.42-acre lot that provides both privacy and presence. A grand wraparound driveway creates a striking approach to the home, of...

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7/9/2026 4:05:03 AM
Active
28 Winding Brook Lane Redding CT
28 Winding Brook Lane

Redding, Connecticut 06896

$910,000 | Active

4 Beds | 4 Baths | 3454 Sqft | 2.11 Acres | 4 Days on Market

Property Type: Single Family For Sale

Nestled on a quiet residential loop in one of Reddings 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 ...

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7/8/2026 2:36:03 PM
Active
7 Long Meadow Lane Redding CT
7 Long Meadow Lane

Redding, Connecticut 06896

$1,599,000 | Active

4 Beds | 5 Baths | 5385 Sqft | 4.39 Acres | 158 Days on Market

Property Type: Single Family For Sale

Sweeping meadow views, privacy & sunsets from an elevated setting 7 Long Meadow Lane is a distinctive property defined by its scale, setting, and versatile layout, offering generous proportions and an architectural presence that supports a wide range of lifestyles. Sited on an el...

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7/8/2026 10:45:00 AM
Active
123A Peaceable Street Redding CT
123A Peaceable Street

Redding, Connecticut 06896

$899,000 | Active

4 Beds | 4 Baths | 3594 Sqft | 2.62 Acres | 5 Days on Market

Property Type: Single Family For Sale

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 ...

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7/7/2026 9:10:46 PM
Under Contract
110 Sport Hill Road Redding CT
110 Sport Hill Road

Redding, Connecticut 06896

$1,695,000 | Under Contract

5 Beds | 6 Baths | 5308 Sqft | 2.09 Acres | 42 Days on Market

Property Type: Single Family For Sale

A rare blend of scale, privacy and value, this beautifully maintained Redding retreat offers over 6,000 square feet of flexible living space. From the gracious front entry, the home unfolds with purpose and ease. To the right, a private library/home office creates a quiet place t...

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7/3/2026 12:27:27 PM
Under Contract CTS
471 Newtown Turnpike Redding CT
471 Newtown Turnpike

Redding, Connecticut 06896

$799,000 | Under Contract - Continue

3 Beds | 3 Baths | 1774 Sqft | 2 Acres | 44 Days on Market

Property Type: Single Family For Sale

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 ...

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7/3/2026 4:05:02 AM
Active
78 Black Rock Turnpike Redding CT
78 Black Rock Turnpike

Redding, Connecticut 06896

$625,000 | Active

2 Beds | 2 Baths | 1688 Sqft | 2.26 Acres | 10 Days on Market

Property Type: Single Family For Sale

Discover the quintessential Redding lifestyle in this charming circa 1898 home, perfectly positioned to enjoy the towns excellent schools, open space, and recreational opportunities like hiking, fishing, and kayaking. This 2/3 bedroom (3rd bedroom being used as a study) residence...

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7/2/2026 3:19:08 PM
Active
71 Picketts Ridge Road Redding CT
71 Picketts Ridge Road

Redding, Connecticut 06896

$499,000 | Active

2 Beds | 1 Baths | 930 Sqft | 2.12 Acres | 100 Days on Market

Property Type: Single Family For Sale

Tucked away like a storybook retreat, 71 Picketts Ridge is a charming and cozy ranch-style home that lives like a private condo alternative, set on two secluded acres and reached by a long, winding driveway that opens to the peaceful serenity of the woods. Surrounded by nature an...

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7/2/2026 3:08:31 AM
Under Contract
121 Picketts Ridge Road Redding CT
121 Picketts Ridge Road

Redding, Connecticut 06896

$1,100,000 | Under Contract

5 Beds | 4 Baths | 4614 Sqft | 2.38 Acres | 42 Days on Market

Property Type: Single Family For Sale

Welcome to 121 Picketts Ridge Road in beautiful West Redding/ Picketts Ridge! This custom built home is the perfect family compound, sitting on massive 2.38 park-like acres. Enjoy level side-by-side, single level living with this Ranch separated by the 3 car garage. The sprawling...

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7/1/2026 6:57:29 PM
Active
16 Shady Lane Redding CT
16 Shady Lane

Redding, Connecticut 06896

$1,149,000 | Active

4 Beds | 3 Baths | 4316 Sqft | 3.64 Acres | 51 Days on Market

Property Type: Single Family For Sale

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 pla...

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7/1/2026 4:12:09 PM
Under Contract
35 Deer Spring Road Redding CT
35 Deer Spring Road

Redding, Connecticut 06896

$799,000 | Under Contract

4 Beds | 4 Baths | 2912 Sqft | 2.05 Acres | 36 Days on Market

Property Type: Single Family For Sale

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 hardw...

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7/1/2026 1:16:58 AM
Under Contract
37 Lamppost Drive Redding CT
37 Lamppost Drive

Redding, Connecticut 06896

$799,000 | Under Contract

4 Beds | 3 Baths | 2602 Sqft | 2 Acres | 33 Days on Market

Property Type: Single Family For Sale

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 Connecticu...

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7/1/2026 12:49:22 AM
Under Contract CTS
240 Umpawaug Road Redding CT
240 Umpawaug Road

Redding, Connecticut 06896

$3,950,000 | Under Contract - Continue

6 Beds | 6 Baths | 3264 Sqft | 18.23 Acres | 24 Days on Market

Property Type: Single Family For Sale

Steeped in history and natural beauty, the Charles Ives House (ca. 1913) is a masterfully restored 18-acre West Redding summer retreat where the famed modernist composer lived and created his signature works. Designed and built by Ives himself, this iconic Arts and Crafts estate ...

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6/30/2026 8:58:14 PM
Under Contract
33 Topledge Road Redding CT
33 Topledge Road

Redding, Connecticut 06896

$929,000 | Under Contract

3 Beds | 3 Baths | 2788 Sqft | 2.24 Acres | 53 Days on Market

Property Type: Single Family For Sale

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 ...

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6/27/2026 4:05:04 AM
Active
33 Old Stagecoach Road Redding CT
33 Old Stagecoach Road

Redding, Connecticut 06896

$1,150,000 | Active

4 Beds | 4 Baths | 3341 Sqft | 2 Acres | 16 Days on Market

Property Type: Single Family For Sale

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.. ...

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6/26/2026 2:34:06 PM
Active
2 Longwood Drive Redding CT
2 Longwood Drive

Redding, Connecticut 06896

$1,745,000 | Active

4 Beds | 5 Baths | 6259 Sqft | 2.72 Acres | 53 Days on Market

Property Type: Single Family For Sale

***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 s...

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6/20/2026 1:46:24 AM
Under Contract
9 Apple Lane Redding CT
9 Apple Lane

Redding, Connecticut 06896

$550,000 | Under Contract

3 Beds | 2 Baths | 1952 Sqft | 1.39 Acres | 31 Days on Market

Property Type: Single Family For Sale

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-bedro...

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6/19/2026 2:51:22 PM
Under Contract CTS
25 Starrs Ridge Road Redding CT
25 Starrs Ridge Road

Redding, Connecticut 06896

$999,000 | Under Contract - Continue

6 Beds | 5 Baths | 4955 Sqft | 5.15 Acres | 29 Days on Market

Property Type: Single Family For Sale

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...

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6/18/2026 9:58:54 PM
Active
70 Dayton Road Redding CT
70 Dayton Road

Redding, Connecticut 06896

$634,000 | Active

4 Beds | 2 Baths | 1632 Sqft | 0.92 Acres | 25 Days on Market

Property Type: Single Family For Sale

Welcome to your dream home, ideally located just steps from Devils 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, youll n...

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6/17/2026 6:10:53 PM
Under Contract CTS
30 Portland Hill Road Redding CT
30 Portland Hill Road

Redding, Connecticut 06896

$699,000 | Under Contract - Continue

4 Beds | 3 Baths | 1756 Sqft | 1.57 Acres | 31 Days on Market

Property Type: Single Family For Sale

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 sl...

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6/16/2026 8:42:30 PM
Under Contract
159 Cross Highway Redding CT
159 Cross Highway

Redding, Connecticut 06896

$629,000 | Under Contract

3 Beds | 2 Baths | 1671 Sqft | 0.86 Acres | 25 Days on Market

Property Type: Single Family For Sale

Charming turn-of-the-century Craftsman farmhouse on one of Reddings 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 m...

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6/16/2026 7:56:51 PM
Under Contract
7 Jeremiah Sanford Road Redding CT
7 Jeremiah Sanford Road

Redding, Connecticut 06896

$1,200,000 | Under Contract

4 Beds | 3 Baths | 3747 Sqft | 2.04 Acres | 31 Days on Market

Property Type: Single Family For Sale

Exceptional custom designed and built 4 bedroom Colonial, bathed in natural sunlight, is nestled perfectly on 2 lush level manicured acres at the end of a small quiet cul-de-sac in a coveted area of town, a perfect tranquil oasis. The open floor plan provides timeless functionali...

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6/16/2026 6:56:01 PM
Active
149 Old Redding Road Redding CT
149 Old Redding Road

Redding, Connecticut 06896

$1,075,000 | Active

3 Beds | 4 Baths | 2754 Sqft | 1.01 Acres | 27 Days on Market

Property Type: Single Family For Sale

Imagine a home where the air is fresh & the pace of life slows. This is a true nature lovers 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 w...

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6/16/2026 5:45:03 PM
Active
37 Highland Avenue Redding CT
37 Highland Avenue

Redding, Connecticut 06896

$399,000 | Active

2 Beds | 1 Baths | 1044 Sqft | 0.7 Acres | 46 Days on Market

Property Type: Single Family For Sale

Charming two-bedroom cottage set on a beautifully level property, offering a private retreat surrounded by a peaceful, bucolic setting. This home is full of potential-bring your vision and transform it into your perfect escape or year-round residence. Enjoy the ease of convenienc...

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6/15/2026 11:59:37 PM
Under Contract
5 Musket Lane Redding CT
5 Musket Lane

Redding, Connecticut 06896

$1,180,000 | Under Contract

4 Beds | 4 Baths | 3650 Sqft | 2.33 Acres | 49 Days on Market

Property Type: Single Family For Sale

Nestled on a tranquil cul-de-sac in bucolic Redding, this expansive 3,650 SqFt, 4 bedroom, 3.5 bath classic Colonial has been completely re-imagined and renovated, both inside and out. This 11 room home offers 5 fireplaces; a new eat-in kitchen with oversized island and large din...

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6/13/2026 1:46:33 PM
Under Contract
76 Pocahontas Road Redding CT
76 Pocahontas Road

Redding, Connecticut 06896

$885,000 | Under Contract

4 Beds | 3 Baths | 3260 Sqft | 2 Acres | 12 Days on Market

Property Type: Single Family For Sale

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 ser...

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6/10/2026 12:08:51 PM
Under Contract
10 Chapman Place Redding CT
10 Chapman Place

Redding, Connecticut 06896

$1,325,000 | Under Contract

4 Beds | 5 Baths | 4414 Sqft | 2.37 Acres | 36 Days on Market

Property Type: Single Family For Sale

Private Luxury Meets Modern Sophistication in Redding! Discover the perfect blend of classic New England charm and cutting-edge convenience. This pristine 4,414 SF Colonial is situated on 2.67 acres at the end of a peaceful cul-de-sac. Inside, you are welcomed through a stately f...

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6/10/2026 4:05:02 AM
Active
207 Redding Road Redding CT
207 Redding Road

Redding, Connecticut 06896

$1,200,000 | Active

4 Beds | 3 Baths | 3124 Sqft | 0.48 Acres | 33 Days on Market

Property Type: Single Family For Sale

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 insid...

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6/10/2026 2:12:37 AM
Under Contract
44 High Ridge Road Redding CT
44 High Ridge Road

Redding, Connecticut 06896

$1,039,000 | Under Contract

4 Beds | 3 Baths | 3519 Sqft | 2.05 Acres | 20 Days on Market

Property Type: Single Family For Sale

Serenity awaits in this classic colonial nestled on two level acres in a walker-friendly cul de sac neighborhood. This turn-key home has perfect flow for entertaining. French double doors off the spacious, quartz countered kitchen open up to the sun-soaked four season room with t...

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6/9/2026 8:55:19 PM
Under Contract CTS
27 Apple Lane Redding CT
27 Apple Lane

Redding, Connecticut 06896

$745,000 | Under Contract - Continue

3 Beds | 2 Baths | 2265 Sqft | 1.1 Acres | 38 Days on Market

Property Type: Single Family For Sale

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 law...

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6/8/2026 3:53:53 PM
Active
299 Redding Road Redding CT
299 Redding Road

Redding, Connecticut 06896

$899,000 | Active

4 Beds | 4 Baths | 3876 Sqft | 2 Acres | 35 Days on Market

Property Type: Single Family For Sale

Experience modern luxury in this beautifully renovated Colonial. A grand double-door entry opens to a bright foyer. The all-new gourmet chefs kitchen boasts a massive waterfall quartz island, high-end appliances, and pot filler. The open-concept main level flows into a spacious l...

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6/8/2026 2:11:28 AM
Active
11 Long Meadow Lane Redding CT
11 Long Meadow Lane

Redding, Connecticut 06896

$1,245,000 | Active

4 Beds | 6 Baths | 5935 Sqft | 2.95 Acres | 38 Days on Market

Property Type: Single Family For Sale

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...

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6/5/2026 8:52:54 PM
Active
268 Umpawaug Road Redding CT
268 Umpawaug Road

Redding, Connecticut 06896

$749,000 | Active

4 Beds | 4 Baths | 3922 Sqft | 2.93 Acres | 103 Days on Market

Property Type: Single Family For Sale

Dont miss the opportunity to live in this special well cared for 8 room Colonial tucked away on 2.93 very private low maintenance acres on sought after Umpawaug Rd, so convenient to Topstone Park, the NY Metro train, walking distance to New Pond Farm, and close to commuting highw...

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6/5/2026 2:04:35 PM
Under Contract
128 Black Rock Turnpike Redding CT
128 Black Rock Turnpike

Redding, Connecticut 06896

$1,499,000 | Under Contract

4 Beds | 4 Baths | 3944 Sqft | 2.02 Acres | 17 Days on Market

Property Type: Single Family For Sale

Set in the heart of charming Redding, Connecticut, this meticulously maintained home offers the perfect blend of New England character, modern efficiency, and everyday convenience. Known for its award-winning schools, scenic walking trails, and peaceful, serene surroundings, Redd...

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6/3/2026 4:05:02 AM
Active
18 Church Street Redding CT
18 Church Street

Redding, Connecticut 06896

$1,275,000 | Active

3 Beds | 3 Baths | 2935 Sqft | 0.72 Acres | 40 Days on Market

Property Type: Single Family For Sale

Known as the Aaron Davis House, ca. 1848, this exceptional historic Georgetown residence blends authenticity, artistic craftsmanship, and modern versatility in one of Reddings most cherished neighborhoods. Set on a beautifully landscaped property, it offers a rare opportunity to ...

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6/1/2026 3:08:59 PM
Under Contract
86 Seventy Acre Road Redding CT
86 Seventy Acre Road

Redding, Connecticut 06896

$938,000 | Under Contract

4 Beds | 3 Baths | 2328 Sqft | 2.05 Acres | 33 Days on Market

Property Type: Single Family For Sale

Set on a level 2-acre property, bordered by over 200 acres of protected nature preserve with scenic trails, this exceptional home offers a rare blend of privacy, convenience, and outdoor beauty. The grounds are meticulously landscaped with exquisite stonework, creating stunning g...

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5/30/2026 3:16:57 PM
Under Contract
42 Topstone Road Redding CT
42 Topstone Road

Redding, Connecticut 06896

$1,595,000 | Under Contract

4 Beds | 4 Baths | 3854 Sqft | 3.01 Acres | 45 Days on Market

Property Type: Single Family For Sale

Nestled on three private acres in highly sought-after Redding, Connecticut, with a private backyard gate entering directly into Topstone Park, this exceptional property offers a lifestyle defined by tranquility, privacy, and space. Surrounded by mature trees and drenched in natur...

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5/29/2026 4:05:02 AM
Active
86 Fire Hill Road Redding CT
86 Fire Hill Road

Redding, Connecticut 06896

$850,000 | Active

4 Beds | 3 Baths | 2329 Sqft | 2.29 Acres | 45 Days on Market

Property Type: Single Family For Sale

Nestled on a peaceful cul-de-sac at the highest point in Redding, this meticulously cared-for 4-bedroom, 2.5-bath home offers the perfect blend of privacy, space, and charm on 2+ gorgeous acres. Surrounded by mature trees and natural beauty, the property provides a serene retreat...

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5/27/2026 2:15:24 PM
Active
74 Black Rock Turnpike Redding CT
74 Black Rock Turnpike

Redding, Connecticut 06896

$1,450,000 | Active

5 Beds | 6 Baths | 4716 Sqft | 2.24 Acres | 112 Days on Market

Property Type: Single Family For Sale

Old Redding charm meets elevated modern living at this exceptional gated Contemporary Colonial offering over 4,700 SF plus approximately 1,800 SF of finished walk-out lower level. Set behind stately iron gates and stone pillars, a private drive leads to a dramatic marble foyer an...

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5/27/2026 4:05:02 AM
Active
28 Goodridge Road Redding CT
28 Goodridge Road

Redding, Connecticut 06896

$1,500,000 | Active

5 Beds | 4 Baths | 4728 Sqft | 2.2 Acres | 47 Days on Market

Property Type: Single Family For Sale

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 farmhous...

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5/21/2026 10:57:17 AM
Under Contract
15 Silversmith Lane Redding CT
15 Silversmith Lane

Redding, Connecticut 06896

$1,585,000 | Under Contract

4 Beds | 4 Baths | 3294 Sqft | 4.04 Acres | 3 Days on Market

Property Type: Single Family For Sale

Artisan Craftsmanship Meets Modern Autonomy - Your Private Oasis Awaits! Nestled on 4 idyllic, professionally landscaped acres at the end of a quiet cul-de-sac, this spectacular 2002 post-and-beam is a perfect blend of artisan craftsmanship and modern design. Built to exacting st...

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5/21/2026 4:05:02 AM
Active
206 Umpawaug Road Redding CT
206 Umpawaug Road

Redding, Connecticut 06896

$7,725,000 | Active

7 Beds | 13 Baths | 13094 Sqft | 7 Acres | 53 Days on Market

Property Type: Single Family For Sale

Exquisite Nantucket-style country estate magnificently sited on seven sprawling acres in Redding, CTs coveted Umpawaug neighborhood. Comprised of three extraordinary residences, this masterfully crafted 2008 HOBI award-winning compound offers 13,904 sf of carefully constructed li...

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5/18/2026 7:44:18 PM
Active
63 Turney Road Redding CT
63 Turney Road

Redding, Connecticut 06896

$7,400,000 | Active

7 Beds | 7 Baths | 9420 Sqft | 39.23 Acres | 211 Days on Market

Property Type: Single Family For Sale

Another Day in Paradise! Timeless grandeur, architectural mastery, and opportunity define this exceptional plantation-style colonial set on 39.23 acres bordered by 100+ acres of protected forestland-a rare opportunity for stately country living in a singular setting.For the sport...

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5/18/2026 12:49:04 AM
Under Contract
313 Umpawaug Road Redding CT
313 Umpawaug Road

Redding, Connecticut 06896

$1,450,000 | Under Contract

4 Beds | 3 Baths | 2944 Sqft | 2 Acres | 21 Days on Market

Property Type: Single Family For Sale

Nestled on a picturesque country road in the heart of Redding, this National Register of Historic Places landmark offers a rare blend of 18th-century soul and modern New England estate living. The homes historic integrity is preserved through twin stone chimneys, original wide-p...

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5/14/2026 8:30:47 PM
Active
5 Side Cut Road Redding CT
5 Side Cut Road

Redding, Connecticut 06896

$995,000 | Active

4 Beds | 4 Baths | 2819 Sqft | 2.37 Acres | 73 Days on Market

Property Type: Single Family For Sale

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 app...

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5/11/2026 2:43:57 PM
Under Contract
15 Dayton Road Redding CT
15 Dayton Road

Redding, Connecticut 06896

$1,399,000 | Under Contract

3 Beds | 4 Baths | 4943 Sqft | 2.76 Acres | 25 Days on Market

Property Type: Single Family For Sale

Impeccable shingle style country cape on park-like 2.76 acres adj. Redding Land Trust conservation property, connecting directly to Devils Den, the largest preserve in CT w/1,800+ acres. Exceptional attention to detail inside & out, w/extensive recent improvements & designer fini...

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5/9/2026 1:19:37 PM
Under Contract
40 Deer Hill Road Redding CT
40 Deer Hill Road

Redding, Connecticut 06896

$1,125,000 | Under Contract

4 Beds | 4 Baths | 3690 Sqft | 2.12 Acres | 18 Days on Market

Property Type: Single Family For Sale

Tucked away on a quiet, tree-lined street in the center of town, 40 Deer Hill Road offers the rare balance of privacy, comfort, and everyday convenience. The moment you step inside, you are greeted by cascading natural light from a dramatic wall of windows. At the heart of the ho...

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5/8/2026 4:05:31 PM
Active
281 Newtown Turnpike Redding CT
281 Newtown Turnpike

Redding, Connecticut 06896

$1,349,000 | Active

5 Beds | 5 Baths | 6170 Sqft | 2.88 Acres | 88 Days on Market

Property Type: Single Family For Sale

Sitting tucked away off a private driveway, this meticulously maintained custom-built colonial is a must-see home offered at an exceptional value. The seamless flow of the main level, sprawling primary suite, private office with porch, and finished basement are just a few of the ...

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4/29/2026 3:54:30 PM
Under Contract
172 Gallows Hill Road Redding CT
172 Gallows Hill Road

Redding, Connecticut 06896

$699,000 | Under Contract

2 Beds | 2 Baths | 2108 Sqft | 0.9 Acres | 35 Days on Market

Property Type: Single Family For Sale

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 bet...

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3/30/2026 2:53:36 PM
Under Contract
429 Rock House Road Redding CT
429 Rock House Road

Redding, Connecticut 06896

$769,900 | Under Contract

4 Beds | 3 Baths | 2576 Sqft | 2.31 Acres | 13 Days on Market

Property Type: Single Family For Sale

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 la...

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5/12/2025 6:16:16 PM
Active
229 Umpawaug Road Redding CT
229 Umpawaug Road

Redding, Connecticut 06896

$7,495,000 | Active

6 Beds | 11 Baths | 7528 Sqft | 6.46 Acres | 427 Days on Market

Property Type: Single Family For Sale

Welcome to 229 Umpawaug Road, the quintessential estate of exceptional quality on the premier scenic road in Redding, Connecticut in Fairfield County. Surround yourself in luxury inside this sun-filled 6 bedroom, 11 bathroom, 6 fireplaces center hall colonial with a flowing floor...

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