159 Cross Highway
Redding, CT 06896
3 Beds
2 Baths
1,671 sqft (on 0.86 acres)
3 Beds
2 Baths
1,671 sqft
(on 0.86 acres)
Local Information
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Description
HIGHEST AND BEST DEADLINE 5/28 5PM. 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 HIGHEST AND BEST OFFERS TO BE SUBMITTED BY THURSDAY 5/28 AT 5PM. We so appreciate your patience through the holiday weekend delay. Heat pump/central air on second floor only. First floor is heated by radiators. Plans for two car garage expansion available. Audio/Video recording device at front and rear door.
Home Highlights
Parking
Open Parking
Outdoor
Porch, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
$376
Listed
7 days ago
Home Details for 159 Cross Highway
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Interior Details Basement: Partial,UnfinishedNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom, Bathroom, Den, Dining Room, Kitchen, Living Room |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2 |
Dimensions and Layout Living Area: 1671 Square Feet |
Appliances & Utilities Utilities: Cable AvailableAppliances: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Lower LevelRefrigeratorWasher |
Heating & Cooling Heating: Hot Water,OilHas CoolingAir Conditioning: Central Air,Window Unit(s)Has HeatingHeating Fuel: Hot Water |
Fireplace & Spa No Fireplace |
Security Security: Security System |
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Exterior Home Features Roof: ShinglePatio / Porch: Porch, DeckOther Structures: Shed(s)Exterior: Rain GuttersFoundation: StoneNo Private Pool |
Parking & Garage No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 6Parking: Driveway,Unpaved,Private,Gravel |
Frontage Not on Waterfront |
Water & Sewer Sewer: Septic Tank |
Finished Area Finished Area (above surface): 1671 Square Feet |
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Days on Market: 7 |
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Year Built Year Built: 1900 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Antique,Farm House |
Building Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty |
Property Information Parcel Number: 268864 |
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Price List Price: $629,000Price Per Sqft: $376 |
Status Change & Dates Possession Timing: Negotiable |
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MLS Status: Active |
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Direction & Address City: ReddingCommunity: Redding Ridge |
School Information Elementary School: ReddingJr High / Middle School: John ReadHigh School: Joel Barlow |
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Listing Agent Listing ID: 24165406 |
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Building Area Building Area: 1671 Square Feet |
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Community Features: Golf, Lake, Library, Park, Stables/Riding, Tennis Court(s) |
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No HOA |
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Lot Area: 0.86 acres |
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BasementMls Number: 24165406Attic: Access Via HatchAttribution Contact: (203) 606-8536Above Grade Unfinished Area: 1671Activation Date: Fri May 22 2026 |
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GolfLakeLibraryParkStables/RidingTennis Court(s) |
Last check for updates: about 13 hours ago
Listing courtesy of Bill Whitehead, (203) 606-8536
Berkshire Hathaway NE Prop., (203) 606-8536
John Talley, (203) 947-1057
Berkshire Hathaway NE Prop., (203) 438-9501
Source: Smart MLS, MLS#24165406
Also Listed on Smart MLS, Berkshire Hathaway HomeServices New England Properties.
Price History for 159 Cross Highway
| Date | Price | Event | Source |
|---|---|---|---|
| 05/22/2026 | $629,000 | Listed For Sale | Smart MLS #24165406 |
| 12/12/2000 | $350,000 | Sold | Smart MLS #98078625 |
| 01/28/1998 | $245,000 | Sold | Smart MLS #97031195 |
| 04/15/1994 | $260,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $8,487 |
| Assessment | $287,300 |
Home facts updated by county records
Comparable Sales for 159 Cross Highway
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.28 | Single-Family Home | $740,000 | 05/11/26 | 3 | 2 | 2,065 | |
0.63 | Single-Family Home | $650,000 | 01/05/26 | 2 | 2 | 1,618 | |
0.81 | Single-Family Home | $650,000 | 11/20/25 | 3 | 2 | 2,009 | |
0.08 | Single-Family Home | $1,600,000 | 09/26/25 | 4 | 3 | 5,072 | |
0.20 | Single-Family Home | $835,000 | 03/02/26 | 5 | 4.5 | 4,801 | |
0.57 | Single-Family Home | $791,000 | 06/16/25 | 4 | 2.5 | 2,735 | |
0.73 | Single-Family Home | $812,500 | 11/10/25 | 4 | 2.5 | 1,886 | |
0.87 | Single-Family Home | $900,000 | 07/30/25 | 4 | 2.5 | 2,484 | |
0.50 | Single-Family Home | $1,675,000 | 09/03/25 | 4 | 3.5 | 4,495 |
Nearby homes
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FOR SALEOPEN FRI, 12-2PM2.2 ACRESColdwell Banker Realty
FOR SALEOPEN SAT, 1-3PM2.88 ACRESColdwell Banker Realty
FOR SALEOPEN SAT, 1-3PM2.24 ACRESCompass Connecticut, LLC
SOLDMAY 11, 2026William Pitt Sotheby's Int'l
FOR SALE4.39 ACRESWilliam Raveis Real Estate
FOR SALE39.23 ACRESWilliam Pitt Sotheby's Int'l
SOLDMAR 2, 2026Coldwell Banker Realty
SOLDFEB 19, 2026William Raveis Real Estate
SOLDJAN 29, 2026Compass Connecticut, LLC
Assigned Schools
These are the assigned schools for 159 Cross Highway.
- John Read Middle School
- 5-8
- Public
- 350 Students
9/10GreatSchools RatingParent Rating AverageJust reviewing my daughter’s school experiences. Student in class photo made the upside down okay sign( signifies white supremacy and alt right). Students reported this to principal with obvious proof of photo). John Read had an opportunity for a teaching moment on diversity. My daughter is a foreign adoptee. School swept under carpet and said it was a joke. No apology from the student to my daughter or other adoptee. Went to Superintendent and No Action Taken.We withdrew our daughter. She attended magnet school and studied for two years in France. Neither administration would have tolerated this behavior. Btw she graduated from high school with high honors. Received Merit scholarships to 2 of 3 colleges. (3rd college did not award merit). Has started a NPO, has had a television spot for her Social Justice work.In summary Redding School System lost a bright student and exceptional human being.Parent Review1y ago - Redding Elementary School
- PK-4
- Public
- 479 Students
8/10GreatSchools RatingParent Rating AverageTerrible. I taught my child almost everything he needed to know. Other than meeting so nice kids and enjoying recess, I feel the time he spent in the classroom was a complete waste of time. I taught him to read, write, spell, add, substract, multiply, divide, sight words, grammar, all of it. I often wondered “what are you doing all day at school”? I would find out there was very little science and social studies. When he was behind in reading, he got sent out for help and it did little to get him up to speed. I ended up getting him up to speed at home. He had never really been taught proper grammar (I was told by 3rd grade teacher it’s not in the curriculum), so I taught him that too. Teachers were having him log onto a computer program called Reflex for basic math skills. There was very little instruction and then reinforcement. They would teach “mini lessons” then have them work on their own. I don’t know, it just didn’t seem like the time spent at school was spent in a meaningful, educational way. A lot of the things they did was “busy work” and silly projects. So he would come home and I would teach him what he needed to know. After RES, we literally left the whole district and enrolled him into private school. What a difference and what a shame that people move to Redding for the schools, pay high taxes because they think they’re getting a good editor their children, but really aren’t. Save your money and don’t move to Redding if it’s just for the education. You’ll find a better education elsewhere.Parent Review5y ago - Joel Barlow High School
- 9-12
- Public
- 768 Students
7/10GreatSchools RatingParent Rating AverageGreat school. Academics are strong and kids are well prepared for college. Classes are small and teachers know all the students. It’s a small school so everyone knows each other though more diversity would be good.Parent Review7mo ago 
Check out schools near 159 Cross Highway.
What Locals Say about Redding
At least 41 Trulia users voted on each feature.
96 % Say there's wildlife
91 % Say parking is easy
88 % Say car is needed
87 % Say there's holiday spirit
86 % Say it's dog friendly
84 % Say it's quiet
76 % Say yards are well-kept
71 % Say they plan to stay for at least 5 years
68 % Say neighbors are friendly
63 % Say there are community events
59 % Say people would walk alone at night
42 % Say kids play outside
33 % Say it's walkable to restaurants
12 % Say it's walkable to grocery stores
12 % Say streets are well-lit
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Bill Whitehead, Berkshire Hathaway NE Prop., (203) 606-8536
Agent Phone: (203) 606-8536
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
159 Cross Highway, Redding, CT 06896 is a 3 bedroom, 2 bathroom, 1,671 sqft single-family home built in 1900. This property is currently available for sale and was listed by Smart MLS on May 20, 2026. The MLS # for this home is MLS# 24165406.