Tucked away on a sought-after cul-de-sac, this open-layout home is crafted for exceptional entertaining. The light-filled, two-story foyer is framed by two sets of French doors: one opening to an office & the other leading to a living room that flows seamlessly into the dining room-an ideal setup for holiday gatherings. The custom kitchen, equipped with granite countertops, a center island, gas cooktop, walk-in pantry & dining area, overlooks the pool & patio. Adjacent to the kitchen is a sitting room & spacious family room featuring a fireplace & built-in bookcase. A generous 20x35 recreation room further enhances the home's entertainment options with a custom bar, vaulted ceiling, full bath & two sets of sliding doors that open to the pool, spa & patio area, creating a perfect indoor-outdoor experience. The upper level boasts a primary suite with a spacious bath & walk-in closet along with two additional bedrooms connected by a Jack & Jill bath. This floor also includes a craft/yoga room & laundry room. On the 3rd floor, a private fourth bedroom with a full bath provides an ideal space for nanny quarters or guests. The lower level offers 715 square feet of flexible finished space, perfect for a workout area with room for a golf simulator & includes ample storage & access to the 3-car garage. Outside, the grounds are complete with a gunite pool, spa, fire pit, stone wall & a fenced area, creating a tranquil oasis for relaxation & entertainment-all just minutes from town!
Sold for $952,000
$952,000
5 Bear Run, Woodbury, CT 06798
4beds
5,915sqft
Single Family Residence
Built in 1997
1.6 Acres Lot
$1,009,100 Zestimate®
$161/sqft
$6,888 Estimated rent
Home value
$1,009,100
Estimated sales range
Not available
$6,888/mo
Zestimate® history
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List your homeWhat's special
Primary suiteStone wallNanny quartersPrivate fourth bedroomLight-filled two-story foyerBuilt-in bookcaseSitting room
Zillow last checked:
Listing updated:
Listed by:
Shelley Drakeley 203-982-7108,
Drakeley Real Estate, Inc. 203-263-4336
Bought with:
Liza C. Reiss, RES.0804920
Elyse Harney Real Estate
Source: Smart MLS,MLS#: 24059188
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Rooms
- Room types: Laundry
Primary bedroom
- Features: Ceiling Fan(s), Full Bath, Walk-In Closet(s), Wall/Wall Carpet
- Level: Upper
Bedroom
- Features: Ceiling Fan(s), Wall/Wall Carpet
- Level: Upper
Bedroom
- Features: Ceiling Fan(s), Wall/Wall Carpet
- Level: Upper
Bedroom
- Features: Ceiling Fan(s), Full Bath, Wall/Wall Carpet
- Level: Upper
Bathroom
- Features: Tile Floor
- Level: Main
Bathroom
- Features: Full Bath, Tile Floor
- Level: Upper
Den
- Features: Hardwood Floor
- Level: Main
Dining room
- Features: French Doors, Hardwood Floor
- Level: Main
Family room
- Features: Built-in Features, Ceiling Fan(s), Fireplace, Wall/Wall Carpet
- Level: Main
Kitchen
- Features: Bay/Bow Window, Granite Counters, Kitchen Island, Pantry, Sliders, Hardwood Floor
- Level: Main
Living room
- Features: French Doors, Hardwood Floor
- Level: Main
Office
- Features: French Doors, Hardwood Floor
- Level: Main
Other
- Features: Wall/Wall Carpet
- Level: Upper
Rec play room
- Features: Vaulted Ceiling(s), Beamed Ceilings, Ceiling Fan(s), Wet Bar, Full Bath, Sliders
- Level: Main
Rec play room
- Features: Wall/Wall Carpet
- Level: Lower
Heating
- Forced Air, Oil
Cooling
- Central Air
Appliances
- Included: Cooktop, Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water Heater, Tankless Water Heater
- Laundry: Upper Level
Features
- Open Floorplan, Entrance Foyer
- Doors: French Doors
- Windows: Thermopane Windows
- Basement: Full,Partially Finished
- Attic: Finished,Walk-up
- Number of fireplaces: 1
Interior area
- Total structure area: 5,915
- Total interior livable area: 5,915 sqft
- Finished area above ground: 5,200
- Finished area below ground: 715
Property
Parking
- Total spaces: 3
- Parking features: Attached
- Attached garage spaces: 3
Features
- Patio & porch: Patio
- Exterior features: Stone Wall
- Has private pool: Yes
- Pool features: Gunite, Heated, Pool/Spa Combo, In Ground
- Spa features: Heated
Lot
- Size: 1.6 Acres
- Features: Subdivided, Level, Cul-De-Sac
Details
- Parcel number: 933533
- Zoning: OS60
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1997
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Green energy
- Energy efficient items: Windows
Community & HOA
Community
- Features: Basketball Court, Library, Park, Playground, Private School(s), Shopping/Mall
- Subdivision: Transylvania
HOA
- Has HOA: No
Location
- Region: Woodbury
Financial & listing details
- Price per square foot: $161/sqft
- Tax assessed value: $547,960
- Annual tax amount: $12,696
- Date on market: 11/15/2024
Price history
| Date | Event | Price |
|---|---|---|
| 4/15/2025 | Sold | $952,000-15.3%$161/sqft |
Source:  Smart MLS #24059188 Report a problem | ||
| 3/27/2025 | Pending sale | $1,124,000$190/sqft |
Source: Smart MLS #24059188 Report a problem | ||
| 12/6/2024 | Price change | $1,124,000-6.3%$190/sqft |
Source: Smart MLS #24059188 Report a problem | ||
| 11/15/2024 | Listed for sale | $1,199,000+59.9%$203/sqft |
Source: Smart MLS #24059188 Report a problem | ||
| 10/14/2010 | Sold | $750,000-3.2%$127/sqft |
Source: Public Record Report a problem | ||
| 7/29/2010 | Price change | $775,000-3.1%$131/sqft |
Source: CENTURY 21 HOME SERVICES SCALZO GROUP #W1057929 Report a problem | ||
| 7/21/2010 | Price change | $800,000-11.1%$135/sqft |
Source: CENTURY 21 HOME SERVICES SCALZO GROUP #W1057929 Report a problem | ||
| 5/22/2010 | Price change | $899,900-7.2%$152/sqft |
Source: Joyce S. Drakeley Real Estate #W1056493 Report a problem | ||
| 4/15/2010 | Listed for sale | $969,900$164/sqft |
Source: Joyce S. Drakeley Real Estate #W1056493 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $13,045 +2.7% | $552,300 +0.8% |
| 2024 | $12,696 -1.6% | $547,960 +23.4% |
| 2023 | $12,904 -0.4% | $444,050 |
| 2022 | $12,953 | $444,050 |
| 2021 | $12,953 | $444,050 |
| 2020 | $12,953 | $444,050 |
| 2019 | $12,953 -9.6% | $444,050 -17.7% |
| 2018 | $14,336 -2.1% | $539,360 |
| 2017 | $14,649 +3.3% | $539,360 |
| 2016 | $14,180 +0.8% | $539,360 |
| 2015 | $14,061 +1.5% | $539,360 |
| 2014 | $13,856 +3% | $539,360 -6.2% |
| 2013 | $13,454 -3.4% | $574,960 |
| 2012 | $13,931 +7.9% | $574,960 |
| 2011 | $12,914 +4.7% | $574,960 |
| 2010 | $12,333 +0.6% | $574,960 -0.9% |
| 2009 | $12,257 -4.8% | $580,080 +9.7% |
| 2008 | $12,879 +58.4% | $528,900 +55.9% |
| 2007 | $8,129 +5.1% | $339,260 |
| 2006 | $7,732 +6.4% | $339,260 |
| 2005 | $7,267 +0.1% | $339,260 +0.1% |
| 2004 | $7,262 +43.4% | $339,040 +82.4% |
| 2003 | $5,064 | $185,840 |
Find assessor info on the county website
Neighborhood: 06798
Nearby homes
- $840,3004 bd3 ba4.1k sqft9 Bear Run, Woodbury, CT 06798Off Market
- $686,5004 bd2 ba2.7k sqft65 Transylvania Rd, Woodbury, CT 06798Off Market
- $795,7004 bd3 ba2.9k sqft55 Transylvania Rd, Woodbury, CT 06798Off Market
- $791,8004 bd2 ba3k sqft10 Bear Run, Woodbury, CT 06798Off Market
- $660,9003 bd2 ba2.5k sqft74 Transylvania Rd, Woodbury, CT 06798Off Market
- $763,5004 bd3 ba3.3k sqft10 Bear Hl, Subdivision Woodbury, CT 06798Off Market
- $767,4004 bd2 ba3.1k sqft17 Bear Run, Woodbury, CT 06798Off Market
- $611,7004 bd2 ba2.2k sqft82 Transylvania Rd, Woodbury, CT 06798Off Market
Nearby schools
GreatSchools rating
- 5/10Mitchell Elementary SchoolGrades: PK-5Distance: 1.1 mi
- 6/10Woodbury Middle SchoolGrades: 6-8Distance: 1.1 mi
- 9/10Nonnewaug High SchoolGrades: 9-12Distance: 2.3 mi
Schools provided by the listing agent
- Elementary: Mitchell
- Middle: Woodbury
- High: Nonnewaug
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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