$549,900
$20K PRICE DROP

Estimated payment $3,718/month

Total Views 72,264
3 Beds
2.5 Baths
2,248 Sq Ft
$245 Price per Sq Ft

Highlights

  • Hot Property
  • Colonial Architecture
  • Attic
  • Pomperaug Regional High School Rated A-
  • Deck
  • 5-minute walk to Bristol Park

About This Home

First Time on the Market - Classic 1930s Colonial in Prime In-Town Location Step into timeless elegance with this rare, stately 1930s Colonial, offered to the open market for the first time. Full of classic charm, the home features original moldings, custom built-ins, and enduring craftsmanship throughout. The main level offers a spacious front-to-back living room with a fireplace and gleaming hardwood floors, a formal dining room perfect for entertaining, a cozy eat-in kitchen, and a thoughtfully added family room providing extra space for everyday living. Upstairs, you'll find three generously sized bedrooms, two full baths, and a bright second-floor landing with additional built-ins. A walk-up attic offers abundant storage or potential future expansion. Set in a hidden gem of a neighborhood, this home sits along the historic trolley bed trail, offering direct access to local shops, restaurants, and all the amenities of in-town living.

Listing Agent

Tim Drakeley

Drakeley Real Estate, Inc. License #REB.0193579 Listed on: 05/24/2025

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $7,863

Year Built

  • Built in 1937

Lot Details

  • 0.28 Acre Lot
  • Level Lot
  • Property is zoned R40

Home Design

  • Colonial Architecture
  • Concrete Foundation
  • Stone Foundation
  • Frame Construction
  • Asphalt Shingled Roof
  • Aluminum Siding

Interior Spaces

  • 2,248 Sq Ft Home
  • 1 Fireplace
  • Thermal Windows
  • French Doors
  • Walkup Attic
  • Storm Windows

Kitchen

  • Oven or Range
  • Dishwasher

Bedrooms and Bathrooms

  • 3 Bedrooms

Laundry

  • Washer
  • Gas Dryer

Unfinished Basement

  • Walk-Out Basement
  • Basement Fills Entire Space Under The House
  • Partial Basement
  • Laundry in Basement

Parking

  • 2 Car Garage
  • Parking Deck
  • Automatic Garage Door Opener

Outdoor Features

  • Deck
  • Porch

Location

  • Property is near shops
  • Property is near a golf course

Schools

  • Middlebury Elementary School
  • Pomperaug High School

Utilities

  • Mini Split Air Conditioners
  • Ductless Heating Or Cooling System
  • Hot Water Heating System
  • Heating System Uses Oil
  • Hot Water Circulator
  • Fuel Tank Located in Basement

Listing and Financial Details

  • Assessor Parcel Number 1193871

Home Details

Home Type

Single Family

Est. Annual Taxes

$7,863

Year Built

Built in 1937

Lot Details

0

Listing Details

  • Neighborhood: N/A
  • Property Type: Single Family For Sale
  • Style: Colonial
  • Sq Ft Est Heated Above Grade: 2248
  • Total Sq Ft: 2248
  • Year Built: 1937
  • New Construction: No/Resale
  • Nearby Amenities: Golf Course, Lake, Library, Medical Facilities, Private School(s), Shopping/Mall
  • Direct Waterfront: No
  • Home Warranty Offered: No
  • Radon Mitigation Air Ynu: Unknown
  • Radon Mitigation Water Ynu: Unknown
  • Directions: 64 to Stevens Road
  • In Law Apartment: No
  • Living Area Sq Ft Per Public Record: 2248
  • Street Type: Road
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Total Bedrooms: 3
  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Fireplaces: 1
  • Attic Description: Walk-up
  • Basement Description: Partial, Full, Unfinished, Full With Walk-Out
  • Interior Amenities: Auto Garage Door Opener
  • Appliances: Oven/Range, Refrigerator, Dishwasher, Washer, Gas Dryer
  • Laundry Room Location: Basement
  • Laundry Room Info: Lower Level
  • Attic: Yes
  • Street Number Modifier: 1

Exterior Features

  • Exterior Features: Sidewalk, Porch, Deck, French Doors
  • Exterior Siding: Aluminum
  • Foundation Type: Concrete, Stone
  • Roof Information: Asphalt Shingle
  • Waterfront Description: Not Applicable
  • Swimming Pool: No
  • Construction Description: Frame

Garage/Parking

  • Garages Number: 2
  • Garage And Parking: Under House Garage

Utilities

  • Cooling System: Ductless, Split System
  • Heat Type: Hot Water
  • Heat Fuel Type: Oil
  • Fuel Tank Location: In Basement
  • Hot Water Description: Other
  • Water Source: Public Water Connected
  • Sewer: Public Sewer Connected

Schools

  • Elementary School: Middlebury
  • High School: Pomperaug

Green Features

  • Energy Features: Storm Windows, Thermopane Windows

Lot Info

  • Acres: 0.28
  • Lot Description: Level Lot
  • Zoning: R40
  • Parcel #: 1193871

Tax Info

  • Tax Year: July 2024-June 2025
  • Property Tax: 7863
  • Total Assessed Value: 241200
  • Mil Rate Total: 32.6

MLS Schools

  • Elementary School: Middlebury
  • High School: Pomperaug

Map

Range of Values:

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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2024 $7,863 $241,200 $57,700 $183,500
2023 $7,781 $241,200 $57,700 $183,500
2022 $7,540 $241,200 $57,700 $183,500
2021 $6,914 $198,500 $65,800 $132,700
2020 $6,967 $198,500 $65,800 $132,700
2019 $6,630 $198,500 $65,800 $132,700
2018 $6,453 $198,500 $65,800 $132,700
2017 $6,251 $198,500 $65,800 $132,700
2016 $6,363 $205,200 $77,400 $127,800
2015 $6,181 $205,200 $77,400 $127,800
2014 $6,021 $205,200 $77,400 $127,800
Source: Public Records

Property History

Date Event Price Change Sq Ft Price
06/03/2025 06/03/25 Price Changed $549,900 -3.5% $245 / Sq Ft
05/24/2025 05/24/25 For Sale $569,900 -- $254 / Sq Ft
Source: SmartMLS

Purchase History

Date Type Sale Price Title Company
Warranty Deed $270,000 --
Warranty Deed $270,000 --
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Open $110,000 Balloon
Open $233,516 No Value Available
Closed $233,516 Purchase Money Mortgage
Source: Public Records

About the Listing Agent

Tim Drakeley

Drakeley Real Estate, Inc.

(475) 265-6768

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Since 1991, Tim Drakeley has solidified his reputation as a premier broker and salesperson, consistently ranked as Woodbury, CT’s #1 selling and listing broker for 12 years and a top producer in the Tri-bury region and all of Litchfield County. A graduate of Holy Cross High School, Northfield Mount Hermon Prep School, and Babson College, where he studied Finance and Entrepreneurial Studies, Tim brings deep expertise to Drakeley Real Estate. Founded in 1986 by his mother, entrepreneur Joyce S.

Tim's Other Listings

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    Introducing this classic 1930s home, now available for the first time on the market! Built to last, this charming residence boasts all the hallmarks of timeless architecture, including arched openings, beautiful hardwood floors throughout, a bay window, exquisite moldings, two staircases, covered porches, and much more. Situated just across the street from Taft School, this peaceful location is

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  • 229 Bacon Pond Rd Unit 322, Woodbury, CT 06798

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    • Unit 322
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    Prime location for affordable living in Woodbury CT! Charming, updated 2-bedroom, 1-bath condo with an open-concept layout. The dining area features sliding doors to a patio, flooding the space with natural light. The living room boasts built-in bookcases flanking a cozy fireplace. Relax on the patio with views of the community's in-ground pool. The Town and Country complex is just 2 minute ride

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  • 1088 Old Waterbury Rd, Southbury, CT 06488

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    Tucked away on 4 acres in the heart of Southbury, this well-cared-for hi ranch home is a quiet escape from the everyday hustle. Set back from the road, it offers two levels of cozy living space, three full bathrooms, and generous family and living rooms with crackling fireplaces and big, inviting windows. The eat-in kitchen sports Corian counters with a touch of style. Downstairs, the main level

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  • 523 Main St N, Woodbury, CT 06798

    $990,000 New Construction

    • 3 Beds
    • 2 Baths
    • 2,300 Sq Ft
    • 523 Main St N
    • Woodbury, CT

    To be built Modern style home with gorgeous southern views and privacy from your neighbors. Enjoy the wall of glass overlooking a bluestone patio, and beautiful views above Main Street North! Just a few minutes from Woodbury's town center, this home provides an open floor with a kitchen/great room, a cathedral ceiling, and a floor-to-ceiling masonry fireplace. The first floor includes a primary

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  • 27 Middle Quarter Rd, Woodbury, CT 06798

    $699,900

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    Discover the charm of this beautifully soon to be restored antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this soon to be renovated vintage gem is just a 2-minute stroll from coffee shops, top-notch restaurants, and the historic Main Street. The home could be meticulously updated from the ground up, featuring wide board antique flooring, a stunning great room

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  • 0 Main St N Unit 24072824, Woodbury, CT 06798

    $399,900

    • Land
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    • $7,104 per Acre
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    • Unit 24072824
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    56 acres in the heart of Woodbury. The perfect spot for a compound or subdivide and create an open space subdivision or a few large parcels. Potential for terrific views over the Nonnewaug Valley. Located a few minutes from downtown and 5 minutes from Nonnewaug High School. Build your dream house and enjoy the views!

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  • 0 Main St N Unit 24072843, Woodbury, CT 06798

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    • $57,095 per Acre
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  • 0 Tulip Tree Village Unit 24086056, Bethlehem, CT 06751

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    Builders take notice of Tulip Tree Village Condominium Complex in Southern Bethlehem! 4 plots available for freestanding residential homes! Owner will sell as a package or staggered sales over time. Owner financing possible with qualified builder. Cul de sac community with existing homes and the 4 additional home sites that are currently for sale. This is a condo complex and Unit 7 is available

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  • 13 Tulip Tree Ln Unit 7, Bethlehem, CT 06751

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    **Brand-New Construction Coming in 2025!** Be the first to own this charming, thoughtfully designed cape-style home. Featuring an open-concept layout, a convenient first-floor primary suite, and a spacious family room perfect for entertaining. Enjoy hardwood flooring throughout the main level, tiled bathrooms, and two versatile upstairs rooms ideal for bedrooms, a home office, or both. The

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Source: SmartMLS

MLS Number: 24098549

SmartMLS

APN: MIDD-000406-000000-000160