Jeff Boucher

Woodbury CT

Drakeley Real Estate, Inc.

68 Closed Sales

$28.8M Total Value

$235K - $905K Price Range

$423.3K Average Price

Prior 5 years

About Jeff

Jeff is a life long resident of Watertown and Woodbury where he lives with his wife Kellie and their daughters. He has worked in the Construction and Service industry caring for many weekend and full time residents of Litchfield County. Jeff is a Licensed REALTOR with Drakeley Real Estate in Woodbury and a Licensed Home Improvement Contractor.

Property and Real Estate is second nature to Jeff and he has been involved with many new construction, renovation and specialty projects for some of the finest estates in Litchfield County and the surrounding area. Modern and unique homes with historic character are a specialty for Jeff. Maximizing reach on the social media and print platform for maximum exposure is paramount in a successful sale.

. He is available 7 days a week for consultation.

Relationships, Trust and Capability are what makes Jeff the right choice for your all your real estate needs.

Home Types: House, Commercial, Condo, Townhouse, Lot/Land, MultiFamily

Years of Experience: 11

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	8
Total Value	$3,119,500
Average Sale Price	$389,938
Price Range	$35K - $860K

Buyer Deals
Total Deals	3
Total Value	$1,322,000
Average Sale Price	$440,667
Price Range	$367K - $495K

1 Year View by Quarter

Seller Deals
Total Deals	18
Total Value	$7,093,500
Average Sale Price	$394,083
Price Range	$35K - $860K

Buyer Deals
Total Deals	10
Total Value	$5,045,000
Average Sale Price	$504,500
Price Range	$365K - $905K

2 Year View by Quarter

Seller Deals
Total Deals	43
Total Value	$16,820,627
Average Sale Price	$391,177
Price Range	$35K - $860K

Buyer Deals
Total Deals	25
Total Value	$11,962,100
Average Sale Price	$478,484
Price Range	$163K - $905K

5 Year View

Neighborhoods Jeff is Experienced In

Jeff's Active Listings

$2,150,000
- 5 Beds
- 4 Baths
- 3,645 Sq Ft
119 Judge Ln

Bethlehem, CT
Discover a rare estate-quality property in the heart of Litchfield County, where timeless character, modern refinement, and more than 40 acres of exceptional natural beauty create an unparalleled retreat. A long private drive winds through rolling landscapes to a thoughtfully reimagined five-bedroom, three-bath residence that seamlessly blends sophisticated updates with the warmth and

Jeff Boucher Drakeley Real Estate, Inc.

$869,000
- 4 Beds
- 2.5 Baths
- 4,148 Sq Ft
131 Woods Way Dr

Southbury, CT
Nestled at the end of a quiet cul-de-sac in one of Southbury's most desirable neighborhoods, this beautifully maintained four-bedroom Colonial offers privacy, comfort, and exceptional spaces for entertaining. Set on a picturesque, tree-lined lot, the home welcomes you with a newly paved driveway, manicured grounds, and fresh paint throughout. Inside, the heart of the home is a stunning living

Jeff Boucher Drakeley Real Estate, Inc.

$335,000
- 2 Beds
- 1.5 Baths
- 1,564 Sq Ft
100 Decicco Rd

Waterbury, CT
One level living in a well established neighborhood of generational homes. Pride of ownership is very apparent in this 2/3 bedroom home with expanded living space in the lower level. All of this on an oversized fenced lot. The 3 season breezeway porch and smaller study off the kitchen adds living space to have coffee, finish your emails for work or use as a guest bedroom. Well maintained

Jeff Boucher Drakeley Real Estate, Inc.

$89,900
- Land
- 0.83 Acre
- $108,313 per Acre
0 Brass Mill Dam Rd

Torrington, CT
Great lot in established subdivision with bordering open space preserve. Buyers and Agents to do their due diligence with town. City utilities available at street. Great location to build your home or opportunity for a builder and spec house. Close to Stillwater Pond State Park for fishing, kayaking and hiking. Close to RT8.

Jeff Boucher Drakeley Real Estate, Inc.

$995,599
- 2 Beds
- 2 Baths
- 1,662 Sq Ft
346 Westside Rd

Goshen, CT
Set along the shores of sought-after Westside Pond in the heart of Litchfield County, this fully refinished waterfront retreat offers the ultimate Connecticut lake lifestyle. Located on one of the area's few non-restrict motorboat lakes, enjoy boating, jet skiing, tubing, kayaking, fishing, or simply relaxing on the water from your own private dock. Designed to maximize its stunning setting, the

Jeff Boucher Drakeley Real Estate, Inc.

$425,000
- 3 Beds
- 3 Baths
- 1,876 Sq Ft
31 Hillcrest Ave

Waterbury, CT
Discover the perfect blend of timeless character and modern updates in this impeccably maintained two-family home on a corner lot in Waterbury. Whether you're seeking a smart investment opportunity or a flexible multigenerational living arrangement, this spacious property delivers. Live on the two-floor upper level and draw income from the three-room garden apartment with a private entrance and

Jeff Boucher Drakeley Real Estate, Inc.

Recently Sold

$659,500

Sold Jul 2, 2026
- 3 Beds
- 3.5 Baths
- 2,304 Sq Ft
577 Lakeside Rd

Southbury, CT
- 2% Below List
- $286/SF
- 58 Days On Market
- Current Est. Value $672K
Jeff Boucher Drakeley Real Estate, Inc.

$590,000

Sold Jun 17, 2026
- 1 Bed
- 2 Baths
- 1,564 Sq Ft
123 Cross Brook Rd

Woodbury, CT
- 1% Above List
- $377/SF
- 73 Days On Market
- Current Est. Value $572K
Jeff Boucher Drakeley Real Estate, Inc.

$310,000

Sold May 27, 2026
- 3 Beds
- 2 Baths
- 2,486 Sq Ft
136 Candee Hill Rd

Watertown, CT
- 5% Above List
- $125/SF
- 31 Days On Market
- Current Est. Value $301K
Jeff Boucher Drakeley Real Estate, Inc.

$860,000

Sold Apr 3, 2026
- 3 Beds
- 2.5 Baths
- 3,373 Sq Ft
182 Magnolia Hill Rd

Bethlehem, CT
- 4% Below List
- $255/SF
- 19 Days On Market
- Current Est. Value $851K
Jeff Boucher Drakeley Real Estate, Inc.

$410,000

Sold Feb 25, 2026
- 5 Beds
- 3 Baths
- 2,547 Sq Ft
69 Johnson St

Naugatuck, CT
- $161/SF
- 129 Days On Market
- Current Est. Value $417K
Jeff Boucher Drakeley Real Estate, Inc.

$35,000

Sold Nov 20, 2025
- Land
- 3.60 Acre Lot
0 Main St N

Unit 24119173

Woodbury, CT
- 46% Below List
- 57 Days On Market
Jeff Boucher Drakeley Real Estate, Inc.

$125,000

Sold Sep 16, 2025
- 1 Bed
- 1 Bath
- 546 Sq Ft
14 Arrowhead Way

Unit 6

Woodbury, CT
- 4% Below List
- $229/SF
- 91 Days On Market
- Current Est. Value $126K
Jeff Boucher Drakeley Real Estate, Inc.

$130,000

Sold Jul 16, 2025
- 1 Bed
- 1 Bath
- 546 Sq Ft
14 Arrowhead Way

Unit 1

Woodbury, CT
- 4% Below List
- $238/SF
- 43 Days On Market
- Current Est. Value $127K
Jeff Boucher Drakeley Real Estate, Inc.

$499,000

Sold Jun 16, 2025
- 3 Beds
- 2.5 Baths
- 1,648 Sq Ft
98 Old Town Farm Rd

Woodbury, CT
- 1% Above List
- $303/SF
- 3 Days On Market
- Current Est. Value $508K
Jeff Boucher Drakeley Real Estate, Inc.

Awards and Designations

NAR - National Association of Realtors

Other Experience

Distressed Properties, First Time Home Buyers, Foreclosures, Investments, Luxury Homes, New Construction, Property Management, Senior Communities, Veteran Programs

Jeff Boucher

(860) 590-8533

Drakeley Real Estate, Inc.

(860) 590-8533

Homes for Sale by City

Jeff Boucher

About Jeff

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

2 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Jeff is Experienced In

Jeff's Listings and Deals

Jeff's Active Listings

Recently Sold

Awards and Designations

Other Experience