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Drakeley Real Estate

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Drakeley Real Estate

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Drakeley Real Estate is a family run business founded in 1986. Located in Woodbury, CT!

11/01/2026

Another successful sale in Woodbury Hill! With extensive experience representing buyers and sellers in this sought-after condominium community, Drakeley Real Estate knows Woodbury Hill inside and out.

Congratulations to the sellers of 25 Woodbury Hill, a beautifully renovated home featuring first-floor living, hardwood floors throughout, and a dramatic floor-to-ceiling brick fireplace under a cathedral ceiling.

Closing at $585,000, we're thrilled to celebrate another successful sale in this wonderful community. Wishing the new owners many happy years in their new home!

📍 25 Woodbury Hill, Unit 25, Woodbury
💰 Sold $585,000

Thinking of buying or selling in Woodbury Hill? Put our local experience to work for you!

11/01/2026

Tucked at the end of a quiet Southbury cul-de-sac, 160 Woods Way Drive pairs a classic center-hall Colonial with 2.7 private, wooded acres and a long driveway that sets it well back from the world.

Inside, the open kitchen and family room gather around a gas fireplace, joined on the first floor by formal living and dining rooms, a bedroom and main-floor laundry. Upstairs are two more bedrooms and a generous primary suite with a walk-in closet. An attached two-car garage, a detached carport and basement storage give you room for everything, and I-84 is about five minutes away.

📍 160 Woods Way Drive, Southbury
🛏 4 beds · 🛁 2.5 baths · 📐 2,532 sq. ft.
💰 $599,000

Reach out to Matthew Amatruda for details or a showing.

11/01/2026

Own a piece of the Litchfield Green. 59 West Street is a standalone 1927 brick commercial building on a corner lot in the heart of Litchfield's downtown retail corridor, now available as a building-only sale.

Completely remodeled from top to bottom, the building offers about 1,000 sq. ft. with central air and public water and sewer. An established business with a loyal customer base currently leases and operates from the space, so an investor or owner gets a well-maintained property with a tenant already in place. Commercial buildings in such a well-known Litchfield County location don't come along often.

📍 59 West Street, Litchfield
📐 1,000 sq. ft. · Commercial building (building only)
💰 $960,000

10/17/2026

Just listed in Newtown! Tucked into a quiet neighborhood, 25 Park Lane is a charming ranch that makes one-level living easy and welcoming.

The living room centers on a fireplace with a wood stove insert, and the oversized sunroom soaks up natural light through its big windows before stepping down to a stone patio and a sweet backyard. Two bedrooms and a remodeled bath keep things simple and cozy.

Recent updates include a newly paved driveway, a newer furnace and hot water heater, fresh paint, and a whole-house generator. A detached one-car garage, a storage shed, and plenty of basement storage round it out, all close to everyday conveniences and commuter highways.

📍 25 Park Lane, Newtown
🛏 2 beds · 🛁 1 bath · 📐 1,158 sq. ft.
💰 $369,000

Reach out to Kat Parlato to schedule a showing.

10/16/2026

Price improvement on this recently renovated Watertown rental — now $1,800/mo (was $1,900). Two bedrooms with an updated kitchen (new cabinets and countertops), upgraded flooring, a renovated full bath, and a shared yard with designated parking. Situated in a great location, close to shopping, restaurants, and commuter routes.

Reach out to Rhya Szymansky for details.

📍 163 Echo Lake Road, Unit #4, Watertown
🛏 2 beds · 🛁 1 bath · 📐 800 sq. ft. · 💰 $1,800/mo (was $1,900)

10/16/2026

1217 Main Street N. is a three-bedroom ranch that's been gutted to the studs and beautifully rebuilt in North Woodbury.

The open-concept layout centers on a gorgeous new kitchen with a center island, opening to a spacious family and dining area with plenty of room for bigger gatherings. All three bedrooms have hardwood floors, and there's a new full bath, a new laundry room and a private side deck just off the entry.

Downstairs, the finished lower level adds valuable space for a family room, home office, gym or rec room. It's a rare chance at a like-new ranch in Woodbury with nothing left to do but move in.

📍 1217 Main Street N., Woodbury
🛏 3 beds · 🛁 1 full bath · 📐 1,960 sq. ft.
💰 $699,900

Reach out to Tim Drakeley to be first in line.

10/16/2026

New to the market in Woodbury! 22 Pilgrim Trail, Unit G1 is a bright lower end-unit condo in Quassuk Heights Gardens, just minutes from Main Street.

Wood floors run through an open living and dining area, the bedroom is spacious, and the front window looks out over Litchfield County’s rolling hills. Out back, a shared patio sits against the greenery. The HOA covers heat, hot water, trash, grounds care, and snow removal — a simple, low-maintenance way to own instead of rent.

📍 22 Pilgrim Trail, Unit G1, Woodbury
🛏 1 bed · 🛁 1 full bath · 📐 546 sq. ft.
💰 $124,900

Reach out to Matthew Amatruda for a private showing.

10/15/2026

Price improvement on a rare Litchfield County estate: 119 Judge Lane in Bethlehem is now $1,995,000.

A long private drive winds through rolling land to this five-bedroom contemporary, set on more than 40 acres of open meadows, mature pines and hemlocks, historic stone walls, fruit trees, gardens, and a tranquil pond. Expansive windows fill the home with natural light and frame the views, and thoughtful updates sit comfortably alongside the warmth of its original design.

A pavilion and patio with a grand stone fireplace is made for gatherings. Equestrians will appreciate the groomed riding trails, and there are miles more for hiking and biking. Above the garage, a guest suite with a living area, kitchenette, and full bath is ready for visitors or an au pair. It's all about 15 minutes from Woodbury, Washington, and Litchfield.

📍 119 Judge Lane, Bethlehem
🛏 5 beds · 🛁 4 full baths · 📐 3,645 sq. ft.
💰 $1,995,000 (was $2,150,000)

Reach out to Jeffrey Boucher at Drakeley Real Estate for a private tour.

10/09/2026

New construction coming to Bethlehem! On Tulip Tree Lane in Tulip Tree Village, this to-be-built Cape Cod brings a finished first floor with two bedrooms and two baths, an open living room with a fireplace, a kitchen with an island, and a primary suite with a walk-in closet and stall shower.

The second floor is left unfinished, and the septic is set up for a future third bedroom when you're ready. There's a full basement, a 2-car attached garage, and a level cul-de-sac setting. The monthly association fee covers road maintenance and insurance; you take care of your own home and grounds.

See plans and specs with the listing, and reach out to Kat Parlato to learn more.

📍 Tulip Tree Lane, Bethlehem
🛏 2 beds · 🛁 2 full baths · 📐 1,445 sq. ft.
💰 $579,900

10/08/2026

Some familiar faces just got a whole lot bigger! 👀

Our new billboard is up on Main Street North in Woodbury, and we couldn’t be more excited!

When it comes to real estate, choose the team with the most character! Keep an eye out next time you're driving through town!

Address

256 Main Street S
Woodbury, CT
06798

Opening Hours

Monday	9am - 5pm
Tuesday	9am - 5pm
Wednesday	9am - 5pm
Thursday	9am - 5pm
Friday	9am - 5pm

Telephone

+12032634336

Website

http://www.drakeley.com/

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