Taylor O'Keefe Real Estate Agent - Drakeley Real Estate, Inc.

286 North St, Watertown, CT For Sale $399,000 - listed by Taylor O'Keefe — For Sale $399,000

Taylor O'Keefe listing and buyer's agent for 25 Cross Rd, Terryville, CT - sold for $150,000 — Sold $150,000

70 East St Unit 1A, Bethlehem, CT For Rent $1,850/month - listed by Taylor O'Keefe — For Rent $1,850/month

379 Smith Pond Rd, Watertown, CT Pending $499,900 - co-listed by Taylor O'Keefe — Pending $499,900 • Co-Listing Agent

Taylor O'Keefe buyer's agent for 116 Frances Ann Dr, Oakville, CT - sold for $410,000 — Sold $410,000

Taylor O'Keefe

Woodbury CT

Drakeley Real Estate, Inc.

97 Closed Sales

$36.2M Total Value

$215K - $837.5K Price Range

$372.8K Average Price

Prior 5 years

About Taylor

Taylor O'Keefe is a proud, life-long Woodbury and Watertown resident who wants to share all that Litchfield, New Haven, and Fairfield Counties have to offer with anyone who shows an interest. Working locally for many years, she is developed numerous connections in the surrounding areas, and prides herself in her local recommendations and resources.

Taylor cares deeply for every client that she is lucky enough to work with. Taylor is known for her around-the-clock availability and dependability, responsiveness, and ability to get the deal done. Her dedication and passion towards real estate is second to none.

A graduate of Nonnewaug High School and The Culinary Institute of America where she received her Bachelors in Professional Studies, Taylor enjoys volunteering her time in the community and sharing her culinary knowledge with local high school students and anyone that she comes in contact with.

When Taylor's not working, she loves spending time with her two dogs, Mack and Reese, her family, and friends, eating at local restaurants, and cooking and baking at home in her kitchen.

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

Years of Experience: 8

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	10
Total Value	$4,061,000
Average Sale Price	$406,100
Price Range	$150K - $700K

Buyer Deals
Total Deals	5
Total Value	$2,435,000
Average Sale Price	$487,000
Price Range	$340K - $600K

Seller Deals
Total Deals	16
Total Value	$6,642,500
Average Sale Price	$415,156
Price Range	$150K - $700K

Buyer Deals
Total Deals	10
Total Value	$4,309,900
Average Sale Price	$430,990
Price Range	$260K - $600K

Seller Deals
Total Deals	58
Total Value	$19,720,400
Average Sale Price	$340,007
Price Range	$65K - $838K

Buyer Deals
Total Deals	39
Total Value	$16,441,000
Average Sale Price	$421,564
Price Range	$155K - $745K

5 Year View

Areas Taylor is Experienced In

Taylor's Listings and Deals

Taylor's Active Listings

$399,000
- 3 Beds
- 2 Baths
- 1,637 Sq Ft
286 North St

Watertown, CT
Cute as a button, this expanded Cape is conveniently located near Taft School and within walking distance to downtown Watertown. Hardwood floors run throughout much of the home, where the first floor offers a spacious living room with a pellet stove, dining room, kitchen, and full bath. Just off the kitchen, the sunken family room is a welcome addition, featuring a propane fireplace flanked by

Taylor O'Keefe Drakeley Real Estate, Inc.

$284,900
- 3 Beds
- 2 Baths
- 1,372 Sq Ft
72 Bee Brook Rd

Washington Depot, CT
Rare opportunity to own a two-family property in the Town of Washington. Multi-family properties in this market are few and far between, making this a unique opportunity for investors, contractors, or buyers looking to renovate and add value. The property offers one, two-bedroom unit, and one, one-bedroom unit. While the property is in need of updates and improvements, it presents an excellent

Taylor O'Keefe Drakeley Real Estate, Inc.

$349,900
- 3 Beds
- 3 Baths
- 1,379 Sq Ft
70 Bee Brook Rd

Washington Depot, CT
Rare opportunity to own a three-family property in the Town of Washington. Multi-family properties in this market are few and far between, making this a unique opportunity for investors, contractors, or buyers looking to renovate and add value. The property offers three one-bedroom units, a detached garage, and a spacious lot. While the property is in need of updates and improvements, it presents

Taylor O'Keefe Drakeley Real Estate, Inc.

$305,000
- 2 Beds
- 2.5 Baths
- 1,504 Sq Ft
319 Thomaston Rd

Unit 13

Watertown, CT
Desirable Watertown Old Farms townhome offering open-concept living, custom stone, natural gas fireplace with built-in shelving, granite kitchen, and a private deck overlooking serene wooded surroundings. The bright living and dining area features warm wood-style flooring, a natural gas fireplace framed by custom stonework and flanked by built-in bookshelves, and a sliding door that leads to a

Taylor O'Keefe Drakeley Real Estate, Inc.

$600,000

Pending
- 9 Beds
- 8 Baths
- 4,492 Sq Ft
137 & 141 Main St S

Woodbury, CT
Rare mixed-use investment opportunity on over an acre along Woodbury's desirable Main Street South. This unique property features a seven-unit residential building, a detached garage with an additional apartment above, and a separate commercial building offering approximately 2,000 square feet with its own dedicated entrance and access. Three of the residential units are currently occupied, while

Taylor O'Keefe Drakeley Real Estate, Inc.

Co-Listing Agent

$499,900

Pending
- 3 Beds
- 2 Baths
- 1,720 Sq Ft
379 Smith Pond Rd

Watertown, CT
Located in a well-established Watertown neighborhood just moments from Smith Pond, this well-maintained 3-bedroom, 2-bath Raised Ranch offers a great combination of space, updates, and convenience. Set on a beautiful 1-acre lot, the property provides plenty of outdoor space while remaining close to shopping, dining, parks, major commuter routes, and the Watertown school district. Inside, you'll

Taylor O'Keefe Drakeley Real Estate, Inc.

$1,850 per month
- 2 Beds
- 1.5 Baths
- 1,000 Sq Ft
70 East St

Unit 1A

Bethlehem, CT
Yearly unfurnished ranch-style rental offering comfortable one-level living with newly refinished hardwood floors throughout. The spacious living/dining room leads into a galley kitchen overlooking the backyard, with two bedrooms and a full bath. The lower level provides additional storage, a half bath with laundry hookups, and access to the one-car garage. Enjoy your own private rear deck and

Taylor O'Keefe Drakeley Real Estate, Inc.

Recently Sold

$375,000

Sold Jul 31, 2026
- 3 Beds
- 2 Baths
- 1,747 Sq Ft
103 Hollow Rd

Watertown, CT
- 132 Days On Market
- $215/SF
- Current Est. Value $375K
Taylor O'Keefe Drakeley Real Estate, Inc.

$150,000

Sold May 15, 2026
- Land
- 9.12 Acres Lot
25 Cross Rd

Terryville, CT
- 6% Below List
- 38 Days On Market
- Current Est. Value $150K
Taylor O'Keefe Drakeley Real Estate, Inc.

$168,000

Sold Dec 31, 2025
- 2 Beds
- 1 Bath
- 913 Sq Ft
229 Bacon Pond Rd

Unit 454

Woodbury, CT
- 9% Below List
- 70 Days On Market
- $184/SF
- Current Est. Value $174K
Taylor O'Keefe Drakeley Real Estate, Inc.

$492,000

Sold Dec 10, 2025
- 3 Beds
- 2.5 Baths
- 1,788 Sq Ft
183 Hulls Hill Rd

Southbury, CT
- 4% Above List
- 36 Days On Market
- $275/SF
- Current Est. Value $497K
Taylor O'Keefe Drakeley Real Estate, Inc.

$490,000

Sold Nov 20, 2025
- 4 Beds
- 3 Baths
- 2,216 Sq Ft
15 Lynns Corner Rd

Woodbury, CT
- 27 Days On Market
- $221/SF
- Current Est. Value $513K
Taylor O'Keefe Drakeley Real Estate, Inc.

$375,000

Sold Oct 27, 2025
- 3 Beds
- 2 Baths
- 1,212 Sq Ft
266 Kasson Rd

Bethlehem, CT
- 1% Below List
- 50 Days On Market
- $309/SF
- Current Est. Value $399K
Taylor O'Keefe Drakeley Real Estate, Inc.

$486,000

Sold Oct 3, 2025
- 3 Beds
- 2 Baths
- 1,850 Sq Ft
15 Wellsville Ave

New Milford, CT
- 1% Above List
- 66 Days On Market
- $263/SF
- Current Est. Value $501K
Taylor O'Keefe Drakeley Real Estate, Inc.

$270,000

Sold Sep 19, 2025
- 2 Beds
- 2.5 Baths
- 1,316 Sq Ft
48 Clubhouse Dr

Woodbury, CT
- 4% Below List
- 40 Days On Market
- $205/SF
- Current Est. Value $283K
Taylor O'Keefe Drakeley Real Estate, Inc.

$555,000

Sold Aug 13, 2025
- 3 Beds
- 4 Baths
- 2,176 Sq Ft
108 Wood Creek Rd

Bethlehem, CT
- 3% Below List
- 45 Days On Market
- $255/SF
- Current Est. Value $599K
Taylor O'Keefe Drakeley Real Estate, Inc.

Agent License: Connecticut RES.0808242

Frequently Asked Questions

Who is Taylor O'Keefe, and what is their real estate background?

How many homes has Taylor O'Keefe sold in Woodbury, CT?

What is Taylor O'Keefe's track record representing buyers?

What is Taylor O'Keefe's track record as a listing agent?

What areas does Taylor O'Keefe serve?

How can I contact Taylor O'Keefe?

Taylor O'Keefe

(475) 263-4675

Drakeley Real Estate, Inc.

(475) 263-4675

Nearby Homes

Taylor O'Keefe

About Taylor

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Areas Taylor is Experienced In

Taylor's Listings and Deals

Taylor's Active Listings

Recently Sold

Frequently Asked Questions

Who is Taylor O'Keefe, and what is their real estate background?

How many homes has Taylor O'Keefe sold in Woodbury, CT?

What is Taylor O'Keefe's track record representing buyers?

What is Taylor O'Keefe's track record as a listing agent?

What areas does Taylor O'Keefe serve?

How can I contact Taylor O'Keefe?