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Deborah Benjamin

Deborah Benjamin
Real Estate Agent (Salesperson)
Oakville CT

Salesperson (CT: RES.0817350)

5 years experience

REALTOR® 5 Active Listings Serves Litchfield County, CT
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Contact Information

Brokerage
Showcase Realty Inc

Office Website
Office Address
216 Davis St
Oakville, CT  06779
(Litchfield County)
Office Phone
860-274-7000
Office Fax
Mobile
203-228-4269
Email
debb**@**********.com
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About Deborah Benjamin

With more than two decades of experience in education, specializing in business, marketing management, personal finance, and accounting, this professional transitioned to a career in real estate in 2020, fulfilling a lifelong aspiration. Joining Showcase Realty in January 2021, they quickly distinguished themselves, ranking among the top ten in production during the first quarter of their inaugural year. Their outstanding performance earned them the "Rookie of the Year Award" for achieving the highest sales among new agents in 2021. The momentum has continued into 2022, setting the stage for further success.

Litchfield County, CT Real Estate Market Analysis (Single Family Homes)

$899,358
Avg. Listing Price
From Deborah's portfolio
3.5 / 2.7
Avg. Beds/Baths
Typical property size
2,514 sf
Avg. Square Footage
Interior living space
609
Active Listings
Current inventory

Litchfield County, Connecticut represents one of the state's most distinctive and affluent real estate markets, characterized by its blend of historic charm, rural luxury, and proximity to major metropolitan areas. This northwestern Connecticut county has become a magnet for high-net-worth individuals seeking country estates, historic properties, and recreational retreats, creating a unique market dynamic that differs significantly from Connecticut's coastal regions.

The county's real estate landscape is supported by 1,069 total actively licensed agents, with all 1,069 agents maintaining email connectivity, reflecting the market's embrace of digital communication tools essential for serving sophisticated clientele. This robust agent presence indicates strong market activity and competition, particularly given the county's relatively rural character and seasonal property fluctuations.

Major Litchfield County, Connecticut Real Estate Markets

The county's primary real estate activity centers around several key municipalities, with Litchfield, New Milford, and Washington leading in luxury home sales and historic property transactions. Kent, Cornwall, and Salisbury have emerged as particularly sought-after destinations for weekend retreats and country homes, while towns like Torrington and Winsted provide more accessible entry points for buyers seeking the county's rural lifestyle at moderate price points.

What's surprising is how the Litchfield Hills region has become a legitimate alternative to the Hamptons for New York City residents, driving a trend toward year-round residency that's reshaping local market dynamics. Towns like Sharon and Norfolk are experiencing unprecedented demand from remote workers and early retirees, creating inventory shortages that have pushed median home prices well above historical norms.

Market Dynamics and Geographic Complexity

Litchfield County's real estate market operates on multiple tiers, from multi-million-dollar estates along Lake Waramaug to modest farmhouses in rural communities like Harwinton and Barkhamsted. The market's complexity stems from its diverse property types, including working farms, historic colonials, modern luxury builds, and lakefront retreats, each requiring specialized knowledge and marketing approaches.

Seasonal fluctuations significantly impact market timing, with spring and early summer driving peak activity as buyers seek to complete transactions before winter. The county's zoning restrictions and historic preservation requirements add layers of complexity that demand experienced local representation, making agent expertise particularly valuable for navigating regulatory challenges and property-specific considerations.

Why Businesses Need Litchfield County, Connecticut Agent Contact Data

Service providers targeting Litchfield County's affluent real estate market require direct access to the county's 1,069 licensed agents to effectively reach high-value clients and luxury property transactions. Mortgage brokers, home inspectors, luxury contractors, and insurance specialists particularly benefit from agent relationships, as referrals drive significant business volume in this relationship-dependent market environment.

The complete email coverage among licensed agents enables efficient digital marketing campaigns and relationship-building initiatives essential for businesses seeking to establish presence in this competitive luxury market. Given the county's geographic spread and the high-touch nature of luxury real estate transactions, maintaining consistent communication with agents across all 26 municipalities becomes crucial for sustained business growth and market penetration.

Current Property Listings

As of 2/17/2026, Deborah Benjamin has 5 properties for sale in Oakville and surrounding areas.

$325,000

Listed 2026-02-07

20 Wolf Hill Rd Unit 1A
Wolcott, CT  06716

Beds: 2.0
Baths: 2.5
Sq Ft: 1,520
Townhomes Map
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$215,000

Listed 2026-01-10

154 Leffingwell Ave
Waterbury, CT  06710

Beds: 3.0
Baths: 1.5
Sq Ft: 1,415
Lot: 6,098 sf
Single Family Map
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$464,900

Listed 2025-10-25

369 Strongtown Rd
Southbury, CT  06488

Beds: 3.0
Baths: 1.5
Sq Ft: 1,634
Lot: 82,764 sf
Single Family Map
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$299,900

Listed 2026-02-04

86 Cannon Ridge Dr Unit 86
Watertown, CT  06795

Beds: 2.0
Baths: 2.0
Sq Ft: 1,110
Townhomes Map
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$350,000

Listed 2025-09-17

22 Irene Ave
Waterbury, CT  06705

Beds: 3.0
Baths: 2.5
Sq Ft: 2,098
Lot: 11,326 sf
Single Family Map
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Current Property Rentals

Deborah Benjamin currently has no rental properties available in Oakville and surrounding areas. Check back later.