165 Whitfield Street, Guilford, Connecticut

$825,000

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2

Beds

3

Baths

2,595

Square feet

0.25

Acres

About 165 Whitfield Street

Historic Charm Meets Exceptional Investment Opportunity in the Heart of Guilford Steeped in history and ideally located just steps from the iconic Guilford Green, this beautifully maintained circa-1850 Greek Revival property offers a rare opportunity to own one of downtown Guilford's most distinctive two-family residences. Once a single family rectory for the neighboring church, this landmark home has been thoughtfully converted into two spacious apartments while preserving its timeless architectural character. The first-floor residence features an inviting living room highlighted by a sun-filled bay window, a generous bedroom, an eat-in kitchen with direct access to a covered rear deck, a full bath complete with both a jetted tub and separate shower, and an additional dining room that easily functions as a home office, den, or guest room. Beautiful hardwood floors add warmth and character throughout the main living spaces. The second-floor apartment offers an open living and dining area, a spacious bedroom with ample closet space, an eat-in kitchen, a full bath with jetted tub and separate shower, an additional half bath with in-unit laundry, and a finished loft for additional living space, ideal for a home office or bedrooms. Major improvements include updated electrical, plumbing, and insulation, along with a complete exterior renovation completed in 2022, updated kitchens & appliances, with new radon system. Both units have ability for additional bedrooms.

Features of 165 Whitfield Street

MLS® # 24188733
Price $825,000
Bedrooms 2
Bathrooms 3.00
Full Baths 2
Half Baths 1
Square Footage 2,595
Acres 0.25
Type Multi-Family For Sale
Sub-Type 2 Family
Style Units on different Floors
Status Active

Community Information

Address 165 Whitfield Street
Area N/A
City Guilford
County New Haven
State Connecticut
Zip Code 06437

Amenities

Parking Spaces 6
Parking Driveway
Is Waterfront No
Waterfront Walk to Water
Has Pool No

Interior

Heating Baseboard, Electric
Cooling None
Fireplace No
Has Basement Yes
Basement Full, Unfinished, Shared Basement

Exterior

Exterior Clapboard, Wood
Lot Description Historic District
Roof Asphalt Shingle
Foundation Brick, Stone

School Information

Elementary Per Board of Ed
High Per Board of Ed

Additional Information

Date Listed July 2nd, 2026
Days on Market 63
Zoning R-1
RE / Bank Owned No

Listing Details

OfficeThomas W. Hulk

Listing Map

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Listing information last updated on September 10th, 2026 at 10:28am EDT.