# 66 High Street #4, Guilford, CT 06437 > **TL;DR:** 2bd/2ba townhouse, $1,200,000 ($634/sqft), built 1884, 1,893 sqft. > Fireplace, A/C, 1-car garage. Est. $7,636/mo. Listed 25 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $1,200,000 | | Price/sqft | $634 | | Bedrooms | 2 | | Bathrooms | 2 full | | Square Feet | 1,893 | | Year Built | 1884 | | Stories | 2 | | Garage | 1-car | | Property Type | Townhouse (Townhouse) | | Status | Active | | Days on Market | 25 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $6,068 | | Estimated Insurance | $350 | | HOA | $1,218 | | **Total** | **$7,636** | ## Nearby Schools - **Elementary:** Per Board of Ed - **High:** Guilford ## Key Amenities - Fireplace - A/C - 1-car garage ## Property Highlights - Built in 1884 - 2 stories - 2 parking spaces - Fireplace ## Description ### Agent Description Just steps from Guilford's historic town green, vibrant boutiques, and gourmet dining-and a short stroll to the town marina and train station-The Residences at 66 High Street offers an extraordinary blend of historic character & cosmopolitan luxury in the award-winning complex. Step inside this stunning two-bedroom unit, once honored as the coveted HOBI (Home Building Industry) Project of the Year. The open-concept main level showcases original exposed brick, seamlessly connecting a living area anchored by a sleek gas fireplace to a gourmet kitchen outfitted with a Wolf range, Sub-Zero refrigerator, quartz countertops, and an entertaining island w seating. Designed for effortless living, the first floor features a convenient guest suite w a connecting full bath, first-floor laundry, & heated bathroom floors. A dramatic wood-and-metal staircase leads to a second-floor loft w a built-in workspace & custom shelving. Retreat to the private primary suite, boasting dramatic 12-foot ceilings, a generous walk-in closet, & a spa-inspired bath. The crown jewel of the home is your very own secret rooftop deck crafted from teak & shaded by a pergola-an outdoor sanctuary offering expansive town views. This unit includes a detached oversized private garage w storage plus an assigned parking space just steps from your door. Residents enjoy an exceptional lifestyle enriched by community amenities, including an in-ground pool, gas fire pit lounge, garden beds, state of the art fitness center and a dedicated dog park, all complemented by an easy commute to New Haven and a convenient two-hour trip to New York City. ## Location - **Address:** 66 High Street #4, Guilford, CT 06437 - **County:** New Haven ## Listing Agent - **Name:** Janet Cronin-Rumanoff - **Brokerage:** William Pitt Sotheby's International Realty - **Broker Phone:** 2034532533 ## Photos ![66 High Street #4 - Photo 1](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f4263235655r.jpg) ![66 High Street #4 - Photo 2](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f2520488813r.jpg) ![66 High Street #4 - Photo 3](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f1532484836r.jpg) ![66 High Street #4 - Photo 4](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f3894621473r.jpg) ![66 High Street #4 - Photo 5](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f238182648r.jpg) ![66 High Street #4 - Photo 6](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f1323435014r.jpg) ![66 High Street #4 - Photo 7](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f61787286r.jpg) ![66 High Street #4 - Photo 8](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f759740371r.jpg) ![66 High Street #4 - Photo 9](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f1940530136r.jpg) ![66 High Street #4 - Photo 10](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f276244418r.jpg) ![66 High Street #4 - Photo 11](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f1004322889r.jpg) ![66 High Street #4 - Photo 12](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f2617532883r.jpg) ![66 High Street #4 - Photo 13](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f3297259150r.jpg) ![66 High Street #4 - Photo 14](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f252107470r.jpg) ![66 High Street #4 - Photo 15](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f3187308274r.jpg) ![66 High Street #4 - Photo 16](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f2271407522r.jpg) ![66 High Street #4 - Photo 17](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f184233120r.jpg) ![66 High Street #4 - Photo 18](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f1382330535r.jpg) ![66 High Street #4 - Photo 19](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f3364429467r.jpg) ![66 High Street #4 - Photo 20](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f2908345227r.jpg) ![66 High Street #4 - Photo 21](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f635567613r.jpg) ![66 High Street #4 - Photo 22](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f2506845812r.jpg) ![66 High Street #4 - Photo 23](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f632197074r.jpg) ![66 High Street #4 - Photo 24](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f3145375580r.jpg) ![66 High Street #4 - Photo 25](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f459317462r.jpg) ![66 High Street #4 - Photo 26](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f2848713320r.jpg) ![66 High Street #4 - Photo 27](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f2806366380r.jpg) ![66 High Street #4 - Photo 28](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f3884813649r.jpg) ![66 High Street #4 - Photo 29](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f4042007720r.jpg) ![66 High Street #4 - Photo 30](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f2533924157r.jpg) ![66 High Street #4 - Photo 31](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f2567025409r.jpg) ![66 High Street #4 - Photo 32](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f1902078831r.jpg) ![66 High Street #4 - Photo 33](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f2015879245r.jpg) ![66 High Street #4 - Photo 34](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f2751401111r.jpg) ![66 High Street #4 - Photo 35](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f1852560794r.jpg) ![66 High Street #4 - Photo 36](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f871790013r.jpg) ![66 High Street #4 - Photo 37](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f415187955r.jpg) ![66 High Street #4 - Photo 38](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f226170501r.jpg) ![66 High Street #4 - Photo 39](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f1488627378r.jpg) ![66 High Street #4 - Photo 40](http://lh.rdcpix.com/c84f8db8dd6fb5028c607efb912d4b01l-f2729941562r.jpg) --- **MLS#:** 24212233 | **Updated:** 2026-10-29 **Source:** listhub *Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://staging.propertysimple.ai/listing/66-high-street-guilford-ct-06437-6f268a4e47e34fcbad75870a5ba59acf) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/66-high-street-guilford-ct-06437-6f268a4e47e34fcbad75870a5ba59acf#listing", "url": "https://staging.propertysimple.ai/listing/66-high-street-guilford-ct-06437-6f268a4e47e34fcbad75870a5ba59acf", "name": "66 High Street #4, Guilford, CT 06437", "description": "Just steps from Guilford's historic town green, vibrant boutiques, and gourmet dining-and a short stroll to the town marina and train station-The Residences at 66 High Street offers an extraordinary blend of historic character & cosmopolitan luxury in the award-winning complex. Step inside this stunning two-bedroom unit, once honored as the coveted HOBI (Home Building Industry) Project of the Year. The open-concept main level showcases original exposed brick, seamlessly connecting a living area anchored by a sleek gas fireplace to a gourmet kitchen outfitted with a Wolf range, Sub-Zero refrigerator, quartz countertops, and an entertaining island w seating. Designed for effortless living, the first floor features a convenient guest suite w a connecting full bath, first-floor laundry, & heated bathroom floors. A dramatic wood-and-metal staircase leads to a second-floor loft w a built-in workspace & custom shelving. Retreat to the private primary suite, boasting dramatic 12-foot ceilings, a generous walk-in closet, & a spa-inspired bath. The crown jewel of the home is your very own secret rooftop deck crafted from teak & shaded by a pergola-an outdoor sanctuary offering expansive town views. 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