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$3,500,000
8 Beds 8 Baths 24158335 MLS
Welcome to The Orange Street Collection, a mixed-use hospitality and residential investment opportunity located in the heart of Downtown New Haven. Positioned steps from Yale University, this asset combines immediate income with meaningful long-term upside in one of the city's most active corridors. The property features over 5,000 square feet of restaurant space across the main and lower levels, including two full kitchens and a flexible layout suited for a flagship dining concept, dual operators, or a hospitality-driven reposition. The lower level offers additional potential for lounge, speakeasy, or private event use. Above, eight residential units provide stabilized income and consistent cash flow, creating built-in diversification and downside protection. This is a rare opportunity to acquire a true mixed-use downtown asset with lease-up potential, strategic location advantages, and strong fundamentals driven by proximity to Yale University, surrounding retail, and vibrant nightlife. Ideal for investors, 1031 exchange buyers, or owner-operators seeking both income and long-term positioning in a growing urban corridor.

99 Orange St, New Haven

$2,199,999
16 Beds 12 Baths 24181250 MLS
Turn-key 6-unit multifamily investment opportunity in New Haven's highly desirable Wooster Square neighborhood! Fully renovated and fully leased with long-term tenants in place, this income-producing asset offers true "collect the keys and collect the rent" ownership. Ideally located just minutes from Downtown New Haven, Yale University, Yale New Haven Hospital, Union Station, I-95, and I-91, the property benefits from strong rental demand driven by education, healthcare, biotech, and technology sectors. The approximately 6,009 SF building features updated units with modern kitchens, renovated bathrooms, contemporary finishes, and attractive layouts that appeal to today's renters. Tenants enjoy walkable access to Wooster Square Park, renowned restaurants including Frank Pepe's and Sally's Apizza, shopping, entertainment, cultural attractions, and direct rail access to New York City. With 5 off-street parking spaces, stable cash flow, and a premier location surrounded by ongoing residential and mixed-use development, this is a rare opportunity to own a fully stabilized multifamily asset in one of Connecticut's strongest rental markets.

177 Chestnut St, New Haven

$1,750,000
16 Beds 16 Baths 24176677 MLS
This newly constructed four-unit townhome asset presents a rare opportunity to acquire a core-plus multifamily property in the New Haven market. Built by a reputable local developer, the property is offered as a single investment asset, ideal for investors seeking stable long-term cash flow with future upside. Each of the four townhome-style units is approximately 2,500 square feet and configured with 4 bedrooms and 3.5 bathrooms. Features include hardwood flooring, tiled bathrooms, central air, stainless steel appliances, in-unit laundry, private decks, and one-car garages. Each unit is separately metered for utilities, supporting efficient management and expense control. Guest parking is also included for added convenience. The property will convey as a single asset with no existing condominium association in place. A future condo conversion may offer additional exit flexibility and potential value enhancement. Located within 7-11 minutes of Yale University, Southern Connecticut State University, and the University of New Haven, the property benefits from consistent rental demand driven by nearby universities, faculty, and medical professionals. Projected market rents are $4,500 per unit per month, supporting an estimated gross annual income of approximately $216,000 based on current assumptions.

15 Colby Ct, New Haven

$1,300,000
22 Beds 11 Baths 24203976 MLS
Attention investors!!! This cash cow is a completely renovated 6 family perfect to add to your portfolio without having to worry about any issues. 6 Brand new furnaces and hot water heaters were just recently installed. Roof is in great condition. All 6 units have brand new hardwood floors throughout apartments, new kitchens, new bathrooms with tiled showers, updated electrical, fresh paint, new windows and much more. 5 of the units consist of 4br 1.5 bath 2 story apartments currently rented for $2,400, $2,300, $2,100, $2,000, last one is vacant and easy to show. The 6th unit is a 2-bedroom, 1 bath currently rented for $1,650. All tenants are up to date on their rents and responsible for their own utilities. Plenty of off street parking for convenience. Laundry hook ups in the basement. Just minutes from I-95, I-91 and downtown New Haven.

767 Congress Ave, New Haven

$1,300,000
9 Beds 9 Baths 24190662 MLS
Exceptional investment opportunity in New Haven's thriving Fair Haven neighborhood! This well-positioned 9-unit apartment building features nine one-bedroom units, offering investors the opportunity to acquire a substantial income-producing asset in one of the city's strongest rental markets. Whether you're looking to expand an existing portfolio or secure a long-term investment, this property presents excellent potential with multiple streams of rental income under one roof. Ideally located in the heart of Fair Haven, residents enjoy convenient access to downtown New Haven, Yale University, Yale New Haven Hospital, local shopping, restaurants, public transportation, and major highways including I-91 and I-95. The neighborhood's proximity to major employers, educational institutions, and everyday amenities continues to drive strong rental demand, making it a desirable location for both tenants and investors alike. The property's location near the Quinnipiac River, neighborhood parks, and local businesses further enhances its appeal while providing easy access to everything New Haven has to offer. With nine one-bedroom apartments, a sizable 7,136-square-foot building, and a location in one of the city's most active multifamily markets, 32 Clinton Avenue represents an outstanding opportunity to invest in a property with strong long-term income potential and portfolio growth.

32 Clinton Ave, New Haven

$1,300,000
6 Baths 24169336 MLS
Exceptional opportunity to acquire or lease a 14,052 SF banquet facility with an attached private club, currently operating as an established catering hall. Situated on 2.35 acres with ample on-site parking for approximately 200 vehicles, this property offers outstanding flexibility for continued hospitality use or redevelopment. Featuring 12-foot ceilings and a well-configured layout, the property is ideally suited for a catering hall, wedding venue, restaurant, or event space. Alternatively, it presents strong potential for adaptive reuse including daycare, nursing home, religious institution, public or private school, two-family homes, or multifamily development. Located just off I-95 (Exit 50), the property offers excellent accessibility and is minutes from downtown New Haven, Yale University, Tweed New Haven Airport, and Yale New Haven Hospital. Zoned RM-1, the site offers redevelopment potential with an estimated yield of approximately 28 residential units (subject to approvals).

560 Woodward Ave, New Haven

$985,000
6 Beds 8 Baths 24206201 MLS
Just two doors in from Orange Street sits this legal two family that is presently being used as a large single-family home with a second-floor studio like apartment. Welcoming front porch leads you into the entry vestibule and spacious foyer with original woodwork and beautiful staircase. The first floor has tall ceilings and features a Living Room, Dining Room, Family Room, Eat in Kitchen, Pantry and Full Bath. The second floor consists of 3 full bedrooms, two full baths and the two room studio apartment that could be converted to a spacious south facing primary bedroom suite. The third floor currently has three rooms and a half bath plus large unfinished attic spaces. Replacement Thermopane windows. Roof 2020. 32'x16' inground pool with new liner. A versatile architectural gem in need of a new buyers vision and updates. Easy walk to downtown and campus and all of the offerings on Orange Street

356 Humphrey St, New Haven

$980,000
13 Beds 6 Baths 24201260 MLS
Rare opportunity to acquire a small multifamily portfolio on Adeline Street in New Haven. The offering consists of a 2 family property at 78 Adeline and a 3 family property at 86 Adeline and a single family at 90 Adeline St. The portfolio is 100% occupied, providing immediate in-place income with separate, tenant-paid utilities throughout. The 2 family features a 1-bedroom unit and a 2-bedroom unit, while the 3 family + single family offers a strong unit mix of three 2-bedroom/1-bath apartments and one 4-bedroom/1-bath unit. Ample off-street parking at both properties adds convenience for tenants + 2 car garage for additional income, tenant amenity or storage. Conveniently located with access to Downtown New Haven, Yale New Haven Hospital, public transportation, shopping, and major commuter routes.

90 Adeline St, New Haven

$979,000
6 Beds 6 Baths 24200440 MLS
Welcome to a home bursting with character and possibility in one of New Haven's most beloved neighborhoods. This stately home sits in East Rock a historic, tree lined enclave prized for its walkability, its mix of architecturally rich homes, and its easy access to East Rock Park, Orange Street's shops and cafes, and the Yale campus just minutes away. Step inside to a grand open staircase that sets the tone the moment you walk through the door. Gleaming parquet flooring flows throughout the home, paired with full length picture windows that flood every room with natural light. A formal dining room just off the entrance offers an elegant space for entertaining, while a beautiful sun room provides the perfect spot to unwind and soak in the light year round. Two full levels of living space offer room to grow, renovate, or reimagine. Outside, a fenced-in yard offers privacy and space to relax, and the detached two car garage adds everyday convenience that's hard to find in this part of the city. With its prime East Rock location and strong bones, 178 Cold Spring presents endless potential whether you're searching for a magnificent single family home to make your own or eyeing a smart investment near Yale for campus housing. Opportunities like this, in a neighborhood this sought after, don't come around often.

178 Cold Spring St, New Haven

$975,000
15 Beds 7 Baths 24103991 MLS
Following strong investor interest and a review of the property's financial performance, the asset has been repositioned to reflect its stabilized income and long-term value. Fully stabilized and well-maintained 5-unit multifamily delivering immediate cash flow and operational stability. The property is 100% occupied with proven tenant history, consistent collections, and strong in-place income exceeding $125,400 annually. Several units feature recent updates and improvements that support tenant retention and continued rent growth. Efficient operating expenses and a solid NOI create a strong overall performance profile. Located in a high-demand rental market in New Haven, this turnkey investment offers both immediate yield and long-term upside. Ideal for investors seeking a stabilized, income-producing asset with reliable performance and DSCR-compatible metrics.

83 James St, New Haven

$859,900
8 Beds 7 Baths 24152633 MLS
Fairhaven Heights' iconic James Babcock House - a classic Victorian Gothic mansion rich in history and architectural beauty. Rumored to have once hosted Abraham Lincoln, this remarkable home features intricate arched woodwork along the eaves and high gables, large windows, and an abundance of original details throughout. Currently operating as a high end 13 bed sober facility with good profit margins! Privately set on a serene interior lot with a secluded driveway connecting East Grand to Clifton Street, this is one of the original Fairhaven Heights estates. A wraparound porch welcomes you into a grand foyer with soaring 11-foot ceilings and a stunning staircase. The formal living room opens to an expansive great room showcasing exquisite woodwork and timeless character. The main level also offers a formal dining room, updated kitchen with butler's pantry, first-floor office with attached half bath, and a bedroom. Five fireplaces are thoughtfully placed throughout the home. Upstairs features eight bedrooms plus two studio apartments, each with its own private bath, along with a total of five full baths and two half baths. The detached two-car garage has been transformed into a wellness space with sauna, cold plunge, and workout area. Ample parking completes the property.This extraordinary estate also offers incredible potential as a private residence, bed and breakfast, or unique investment opportunity. A rare chance to own a true piece of Fairhaven Heights history

89 Sherland Ave, New Haven

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