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$769,000

A Legacy Address Ready for Its Next Visionary. Rising with quiet confidence along the historic Grand Avenue commercial spine, 922 Grand Avenue stands as one of the city's most architecturally honest and socially resonant commercial buildings. A mid-century civic structure that has outlived trends and weathered cycles, it now emerges as a rare canvas for the next chapter of neighborhood innovation. Built in 1963 during a wave of community-minded construction across the Elm City, the 4,500-square-foot masonry building is an enduring example of New Haven's post-industrial commercial architecture: solid, straightforward, purpose-built. Constructed of concrete, cinder block, and brick, with a flat rubber roof, 12-foot wall heights, and a full 4,500-square-foot basement, the property was engineered for longevity, adaptability, and public use - traits that have allowed it to remain structurally intact for more than six decades. Its original use classification - Clubs/Lodges with a modern STORE/SHOP (MDL-94) designation - reflects its history as a gathering place, a service hub, and a point of local connectivity. The unfinished basement offers expansion potential. The property invites reinvention - fitness and wellness programs, neighborhood brewery, grocery store, performance spaces, coworking studios, nonprofit headquarters, boutique commercial concepts, retail and more possibility subject to city approval. Seize this rare opportunity now.

1 Baths ⋅ 24203165 MLS

A Legacy Address Ready for Its Next Visionary. Rising with quiet confidence along the historic Grand Avenue commercial spine, 922 Grand Avenue stands as one of the city's most architecturally honest and socially resonant commercial buildings. A mid-century civic structure that has outlived trends and weathered cycles, it now emerges as a rare canvas for the next chapter of neighborhood innovation. Built in 1963 during a wave of community-minded construction across the Elm City, the 4,500-square-foot masonry building is an enduring example of New Haven's post-industrial commercial architecture: solid, straightforward, purpose-built. Constructed of concrete, cinder block, and brick, with a flat rubber roof, 12-foot wall heights, and a full 4,500-square-foot basement, the property was engineered for longevity, adaptability, and public use - traits that have allowed it to remain structurally intact for more than six decades. Its original use classification - Clubs/Lodges with a modern STORE/SHOP (MDL-94) designation - reflects its history as a gathering place, a service hub, and a point of local connectivity. The unfinished basement offers expansion potential. The property invites reinvention - fitness and wellness programs, neighborhood brewery, grocery store, performance spaces, coworking studios, nonprofit headquarters, boutique commercial concepts, retail and more possibility subject to city approval. Seize this rare opportunity now.

922 Grand Ave, New Haven

$680,000

Discover a prime investment opportunity with this exceptional multi-family property located in the heart of New Haven, CT. This well-maintained building offers a total of 2 spacious units, each designed for comfort and convenience. Amenities include off-street parking, on-site laundry, beautifully landscaped yard. Situated in a vibrant neighborhood, this property is just minutes away from Yale University, downtown New Haven, and a variety of dining, shopping and cultural attractions. Public transportation is easily accessible, making it convenient for tenants. Potential for increased revenue. Don't miss out on this rare opportunity to own a two-family home in one of Connecticut's most sought-after area. Walking distance to New Haven's Best! And let's not forget to mention the BEAUTIFUL back yard! You will never see another with such awesome plantings designed to cater to a multifamily residence with lush greenery and thoughtfully arranged spaces that invite both relaxation and community bonding. A true city oasis! This is a must-see property!

4 Beds ⋅ 2 Baths ⋅ 24197946 MLS

Discover a prime investment opportunity with this exceptional multi-family property located in the heart of New Haven, CT. This well-maintained building offers a total of 2 spacious units, each designed for comfort and convenience. Amenities include off-street parking, on-site laundry, beautifully landscaped yard. Situated in a vibrant neighborhood, this property is just minutes away from Yale University, downtown New Haven, and a variety of dining, shopping and cultural attractions. Public transportation is easily accessible, making it convenient for tenants. Potential for increased revenue. Don't miss out on this rare opportunity to own a two-family home in one of Connecticut's most sought-after area. Walking distance to New Haven's Best! And let's not forget to mention the BEAUTIFUL back yard! You will never see another with such awesome plantings designed to cater to a multifamily residence with lush greenery and thoughtfully arranged spaces that invite both relaxation and community bonding. A true city oasis! This is a must-see property!

100 William St, New Haven

$875,000

This Wooster Square brick and frame 4 family is an amazing opportunity. Good size apartments, separate utilities with gas heat and hot water heaters, replacement windows, washers and dryers in each unit and off-street parking for 6 cars. The building has been well maintained. The current rents are under market value, but some updates will bring this building to its' full potential. Located in an ideal location close to Yale, YNHH, the train station and downtown New Haven.

8 Beds ⋅ 4 Baths ⋅ 24199790 MLS

This Wooster Square brick and frame 4 family is an amazing opportunity. Good size apartments, separate utilities with gas heat and hot water heaters, replacement windows, washers and dryers in each unit and off-street parking for 6 cars. The building has been well maintained. The current rents are under market value, but some updates will bring this building to its' full potential. Located in an ideal location close to Yale, YNHH, the train station and downtown New Haven.

191 Saint John St, New Haven

$1,200,000

Prime Wooster Square 4-Unit Investment Opportunity! Ideally located just steps from Wooster Square and minutes from Yale University, this beautifully updated four-unit property offers an exceptional opportunity for investors, owner-occupants, or those seeking flexible rental options. The property has been tastefully renovated while thoughtfully preserving its original character, including exposed brick and charming architectural details. All four units are being offered fully furnished, creating a truly turnkey opportunity. Select units have been utilized as Airbnb rentals, while the property's proximity to Yale makes it ideally positioned for strong rental demand. Whether continuing with short-term rentals, transitioning to traditional leases, or exploring a combination of both, this property offers tremendous flexibility. Enjoy the best of New Haven with world-class dining, cafes, parks, Yale University, and downtown amenities all close by. A rare opportunity to own a distinctive four-family property in one of New Haven's most sought-after neighborhoods, combining historic charm, modern updates, prime location, and multiple income-producing possibilities.

5 Beds ⋅ 4 Baths ⋅ 24198627 MLS

Prime Wooster Square 4-Unit Investment Opportunity! Ideally located just steps from Wooster Square and minutes from Yale University, this beautifully updated four-unit property offers an exceptional opportunity for investors, owner-occupants, or those seeking flexible rental options. The property has been tastefully renovated while thoughtfully preserving its original character, including exposed brick and charming architectural details. All four units are being offered fully furnished, creating a truly turnkey opportunity. Select units have been utilized as Airbnb rentals, while the property's proximity to Yale makes it ideally positioned for strong rental demand. Whether continuing with short-term rentals, transitioning to traditional leases, or exploring a combination of both, this property offers tremendous flexibility. Enjoy the best of New Haven with world-class dining, cafes, parks, Yale University, and downtown amenities all close by. A rare opportunity to own a distinctive four-family property in one of New Haven's most sought-after neighborhoods, combining historic charm, modern updates, prime location, and multiple income-producing possibilities.

341 Saint John St, New Haven

$285,000

Your chance to experience modern townhouse living in New Haven's most iconic and legendary neighborhood awaits! Welcome to this open and sun filled 2 bedroom, 1.5 bath townhouse located on sought after Wooster Street. This move in ready home with new windows features a bright, flowing layout with freshly painted interiors that create a clean, modern feel throughout. The main level offers an inviting open living and dining area, ideal for everyday comfort and entertaining. Upstairs, both bedrooms are generously sized, and the full bath plus main level half bath add convenience for residents and guests. A garage located underneath provides secure parking and protection from the elements, while an additional private storage unit offers valuable extra space for seasonal items and belongings. Live steps from world famous Wooster Street eateries - Pepe's, Sally's, and a lineup of neighborhood favorites - while enjoying easy access to downtown, Yale, parks, and transit. Whether you're grabbing a slice, commuting, or exploring the city, everything is right at your fingertips. Commuters will appreciate the easy access to major highways, including I-95 and I-91. This home is also eligible for the Yale Homebuyer Program for Yale employees. Ask for details!

2 Beds ⋅ 2 Baths ⋅ 24198228 MLS ⋅ Wooster Court BLDG.

Your chance to experience modern townhouse living in New Haven's most iconic and legendary neighborhood awaits! Welcome to this open and sun filled 2 bedroom, 1.5 bath townhouse located on sought after Wooster Street. This move in ready home with new windows features a bright, flowing layout with freshly painted interiors that create a clean, modern feel throughout. The main level offers an inviting open living and dining area, ideal for everyday comfort and entertaining. Upstairs, both bedrooms are generously sized, and the full bath plus main level half bath add convenience for residents and guests. A garage located underneath provides secure parking and protection from the elements, while an additional private storage unit offers valuable extra space for seasonal items and belongings. Live steps from world famous Wooster Street eateries - Pepe's, Sally's, and a lineup of neighborhood favorites - while enjoying easy access to downtown, Yale, parks, and transit. Whether you're grabbing a slice, commuting, or exploring the city, everything is right at your fingertips. Commuters will appreciate the easy access to major highways, including I-95 and I-91. This home is also eligible for the Yale Homebuyer Program for Yale employees. Ask for details!

120 Wooster St Unit Q, New Haven

$595,000

Wooster Square condo living with direct park views and historic character. This twolevel, 2 bedroom, 2 bath home offers oversized windows overlooking the cherrytreelined square, 11+ ft ceilings, exposed brick, and hardwood floors. The main level includes a bright living area with dramatic 8 ft windows, an office nook ideal for remote work, and a kitchen with granite counters, an island, and gas cooking. A full bath with walkin shower and a flexible second bedroom-complete with Murphy bed and access to a shared back deck-round out this floor. The lower level features a spacious primary suite with a walkin closet, full bath, and inunit laundry, creating a quiet, comfortable retreat. The association offers a common patio for grilling, relaxing, and outdoor dining. Additional basement storage, updated mechanicals, and central A/C add everyday convenience. Located on a quiet block in one of New Haven's most beloved neighborhoods, you're steps from worldfamous Apizza, downtown, the Wooster Square Farmers Market, and major highways. Pets allowed (with restrictions). Onstreet parking. A rare chance to live directly on Wooster Square with character, comfort, and unbeatable walkability.

2 Beds ⋅ 2 Baths ⋅ 24194029 MLS ⋅ On The Park BLDG.

Wooster Square condo living with direct park views and historic character. This twolevel, 2 bedroom, 2 bath home offers oversized windows overlooking the cherrytreelined square, 11+ ft ceilings, exposed brick, and hardwood floors. The main level includes a bright living area with dramatic 8 ft windows, an office nook ideal for remote work, and a kitchen with granite counters, an island, and gas cooking. A full bath with walkin shower and a flexible second bedroom-complete with Murphy bed and access to a shared back deck-round out this floor. The lower level features a spacious primary suite with a walkin closet, full bath, and inunit laundry, creating a quiet, comfortable retreat. The association offers a common patio for grilling, relaxing, and outdoor dining. Additional basement storage, updated mechanicals, and central A/C add everyday convenience. Located on a quiet block in one of New Haven's most beloved neighborhoods, you're steps from worldfamous Apizza, downtown, the Wooster Square Farmers Market, and major highways. Pets allowed (with restrictions). Onstreet parking. A rare chance to live directly on Wooster Square with character, comfort, and unbeatable walkability.

42 Academy St Unit 2, New Haven

$775,000

Rare historic Wooster Square compound featuring a detached carriage house and private garden retreat. Opportunities like this seldom come to market in New Haven's iconic Wooster Square Historic District. Built in 1870, this distinguished brick residence offers 3 BR, 2 full baths, and a rare blend of architectural character, flexible living space, and private outdoor living. Behind the historic brick facade, soaring ceilings, original details, and two decorative fireplaces evoke the craftsmanship & charm of a bygone era, while thoughtful updates provide modern comfort, including a remod 2nd bath. The unfinished third floor offers expansion potential and a lookout perch overlooking the neighborhood. The walk-out lower level has been transformed into a cozy cabin-inspired retreat, ideal for entertaining or relaxing, with abundant storage. Set on a fenced corner lot, the property lives like a private compound with mature landscaping, intimate garden spaces, and off-street parking-an unexpected retreat in the heart of the city. The detached carriage house has been extensively upgraded into a sophisticated home office & fitness studio, offering flexibility and potential Yale Homebuyer Program eligibility, with the option to convert back to a 2-car gar. Just moments from Wooster Square's cherry blossoms, farmers market, world-famous pizza, Union Station,Yale,Yale NH Hospital, downtown, restaurants, and major highways. Historic. Private. Flexible. Walkable.

3 Beds ⋅ 2 Baths ⋅ 24187215 MLS

Rare historic Wooster Square compound featuring a detached carriage house and private garden retreat. Opportunities like this seldom come to market in New Haven's iconic Wooster Square Historic District. Built in 1870, this distinguished brick residence offers 3 BR, 2 full baths, and a rare blend of architectural character, flexible living space, and private outdoor living. Behind the historic brick facade, soaring ceilings, original details, and two decorative fireplaces evoke the craftsmanship & charm of a bygone era, while thoughtful updates provide modern comfort, including a remod 2nd bath. The unfinished third floor offers expansion potential and a lookout perch overlooking the neighborhood. The walk-out lower level has been transformed into a cozy cabin-inspired retreat, ideal for entertaining or relaxing, with abundant storage. Set on a fenced corner lot, the property lives like a private compound with mature landscaping, intimate garden spaces, and off-street parking-an unexpected retreat in the heart of the city. The detached carriage house has been extensively upgraded into a sophisticated home office & fitness studio, offering flexibility and potential Yale Homebuyer Program eligibility, with the option to convert back to a 2-car gar. Just moments from Wooster Square's cherry blossoms, farmers market, world-famous pizza, Union Station,Yale,Yale NH Hospital, downtown, restaurants, and major highways. Historic. Private. Flexible. Walkable.

161 Olive St, New Haven

$2,199,999

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.

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

$3,500,000

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.

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