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$3,990,000
4 Baths ⋅ 24135654 MLS
Rare opportunity to acquire a beautifully restored 21-unit multifamily asset in New Haven's sought-after East Rock neighborhood. Once home to the YMCA and historic Railroad Boarding House, this timeless brick building blends classic architecture with modern luxury and a true sense of community. The unit mix includes 6 studios, 10 one-bedrooms, and 5 two-bedrooms (some with two baths), all featuring granite countertops, stainless steel appliances, in-unit washer/dryers, and individual heating, hot water, and central air. Four ground-floor units offer private rear entrances for added convenience and privacy. Outdoor amenities include six EV charging stations set on handsome pavers, community garden boxes, and a picnic area that enhances the building's inviting atmosphere. Additional features include secure access, a fitness room, and off-street parking. Ideally located minutes from Yale University, East Rock Park, downtown, and area restaurants and shops. Tenant-paid utilities and an assumable Freddie Mac loan at 3.8% (1% assumption fee) make this a turnkey, efficient investment in one of Connecticut's strongest rental markets.

1435 State St, New Haven
$3,500,000
4 Baths ⋅ 24153679 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
$2,250,000
4 Baths ⋅ 24163167 MLS
Ideal property for a 1031 Exchange! Situated in the heart of the Yale Medical Community, and directly across from Saint Raphael's, this offering includes two parcels, both in an RO zone. The first is 1455 Chapel which is a 6,343 square foot medical office / residence sitting on .35 acres. The second is an additional .16 acre parking lot adjacent to 1455 Chapel on Sherman Avenue. The Sherman Lot has a 15 foot entrance off Sherman Avenue. 1455 Chapel has 71 feet of frontage on Chapel Street. Perfect opportunity for parking as both parcels currently boast a total of 52 parking spaces. Other uses might include a "walk-thru restaurant catering to the thousands of Yale Medical employees and millions of in and out patients seen by Saint Raphael's and Yale. Maybe a food truck park satisfy the impressive level of traffic looking to eat as well as park? Possibilities are endless given the foot and car traffic. Price, acreage and taxes all reflect both parcels. Please watch and listen to the video.

1455 Chapel St, New Haven
$2,100,000
4 Baths ⋅ 24173993 MLS
475 Whitney Avenue presents a rare opportunity to restore & reposition one of New Haven's most architecturally significant properties into a signature residential asset. The building has been used by a prominent law firm since 1971. Originally constructed as a grand private residence in 1896, the building is ideally suited for conversion back to a luxury single-family estate or redevelopment from the current office configuration as a boutique multi-family or condominium offering. The structure's scale, craftsmanship & layout-featuring expansive rooms, high ceilings & formal entertaining spaces-lend themselves naturally to residential reuse. The architectural details including the yellow venetian brick & copper gutters & flashing make this prohibitively expensive to replicate today. In addition to the main residence the property includes a detached rear structure (originally a garage later converted to conference space) that can possibly be repositioned into 1 or 2 addtl residential units, guest accommodations or accessory dwelling space creating meaningful added value & flexibility. The current site configuration includes a large, paved parking area, which offers a unique opportunity to reclaim a portion of the grounds for landscaped lawns, private outdoor space & a formal residential driveway, restoring the property's original estate-like setting while maintaining functional access. 475 Whitney is widely regarded as one of the most distinctive residences along Whitney Ave.

475 Whitney Ave, New Haven
$1,595,000
4 Beds ⋅ 4 Baths ⋅ 24201633 MLS
An address of true distinction, 8 Saint Ronan Terrace offers a rare opportunity to reside within a private enclave in the heart of Prospect Hill. Set upon a nearly quarter-acre lot, this residence serves as a secluded sanctuary just moments from the Yale University campus. It is a home where historic architectural integrity meets a sophisticated, modern lifestyle, complete with forward-thinking amenities like a newly installed EV charger. Inside, the scale and finish are exceptional. The floor plan offers four generous bedrooms, a tranquil library, and two versatile flex rooms perfectly suited for additional bedrooms, an office, gym or professional studio. Culinary pursuits are elevated in the renovated chef's kitchen, a space defined by the precision of Wolf and Sub-Zero appliances. The primary suite is a true destination, featuring a light-filled sunroom, a custom boutique closet, and a newly reimagined spa bath. The location offers a lifestyle defined by culture and convenience. Positioned moments from Yale, the residence provides effortless access to the energy of Downtown New Haven and the scenic beauty of East Rock. Residents can enjoy world-class museums and the city's renowned fine dining scene, all while benefiting from the property's inclusion in the Worthington Hooker Elementary district. Every inch of this property has been thoughtfully curated, offering a polished retreat in New Haven's most storied and prestigious district.

8 Saint Ronan Ter, New Haven
$1,295,000
4 Baths ⋅ 24178859 MLS
Built in 1901 by S.G. Taylor in New York, the "John Slade Ely House" was built as a residence for John Slade, a physician and professor in theory and practice of medicine at Yale. The 6,651 SQ FT Tudor style building is at the gateway between East Rock and Downtown on Trumbull Street. Its historical origins remain intact with the grand staircase, elaborate fireplaces, leaded glass windows, arched doorways, coffered ceilings and detailed woodwork. Spread across three levels, with an additional 2,672 sq ft in the unfinished basement, the possibilities are endless. New Haven City Plan recently approved a conversion into ten apartments. The property would also be perfect for a conversion back to a primary residence, a live/work space, or non-profit use. The building has oil heat, a brand new roof, a handicap ramp, and a large backyard. This is a landmark property that will not last long!

51 Trumbull St, New Haven
$1,200,000
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
$1,200,000
4 Baths ⋅ 24171998 MLS
46 Clinton Ave, New Haven, CT presents a rare opportunity for an end user, business owner, or investor to own a versatile mixed-use property with 6 total units, including 2 large bay/warehouse-style units. The layout offers excellent flexibility for a wide range of uses, including contractor storage, auto-related use, light industrial, workshop space, distribution, warehousing, construction/trades business, equipment storage, or an owner-operated business with additional rental income from the remaining units. With functional bay space and multiple income-producing components, this property gives an owner-user the ability to operate their business on-site while offsetting expenses through rental income. Conveniently located in New Haven with access to major roads, local businesses, and neighborhood amenities, 46 Clinton Ave is a strong fit for a user looking for space, flexibility, and long-term upside.

46 Clinton Ave, New Haven
$1,100,000
5 Beds ⋅ 4 Baths ⋅ 24188743 MLS
An absolute Westville treasure! This home, known as the Frederick Penny House is a Queen Anne Renaissance Revival and has been extensively renovated and restored to its original glory. The home boasts 5 bedrooms, including 2 primary suites, 3 other bedrooms, and 3.5 updated baths with climate control showers. A grand entryway has a magnificent mohogany staircase, arched entryways, original woodwork and moldings, beautifully maintained hardwoord floors and high ceilings.The Living Room and the Family Room with built ins and reading nooks, both have fireplaces. Spacious dining room off the butlers pantry with wine fridge. The fully renovated kitchen has an island, granite countertops and stainless steel appliances and door to access the private deck. 2nd floor of the home has 4 large bedrooms (one with full en suite bath) and a renovated full bath off the hallway. 3rd floor has the beautiful primary suite with full bath containing a soaking tub and climate control shower. Large walk-in closet that can also serve as a dressing room. Full laundry Room with sink is located in the basement, which is finished. Newer gas furnace, central air and roof. Huge level backyard and two car detached garage round out this spectacular home. This home has been beautifully renovated to preserve its historic charm and remains one of the last homes of its kind that has not been converted into a multi-family residence. Photos will be uploaded soon!

329 Alden Ave, New Haven
$950,000
6 Beds ⋅ 4 Baths ⋅ 24166780 MLS
Wonderful three family home with excellent income in East Rock. The three apartments have been an excellent income producer. The first floor apartment has a living room, eat-in kitchen, 2 bedrooms and a full bath. It has a stairway to the lower level which offers two large finished rooms and a bath. The second floor apartment includes a living room, kitchen, two bedrooms and a bath. The third floor has two levels of living space. There are four rooms with 2 bedrooms and a bath, plus there is a staircase to the top floor which offers a sitting room ad on additional room. The three apartments have separate utilities and the tenants are responsible for their heat, cooking gas, hot water and electric usage. There is a one car garage that has good size storage room behind it. Three cars can park in front of the garage. The wide yard has a patio and lots of space for outdoor living. The property is close to neighborhood cafes, markets, East Rock Park and the Yale Shuttle. The property has been meticulously maintained and is an ideal opportunity.

117 Nicoll St, New Haven
$875,000
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
$695,000
3 Beds ⋅ 4 Baths ⋅ 24186548 MLS
Rare opportunity to own a mixed use investment property in the heart of Westville village with excellent long term commercial business/tenant on the ground level. The building consist of 2714 SQ FT on the main and second floor plus an unfinished walk up attic with incredible expansion possibilities. The main level is leased to an established and loved restaurant/bar with a strong rent. The second level of the building features a spacious two bedroom apartment currently rented for $1550 per month. The apartment features a 5 room layout with large carpeted living room, separate dining room, large eat in kitchen, 2 bedrooms and one full bath. If needed, the living room could be used as a third bedroom. The apartment has a staircase that leads to the unfinished attic with expansion possibilities - perfect for two additional bedrooms and a full bath. The building has separate utilities (oil and electric), mid-aged boilers, a newer roof and a large parking lot in the rear for ~6-8 cars. This is an investment opportunity you don't find often, don't miss your chance to own this rare property in Westville!

879 Whalley Ave, New Haven
$674,900
4 Beds ⋅ 4 Baths ⋅ 24198229 MLS
Experience refined waterfront living on the Quinnipiac River,where this 2001 custombuilt residence rises above the shoreline to capture sweeping,unobstructed views of the Quinnipiac Meadows Nature Preserve.Protected marshland stretches out before you, with egrets, ospreys, swans, ducks, and even bald eagles creating a daily natural spectacle. Private river access allows effortless launching of kayaks, canoes, or small craft, blending recreation with tranquility.Outdoor living feels resortlike, with a generous upper deck for morning light and evening breezes, a covered lower patio for shaded relaxation, and terraced lawns framed by stone walls and mature trees. Adirondack seating at the water's edge invites quiet moments overlooking the tide and preserve.Inside, the main level is bright and open, anchored by a white kitchen with stainlesssteel appliances, butcherblock island, and classic subway tile. Sunfilled dining and living areas feature hardwood floors and expansive windows that frame the river. The primary suite enjoys panoramic water views and sliding doors, while additional bedrooms offer flexible, wellappointed space. A lowerlevel family room provides a dramatic vantage point over the marsh, ideal for intimate gatherings. A rare luxury amenity, the detached 1,025sf garage with soaring ceilings accommodates vehicles, boats, kayaks, or workshop space. This home is a private waterfront sanctuary offering beauty, serenity, and a lifestyle few properties can match!

866 Quinnipiac Ave, New Haven
$600,000
10 Beds ⋅ 4 Baths ⋅ 24201256 MLS
Unique investment opportunity at 86 & 90 Adeline Street in New Haven, consisting of two parcels featuring a three-family, single-family home, and detached two-car garage. The unit mix includes three 2-bedroom/1-bath apartments and one 4-bedroom/1-bath home, all 100% occupied and providing immediate rental income. All units have separate, tenant-paid utilities (gas heat and hot water). The properties also offer ample off-street parking in addition to the detached garage. Conveniently located with access to Downtown New Haven, Yale New Haven Hospital, public transportation, shopping, and major commuter routes. For investors seeking additional scale, this can be purchased together with the neighboring two-family property and lot at 78 Adeline Street. A strong opportunity to expand an existing portfolio or establish a larger multifamily presence in the New Haven market.

86 Adeline St, New Haven
$599,900
4 Beds ⋅ 4 Baths ⋅ 24195560 MLS
**OPEN Saturday, Sept. 12, 2026 - 11AM to 1PM** This beautiful 4-bedroom, 3.5-bath Cape is a must-see and won't last long! From the moment you step through the front door, you'll feel right at home. The spacious living room flows into the dining room, which opens to the inviting kitchen-perfect for everyday living and entertaining. The main level also features two bedrooms and a full bath, offering flexible living space for family, guests, or a home office. Upstairs, you'll find a spacious primary bedroom complete with two walk-in closets, along with a second bedroom featuring its own walk-in closet. With abundant storage throughout, there's plenty of room for all your treasures. The finished basement provides even more living space with a comfortable recreation room, utility area, and convenient half bath. Step outside to enjoy the spacious paver patio, thoughtfully designed for entertaining, with plenty of room for outdoor dining, a firepit, and a covered barbecue area complete with a pizza oven. With its versatile layout, generous storage, finished lower level, and incredible outdoor entertaining space, this home truly has room for everyone. Don't miss the opportunity to make it yours! Permits for the additional bathroom have been closed. Town card will be updated to reflect three full bathrooms one half bath please see attached documents to provide further information.

203 Russell St, New Haven
$599,900
4 Baths ⋅ 170613179 MLS
Listen up investors, here is your opportunity to own a store front, multi unit 3 rental apartments: (2) 1 bedroom apartment and (1) 3 bedroom apartment. Listing price includes the: (liquor, beer, soda, juice and cigarettes inventories, liquor and lottery licenses. This can be used as a multi-function property.

578 Winchester Ave, New Haven
$595,000
9 Beds ⋅ 4 Baths ⋅ 24178401 MLS
A well maintained 3 family investment with all 3 bedrooms in the Dwight neighborhood of New Haven! Very close to Yale University, Yale Hospital, and the downtown shops and restaurants. The rental prices for three bedroom units in the area are averaging $1,800 per month and trending towards $2,000 per month. The property features in-unit washer and drier hookups for all units and paved off-street parking.

607 Elm St, New Haven
$549,900
9 Beds ⋅ 4 Baths ⋅ 24206142 MLS
169 Chatham Street, a legal four-family property, is being offered for the first time in approximately 25 years. This well-maintained property offers a rare opportunity with tremendous flexibility for both an owner-occupant and an investor looking to add to their portfolio. The lower level features an efficiency apartment currently occupied by the owner. The spacious first-floor apartment is ideal for a homeowner who wants plenty of living space while allowing rental income from the additional units to help offset the mortgage. This unit offers 3 bedrooms, 2 full bathrooms, a living room, dining room and kitchen, along with engineered hardwood flooring and fresh paint. The second-floor apartment is occupied by long-term tenants and features 3 bedrooms and 1 full bathroom. The third-floor apartment offers 2 bedrooms and 1 full bathroom. The existing tenants are leased through January 2027, providing immediate rental income for the new owner. Additional features include separate utilities, a garage and a private driveway. Whether you are looking to owner-occupy while building equity or add a solid four-family property to your investment portfolio, 169 Chatham Street offers space, income potential and endless possibilities. Sold as is.

169 Chatham St, New Haven
$536,000
8 Beds ⋅ 4 Baths ⋅ 24204097 MLS
Exceptional investment opportunity in New Haven. This well-maintained two-family property offers strong potential cash flow making it an excellent addition to any investor's portfolio or an ideal owner-occupied opportunity. The first floor features 3 bedrooms and 2 bathrooms. and second and third level features 5 bedrooms and 2 full bathrooms. All units have been updated with modern kitchens and bathrooms and beautiful hardwood floors throughout, providing comfortable and attractive living spaces for tenants. Each unit also benefits from its own dedicated parking space located at the rear of the property, adding convenience for residents. Ideally situated in New Haven offers easy access to I-95, Yale University. Making this a highly desirable rental location with lasting appeal. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the others, this income-producing property is one you won't want to miss

New Haven
$535,000
5 Beds ⋅ 4 Baths ⋅ 24183907 MLS
Opportunity knocks with this spacious 3 family property, located just minutes from Yale New Haven Hospital Saint Raphael Campus, Downtown New Haven, Route 34, and major commuter routes. Featuring two spacious 2-bedroom units and one 1-bedroom unit, each offering hardwood floors, large living rooms, dining rooms, and generous layouts. The second-floor unit includes 1.5 baths. Additional features include off-street parking, a large backyard, and a balcony with views of Downtown New Haven. Ideal for owner-occupants or investors seeking strong rental demand in a convenient location.

65 Parmalee Ave, New Haven
$499,900
6 Beds ⋅ 4 Baths ⋅ 24189456 MLS
Exceptional value-add opportunity in the heart of New Haven's desirable Edgewood neighborhood! This unique multi-family property offers an exciting opportunity for investors, developers, and visionaries looking to unlock its full potential. Currently configured as a 2-family with 6 bedrooms and 6 full bathrooms, the property also comes with zoning-approved plans to convert it into a 5-family residence, creating a rare opportunity to significantly increase its income-producing potential. With generous square footage and a flexible layout, this property provides a strong foundation for a transformative renovation. Whether you're an experienced investor or looking for your next development project, the possibilities are substantial. Bring your contractor, your vision, and the right team to reimagine this property into a standout asset in one of New Haven's most established neighborhoods. Located in the sought-after Edgewood neighborhood, you'll enjoy convenient access to Edgewood Park, Yale University, Yale New Haven Hospital, local restaurants, shopping, public transportation, and major highways, making this an attractive location for future tenants. While the property requires significant renovation and is being offered as an opportunity for someone ready to add value, the approved conversion plans and prime location make it a truly compelling investment. Don't miss your chance to bring new life to a property with exceptional upside and long-term potential.

244 Sherman Ave, New Haven
$469,000
6 Beds ⋅ 4 Baths ⋅ 24189597 MLS
Welcome to 115 Dewitt Street, an excellent opportunity for homeowners looking to build equity while reducing their monthly housing expenses. This spacious multifamily property offers six bedrooms, three full bathrooms plus one half bathroom, and approximately 2,255 square feet of living space. Live comfortably in one unit while collecting rental income from the additional unit to help offset your mortgage. Conveniently located in New Haven's Hill neighborhood near downtown, Yale New Haven Hospital, shopping, dining, and public transportation, this property offers both comfortable living and long-term financial potential.

115 Dewitt St, New Haven
$459,990
9 Beds ⋅ 4 Baths ⋅ 24197366 MLS
Investors take notice! This turnkey, income-producing 9-bedroom, 4-bath investment property offers strong cash flow with long-term tenants already in place, making it an excellent opportunity for both first-time and seasoned investors. The property features generously sized bedrooms, spacious bathrooms, durable vinyl flooring, and newer appliances throughout. With stable rental income already established, this is a low-maintenance addition to any investment portfolio. Conveniently located just minutes from downtown New Haven, Yale University, Yale New Haven Hospital, shopping, restaurants, public transportation, and major highways including I-95 and I-91, this property offers easy access to everything tenants need, helping support long-term occupancy and rental demand.

79 Hallock St, New Haven
$449,900
4 Beds ⋅ 4 Baths ⋅ 24189784 MLS
Beautifully restored historic Colonial offering the perfect blend of timeless character and thoughtful modern updates. Originally taken down to the studs and completely renovated by a respected local nonprofit, this home has since been beautifully redesigned and further upgraded by the current owners with exceptional attention to detail. The tastefully updated interior features an upgraded kitchen, four bedrooms, two full bathrooms, two half bathrooms and a fully finished walk up attic. Pride of ownership is evident throughout, from the recently painted exterior to the meticulously maintained living spaces. Outside, the property offers established gardens, greenhouse structures, and inviting outdoor spaces for gardening, entertaining, or simply enjoying the surroundings. Ideally located within walking distance of Science Park, the Farmington Canal Heritage Trail, and the exciting new retail and commercial developments transforming the Winchester Avenue corridor, this home combines historic charm, modern comfort, and outstanding convenience in one of New Haven's most dynamic neighborhoods.

653 Winchester Ave, New Haven

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