Vintage homes for sale & real estate in Prospect Hill, CT

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590 Whitney Ave, New Haven, CT 06511

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
In the heart of the East Rock section of New Haven there's an amazing three-family home waiting for you! Each unit has nice sized bedrooms. The tenants take pride in their spaces keeping everything neat and tidy. Plus there's plenty of parking. This property is available for owner occupied or investment. This property is sold as-is giving you the chance to make it your own!

$799,000

6 beds3 baths3,103 sq ft

590 Whitney Ave, New Haven, CT 06511

7,405 sq ft lot • Somewhat walkable

152 Sheffield Ave, New Haven, CT 06511

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
Multi-family style home perfectly blending charm with modern comfort. Spanning an impressive 3,184 square feet, this property offers two distinct units on separate floors, making it ideal for large families or those seeking extra rental income. With a total of 7 bedrooms and 2 full bathrooms, ensuring ample space for relaxation and privacy. One of the standout features of this home is the off-street parking, providing convenient accessibility, a rare luxury in this prime location. For outdoor enthusiasts, the private fenced backyard serves as a tranquil retreat, perfect for gatherings, barbecues, or simply unwinding after a long day. Situated in a desirable neighborhood, you're just moments

$357,500

7 beds2 baths3,184 sq ft

152 Sheffield Ave, New Haven, CT 06511

5,662 sq ft lot • Somewhat walkable

721 Winchester Ave, New Haven, CT 06511

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
Diamond in the rough! This prime Newhallville value add 3 family opp is situated close to Albertus Magnus and Yale University and nestled among several other investment opps that have taken the opportunity and run with some TLC and bringing in tenants at market rent! With vinyl siding and newer replacement windows and ample off-street parking, the exterior of the property is ready for its new owner. There are 3 units all with 2 bedrooms filled with month-to-month tenants with below market rents. Separate utilities make for lower maintenance costs as an owner. Take advantage of this amazing opportunity for upside and schedule your viewing today! Can also be purchased with 718 Winchester Ave

$400,000

6 beds3 baths2,952 sq ft

721 Winchester Ave, New Haven, CT 06511

5,227 sq ft lot • Somewhat walkable

331 Saint Ronan St, New Haven, CT 06511

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
One of the finest examples by renown architect R. W. Foote, know for designing most significant residences in New Haven. This renovated stucco & red tile roof house was built in the Modern English style in 1917. Surrounded by mature landscaping, the house reveals its outstanding detailing as you open the front door. 10 ft ceilings throughout the 1st fl: Grand Entry Foyer, gleaming chestnut paneling clad the walls of the Foyer & Living Room. LR with impressive FP opens to an east-facing sitting rm perfect for relaxing in the morning sun. Formal Dining Room has 2 sets of French doors, FP & opens to a private balcony. Capacious butler's pantry leads to the large eat-in Kitche

$2,150,000

7 beds4.5 baths6,971 sq ft

331 Saint Ronan St, New Haven, CT 06511

0.32 acre lot • 2 garage spots • Somewhat walkable

1 Reservoir St, New Haven, CT 06511

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
Unique opportunity to purchase a 100-year-old converted stable that features 3124 square feet of main floor living space plus an additional 3000 square feet of above grade garden level space with large oversize windows and high ceilings. This dramatic light filled enchanting home offers flexible floor plan of four plus bedrooms including a main level Primary bedroom suite that features two full baths as well as two dressing rooms. Soaring cathedral ceilings, skylights and a loft study just add to the drama. Set on a combined . 31-acre parcel. Additional common space land as well all adds to the magic of this intown enclave. The assessment, taxes and land size reflect the two combined proper

$1,695,000

4 beds4 baths6,124 sq ft

1 Reservoir St, New Haven, CT 06511

0.31 acre lot • $25 HOA • Car-dependent

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35 Eld St, New Haven, CT 06511

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
Fantastic four family in the heart of lower East Rock, steps to Yale SOM, gourmet markets & restaurants, and a short walk to Downtown New Haven & Yale. The first floor of the building has 2 apartments: one 4 room, 1 bed/1 bath, and a two room studio. The one bedroom has been fully renovated with new vinyl flooring, and has high ceilings, a bay window, separate formal living & dining room, a remodeled eat-in kitchen, and tile bathroom. The two room studio has hardwood floors, an updated kitchen and a remodeled full bathroom. The third apartment is a rare two story townhouse sited on half of the second floor and the whole third floor. This spacious 7 room, 4 bedroom, 2.5 bat

$995,000

6 beds5.5 baths3,410 sq ft

35 Eld St, New Haven, CT 06511

6,534 sq ft lot • Walker's paradise

6 Prospect Ct, Hamden, CT 06517

OPEN SUN, 1PM TO 4PM

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
Nestled in the prestigious East Rock/Prospect Hill neighborhood, this stunning Tudor mansion boasts 8,430 square feet of historic charm and modern luxury. Originally home to Edward T. and Adele K. Paier, it served as the Paier College of Art from 1960 to 1963, adding historical significance. Just minutes from Yale University, the estate is surrounded by top-tier educational institutions such as Choate Rosemary Hall and Hopkins School, along with Yale Teaching Hospital, making it ideal for families seeking access to world-class education and healthcare. New Haven's cultural offerings, including dining, museums, theaters, parks, and Long Island Sound beaches, are also within easy reach. The p

$2,499,000

6 beds7 baths8,430 sq ft

6 Prospect Ct, Hamden, CT 06517

0.78 acre lot • 3 garage spots • Pool

165 Starr St, New Haven, CT 06511

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
Prime Investment Opportunity in Newhallville! This fully occupied 2-family property offers a solid investment in a sought-after New Haven location near Yale New Haven Hospital and Edgerton Park. The 2,099 SF residence includes a charming open porch on the second floor and tenant-paid utilities for added convenience. Both units are on month-to-month leases, with the first floor renting at $975/month and the second floor at $1,450/month-both below the area's market rent starting at $1,600, allowing potential for increased income. Sold as-is, with inspections for informational purposes only. Comparable sales: 323 Division St $285,000 (full rehab); 141 Newhall St (good condition). Seller is off

$270,000

4 beds2 baths2,099 sq ft

165 Starr St, New Haven, CT 06511

2,613 sq ft lot • Somewhat walkable

229 Goodrich St, Hamden, CT 06517

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
Welcome to 229 Goodrich St, Hamden - a prime three-unit multifamily property offering income-generating opportunities. Each unit features spacious, well-lit living areas, comfortable bedrooms, and a functional layout, making it appealing to tenants and investors alike. This well-maintained property includes separate entrances and utilities for each unit, providing privacy and convenience. With ample off-street parking and a backyard area for outdoor enjoyment, it offers great appeal for residents. Ideally located in Hamden, 229 Goodrich St is close to local amenities, shops, dining, schools, and public transportation, ensuring easy access to everything the area has to offer. Whether you're

$449,900

7 beds3 baths3,010 sq ft

229 Goodrich St, Hamden, CT 06517

3,920 sq ft lot • Somewhat walkable

80 Shepard St, New Haven, CT 06511

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
Welcome to 80 Shepard St, New Haven, CT - a fantastic three-unit property with outstanding value-add potential. Offering 6 bedrooms and 3 bathrooms, this multi-family home provides ample living space for tenants or owner-occupants looking for rental income. Each unit is spacious and filled with natural light, providing the perfect opportunity to update and customize to your liking. The property features a generous backyard, ideal for outdoor relaxation or entertaining. Conveniently located near schools, parks, shopping, and dining, 80 Shepard St offers easy access to all that New Haven has to offer. Whether you're an investor seeking a profitable multi-family property or looking to live in

$440,000

6 beds3 baths2,956 sq ft

80 Shepard St, New Haven, CT 06511

4,356 sq ft lot • Somewhat walkable

92 Shepard St, New Haven, CT 06511

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
Welcome to 92 Shepard St, New Haven, CT - a wonderful three-unit property with great value-add potential. Featuring 5 bedrooms and 3 bathrooms, this property offers ample space and flexibility for investors or owner-occupants seeking rental income. Each unit provides comfortable living areas filled with natural light, with plenty of opportunities for upgrades and customization. The property includes a spacious backyard, perfect for outdoor activities or relaxing in a private setting. Located near schools, parks, shopping, and dining, 92 Shepard St ensures easy access to everything New Haven has to offer. Whether you're looking to invest in a multi-family property or want to live in one unit

$434,900

5 beds3 baths3,017 sq ft

92 Shepard St, New Haven, CT 06511

4,356 sq ft lot • Somewhat walkable

133 Butler St, New Haven, CT 06511

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
An Amazing Opportunity for First-Time Homebuyers! Welcome to this charming 3-bedroom, 2-bathroom home, perfect for those seeking comfort and convenience. Step into a cozy foyer and enjoy a bright, updated space filled with tons of natural light. The home features fully remodeled spaces, including beautiful hardwood floors, modern recessed lighting, and a brand-new kitchen equipped with stainless steel appliances. The main level also offers a washer/dryer hookup for added convenience. You'll love the extra room, perfect for an office or den, ideal for work-from-home needs. The level, oversized backyard and private driveway provide ample outdoor space for relaxation and entertainment, along

$299,999

3 beds2 baths1,350 sq ft

133 Butler St, New Haven, CT 06511

6,098 sq ft lot • Somewhat walkable

407 Shelton Ave, New Haven, CT 06511

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
Welcome to 407 Shelton Ave. This lovely colonial is looking for a new owner. . Step into this 3 Bedroom 2 Bath home with 2 additional Bedrooms on the 3rd floor. New carpet and more! Off the living room is the spacious open concept kitchen and dining room which makes entertaining a breeze. . Walk upstairs to the large primary bedroom that has its own full bath. Second floor includes 2 others spacious Bedrooms and lots of natural light. The 3rd floor also includes many closets and skylights that just need the glass added back. The nicely sized backyard is perfect for relaxing after a long day. As-is Sale. Subject to Probate.

$249,900

3 beds2 baths1,302 sq ft

407 Shelton Ave, New Haven, CT 06511

4,791 sq ft lot • Somewhat walkable

16 Eld St, New Haven, CT 06511

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
Great investment property or owner occupied, 2 family, EastRock neighborhood, can be converted to a single family, off street parking, 2 car garage, nice patio, garden area, first floor has 9 foot ceilings, newer ACs, newer furnaces, newer windows, converted from oil to gas, walking distance to downtown, restaurants, shops and Yale. located near the Yale business school.

$699,840

4 beds2 baths2,226 sq ft

16 Eld St, New Haven, CT 06511

5,227 sq ft lot • 2 garage spots • Walker's paradise

718 Winchester Ave, New Haven, CT 06511

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
Discover this 3-family property on Winchester Ave, perfect for both owner-occupants and savvy investors. The home features a fenced front yard, durable vinyl siding, and separate utilities, with 3-bedroom units on the 1st and 2nd floors, and a 2-bedroom unit on the 3rd floor. With one tenant currently on a month-to-month lease and below-market rent, you have the potential to increase income, with market rates around $1,700+/month for the remaining units. Can also be purchased with 721 Winchester Ave just across the street. Great start or addition to your investment portfolio! MLS# 24055834. Comparable closed sales nearby include: Enjoy the Sweat Equity/Appreciation or pull Equity Out and b

$380,000

8 beds3 baths2,767 sq ft

718 Winchester Ave, New Haven, CT 06511

4,356 sq ft lot • Somewhat walkable

57 Bassett St, New Haven, CT 06511

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
Large 3 family in Newhalville, a block away from Albertus Magnus College! All 2-bedroom units with the 1st and 3rd floor units occupied with long term tenants paying below market rent. 2-bedroom units in the area are going for $1800/mth! 2nd floor vacant unit has an office or nursery space right off the primary bedroom and room for laundry in the pantry area off the kitchen! Large units with ample natural light and eat-in kitchens! Separate and tenant paid utilities make for low owner-expenses. Large backyard that is partially fenced in. Awesome opportunity for upside on this one-start reaping the benefits of this prime location and competitive rental market!

$385,000

6 beds3 baths3,085 sq ft

57 Bassett St, New Haven, CT 06511

4,791 sq ft lot • Somewhat walkable

64 Lilac St, New Haven, CT 06511

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
Amazing opportunity for investor or owner occupant buyers in Newhallville! This over 3,000 SF property has a total of 6 bedrooms and 3 bathrooms. There is low maintenance vinyl siding and separate utilities. All tenants are long term, month to month.

$375,000

6 beds3 baths3,075 sq ft

64 Lilac St, New Haven, CT 06511

6,098 sq ft lot • Somewhat walkable

Undisclosed address, Hamden, CT 06517

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
INVESTORS OR OWNERS OCCUPIED TAKE NOTICE!!! Well-kept 2 families in the Highwood neighborhood section of Hamden. 1st floor has 2 bedrooms and 1 full bathroom. The 2nd-floor unit has 3 bedrooms, one in the finished attic, and 1 full bathroom. All gas utilities. Call for a private showing today! Immediate CASH FLOW!

$349,000

5 beds2 baths1,744 sq ft

Undisclosed address, Hamden, CT 06517

5,227 sq ft lot • Somewhat walkable

383 Shelton Ave, New Haven, CT 06511

ABOUT THIS HOME
Vintage Home for sale in Prospect Hill, CT:
2 for 1 DEAL! 383 SHELTON ST ALONG WITH 123 READ ST PRESENTS AN EXCELLENT INVESTMENT OPPORTUNITY - Rare find! Mixed-use property with a convenience store in need of total rehab. This property is perfect for investors looking to restore and redevelop for potential long-term gains. Located in a high-traffic area, this property offers great visibility and accessibility for businesses. Whether you are looking to renovate and lease out the units or redevelop for a new purpose, this property has endless potential. Don't miss out on this chance to explore the possibilities of this unique investment opportunity. 383 Shelton St at one point offered a convenience store on the 1st floor and 2 apartme

$550,000

10 beds5 baths6,464 sq ft

383 Shelton Ave, New Haven, CT 06511

5,662 sq ft lot • Garage • Somewhat walkable

Vintage Homes for Sale in Prospect Hill

There are currently 5 vintage homes for sale in Prospect Hill at a median listing price of $687K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Prospect Hill stay on the market for 103 days. Popular neighborhoods include Fair Haven, Westville, Wooster Square, West New Haven, and Long Island. This map is refreshed with the newest listings in Prospect Hill every 15 minutes.

In the past month, 1 home has been sold in Prospect Hill. In addition to houses in Prospect Hill, there was also 1 condo, 0 townhouses, and 4 multi-family units for sale in Prospect Hill last month. Prospect Hill is a moderately walkable neighborhood in New Haven with a Walk Score of 54. Prospect Hill is home to approximately 3,896 people and 1,408 jobs. Find your dream home in Prospect Hill using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Prospect Hill are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Prospect Hill. If you're looking to sell your home in the Prospect Hill area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Prospect Hill with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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