Homes for Sale in New Haven County CT with 5-Bedrooms

/38
$1,895,000
- 5 Beds
- 3.5 Baths
- 3,912 Sq Ft
30 Meeting House Ln, Madison, CT 06443

Once known as "Hartsbourne," this storied Madison residence is celebrated for its premier location overlooking the town green and its timeless architectural presence. A true local landmark, the home is distinguished by its striking curved eaved roofline, reminiscent of a pagoda with a unique flat seamed copper roof center. Beautifully aligned with the neighboring Congregational Church, the home

Cathy Lynch

Coldwell Banker Realty

(475) 252-9212

30 Meeting House Ln, Madison, CT 06443
/40
$925,000
- 5 Beds
- 4 Baths
- 4,681 Sq Ft
20 Upson Rd, Wolcott, CT 06716

Stunning property consisting of a contemporary 4,680 SF home with 18 rooms on 36+/- acres that are sub-dividable with 16+/- building lots in Wolcott, CT. Country living at its finest at this resort type property with surrounding private woods. Perfect for equestrian, hiking, motorsports and entertaining. From the main house you enter the original 1800's log cabin with exquisite hand polished

Don Orsini

Don Orsini Realty, LLC

(203) 463-5463

20 Upson Rd, Wolcott, CT 06716
/40
$599,900 Open Sat 11:30AM - 1:30PM
- 6 Beds
- 3 Baths
- 3,763 Sq Ft
356 Winthrop Ave, New Haven, CT 06511

Great opportunity to own a well-maintained 3-family in a prime New Haven location. Features 3 units with separate utilities and a spacious basement for storage, offering flexibility and endless possibilities for investors or owner-occupants. Conveniently located near Yale University, major hospitals, and Downtown New Haven, with easy access to shopping, dining, public transportation, and major

John Armellino

William Raveis Real Estate

(475) 290-6540

356 Winthrop Ave, New Haven, CT 06511
/19
$1,100,000
- 12 Beds
- 6 Baths
- 1,238 Sq Ft
111 Sunset Ave Unit 111, 113, 115, Meriden, CT 06450

Unique investment opportunity. 4 total 'condo' units. 1 building with 3 attached units on Sunset Avenue, and another single free-standing unit with the driveway on Liberty St. There is an HOA in place, but current owner does not collect from himself. All units are rented.

Amy Rio

Executive Real Estate Inc.

(203) 693-9315

111 Sunset Ave Unit 111, 113, 115, Meriden, CT 06450
/38
$499,900
- 5 Beds
- 3 Baths
- 2,168 Sq Ft
38 Brown St, West Haven, CT 06516

Built in 2023, this beautiful Raised Ranch with a Colonial feel offers 2,600 square feet of living space with 5 bedrooms and 3 full baths. The home features an open-concept kitchen with a 6-foot granite island, white shaker cabinets with crown molding, and stainless steel appliances. The upper level boasts high end vinyl flooring and skylights in the vaulted ceiling, while the lower level

Ariel Edery

mygoodagent

(475) 356-3131

38 Brown St, West Haven, CT 06516
/11
$419,900
- 6 Beds
- 4 Baths
- 2,826 Sq Ft
110 Dickerman St, Hamden, CT 06518

Endless potential awaits at 110 Dickerman St in the heart of Hamden! Featuring a brand-new roof and siding, this property is already off to a strong start. Originally being transformed into a single-family home, this space offers the perfect blank canvas for those with vision. Whether you're an investor, contractor, or person looking to add your own personal touch, this home presents a unique

Guillermo Araujo

Five Stars Realty

(203) 769-9191

110 Dickerman St, Hamden, CT 06518
/19
$975,000
- 15 Beds
- 7 Baths
- 5,600 Sq Ft
83 James St, New Haven, CT 06513

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

Marie Matta-Isona

iVision Real Estate

(203) 941-6809

83 James St, New Haven, CT 06513
/2
$475,000
- 6 Beds
- 2 Baths
- 2,208 Sq Ft
677 Washington Ave, West Haven, CT 06516

Well maintain 2 family home. Fully rented. Convenient to shopping, restaurants, bus line, beaches and highways. Financials available upon request.

Steven Miller

Coldwell Banker Realty

(203) 350-7360

677 Washington Ave, West Haven, CT 06516
/12
$729,900
- 8 Beds
- 4 Baths
- 4,360 Sq Ft
387 S Main St, Seymour, CT 06483

Excellent investment opportunity in a prime location! This well maintained 4 family property sits on a corner 1acre lot and offers a true turnkey experience for investors. Featuring city water and sewer, separate entrances and utilities, and off street parking, this asset is designed for easy management and long term stability. The building includes four basement storage units plus a walkup attic

David Fiske

Houlihan Lawrence WD

(475) 255-3180

387 S Main St, Seymour, CT 06483
/20
$529,900
- 5 Beds
- 2.5 Baths
- 2,107 Sq Ft
16 Raymond Rd, Woodbridge, CT 06525

Welcome to this spacious and versatile Cape Cod-style home, ideally situated on a level corner lot in a highly sought-after, top-rated school district. Offering 9 rooms, this home features 5 bedrooms and a dedicated home office, providing flexibility for today's lifestyle needs. Inside, you'll find 2.5 bathrooms, hardwood floors throughout, and a cozy fireplace perfect for relaxing winter nights.

Frances DeMaio

Square Feet Realty LLC

(475) 251-7009

16 Raymond Rd, Woodbridge, CT 06525
/15
$725,000
- 6 Beds
- 6 Baths
- 4,705 Sq Ft
111 Chapel St, New Haven, CT 06513

Exceptional investment opportunity in the heart of New Haven! This well-maintained six-family property generates a strong $93,000 in annual gross revenue and is fully occupied. The building features three floors with side-by-side units, totaling six spacious one-bedroom apartments. Each unit offers hardwood flooring, generous living space, and excellent natural light, creating comfortable living

Javyn Roundtree

Roundtree Realty LLC

(475) 258-7166

111 Chapel St, New Haven, CT 06513
/23
$1,000,000
- 13 Beds
- 7 Baths
- 4,796 Sq Ft
33 Allen Place, New Haven, CT 06512

Legal six-family property located at the end of a quiet dead-end street in a growing area of New Haven. The asset consists of a five-unit brick building with an attached single-family home, offering strong and diversified rental income within one property. Current rents are solid, providing immediate cash flow with additional upside potential. Value-add opportunity through strategic rent

Javyn Roundtree

Roundtree Realty LLC

(203) 204-6750

33 Allen Place, New Haven, CT 06512
/25
$1,100,000
- 12 Beds
- 6 Baths
- 1,238 Sq Ft
111,113 & 115 Sunset Ave, Meriden, CT 06450

Unique investment opportunity. 4 total 'condo' units. 1 building with 3 attached units on Sunset Avenue, and another single free-standing unit with the driveway on Liberty St. There is an HOA in place, but current owner does not collect from himself. All units are rented. 1 unit with central air

Amy Rio

Executive Real Estate Inc.

(475) 271-4948

111,113 & 115 Sunset Ave, Meriden, CT 06450
/37
$975,000
- 5 Beds
- 3 Baths
- 2,605 Sq Ft
194 Canner St, New Haven, CT 06511

This charming bright 1910 East Rock treasure is a classic and is filled with character and personality. Wonderful period details include columns, original woodwork and HW floors. The living room has a wood burning fireplace and French doors that lead to a peaceful side porch. The dining room offers built-in shelving and a large opening to the spacious renovated kitchen, which boasts lots of

Betsy Grauer Betsy Grauer Realty, Inc

194 Canner St, New Haven, CT 06511
/38
$1,975,000
- 5 Beds
- 4.5 Baths
- 5,810 Sq Ft
1085 Ridge Rd, Hamden, CT 06517

This elegant estate type home has just received a magnificent, tasteful renovation. Everything has been done for you with a new slate roof, new primary bedroom suite, renovated kitchen and bathrooms, all new Thermopane windows, heat, air conditioning and updated electric. Sitting on a large lot on a distinctive part of Ridge Road, this classic Tudor is timeless. The spacious rooms are filled with

Betsy Grauer Betsy Grauer Realty, Inc

1085 Ridge Rd, Hamden, CT 06517
/40
$939,900
- 8 Beds
- 7 Baths
- 6,200 Sq Ft
89 Sherland Ave, New Haven, CT 06513

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. Privately set on a serene interior lot with a secluded driveway connecting

Betsy Purtell Purtell Realty LLC

89 Sherland Ave, New Haven, CT 06513
/37
$999,000
- 5 Beds
- 5.5 Baths
- 5,081 Sq Ft
435 Maple Ave, Cheshire, CT 06410

Your Dream Home in the Heart of Cheshire! Welcome to this stunning 5-bedroom/potential 7 bedroom, 5.5-bath Colonial located in the center of Cheshire. With over 5,000 sq. ft. of living space and set on more than an acre, this masterpiece offers the perfect blend of luxury, comfort, and convenience. The seller has spared no detail in the design and upkeep of this exceptional home. Main Floor

Amy LaMaster The Bella Group, LLC

435 Maple Ave, Cheshire, CT 06410
/37
$1,975,000
- 5 Beds
- 4.5 Baths
- 5,345 Sq Ft
1050 Whitney Ave, Hamden, CT 06517

Perhaps the most beautiful house you will ever see! This exquisite estate type property is surrounded by 2.25 acres of mature landscaping and woodlands. The grand entry hall with a fireplace and double height ceiling has a graceful double staircase. A decorative arched entry archway leads to a spectacular living room with walls of glass, a fireplace, and a tasteful original fountain. The spacious

Betsy Grauer Betsy Grauer Realty, Inc

1050 Whitney Ave, Hamden, CT 06517
/38
$699,500
- 6 Beds
- 3 Baths
- 2,930 Sq Ft
45 Lyon St, New Haven, CT 06511

Nestled in the heart of New Haven is this lovely Wooster Square area 2 family which has been beautifully maintained. The house has lots of updates, newer vinyl siding, Thermopane windows, gas heating units, blown-in insulation and updated electric. The first floor has five rooms and can be used as a 2- or 3-bedroom apartment. The second and third floors are combined to make a large, sunny duplex

Betsy Grauer Betsy Grauer Realty, Inc

45 Lyon St, New Haven, CT 06511
/39
$2,499,000
- 5 Beds
- 4.5 Baths
- 4,430 Sq Ft
590 Gulf St, Milford, CT 06460

Perched high atop a scenic bluff, this extraordinary coastal retreat offers some of the most breathtaking water views in all of Milford, with sweeping, nearly 360-degree vistas of Long Island Sound and the neighboring bay. Set on over an acre of land, this is a truly rare opportunity to own one of the area's largest parcels with such expansive, unobstructed waterfront scenery. Originally built in

Stacy Blake Stacy Blake Realty LLC

590 Gulf St, Milford, CT 06460
/13
$399,900
- 5 Beds
- 3 Baths
- 2,522 Sq Ft
85 Rolling Ridge Rd, Hamden, CT 06518

Nicely maintained Raised Ranch with room for the whole family! 5 bedroom and 3 full baths . Main level offers plenty of light and hardwood flooring! Spacious Living Room and Dining Room with slider to deck. Eat-in Kitchen boasts plenty of cabinetry. Primary bedroom suite and two additional bedrooms with a second full bathroom complete the main level. Potential in-law setup in lower level with

Lou Mihalakos Spartan Property

85 Rolling Ridge Rd, Hamden, CT 06518
/21
$489,900
- 12 Beds
- 3 Baths
- 3,807 Sq Ft
141 Draher Ave, Waterbury, CT 06708

Outstanding Town Plot 3-Family w/3 car-garage! Perfect for Owner-Occupants or Investors! This spacious multi-family property offers a turn-key investment opportunity with three oversized units, each featuring 4 bedrooms, 1 bath, an eat-in kitchen, and a generous living room. Tenants enjoy separate, tenant-paid utilities, including electric heat and hot water, with individual electric panels

Amanda Sheehan Oxford Realty

141 Draher Ave, Waterbury, CT 06708
/40
$369,000
- 6 Beds
- 2 Baths
- 2,784 Sq Ft
905 Cooke St, Waterbury, CT 06704

Spacious two-family home set on a desirable corner lot, enhanced by a charming white picket fence, an oversized side yard, and a detached two-car garage with a brand-new roof-matching the newly installed roof on the main house for added peace of mind. This well-maintained property also features newer windows, adding to its overall value and efficiency. Each unit offers a welcoming foyer entry

Lucy Larracuente-Johnson Larracuente & Johnson Realty, LLC

905 Cooke St, Waterbury, CT 06704
/38
$759,900
- 5 Beds
- 2 Baths
- 2,496 Sq Ft
258 Saint John St, New Haven, CT 06511

Classic charm meets modern updates in this timeless home in the heart of historic Wooster Square, featuring a welcoming columned entry with subtle Greek Revival-inspired details. The main level welcomes you with a beautifully designed blue family room with built-in bookshelves and a decorative fireplace, perfect for seasonal decor, flowing into the living room, followed by a well-sized bedroom,

Cecilia Jaoude Pearce Real Estate

258 Saint John St, New Haven, CT 06511
/35
$475,000
- 8 Beds
- 3 Baths
- 2,747 Sq Ft
766 Winchester Ave, New Haven, CT 06511

Welcome to 766 Winchester Avenue, a spacious and sun-filled 2-family home located just steps from Albertus Magnus College and minutes to Yale's campus and downtown New Haven. This location places you in a consistently strong rental market, making it an exceptional opportunity for both investors and owner-occupants alike. The entire property was gutted and fully remodeled in 2015, offering modern

Sarah Beth Luce-Del Prete Coldwell Banker Realty

766 Winchester Ave, New Haven, CT 06511
/34
$2,500,000
- 5 Beds
- 5.5 Baths
- 4,892 Sq Ft
32 Millwood St, Milford, CT 06460

A rare coastal offering set along the coveted shores of Fort Trumbull Beach in Milford. This exceptional waterfront residence spans three levels and features 5 bedrooms and 5.5 bathrooms, thoughtfully designed to capture sweeping views of Long Island Sound and Charles Island. Expansive outdoor living is seamlessly integrated with multiple decks extending from the main level and second-floor

Luke Porto William Raveis Real Estate

32 Millwood St, Milford, CT 06460
/38
$1,595,000
- 5 Beds
- 4.5 Baths
- 5,575 Sq Ft
76 High Hill Cir, Madison, CT 06443

Perched back from and above a quiet cul-de-sac, in one of Madison's most prestigious communities, this stately five bedroom Colonial is minutes from I-95 and Madison's Town Green and beaches. The home is perfect for entertaining boasting a renovated chef's kitchen with dining area; adjacent to the home's covered deck overlooking an inviting in-ground pool, and spacious family room with fireplace.

John Campbell Compass Connecticut, LLC

76 High Hill Cir, Madison, CT 06443
/34
$1,199,000
- 6 Beds
- 5 Baths
- 3,685 Sq Ft
525 Whitney Ave, New Haven, CT 06511

Welcome to a rare and meticulously maintained legal four-family residence in the heart of New Haven's most prestigious neighborhood. Situated within the highly coveted Worthington Hooker School district, 525 Whitney Avenue offers a lifestyle of sophisticated urban living combined with exceptional financial upside. Whether you are a savvy investor or an owner-occupant looking to live in luxury

Jake Smith Alpha Capital Realty, LLC

525 Whitney Ave, New Haven, CT 06511
/36
$1,175,000 Open Sat 12PM - 2PM
- 5 Beds
- 4.5 Baths
- 3,194 Sq Ft
37 Lovers Ln, Madison, CT 06443

Location, Location, Location!! Timeless elegance meets modern living in this beautifully appointed 5-bedroom Colonial, ideally situated just moments from Madison's beaches and charming town green. Thoughtfully designed for both refined living and effortless entertaining, the home offers expansive gathering spaces, gracious proportions, and seamless indoor-outdoor flow. Inside, sun-filled living

Melanie Scull William Pitt Sotheby's Int'l

37 Lovers Ln, Madison, CT 06443
/35
$1,275,000
- 5 Beds
- 3 Baths
- 2,117 Sq Ft
98 Morgan Ave, East Haven, CT 06512

The most magical Morgan Point DIRECT WATERFRONT home. This exquisite residence boasts 4-5 bedrooms and 3 full baths, offering a perfect blend of comfort and luxury. The entire home has been fully renovated inside-out & top to bottom with replacement windows, new Hardie board siding, a new roof, Wi-Fi lighting, nest thermostats & more ensuring both beauty and durability. Inside you will find a

Susan Santoro William Pitt Sotheby's Int'l

98 Morgan Ave, East Haven, CT 06512
/39
$627,500
- 6 Beds
- 3 Baths
- 3,050 Sq Ft
43 Gorham Ave, Hamden, CT 06514

Great Location and opportunity. Live in one Unit and Let the other Unit Contribute to your monthly mortgage. It boasts a generous layout with 6 bedrooms and 3 full bathrooms, Also, each unit has an ample formal dining room. Thoughtfully designed for comfort and functionality. Every detail has been meticulously addressed in a professional remodel, showcasing the use of quality materials and

Angela Caban Realty ONE Group Connect

43 Gorham Ave, Hamden, CT 06514
/40
$679,000
- 5 Beds
- 3 Baths
- 2,842 Sq Ft
63 Sea St, New Haven, CT 06519

Immaculate, turnkey 3 family house in City Point neighborhood of New Haven has been beautifully maintained. Great location near the water, I 95, Yale University, downtown, the the hospitals, train station and more. All units occupied, easy to rent. 1st floor is 5 rooms, 2 BR, 1 bath. 2nd floor 5 rooms, 2 BR, 1 bath. 3rd floor is 4 rooms, 1 BR, 1 bath with new HVAC heat and central A/C. New new

Nancy Nishball Ivy Realty LLC

63 Sea St, New Haven, CT 06519
/5
$525,000
- 8 Beds
- 3 Baths
- 2,938 Sq Ft
41 Diane Terrace, Waterbury, CT 06705

Conveniently located just minutes from the highway, shopping, schools and restaurants, this very well-maintained 3 family property offers comfort, flexibility and strong investment potential. The first floor unit features 3 bedrooms, an eat-in kitchen, and a spacious living room with fireplace. The second unit offers a similar layout with 3 bedrooms, an eat-in kitchen, and a spacious living room

Gerald Donorfio, Jr. Fercodini Properties, Inc.

41 Diane Terrace, Waterbury, CT 06705
/40
$1,995,000
- 5 Beds
- 9 Baths
- 5,414 Sq Ft
173 Highwoods Dr, Guilford, CT 06437

A MAGNIFICENT REVIVAL & TIMELESS BLEND OF SOMETHING OLD & SOMETHING NEW. One of the finest restorations in New England, the Pitkin mansion is a true historical treasure. Carefully dismantled & moved to its current site in 1955, the property is nestled within nearly 4 acres of mature trees, manicured lawns, & magical gardens. This classic revival will be celebrated by the most discerning antique

Kiara Rusconi William Raveis Real Estate

173 Highwoods Dr, Guilford, CT 06437
/7
$525,000
- 6 Beds
- 2 Baths
- 2,688 Sq Ft
20 Columbia St, Ansonia, CT 06401

This is a great opportunity for an owner-occupant or investor to own this well-maintained 2-unit property. The first and second levels feature three bedrooms and one full bathroom, providing ample living space. The second level was updated in 2018 and is separately metered, offering flexibility for tenants or owners. Additionally, the second level could be expanded into the third floor for even

Sebastian Barneby Anchor Point

20 Columbia St, Ansonia, CT 06401
/38
$490,000
- 6 Beds
- 2.5 Baths
- 1,998 Sq Ft
347 Amity Rd, Bethany, CT 06524

Set on 2.5 level acres just ten minutes from the Merritt Parkway, this sunny Bethany ranch is ready for new owners! Move-in ready- you could be enjoying the pool, patio, gazebo, and fire pit before summer! With four bedrooms, two full and one half baths, and laundry on the main level, this easy-to-live-in home also offers ample storage and plentiful possibilities in the partially finished

Stephanie Blake BHGRE Gaetano Marra Homes

347 Amity Rd, Bethany, CT 06524
/37
$2,250,000
- 18 Beds
- 10 Baths
- 8,071 Sq Ft
334 Saint John St, New Haven, CT 06511

Turnkey & fully occupied 6 unit investment property in the heart of the Wooster Square neighborhood steps to Downtown New Haven & Yale! The building offers the best of both worlds: its historic brick facade and original details complement its modern, sparkling interior. The building features fantastic apartment layouts, including two four-bedroom, two-bath townhouse units on the first floor and

Jack Hill Seabury Hill REALTORS

334 Saint John St, New Haven, CT 06511
/40
$450,000
- 5 Beds
- 2 Baths
- 1,882 Sq Ft
49 3rd St, Hamden, CT 06514

Welcome to 49 3rd Street in Hamden! A beautifully fully renovated two-family home with a finished basement located in a good neighborhood. This turnkey property offers the perfect opportunity for both owner-occupants or investors. The first-floor unit features 2 spacious bedrooms and 1 full bathroom, highlighted by gleaming hardwood floors and a brand-new modern kitchen with updated finishes. The

Mateo Avila Keller Williams Prestige Prop.

49 3rd St, Hamden, CT 06514
/34
$599,000 Open Sat 10AM - 1PM
- 6 Beds
- 3.5 Baths
- 2,755 Sq Ft
26 Union St, Seymour, CT 06483

Welcome to your dreaming and beautifully preserved single family Brick Colonial House, initially built in 1911 and remodeled in 2019, blending timeless charm with modern fashion. This home is bathed in natural light from oversized windows, complemented by soaring over 9 ft ceilings. The first floor showcases an open living room with exposed beams and a fireplace, an eat-in kitchen, a half bath,

Michael Jiang Century 21 AllPoints Realty

26 Union St, Seymour, CT 06483
/13
$2,575,000
- 20 Beds
- 16 Baths
- 10,394 Sq Ft
83 E Grand Ave, New Haven, CT 06513

Updated and well-maintained, fully rented, 13-unit multifamily portfolio located on East Grand Ave in New Haven's Fair Haven Heights neighborhood. The property consists of three buildings with a desirable unit mix including 1-bedroom townhome-style units, ADA-compliant 2-bedroom units, and larger 3 and 4 bedroom apartments. Units feature quality interior finishes such as tile flooring, wood

Douglas Ledewitz Pulse Realty LLC

83 E Grand Ave, New Haven, CT 06513

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