Homes for Sale in Fairfield County CT with 5-Bedrooms

/4
$559,900
- 6 Beds
- 2 Baths
- 1,600 Sq Ft
59 Pleasant St, Danbury, CT 06810

Rarely available two-family in the desirable Pleasant Street neighborhood of Danbury. Property has had a long-term owner and under market rents. Perfect opportunity for an investor or owner occupant. Property conveys "as is" with occupants on a month-to-month lease.

Michael Dziedzic Precision Realty LLC

59 Pleasant St, Danbury, CT 06810
/40
$4,750,000
- 6 Beds
- 4.5 Baths
- 6,106 Sq Ft
23 Meeting House Rd, Greenwich, CT 06831

2021 fully gut-renovated modern farmhouse awaits! Park-like property, secluded backcountry environment, on a charming cul-de-sac. A total transformation brings the traditional home into the 21st century with modern style. This home offers generous space, large walls of sunny windows, and a versatile floor plan for everyday living and entertaining. Situated on a private road without through

Mikhail Faifman William Raveis Real Estate

23 Meeting House Rd, Greenwich, CT 06831
/20
$1,600,000
- 6 Beds
- 5 Baths
- 2,550 Sq Ft
61 Aberdeen St, Stamford, CT 06902

This exceptional four-family house, located in a sought-after Stamford neighborhood, offers a unique blend of modern luxury and investment practicality. Situated just minutes from vibrant local shopping centers and easily accessible to major highways, it is a prime location for professionals and working families seeking both convenience and a suburban feel. The property is designed with a clear

Scott Kadison Scott Kadison Real Estate

61 Aberdeen St, Stamford, CT 06902
/15
$824,990
- 6 Beds
- 4 Baths
- 2,758 Sq Ft
7 Hayestown Heights, Danbury, CT 06811

Welcome to 7 Hayestown Heights, a versatile multi-family residence in Danbury's desirable Pembroke neighborhood. This thoughtfully maintained property offers ample living space with a total of 6 bedrooms and 4 full baths, spanning approximately 2,758 sq ft - making it ideal for families, multi-generational living, or rental opportunities. This home was rebuilt from the ground up in 2012 with many

Randall Corprew HomeSmart Homes and Estates

7 Hayestown Heights, Danbury, CT 06811
/33
$1,749,999
- 16 Beds
- 8 Baths
- 5,824 Sq Ft
25 Whittier St, Bridge Port, CT 06605

Exceptional investment opportunity in Bridgeport's desirable Black Rock neighborhood. This 8-unit multifamily property features eight 2-bedroom, 1-bathroom units, each with spacious layouts ideal for tenants seeking comfort and convenience. The building is well-maintained, with separate utilities and strong rental history, making it a turnkey addition to any portfolio. Located just minutes from

Zach Pinto Alpha Capital Realty, LLC

25 Whittier St, Bridge Port, CT 06605
/34
$1,749,999
- 16 Beds
- 8 Baths
- 5,824 Sq Ft
31 Whittier St, Bridge Port, CT 06605

Excellent investment opportunity in the heart of Bridgeport's Black Rock neighborhood. This 8-unit multifamily building features eight 2-bedroom, 1-bathroom units, each with spacious layouts and strong rental potential. The property includes separate utilities for each unit and has been well-maintained, making it ideal for investors seeking a stable, income-producing asset. Located just minutes

Zach Pinto Alpha Capital Realty, LLC

31 Whittier St, Bridge Port, CT 06605
/9
$560,000
- 5 Beds
- 2 Baths
- 1,600 Sq Ft
78 Fairmount Ave, Bridgeport, CT 06606

Ready for a new owner, Great location two family , home owner used the property like single family , new baths , great condition , big back yard new roof . Sold As-is .

Marta Arroyo William Raveis Real Estate

78 Fairmount Ave, Bridgeport, CT 06606
/38
$1,599,999
- 18 Beds
- 6 Baths
- 6,276 Sq Ft
746 Maple St, Bridgeport, CT 06608

Well-positioned 6-unit multifamily property in Bridgeport's East Side-ideal for investors seeking immediate cash flow and long-term upside. This income-producing asset features six residential units, each with functional layouts and solid rental appeal. The building includes separate utilities, and with a mix of unit sizes, it attracts consistent tenant demand. Located near public transportation,

Justin Sudol Alpha Capital Realty, LLC

746 Maple St, Bridgeport, CT 06608
/31
$799,900
- 6 Beds
- 2 Baths
- 3,725 Sq Ft
1867 Main St, Stratford, CT 06615

Amazing opportunity to own this beautifully kept multi family home in the heart of Stratford. This unique multi family home is currently being used as a two family dwelling with the second floor unit utilizing both the second and third floor of the home which has already passed zoning petition to convert into a third unit. This is a wonderful opportunity to own an income producing property and

Davis Owen Davis Owen Real Estate

1867 Main St, Stratford, CT 06615
/47
$3,499,000 Open House 4/12
- 5 Beds
- 4.5 Baths
- 5,389 Sq Ft
399 Stanwich Rd, Greenwich, CT 06830

Set amid scenic beauty, this custom-built Colonial offers over 5,300± square feet of elegant living space across four levels, complete with an indoor swimming pool and a charming guest cottage. Sun-filled formal living and dining rooms showcase soaring ceilings and beautiful natural light, while the kitchen with breakfast room opens to a comfortable family room. The serene primary suite provides

Leslie McElwreath Sotheby's International Realty

399 Stanwich Rd, Greenwich, CT 06830
/50
$1,795,000
- 5 Beds
- 5.5 Baths
- 4,962 Sq Ft
6A Rock Ridge Ct, New Fairfield, CT 06812

Perched high above Candlewood Lake, this extraordinary custom-built residence was crafted by a six-time HOBI Award-winning builder for himself and embodies the finest craftsmanship with timeless sophistication. Spanning 4,962 sq. ft., the home blends classic Southern Fairfield County architectural details with breathtaking four-season mountain and Candlewood Lake views. Inside, rich

Angelina Valentini Coldwell Banker Realty

6A Rock Ridge Ct, New Fairfield, CT 06812
/40
$1,269,000 Open Sun 11AM - 1PM
- 5 Beds
- 2.5 Baths
- 5,035 Sq Ft
93 Putting Green Rd N, Trumbull, CT 06611

Welcome to 93 Putting Green Road North - A Grand, Fully Renovated Colonial in Trumbull's Desirable Daniel's Farm District. Step through the front door into a stunning two-story foyer and discover this beautifully reimagined center hall colonial offering over 4,100 sq. ft. of elegant living space, plus an additional 900 sq. ft. of finished, lower level. Every inch of this 5-bedroom, 3.5-bath home

Sam Granata Preston Gray Real Estate

93 Putting Green Rd N, Trumbull, CT 06611
/24
$698,000
- 5 Beds
- 4 Baths
- 3,586 Sq Ft
184 Putting Green Rd, Trumbull, CT 06611

Spacious 5 Bedroom Home with In-Law Setup and pool in the desirable Hillandale area. Ideal for Fix & Flip or Multi-Generational Living. Discover potential and opportunity in this spacious five bedroom, four bath home perfectly located near shopping, schools, and Route 15. Set on a desirable 1.06 acre corner lot, this property offers a versatile layout with an in-law setup, wood-burning fireplace,

Catherine Aaron Berkshire Hathaway NE Prop.

184 Putting Green Rd, Trumbull, CT 06611
/38
$1,199,000
- 5 Beds
- 4 Baths
- 3,581 Sq Ft
198 Steep Hill Rd, Weston, CT 06883

Exceptional 5-BR stone home blending contemporary design w natural tranquility sits atop 2 private acres in Weston. Expertly engineered & beautifully constructed, this freshly painted home welcomes you through a dramatic 2-story foyer into a sun-filled living room with floor-to-ceiling windows, sweeping woodland views, and a custom 2-sided fireplace. Open chef's kitchen features granite

Elaine Schanzenbach William Raveis Real Estate

198 Steep Hill Rd, Weston, CT 06883
/31
$700,000
- 10 Beds
- 4 Baths
- 2,988 Sq Ft
1922 Boston Ave Unit 1924, Bridgeport, CT 06610

Beautifully renovated and move-in ready, this spacious 2-family brick home sits proudly on a corner lot and offers the perfect blend of modern style and investment potential. Featuring new kitchens, new bathrooms, new flooring, and fresh paint throughout, this home boasts a bright, open layout with excellent natural light. The finished basement provides extra living or entertainment space, while

Angel Mora eXp Realty

1922 Boston Ave Unit 1924, Bridgeport, CT 06610
/53
$5,450,000
- 6 Beds
- 9 Baths
- 7,738 Sq Ft
897 Lake Ave, Greenwich, CT 06831

This exceptional contemporary home on a quiet cul-de-sac has been transformed with a complete meticulous custom renovation. The dramatic yet highly functional home is being offered fully furnished with Roche Bobois furniture in addition to Barovier & Toso Venetian light fixtures throughout the home. The beautiful parklike grounds encompass 4 acres including a tennis court, pool with spa and large

Christopher Finlay Brown Harris Stevens CT, LLC

897 Lake Ave, Greenwich, CT 06831
/39
$1,849,000
- 6 Beds
- 5 Baths
- 5,500 Sq Ft
6 Brinsmade Ln, Sherman, CT 06784

Discover a private country retreat just 90 minutes from New York City in Sherman, CT, set on approximately 10 acres near Candlewood Lake with beach and boat rights. This exceptional estate blends historic New England charm with modern luxury and low taxes. Three residences-the Main House, Carriage House, and Pool House-offer 5,200 sq ft with six bedrooms and five full baths, ideal for

Ginny Gordon-O’Neill William Raveis Real Estate

6 Brinsmade Ln, Sherman, CT 06784
/40
$1,495,000
- 5 Beds
- 3.5 Baths
- 3,888 Sq Ft
4 Trails End Rd, Weston, CT 06883

This beautifully renovated 4-bedroom Colonial in Lower Weston, Connecticut, exemplifies exceptional craftsmanship and attention to detail throughout. Set on a level, two-acre corner lot, the home offers both privacy and a tranquil setting. The modern kitchen features top-quality finishes and flows seamlessly into the family and dining rooms, overlooking a picturesque backyard. The living room,

Bozena Tisch Coldwell Banker Realty

4 Trails End Rd, Weston, CT 06883
/34
$3,895,000
- 7 Beds
- 8 Baths
- 9,267 Sq Ft
43 Sterling Rd, Greenwich, CT 06831

Opportunity to acquire an exceptional 6.5 acre Greenwich country compound set amongst very high-end homes in a private, gated association. There are stunning vistas & a bucolic setting w/manicured & mature plantings plus expansive lawns for horses. Amenities include pool & spa, pool house, tennis & basketball courts, spaces for vegetable & flower gardens, carriage house or art studio & office.

Barbara Wells Houlihan Lawrence

43 Sterling Rd, Greenwich, CT 06831
/28
$479,000
- 6 Beds
- 2 Baths
- 2,156 Sq Ft
39 Jane St, Bridgeport, CT 06608

Assumable financing at 4.8 percent available! Well-maintained two-family home located on Bridgeport's East Side, ideal for both investors and owner-occupants. The first-floor unit offers 1 bedroom and 1 bath with a bright, open layout. The spacious second-floor duplex features 5 bedrooms and 1 bath, providing excellent rental income potential or flexible living arrangements. Each unit is

Michelle Lorenzetti Premier Re Group LLC

39 Jane St, Bridgeport, CT 06608
/38
$1,395,000
- 8 Beds
- 8.5 Baths
- 5,530 Sq Ft
75 Coolidge Ave, Stamford, CT 06906

Don't miss this fabulous two-family home, where each unit lives like a 4-5 bedroom single-family house. Newly re-built in 2023, this 5530 sq ft home has so much to offer, with enough room for the whole family. Four to five bedrooms and 4 full bathrooms in each unit plus a large finished walk-up third floor in each unit and a full finished basement in unit 2, both can be used as an office, play

Stefanie Lacoff Berkshire Hathaway NE Prop.

75 Coolidge Ave, Stamford, CT 06906
/37
$1,399,000
- 5 Beds
- 6 Baths
- 5,630 Sq Ft
70 Obtuse Hill Rd, Brookfield, CT 06804

Welcome to Arundel, a one-of-a-kind estate envisioned by playwright Joseph Hayes, whose passion for medieval theatre inspired its dramatic architecture and timeless design. Nestled on nearly 6 pristine acres, this enchanting retreat features sweeping lawns, shimmering ponds with fountains, private putting green, a charming guest cottage, and a six-car garage. Inside the main residence, luxury

Kellie Martone William Pitt Sotheby's Int'l

70 Obtuse Hill Rd, Brookfield, CT 06804
/25
$5,500,000
- 6 Beds
- 3.5 Baths
- 4,416 Sq Ft
62 Codfish Hill Rd, Bethel, CT 06801

Subdivision Potential! One of the Largest Land Parcels in Bethel - Over 61 Acres! A rare opportunity for investors, developers, and visionaries to own more than 61 acres in the highly sought-after Codfish Hill area. This former farmland, once a thriving homestead, offers a unique combination of development potential and the charm of an existing colonial farmhouse with multiple outbuildings. The

Rich Lechthaler Great Estates, CT

62 Codfish Hill Rd, Bethel, CT 06801
/20
$995,000
- 15 Beds
- 4,570 Sq Ft
357 Norman St, Bridgeport, CT 06605

Excellent Investment Opportunity! This historic and well-maintained apartment building offers an exceptional chance to expand your portfolio with a strong performing asset. Spanning approximately 4,570 sqft., the property features 15 residential units plus an on-site office, ideal for property management convenience. This building offers a varied floor plan of efficient studio units, appealing to

Catherine Aaron Berkshire Hathaway NE Prop.

357 Norman St, Bridgeport, CT 06605
/12
$630,000
- 6 Beds
- 3 Baths
- 3,069 Sq Ft
195 Lenox Ave Unit 197, Bridgeport, CT 06605

Welcome to 195 Lenox Avenue - a modern and versatile 3-family home perfect for both investors and first-time buyers. With 6 bedrooms, 3 full bathrooms, and a full basement, this property offers plenty of space and excellent rental potential. The first and second floors each allow for an extra bedroom conversion, maximizing cash flow. Inside, the units are updated and well-maintained, providing

Shafran Salim Guy Bocicaut Real Estate

195 Lenox Ave Unit 197, Bridgeport, CT 06605
/27
$2,750,000
- 5 Beds
- 3.5 Baths
- 3,200 Sq Ft
44 Benedict Hill Rd, New Canaan, CT 06840

Welcome to the iconic Evans House - a striking work of mid-century modern architecture. Designed in 1961 by renowned architect James Evans, this one-of-a-kind residence showcases a striking hyperbolic paraboloid roof that allows for a completely open main level filled with soaring floor-to-ceiling windows. Every room is immersed in natural light and surrounded by serene wooded views, offering

John-Michael Rachinsky-Wood Harbor Bridge Realty

44 Benedict Hill Rd, New Canaan, CT 06840
/30
$8,750,000
- 5 Beds
- 8 Baths
- 9,619 Sq Ft
10 Birch Ln, Greenwich, CT 06830

Impeccably constructed colonial in Greenwich's Golden Triangle on 1.35 acres with pool bordered by a scenic pond. A double-height foyer leads to the formal living room and library, both with fireplaces. Chef's kitchen adjoins the family room with fireplace, butler's pantry, and formal dining room. French doors open to terrace with heated pool, barbecue and firepit. Mudroom and attached 4-car

Joseph Barbieri Sotheby's International Realty

10 Birch Ln, Greenwich, CT 06830
/40
$13,995,000
- 6 Beds
- 8 Baths
- 10,286 Sq Ft
7 Parsonage Rd, Greenwich, CT 06830

An extraordinary newly constructed residence in the heart of Greenwich, Seven Parsonage Road is a masterfully crafted white brick manor on 1.12 acres, defined by timeless elegance and modern sophistication. Spanning four expansive light filled levels served by an elevator, this six-bedroom, six full and two half-bathroom home offers over 10,200+/- square feet of meticulously designed living

Leslie McElwreath Sotheby's International Realty

7 Parsonage Rd, Greenwich, CT 06830
/36
$8,500,000
- 7 Beds
- 10 Baths
- 9,649 Sq Ft
18 Tokeneke Trail, Darien, CT 06820

This magnificent Round Meadows estate with a fantastic 9700 sf house on 5.346 acres of private property is now on the market for the first time in more than 54 years. Located in the private Tokeneke Association with protected land trust property to the East and West of it, Round Meadows is the ultimate in privacy and natural beauty. The owners had the vision to preserve, restore and ultimately

Robin Stineman William Pitt Sotheby's Int'l

18 Tokeneke Trail, Darien, CT 06820
/40
$1,625,000
- 6 Beds
- 7 Baths
- 7,071 Sq Ft
132 Merrimac Dr, Trumbull, CT 06611

Welcome to this one-of-a-kind property in Trumbull, offering over 7,000 sf of living space across two separate ranch-style units-perfect for multi-generational living, extended family, or flexible use. With a total of 17 rooms, 6 bedrooms, 5 full & 2 half baths, these two residences blend spaciousness, comfort, and luxury in a breathtaking setting. Upper level has a private entrance. Each unit

Carl Surrusco William Raveis Real Estate

132 Merrimac Dr, Trumbull, CT 06611
/7
$755,000
- 5 Beds
- 3 Baths
- 2,483 Sq Ft
855 Brewster St Unit 857, Bridgeport, CT 06605

An incredible investment opportunity in a highly desirable Black Rock Neighborhood. This well maintained 3 Family property is perfect for investors or owner occupied. Ideally located within walking distance to the Fairfield Metro Train Station, shops and restaurants along Fairfield Ave. It's a short drive to I-95 and Downtown Fairfield and Black Rock Turnpike. This 3 Family home has 5 Bedrooms, 3

Doug Munson Munson Real Estate

855 Brewster St Unit 857, Bridgeport, CT 06605
/40
$1,100,000
- 5 Beds
- 6 Baths
- 5,189 Sq Ft
40 Walnut St, Monroe, CT 06468

Welcome to this magnificent custom-built raised ranch known as 40 Walnut Street located in Fairfield County in the Town of Monroe. Monroe is a beautiful community that offers a balanced blend of suburban amenities, many opportunities for recreation, scenic beauty and rural character. Whitney Farms Golf Course is a three-minute drive and features a clubhouse, pro-shop and catering facility for all

Stephen Hodson Hodson Realty, Inc.

40 Walnut St, Monroe, CT 06468
/40
$25,500,000
- 9 Beds
- 14 Baths
- 14,266 Sq Ft
104 Dans Hwy, New Canaan, CT 06840

Clark House, a legacy property with extraordinary provenance, was re-imagined by design legends Delphine and Reed Krakoff, adding their imprimatur of spare modern elegance. Reminiscent of a French hunting lodge and built like a fortress from steel and concrete in 1937, the property was purchased as a country residence by copper heiress Huguette Clark, and remained unoccupied and untouched until a

Leslie Razook William Pitt Sotheby's Int'l

104 Dans Hwy, New Canaan, CT 06840
/39
$2,200,000
- 6 Beds
- 2 Baths
- 2,180 Sq Ft
2142 Fairfield Beach Rd, Fairfield, CT 06824

OPPORTUNITY KNOCKS TWICE with the only two-family home on Fairfield beach road Peninsula. Great rental income. Newly painted inside and out and completely furnished. This duplex features a spacious four-bedroom unit and a two-bedroom unit on the creek side with private gate access to the beach just across the road. Features include a wrap-around deck on the creek side with boat access to Long

Michael Menillo Collage Realty

2142 Fairfield Beach Rd, Fairfield, CT 06824
/38
$2,490,000
- 5 Beds
- 5.5 Baths
- 2,885 Sq Ft
65 Sherwood Place, Greenwich, CT 06830

Exquisite individual custom built 2014 condominium unit it a two unit complex. Prime In Town location, walk to Greenwich Avenue. Unit has four levels with four bedrooms and three baths on second floor, Bedroom and bath on attic level. Bedroom and full bath with fireplace on lower level.

Scott Kelland CLS Group

65 Sherwood Place, Greenwich, CT 06830
/40
$1,930,000
- 7 Beds
- 10 Baths
- 5,883 Sq Ft
49 Great Ring Rd, Sandy Hook, CT 06482

Welcome to 49 Great Ring Road-an iconic estate with breathtaking views and a classic 1940 built home full of charm and elegance. Step into the front-to-back foyer and take in the sight lines to the expansive stone patio and sparkling pool. At the heart of the home is the great room, featuring a soaring ceiling and a grand fireplace-perfect for gatherings. The custom cherry sunroom is a

Connie Widmann William Raveis Real Estate

49 Great Ring Rd, Sandy Hook, CT 06482
/34
$7,495,000
- 6 Beds
- 11 Baths
- 7,528 Sq Ft
229 Umpawaug Rd, Redding, CT 06896

Welcome to 229 Umpawaug Road, the quintessential estate of exceptional quality on the premier scenic road in Redding, Connecticut in Fairfield County. Surround yourself in luxury inside this sun-filled 6 bedroom, 11 bathroom, 6 fireplaces center hall colonial with a flowing floor plan, formal and informal rooms, embracing the incredibly private 6.5 acres of hand-stacked walls, privacy gates and

Stacy Young William Raveis Real Estate

229 Umpawaug Rd, Redding, CT 06896
/44
$18,500,000
- 6 Beds
- 9 Baths
- 10,275 Sq Ft
41 Meadow Wood Dr, Greenwich, CT 06830

With breathtaking views of Long Island Sound, this custom-built Mediterranean-style home is nestled in an exclusive gated community known as Quarry Farm in Belle Haven. Featuring a terracotta-tiled roof, this luxurious home boasts 6-bedrooms and 6.3 baths on 4.7 acres of land. The central courtyard, which serves as the heart of the home, is surrounded by common living areas with extra-height

Jennifer Ho Douglas Elliman of Connecticut

41 Meadow Wood Dr, Greenwich, CT 06830
/47
$6,395,000
- 5 Beds
- 10 Baths
- 7,632 Sq Ft
21 Calhoun Dr, Greenwich, CT 06831

Welcome to ''Park Hill'', a reimagined 1923 English Manor in a Prestigious Private Association. Thoughtfully refreshed for modern living while preserving the architectural character that makes it timeless. Set on 1.81 private, park-like acres, this 7,632 sq. ft. manor blends historic charm with contemporary luxury in a way few properties can. 1923 English Tudor Revival with 2025 updates. Rare

Danielle Claroni Sotheby's International Realty

21 Calhoun Dr, Greenwich, CT 06831
/40
$1,779,000
- 5 Beds
- 5.5 Baths
- 7,611 Sq Ft
28 Old Orchard Dr, Weston, CT 06883

Experience dramatic, modern living in this grand home with a glorious gunite pool & exceptional architectural appeal. Custom-designed, the quality of this residence is readily apparent as you approach from the centrally-located, multi-million dollar neighborhood of fine homes. The stone front, Belgium block-lined drive and specimen landscaping greet you, leading to the soaring two-story foyer.

Barbara Bross Coldwell Banker Realty

28 Old Orchard Dr, Weston, CT 06883

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