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    Showing Homes Nearby Southport, CT
    Beds:
    4
    Baths:
    2.50
    Sq.Ft.:
    2,464
    Status:
    Active
    MLS#:
    24012971
    Type:
    Single Family
    Lot size:
    0.2 Acres
    Year built:
    1940
    Courtesy: Shoshana Carter - William Raveis Real Estate Shoshana Carter
    View additional info

    Welcome home to 101 Smedley Rd, where era charm meets modern convenience on a street celebrated for its friendly vibe & prime location. Nestled in a neighborhood w/ highly-rated schools and close to all amenities, this classic colonial blends character w/ the amenities of today's lifestyle. Inside, hardwood floors usher you through traditional spaces enriched w/ modern touches. The inviting formal living room, complete w/ a cozy fireplace, is an elegant spot to entertain guests. Across the entry, the formal dining room sets the stage for memorable dinners. The eat-in kitchen, equipped w/ granite countertops & a sunken dining area, overlooks the backyard & offers easy access to the patio-perfect for seamless indoor-outdoor living.The family room features built-ins & a 2nd fireplace, adding warmth & charm, & leads conveniently to the mudroom & backyard. A laundry area & half bath complete the 1st floor. Upstairs, an oversized landing introduces 4 bedrooms and 2 full bathrooms, including a luxurious primary suite w/ its own fireplace, walk-in closet, & a renovated bathroom adorned w/ shiplap & a subway-tiled shower. The lower level offers a versatile bonus space, perfect for a playroom or man-cave. Outside, the home continues to impress w/ a private, landscaped backyard framed by greenery, featuring a bluestone patio ideal for hosting BBQs & outdoor parties. This home doesn't just offer a place to live-it offers a lifestyle in a location that defines convenience. Welcome Home!

    Beds:
    7
    Baths:
    7.50
    Sq.Ft.:
    9,035
    Status:
    Active
    MLS#:
    170623903
    Type:
    Single Family
    Lot size:
    0.83 Acres
    Year built:
    2024
    Courtesy: John Schiaroli - William Pitt Sotheby's Int'l John Schiaroli
    View additional info

    **UNDER CONSTRUCTION NOW!**POTENTIAL POOL SITE**Step into a world of sophisticated living at Sherwood Estates. This meticulously crafted 4-story residence at 26 Morningside Drive South seamlessly blends the charm of Westport's heritage with the finest features of modern design. Here, you'll discover a haven for grand entertaining, comfortable family living, and unparalleled relaxation. A Culinary and Social Hub: The first floor captivates with its expansive open floor plan. The heart of the home is undoubtedly the eat-in kitchen, featuring a custom-built, oversized island that's perfect for meal preparation or casual gatherings. A walk-in pantry ensures ample storage, while custom cabinetry throughout this entire level creates a sense of refined elegance. The mudroom, conveniently located off the spacious 3-car garage, provides a designated space for organization. Unwind in the inviting family room, lose yourself in a captivating read in the dedicated library, or host formal dinners in the elegant dining room - all warmed by the ambiance of two fireplaces. Additionally, a walk-out feature to the rear allows for seamless indoor-outdoor living.

    Beds:
    7
    Baths:
    7.50
    Sq.Ft.:
    8,203
    Status:
    Active
    MLS#:
    170623646
    Type:
    Single Family
    Lot size:
    0.82 Acres
    Year built:
    2024
    Courtesy: John Schiaroli - William Pitt Sotheby's Int'l John Schiaroli
    View additional info

    Unwind in Unparalleled Space: The expansive first floor boasts a truly open concept design, perfect for grand entertaining or intimate gatherings. Imagine seamless flow between the gourmet kitchen, complete with a butler's pantry and walk-in pantry, to the inviting living room, elegant dining room, and cozy family room - all warmed by the ambiance of three fireplaces. A dedicated library provides a tranquil escape for reading or reflection. A Haven for Every Member of the Family: The second floor offers a private sanctuary. Retire to the luxurious primary suite, featuring a spa-like bathroom and a custom-designed walk-in closet. Four additional bedrooms, each with en-suite bathrooms, ensure comfort and privacy for all. Entertainment Extravaganza: Ascend to the third floor and discover a haven for entertainment. Immerse yourself in the fully equipped movie room, the perfect venue for blockbuster nights. A spacious game room invites friendly competition, while a well-appointed bedroom with a full bath offers additional guest accommodations. Ample storage space ensures a place for everything. Unwind and Recharge: The possibilities are endless in the expansive lower level. Maintain your fitness goals in the dedicated gym, followed by relaxation in the rejuvenating sauna. For the discerning wine connoisseur, a temperature-controlled wine room awaits. A full bathroom and bedroom provide additional living space, while a wet bar and playroom cater to all.

    Beds:
    3
    Baths:
    1.50
    Sq.Ft.:
    1,344
    Status:
    NEW LISTING
    MLS#:
    24005734
    Type:
    Single Family
    Lot size:
    0.11 Acres
    Year built:
    1937
    Courtesy: Laura Hoglund - Berkshire Hathaway NE Prop. Laura Hoglund
    View additional info

    Charming 3 bedroom colonial with the outdoor entertaining space you've been dreaming of! This sun-filled home boasts a traditional layout with a kitchen open to an office or dining nook. Dining room, living room, half bath and a bonus sunroom complete the main level. Upstairs, the primary bedroom offers comfort and privacy, with two additional bedrooms, perfect for guests or a home office. The beautifully landscaped yard offers outdoor space for gatherings or gardening enthusiasts. One car detached garage. Located in the desirable Fairfield University neighborhood, walking distance to two parks, easy access to all of Fairfield's amenities including downtown, shopping, Whole Foods, I-95 and Metro North. Great opportunity to get into one of Fairfield's sought-after neighborhoods! ***Highest and Best due by Monday, 5/13 at 8pm***

    Beds:
    5
    Baths:
    7.50
    Sq.Ft.:
    9,280
    Status:
    Active
    MLS#:
    24015830
    Type:
    Single Family
    Lot size:
    1.03 Acres
    Year built:
    2010
    Courtesy: Linda Skolnick - Coldwell Banker Realty Linda Skolnick
    View additional info

    5BR Colonial, built by Mattera Construction, blends timeless elegance with modern luxury! Nestled in a tranquil setting, this home is an entertainer's dream, boasting exceptional features that cater to comfort, style, and convenience.Outside, enjoy your personal oasis w/sparkling Pebble Tech Pool & Spa. The pool house is a haven w/ full bath, changing room, washer/dryer, and a wet bar complete with icemaker and Sub-Zero drawers. Crank up the tunes with the built-in sound system and enjoy poolside gatherings or relax under the upper patio's gas fire pit. For the ultimate outdoor cooking experience, fire up the Lynx grill & take in the warmth from the covered patio's wood-burning fireplace.The kitchen is a chef's paradise, featuring a Sub-Zero refrigerator & separate Sub-Zero freezer, along with a Wolf Range. The open layout flows into a spacious living area, perfect for family and friends to gather.Retreat to the Primary Bedroom, where luxury awaits. A Miele coffee maker ensures a perfect start to your day, while Sub-Zero drawers offer convenience for late-night snacks. The Primary Suite features heated floors for those chilly mornings.The garage is as impressive as the rest of the home, outfitted w/ a Garage-Tek organizer system & specialized flooring for durability &easy maintenance. The state-of-the-art HVAC system ensures optimal air quality & humidity control w/ Blue air purifiers. This remarkable property truly has it all. Don't miss your chance to own a slice of paradi

    Beds:
    4
    Baths:
    2.00
    Sq.Ft.:
    2,250
    Status:
    Active
    MLS#:
    24012362
    Type:
    Single Family
    Lot size:
    0.16 Acres
    Year built:
    1946
    Courtesy: Lisa Mancini - William Raveis Real Estate Lisa Mancini
    View additional info

    Welcome to 64 Woodside Avenue! This picture-perfect Colonial ideally located in the sought-after University area offers a peaceful setting while just minutes from bustling downtown Fairfield. Relax on your front porch or entertain in your fenced-in backyard. Inside, enjoy the open floor plan with 3 levels of spacious living, hardwood floors, four generous sized bedrooms (including one on the main level), 9 rooms and two full baths. The main level features a living room with a wood-burning fireplace, built-ins and bow window, eat-in kitchen that seamlessly flows into the family room featuring vaulted ceilings and an abundance of natural light, a dining room with sliding barn doors (currently used as a playroom) and the 4th bedroom. Upstairs, the front to back primary bedroom includes a walk-in closet, two additional bedrooms and a full bath. The partially finished lower level adds 390 square feet of gracious living space, ideal for a home office/media room or bonus room PLUS storage. Step outside, the fenced-in backyard is perfect for extending your entertaining to the outdoors with the lush yard and patio. With easy access to downtown Fairfield, shopping, dining, theatre, Metro North, and beaches this home truly is exceptional!

    Beds:
    6
    Baths:
    7.00
    Sq.Ft.:
    5,324
    Status:
    Active
    MLS#:
    170624891
    Type:
    Single Family
    Lot size:
    1 Acres
    Year built:
    2011
    Courtesy: Kim Harizman - Compass Connecticut, LLC Kim Harizman
    View additional info

    This stunning transitional colonial house, custom built in 2011 and substantially renovated in 2022, is privately situated on a flat, dry professionally landscaped acre of property in the Long Lots school district. Boasting 6 spacious bedrooms, 6 full and 2 half baths, and 4 levels of finished space, the possibilities are endless. Every detail of this custom built Able Construction home has been carefully designed and meticulously maintained. The chef's kitchen, recently renovated with Voytek custom cabinets and Caesar stone concrete countertops and island, opens graciously to an eat in area with double height ceiling and comfortable family room with wood burning fireplace. Walls of windows provide exceptional natural light and the open floor plan allows for easy living. Built in wet bar in the formal living area makes this home an entertainers dream. Modern features abound. The mudroom bathroom doubles as a pool house with access from the pool patio. Complete with heated gunite saltwater pool and spa, no detail has been overlooked. Home gym, craft room, and game room on the lower level, bonus space and 6th bedroom on the 3rd floor, give the discerning buyer plenty of options and versatility. See addendum for recent upgrades.

    Beds:
    4
    Baths:
    2.50
    Sq.Ft.:
    2,496
    Status:
    NEW LISTING
    MLS#:
    24015779
    Type:
    Single Family
    Lot size:
    1 Acres
    Year built:
    1975
    Courtesy: Meredith Cohen - William Raveis Real Estate Meredith Cohen
    View additional info

    Classic center hall colonial can be your home. Priced to sell. Centrally situated within Westport- convenient to town, schools, beach and Post Rd. This home is in an ideal location. Large, bright and sunny bedrooms all with hardwood floors. Natural gas and connected to town sewer. Finished walk-out basement. Home being sold "as is" so come with your decorating ideas and enjoy this house for years to come. 1-acre lot!!

    Beds:
    3
    Baths:
    3.50
    Sq.Ft.:
    3,072
    Status:
    Active
    MLS#:
    24004361
    Type:
    Single Family
    Lot size:
    0.37 Acres
    Year built:
    1950
    Courtesy: Michele Berardo - Brown Harris Stevens Michele Berardo
    View additional info

    Welcome to 1436 North Benson Rd. An elegant five bedroom 3 1/2 bath colonial in the University area is a better than new, impeccably crafted home that offers luxurious living in a prime location. With a "park like" backyard including 20x20 flagstone patio and architectural fireplace provides all the privacy you could want, perfect for entertaining. The main level includes a cozy living room with fireplace, intimate dining area with sliders to the stone patio and outdoor fireplace. Kitchen with pantry/mudroom, separate laundry as well as an bonus Aupair/Inlaw suite with bedroom, office and full bath. A staircase leads from the kitchen to the three upstairs bedrooms. The primary bedroom boasts a walk-in closet and large shower with two person spa tub. Three zone smart climate control thermostats and wired speakers throughout. As if all this were not enough there is also a large bonus room/family room with French doors and beautiful molding/lighting. As well, there is a partially finished basement with a 1/2 bath, additional laundry hookup and cedar closet. The remaining 1/2 of the basement has ample storage. The home has an extra large, three car garage with epoxy floor perfect for extra storage or toys. A very large elegant semi circular gated driveway ensures room to receive guests. Agent/Owner.

    Beds:
    4
    Baths:
    3.50
    Sq.Ft.:
    4,215
    Status:
    Active
    MLS#:
    24009475
    Type:
    Single Family
    Lot size:
    2 Acres
    Year built:
    2022
    Courtesy: Jackie Davis - William Raveis Real Estate Jackie Davis
    View additional info

    Welcome home to 100 Mine Hill Road, where luxury meets modernity in the heart of Lower Greenfield Hill. This stunning, custom new construction, 13 room home is a stand-out positioned on a prime 2-acre professionally landscaped lot w/ gorgeous stone masonry. Step inside to an open floor plan, w/ soaring ceilings & 3 levels of meticulously crafted living space designed for ultimate comfort & style. 1st & 2nd-floor primary suite ensures flexibility for modern living. Designed for maximum energy efficiency & comfort featuring European triple-pane tilt-turn windows & doors by KLAR Studio in Westport. 2 ERV fresh air exchange systems ensure continuous circulation of filtered & tempered fresh air. Every detail has been carefully considered, from the custom cabinetry by JEM Woodworking in Greenwich, CT, to the solid brass hardware handmade in England by Armac Martin. Prime grade European white oak floors & high-efficiency LED lighting grace each room, creating an ambiance of sophistication & warmth. Experience unparalleled control w/ a Lutron Radio RA 3 lighting & shading automation system, complemented by the Josh home voice control automation system. Your security & peace of mind are assured with Lorex 4K night vision security cameras & a Generac whole home generator. Ethernet wiring, high-end appliances, spray foam insulation & 1 &1/8" subfloors. Ideally located close to town, train, parks, dining and shopping. This luxurious estate is truly one of a kind!

    Beds:
    4
    Baths:
    4.50
    Sq.Ft.:
    2,716
    Status:
    Active
    MLS#:
    24010562
    Type:
    Single Family
    Lot size:
    1.11 Acres
    Year built:
    1967
    Courtesy: Walt Dobosz - Higgins Group Real Estate Walt Dobosz
    View additional info

    This meticulously maintained colonial is best described as one of Greens Farms hidden gems. This warm and welcoming 4BR/4.5 BA home sits on a delightful, verdant acre with beautiful mature landscaping at the end of a storybook private cul-de-sac The main living area offers a spacious formal living room with sliders that lead to the wrap around deck. The updated gourmet kitchen includes an oversized island, plus separate dining area, pantry, and more sliders that open to the backyard deck overlooking the garden area. The kitchen opens to the family room with fireplace and more access to the outdoors. The main level also offers a large formal dining room adjacent to the kitchen. Upstairs you will find a spacious primary suite with walk in closet, full bath and a sunny loft that overlooks the family room. This flexible space might be a study, office or exercise area. There are three additional bedrooms, one is en suite. The laundry is also conveniently located on the upper level. The lower level features a large recreation area, a workshop, a bonus guest/au pair room, plus an additional full bath. This well loved home is a serene retreat, in the heart of Greens Farms, just minutes to shops, schools, the beach and train.

    Beds:
    6
    Baths:
    7.00
    Sq.Ft.:
    8,641
    Status:
    Active
    MLS#:
    24001387
    Type:
    Single Family
    Lot size:
    1.46 Acres
    Year built:
    2024
    Courtesy: Jillian Klaff - Coldwell Banker Realty Jillian Klaff
    View additional info

    Luxury living awaits in this exceptional new construction home on 1.5 level acres in a quiet Westport CT sought after cul-de-sac. Enjoy the splendor of the park-like property featuring an oversized salt water pool, spa & outdoor kitchen perfect for entertaining. Savor the tranquility of the front covered porch & convenience of rear covered porch with electric retractable screens.With room for a sports court for pickle ball & basketball this estate offers unparalleled recreation.Spanning 8641 SF across 4 floors, the home features 6 BRS ,6 full/2half BTHS. The 1st floor boasts a custom chef's kitchen, scullery, a temp controlled custom all-glass wine room, a primary suite, office,DR, sun filled FR with sliders to rear porch & back yard, fabulous mud room to heated 3 car garage, rear staircase and powder room.The 2nd floor features a luxury primary suite with cathedral ceilings, natural beams, FP, breakfast bar with refrigerator, sink & coffee maker, oversized custom walk-in closets, office or nursery & spa-like bath, 3 ensuite BRS, study nook w/ custom cabinetry & laundry. The finished 3rd floor offers a bonus room, bath & reading/play nook. The walk-out lower level is flooded with light & includes a gym, BR, full BTH, beverage center, wet bar, carpeted movie room wired for sound & projector and 2nd laundry.Complete with a whole house sound speaker system, generator, wide, white oak floors & 3 fireplaces, experience unparalleled luxury living in this meticulously crafted home.

    Beds:
    4
    Baths:
    5.00
    Sq.Ft.:
    3,900
    Status:
    Active
    MLS#:
    170614734
    Type:
    Single Family
    Subdivision:
    The Homes at Ross Meadow
    Lot size:
    0.28 Acres
    Year built:
    2024
    Courtesy: Linda Blackwell - Houlihan Lawrence Linda Blackwell
    View additional info

    The Homes at Ross Meadow-a beautiful enclave of 9 new homes crafted by SandDollar Development using quality materials and thoughtful design that embodies a timeless and elegantly fresh aesthetic of quiet luxury. Perfect for today's busy lifestyles and diverse life stages. 3900 sqft on 3 levels, 4 bedrooms and 5 full baths. Exceptional finishes include 9' ceilings on main level, modern moldings, custom millwork, and spacious open floor plan, great room scale and natural light. Main level has beautiful chef's kitchen, with large island, ample cabinets topped with quartz counters, top appliances, and walk-in pantry. Great room, adorned with gas fireplace, beautiful custom built-ins and connects to covered terrace for ideal indoor/outdoor entertaining. Additional versatile room with a full bath offers flexibility as a study/office or 5th bedroom option. Expansive primary bedroom suite with custom-fitted walk-in closet and luxuriously appointed bath that has radiant heat floor, 8-foot double vanity with quartz top, designer tile, soaking tub and large shower. Generous second bedroom has walk-in closet and ensuite bath. 2 additional large bedrooms have baths ensuite. Second floor completed with hall linen closet and laundry room. Buyer has option to finish 3rd floor OR lower level. Conveniently located in sought after University area, minutes to schools, beaches, downtown shops, restaurants and commuting options.Completed summer 2024

    Beds:
    5
    Baths:
    4.00
    Sq.Ft.:
    3,900
    Status:
    Active
    MLS#:
    170617109
    Type:
    Single Family
    Subdivision:
    The Homes at Ross Meadow
    Lot size:
    0.28 Acres
    Year built:
    2024
    Courtesy: Linda Blackwell - Houlihan Lawrence Linda Blackwell
    View additional info

    The Homes at Ross Meadow is a beautiful enclave of 9 new homes meticulously crafted by SandDollar Development using quality materials and thoughtful design that embodies a timeless and elegantly fresh aesthetic of quiet luxury. Perfect for today's busy lifestyles and diverse life stages. 3900 sqft on 3 levels, 4/5 bedrooms and 4/5 full baths. Exceptional finishes include 9' ceilings on main level, modern moldings, custom millwork, and spacious open floor plan, great room scale and natural light. Main level has beautiful chef's kitchen, with large island, ample cabinets topped with quartz counters, top appliances, and walk-in pantry. Great room, adorned with gas fireplace, beautiful custom built-ins and connects to covered terrace for ideal indoor/outdoor entertaining. Additional versatile room with a full bath offers flexibility as a study/office or 5th bedroom option. Expansive primary bedroom suite with custom-fitted walk-in closet and luxuriously appointed bath that has radiant heat floor, 8-foot double vanity with quartz top, designer tile, soaking tub and large shower. Generous second bedroom has walk-in closet and ensuite bath. 2 additional large bedrooms share a Jack and Jill bath. Second floor completed with hall linen closet and laundry room. Buyer has option to finish 3rd floor OR lower level. Conveniently located in sought after University area, minutes to schools, beaches, downtown shops, restaurants and commuting options. Lot 9 to be completed summer '24

    Beds:
    5
    Baths:
    6.00
    Sq.Ft.:
    4,934
    Status:
    Active
    MLS#:
    24008161
    Type:
    Single Family
    Lot size:
    2.15 Acres
    Year built:
    2008
    Courtesy: Douglas Bross - Coldwell Banker Realty Douglas Bross
    View additional info

    This distinctive estate in Lower Greenfield Hill offers the ideal blend of Old World style and character with the benefits of high-quality, recent construction. Set on over two acres of exquisite grounds with rich history and provenance, this is a rare find that will enchant you upon arrival. The stone and shingle design of this residence speaks to the quality and timeliness of the interiors that await your discovery. The open floor plan lends itself to effortless entertaining, while stone fireplaces, custom beams and tasteful millwork infuse a sense of history and warmth to the gracious spaces. Distinctive features include the custom gourmet kitchen with Wolf, Miele and Sub Zero appliances, artisanal cabinetry, a butler's pantry and great flow into the family room with an incredible fireplace and cathedral ceiling. The first floor primary suite is a luxurious retreat, complete with a fireplace, elegant private bath and an expansive custom closet. The flexible layout includes spaces for fantastic home office space, in-law suite, staff quarters and much more. Auto enthusiasts will want to take note: this property offers both a three-car attached garage, as well as an incredible five-car heated carriage house offering a total of eight garage bays. The postcard-worthy acreage includes a pool and sunken garden, featured in prestigious garden tours. Imagine an incredibly tranquil retreat that offers direct convenience to town, commuting, and all amenities.

    Beds:
    7
    Baths:
    7.00
    Sq.Ft.:
    6,200
    Status:
    Active
    MLS#:
    24013922
    Type:
    Single Family
    Lot size:
    0.71 Acres
    Year built:
    2024
    Courtesy: Patricia A. Shea - Coldwell Banker Realty Patricia A. Shea
    View additional info

    Move in this Summer! Professionally curated new home with a clean aesthetic incorporating the latest design ideas and finest materials. The crisp look of nickel-gap siding from the JamesHardie Aspyre Collection complimented by large Marvin windows and doors welcome you. Walking through the first floor you'll see spaces perfect for both entertaining and casual living blended together on beautiful white oak flooring. Top-of-line Thermador appliances will catch your eye in the kitchen as will the walk-in pantry and scullery leading to a spacious dining room. Bathed in natural light, the open kitchen family room space is a wonderful place to cook, eat and live. Before looking upstairs don't miss the first-floor office with an adjacent bar area and private patio. Once upstairs, the primary bedroom steals the show. Bright and airy with oak beams, a cozy fireplace, enormous closet space and a super luxurious bath including a shower room with two shower set ups and comfy soaking tub...you'll never want to leave! Two ensuite bedrooms plus a Jack and Jill bedroom with connecting bath round out the second level. The third floor could be an amazing teen-suite or an equally wonderful office suite with full bath and viewing deck area overlooking conservation land. Completing four finished levels is the lower-level family room, bedroom and cabana bathroom leading to a stunning Signature Pool sited on .71 acres at the end of a quiet cul-de-sac, centrally located near all Westport amenities

    Open House:

    Sunday, 5/19 1:00-3:00PM

    Beds:
    3
    Baths:
    1.50
    Sq.Ft.:
    1,956
    Status:
    Active
    MLS#:
    24013190
    Type:
    Single Family
    Lot size:
    0.14 Acres
    Year built:
    1924
    Courtesy: Melissa Makris - William Raveis Real Estate Melissa Makris
    View additional info

    RARE OPPORTUNITY! LOCATION-LOCATION-LOCATION ! Much sought after solid neighborhood that rarely ever turns over. This colonial has charm, style and lots of modern lifestyle possibilities. It is a primarily level lot situated on top of hill with garden and city views. It is at the end of the street and tucked back from street, very private level back yard. 3 bedroom with option for a fourth, and large 3rd floor loft like space. Front porch and back deck patio. Convenient to I95, walkable to MetroNorth, shopping, restaurants and nightlife only a short distance. Beach and parks are a short drive. A MUST SEE! (Note: 14 Massachusetts Avenue in Fairfield also for sale, it has a possibility for a double property. It has a detached garage also suitable for 3-season workshop or auxiliary use.)

    Open House:

    Sunday, 5/19 1:00-3:00PM

    Beds:
    3
    Baths:
    1.50
    Sq.Ft.:
    1,374
    Status:
    Active
    MLS#:
    24013184
    Type:
    Single Family
    Lot size:
    0.14 Acres
    Year built:
    1928
    Courtesy: Melissa Makris - William Raveis Real Estate Melissa Makris
    View additional info

    RARE OPPORTUNITY in sought after neighborhood, never turns over! Either use as investor property, expansion possibilities for design-builder, or move right in! This home offers all the lifestyle conveniences. LOCATION-LOCATION-LOCATION! Character rich 1928 colonial with gambrel roof, architectural classicism and new england charm with lots of EXPANSION possibilities! Situated on a flat-topped hill, multi-tier lawn areas. It's very private, at end of quiet street, abutting a town owned wooded lot. 3-bedrooms, option for fourth, and walk-up 3rd floor loft-like space (fantastic for media room, home office, art/yoga studio, playroom, or bonus bedroom). This home is bright and sunny with city views from the front paired with bucolic views of side and back yards. With a remodel, an in-law suite with separate exterior access is possible. Walk to the Metro, WholeFoods/Home Depot and nearby restaurants with night life. I-95 is very close and beach a 5-10 min drive. NEW kitchen, with NEW EnergyStar appliances (natural gas range/oven), and glass subway tile backsplash. Interior/exterior freshly painted, hardwood floors refinished throughout, updated baths, and a NEW roof. The darling detached garage, functional also serves as a folly focal point with a NEW cement floor. Suitable for a sporty convertible, 3-season workshop or party barn. (NOTE: 16 Massachusetts Ave is also for sale creating this RARE opportunity. Combined, it has the possibility for a double property) A MUST SEE!

    Beds:
    3
    Baths:
    2.00
    Sq.Ft.:
    1,370
    Status:
    NEW LISTING
    MLS#:
    24015410
    Type:
    Single Family
    Lot size:
    0.25 Acres
    Year built:
    1961
    Courtesy: Virginia Klein - RE/MAX Heritage Virginia Klein
    View additional info

    Tucked away at the end of a cul-de-sac in the University area this little gem is sited on a level quarter acre. The home has great bones, some quality updates and is ready for a glow-up. The first floor offers a living room with a fireplace, dining room, kitchen, and a light and airy family room with vaulted ceilings. On the second floor there are three generous sized bedrooms and one large full bath. The lower level has a second full bath and a bonus room. Laundry and storage are available in the basement. Located between Post Rd and Black Rock Turnpike you've got the best of all the Fairfield conveniences.

    Beds:
    11
    Baths:
    8.50
    Sq.Ft.:
    15,118
    Status:
    Active
    MLS#:
    170612636
    Type:
    Single Family
    Lot size:
    3.07 Acres
    Year built:
    1928
    Courtesy: Gail S. Robinson - William Raveis Real Estate Gail S. Robinson
    View additional info

    Experience the timelessness of The Chimneys, an architectural gem designed by the legendary Charles Wellington Walker in 1928. Originally built with the finest materials, this Georgian Revival style home garnered the prestigious America's Finest Home Award in 2015, acknowledging the attention to detail that has gone into its restoration. A 54-foot front-to-back Grand Hall, centered by a sweeping staircase with unique hand-wrought iron balustrades, exudes a sense of elegance. The 11 fireplaces, each a work of art, adorn the rooms with distinct style, adding warmth and character. The main floor includes a front-to-back living room with twin fireplaces, billiard room, library, formal dining room, office, and a kitchen/family room combination. Two extra rooms could become an in-law suite w. separate entrance and full bath. On the 2nd floor, the primary suite beckons with a full bathroom, dressing room with a fireplace and terrace, and a Juliette balcony, offering views of Long Island Sound. Five of the bedrooms on the 2nd level are ensuite, and boast their own fireplaces. In total, there are 11 BR, 7 full BA, and 3 partial BA. Adjacent to the 6-car garage, a townhouse-style carriage house provides a guest area. The two-story columned porch on the side invites you to the in-ground pool and cabana, complete with statuary. There is a full-length stone patio in the rear, overlooking the fountain and perennial gardens. Land may be subdividable, due to .20 acre zoning.

    Beds:
    6
    Baths:
    10.00
    Sq.Ft.:
    10,414
    Status:
    Active
    MLS#:
    24000586
    Type:
    Single Family
    Subdivision:
    Hunt Club
    Lot size:
    1.85 Acres
    Year built:
    2002
    Courtesy: Karen K. Scott - Compass Connecticut, LLC Karen K. Scott
    View additional info

    Introducing 5 Boxwood Lane, a luxurious haven in Westport's serene Hunt Club neighborhood. This exceptional property blends luxury, comfort, and tranquility on a private cul-de-sac. Meticulously designed with exquisite details and custom amenities, this home stands apart. Four levels, high ceilings, and a thoughtful layout offer grandeur and ease. Discover the gourmet kitchen, top-of-the-line appliances, custom cabinetry, and a generous island. The formal dining room and fireplace-centered living room create perfect gathering spaces. A handsome library/office caters to luxury work-from-home needs. The upper levels reveal a sprawling primary suite with two ensuite bathrooms, walk-in closets, and an office/relaxation niche. Additional bedrooms with bathrooms ensure privacy. A bonus room + ensuite bedroom offers versatility for guests, au pair, or studio. The lower level is an expansive recreational area for games and movie nights, the ultimate "hang-out space." Once outdoors, a manicured oasis awaits, with stunning perennial gardens, velvety lawns, and a blissful poolside retreat featuring a charming cabana. This one-of-a-kind residence transitions effortlessly between lavish soir?es and cherished family moments. Private yet convenient, enjoy Westport's attractions, including commuter trains, beaches, shopping, dining, recreation, arts, and top-rated schools. For those seeking sophistication and an unparalleled lifestyle, welcome to your dream home at 5 Boxwood Lane.

    Beds:
    3
    Baths:
    1.50
    Sq.Ft.:
    1,000
    Status:
    Active
    MLS#:
    24008687
    Type:
    Single Family, Ranch
    Lot size:
    0.22 Acres
    Year built:
    1956
    Courtesy: Kelly Finn - Coldwell Banker Realty Kelly Finn
    View additional info

    Are you a first time home buyer ? downsizing ? or looking for a solid investment in the coveted University area ? This ranch-style sanctuary offers a thoughtfully designed layout and a bright and airy ambiance. The main floor features a welcoming living space bathed in natural light adorned from oversized windows and beautiful hardwood floors thruout. The kitchen has ample cabinet space and accesses the spacious rear deck with the added bonus of a three season, screened porch with views of the lush rear property. The spacious dining area provides an ideal setting to enjoy delicious meals. Three comfortable bedrooms share the updated hall bath, completing the main level. Descend to the freshly, painted finished basement with a half bath, adding approx 400 sqft and offering a versatile space, whether a home office, media room or additional living space that can be customized to suit your needs. Situated on a beautiful .22 acres, oversized two car attached garage, central air, city water, sewer and efficient solar panels. This home is ideally located close to town, highways, train, top schools, and beaches. Don't miss the chance for this convenient gem with unlimited expansion possibilities and be in to enjoy your summer.

    Beds:
    2
    Baths:
    2.00
    Sq.Ft.:
    1,145
    Status:
    NEW LISTING
    MLS#:
    24016222
    Type:
    Condo, Townhouse
    Year built:
    2006
    Courtesy: Nicholas Molinaro - Keller Williams Realty Partner Nicholas Molinaro
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    This charming 1,145 square foot unit features 2 bedrooms and 2 bathrooms, perfectly situated in the desirable Black Rock Neighborhood, offering convenience for commuters. The cozy living spaces are ideal for relaxation and entertaining, boasting a seamless flow from the living room to the dining area. Step outside onto the deck and enjoy serene views of Ash Creek, creating a tranquil backdrop for morning coffee or evening gatherings. The primary bedroom provides a peaceful retreat with an en-suite bathroom, while the second bedroom offers flexibility for guests or a home office. Both bathrooms are tastefully appointed with modern fixtures and finishes. Convenience is ensured with a dedicated laundry room and utility closet, providing added storage space for your comfort. Nestled in the sought-after Black Rock neighborhood, residents can easily access local shops, restaurants, parks, and waterfront activities. Commuting is effortless with nearby highways and public transportation options. Don't miss out on this opportunity to own a piece of paradise in Black Rock. Schedule an appointment today and experience the beauty and charm of this exceptional home!

    Open House:

    Sunday, 5/19 11:00-1:00PM

    Beds:
    3
    Baths:
    1.50
    Sq.Ft.:
    2,080
    Status:
    NEW LISTING
    MLS#:
    24015428
    Type:
    Single Family
    Lot size:
    0.14 Acres
    Year built:
    1938
    Courtesy: Janice Mattioli - Coldwell Banker Realty Janice Mattioli
    View additional info

    This charming 2080 square feet colonial on the Fairfield line has its original features, such as ornate original wooden floors, doors, and windows, an a fireplace, and more. A beautiful landscaped well-maintained lawn and a large back deck to die for with a pergola overhang to entertain all your friends and family. Bring your TLC to make this solid 1938 home shine. This home makes a statement with its large foyer and charming archway with pillar entrances to the living room and dining room. The living room also features built-in bookshelves, a fireplace, and a separate entrance on either side of the f/p with single French doors to an enclosed sun porch. The large dining room holds its value for having those wonderful holiday gatherings. The kitchen has a pantry closet, gas stove, 1/2 bth, and open stair case that either leads to the second level or back to the front foyer. The second floor has 3 large bedrooms, a full bath, and a walk-up finished attic that can be made into 4th bedroom or anything that you like, it includes a cedar closet and sink and has its a/c unit. Central air throughout the home, interior entrance, and side entrance to the full unfinished basement. If you love charming homes this is the home for you!

    Beds:
    3
    Baths:
    3.00
    Sq.Ft.:
    1,769
    Status:
    NEW LISTING
    MLS#:
    24012817
    Type:
    Condo, Townhouse
    Year built:
    2005
    Courtesy: Lisa Fratarcangeli - William Raveis Real Estate Lisa Fratarcangeli
    View additional info

    Stone Ridge at Fairfield is a beautiful gated community. This elegant second floor unit has 3 Bedrooms, 3 full Bathrooms, and 2 spacious decks. Coveted GARAGE SPACE and STORAGE ROOM are included with this unit in addition to an exterior reserved parking space. There are extraordinary appointments and impeccable design elements such as 10' ceilings, hardwood floors, lovely kitchen with stainless steel Viking appliances. The Primary Bedroom suite includes hardwood floors and three closets for plenty of storage. Primary Bathroom has double sinks, marble flooring, spa tub, and large shower stall which are all hallmarks of a Stone Ridge home. Recent updates include new refrigerator, dishwasher, microwave, garbage disposal, washer, dryer and tankless hot water heater. Gorgeous plantation shutters in living room and primary bedroom. New blinds in guest room. The elegant Ridge Club includes a continental breakfast daily in the Community Room, a Fitness Room, Concierge/Manager and Porter/Handymen which elevates condominium living to new heights. Located across from the new Fairfield Metro Train Station. Close to Whole Foods shopping center. Enjoy the easy living of Condo life! Garage Space No. 17, Storage Room No. 5, and Exterior Reserved Space No. 61

    This Information is from Smart MLS and has been compiled from various sources, all of which may not be completely accurate. Smart MLS makes no warranty or representation as to the accuracy of listing information. All information that influences a decision to purchase a listed property should be independently verified by the purchaser. Copyright 2017 Smart MLS, Inc. All rights reserved.

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