Homes for Sale near Roger Ludlowe Middle School

Welcome to one of Greenfield Hill's most distinguished residences-an extraordinary 9,700+ sq. ft. Colonial estate nestled on 2 pristine acres in one of Fairfield's most prestigious enclaves. This 5-6 bedroom architectural masterpiece combines timeless elegance with modern luxury, offering an unparalleled lifestyle just moments from town. From first look, the home's unrivaled curb appeal

Michael Debiase Keller Williams Realty

Experience Coastal Luxury in this Brand New Custom Colonial just steps away from the soothing sands & sea breeze of Penfield Beach, featuring a brand-new pavilion for the ultimate Gold Coast lifestyle! Perfectly situated on one of Fairfield's most coveted streets, this FEMA-compliant custom home offers 4 Bedrooms, 3 Full bathrooms & over 3,000 square feet of thoughtfully designed living space

Melissa Montagno Higgins Group Real Estate

Welcome to a truly exceptional opportunity-a direct waterfront compound offering expansive views of Long Island Sound, a dock, &endless showstopping sunsets. This remarkable property features 2 residences: a fully renovated, FEMA-compliant main house AND a charming, income-generating guest cottage.The Main Residence (320)is a modern coastal retreat offering 3,129 sq ft of sun-drenched living

Deirdre Andreoli Compass Connecticut, LLC

Live the ultimate coastal lifestyle in this sensational 5-6 bedroom, 4.5 bathroom Nantucket-style Colonial w/brand new Gunite pool. Set on an oversized, wide lot, this home was recently reimagined by one of Fairfield County's most acclaimed interior designers. Sun-flooded w/9' ceilings & a breezy beach-inspired layout, every detail feels custom & elevated: coffered ceilings, transom doorways,

Kate Cacciatore William Raveis Real Estate

A Rare Opportunity in the Beach Area- Set on an oversized .42-acre lot at the end of a quiet cul-de-sac, this custom-built home offers a rare combination of space, quality, and location. Uniquely positioned with a deep front setback and an expansive backyard-this property stands apart from typical neighborhood lots. Ample room for a pool and more! Thoughtfully designed for both comfort and

Wendy Ryan Brown Harris Stevens

Imagine starting each day with breathtaking sunrises over the water, the salty breeze on your face, and your toes in the sand. This magnificent custom-built waterfront estate offers 126 feet of direct beachfront along Fairfield's highly sought-after South Pine Creek Beach Area. Perfectly situated on nearly an acre of property, this stately Federal Colonial was custom built in 2005 and showcases

Melissa Montagno Higgins Group Real Estate

Located in the heart of Greenfield Hill at the top of Bronson Road, this iconic Connecticut estate sits on 2+ beautifully landscaped acres with distant water views of Long Island Sound. Across from a majestically developed family and horse-farm compound and outside the historic district, this home blends old-world charm with modern comforts. Originally built in 1844 and significantly expanded and

Tara Hawley Coldwell Banker Realty

New Construction in coveted BEACH AREA! This 4,000 sqft custom Colonial blends coastal charm with modern luxury-just a short walk to Penfield Beach, Fairfield Beach Club, vibrant downtown, the train, and top-rated schools. With 5-6 bedrooms, 4.5 baths, and 3 finished levels, this elevator-ready home offers exceptional design, flow, and comfort. The open concept kitchen is both functional and

Julie Vanderblue Higgins Group Real Estate

Spectacular New Construction in the Sasco Beach Area. Don't miss the rare opportunity to customize and make this home your own.Located on almost a half acre of peaceful, private property, last house on a cul-de-sac, backing up to open land on Sasco Hill. Distant water views, serenity, extensively manicured yard and just steps to South Pine Creek Beach.. a very special quaint beach with life

Bette Gigliotti William Raveis Real Estate

Charming 3-bedroom, 1-bath Ranch nestled on a private lot surrounded by mature privacy hedges in a phenomenal Fairfield neighborhood. Hardwood floors lie beneath all carpeting (excluding kitchen and porch), offering excellent potential for easy updates. The spacious 3-season porch provides opportunity for year-round use with a simple conversion. The finished lower level adds 480 sq ft of living

Frank D'Ostilio Houlihan Lawrence WD

Situated near the head of Southport Harbor and within walking distance to the village, train station, and all the charm of Southport life, this 1904 jewel-box home blends historic character with elevated, designer-informed updates. With two bedrooms, two full and one half baths, charming public rooms, a finished third floor (ideal to use for additional bedroom or home office), and an attached

Wendy Ryan Brown Harris Stevens

Set in one of Fairfield's most beloved waterfront communities, 73 Old Dam Rd is the perfect blend of contemporary style and laid back coastal living with Dock, Private Beach Access, & calming water views of the Creek and Long Island Sound. Recently and tastefully renovated, this home offers a light and bright open floor plan. You'll love the new kitchen featuring high end appliances and custom

Jaclyn Picarillo Higgins Group Bedford Square

Introducing a breathtaking & architecturally striking waterfront estate on the Gold Coast - a treasure combining elevated design, top tier craftsmanship & smart luxury. Set on a rare .53 acre beachfront lot w/ 80+ ft of direct shoreline, this exceptional home offers 5,400sf of elegant living across 3 levels + a 560sf studio w/ a half bath - ideal for a guest suite or creative retreat. Wrapped in

Jackie Davis William Raveis Real Estate

Welcome to 1477 Mill Plain Road - a timeless expanded Cape in Fairfield's coveted University neighborhood, boasting an incredible location and exceptional convenience. Ideally located steps to Riverfield Elementary, offers walkability to downtown shops and restaurants, train station, middle and high schools, and Fairfield University, and close to the beautiful beaches the nature trails, this home

Wendy Ryan Brown Harris Stevens

Greenfield Hill Colonial Home on 2-Acre Lot - Great Potential This sweet colonial home has wonderful curb appeal. Situated on a spacious 2-acre lot and just waiting for the perfect buyer to polish this pearl. With a classic floor plan and options for expansion. The first floor includes a living room, dining room, den/office, and a kitchen, along with a full bath. Upstairs, there are four bedrooms

Karen Waldvogel William Raveis Real Estate

A prime Southport country setting at the Westport line is home to this gracious five bedroom colonial featuring a rarely found attached main level IN-LAW / AU PAIR APARTMENT with a private entrance, Living/Dining Room, Bedroom and a full Bath. Additionally appreciated, and perfect for today's work from home buyer, is an office/studio over the barn style oversized detached two car garage.

Paul Triantafel William Pitt Sotheby's Int'l

Extremely rare opportunity to own a side-by-side, Colonial style duplex with over 4400sqft in total and 10 bedrooms-in the heart of the Fairfield beach area. The home is currently rented each academic year through May 2028. Cap spreadsheet is in attachments, illustrating the very positive income flow. Academic rental $19,000-$21,000 per month for entire house. Converting to a 10-month lease after

Jessica Walsh William Raveis Real Estate

Prime Corner Lot In a Coveted Fairfield Beach Neighborhood. This exquisite four bedroom, three full & two half bath home blends luxury with modern convenience, with nine-foot ceilings and rich paneling throughout. The heart of the home is the open concept gourmet kitchen & living room.The kitchen has Carrera marble, a spacious island w seating, a walk-in pantry & flows seamlessly into the

Sally Bohling Coldwell Banker Realty

Sprawling ten room ranch style residence offering three acres on a prime estate street in Greenfield Hill. This stately home is discreetly positioned behind a brick wall and approached by a sweeping circular drive creating a grand sense of arrival. Inside this impressive home discover a striking Indoor Pool housed in its own sun lit pavilion. This dramatic recreation space adjoins the Kitchen and

Paul Triantafel William Pitt Sotheby's Int'l

Savor the coastal lifestyle in this chic, modern 2021 construction home in the highly desirable Fairfield Beach neighborhood. Just a quick stroll to the beach with pavillion, Fairfield town marina & Sand Castle Park. Hard to find beach area NOT in Flood Zone! No flood insurance required. Thoughtfully designed for open & airy living. Step into open concept living with a spacious living room that

Katie O'Grady Compass Connecticut, LLC

Welcome to 260 Willow Street-where timeless design meets modern luxury. Thoughtfully reimagined and meticulously executed, this exceptional Southport Village residence embodies architectural refinement and effortless elegance. Renowned architect Christopher Pagliaro's philosophy of "addition by subtraction" is evident throughout, resulting in a home that is both sophisticated and serene. Every

Elizabeth Tritschler William Raveis Real Estate

Experience elevated coastal living in this stunning new-construction modern Colonial, ideally situated in the heart of Fairfield's desirable beach area. Just a short stroll to South Pine Creek Beach, the train, tennis courts, golf course, and vibrant downtown shops and dining, this home offers an unmatched blend of luxury and lifestyle. Spanning approximately 3,500 square feet, this custom

Michael Puff RE/MAX Town & Country

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

Opportunity Knocks for this perfect opportunity for renovation or expansion in prime Location! Nestled on a quiet lower Greenfield Hill cul-de-sac with a peaceful yard, this solidly built home is being sold as-is, where-is with no representation of electric, plumbing, or mechanical systems. TOWN VARIANCE IS IN PLACE FOR EXPANSION and for adding a second story, providing incredible potential to

Michael Traum RE/MAX Heritage

Located on a quiet cul-de-sac in one of Southport's premier family neighborhoods, this elegant 4-bedroom, 2 full and 2 half-bath Colonial by Toll Brothers combines timeless design with modern comfort. The stately "Cedarbrook" Federal Colonial model welcomes you with a grand two-story foyer, setting the stage for the sophisticated interiors. Formal living and dining rooms are ideal for

Julie Vanderblue Higgins Group Real Estate

Stunning NEW construction nestled in the desirable Fairfield Beach neighborhood. This fabulous home is crafted by premier Fairfield County builder with over 43 years of esteemed reputation and results. Premium materials, thoughtful design, and masterful workmanship are showcased throughout. Step inside to find a clean, modern, open living space with 9' ceilings. The inviting living room,

Katie O'Grady Compass Connecticut, LLC

Sasco Point- A Rare Waterfront Estate. Perched on over 11 acres with 450 feet directly on Long Island Sound, Sasco Point is an extraordinary coastal retreat. Nestled at the end of prestigious Sasco Hill Road, this architecturally stunning estate blends Swedish, Dutch, and Moorish influences, creating a residence that is as elegant as it is timeless. A discreet gated entrance leads to a winding

Andrew Whiteley Brown Harris Stevens

"Pebbles" | Iconic Sasco Hill Estate Timeless Design. Storied Past. Unrivaled Views. A distinguished Georgian Revival estate set on nearly 3 acres, the largest lot along this coveted stretch of Sasco Hill. With sweeping, unobstructed views of the Country Club of Fairfield, Southport Harbor, Long Island Sound, and the Manhattan skyline, this iconic property offers an extraordinary blend of

Wendy Ryan Brown Harris Stevens

Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7 bedrooms, 5 baths, library with

Helene Salerno Preoh, LLC

Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7 bedrooms, 5 baths, library with

Helene Salerno Preoh, LLC

Welcome to Turning Point at Pine Creek, where the coastline bends to a point creating some of the most magnificent side-to-side sweeping views the Gold Coast has to offer. This very special beachfront site will offer Connecticut Home's latest architectural masterpiece. A 4000sf state of the art custom build with ultra high-end finishes which will no doubt be one of CT's most remarkable coastline

Basil Amso RE/MAX Right Choice

First Time on the Market - A Southport Treasure with Endless Possibilities For the first time since 1912, this cherished Southport residence is being offered for sale. Passed down through generations, this classic colonial has been a cornerstone of one family's legacy for over a century - and now it's ready for its next chapter. Set on nearly a half-acre in the heart of Southport, this property

Vienna DiPiave William Pitt Sotheby's Int'l

This is the iconic property everyone is talking about! Introducing an extraordinary new custom residence set in the beloved estate area of Upper Southport near private equestrian facilities and public trails, beaches, restaurants, train, and shopping. Masterfully designed and customized to YOUR every whim with exquisite main house, separate party barn and/or guest house, pool with spa, tennis

Jaclyn Picarillo Higgins Group Bedford Square

Welcome to the pinnacle of luxury coastal living at 1008 Fairfield Beach Road- where modern luxury meets coastal elegance. Presented by one of Fairfield County's premier celebrity developers, this extraordinary new construction beach home offers an unparalleled lifestyle with panoramic, unobstructed views of the Long Island Sound with jaw-dropping sunsets. Stand out in the neighborhood with one

Valerie Alvarez Higgins Group Real Estate

Enjoy the beach life year round at this perfect walk everywhere location .. just steps to Jennings Beach, Sand Castle Park and the Fairfield Marina. Located on a quiet cul-de-sac with privacy. Don't miss this opportunity to customize your gorgeous New home which will be underway soon and should be complete by the end of the year. Meet with the builders and choose your finishes! 4 bedrooms, 3.5

Bette Gigliotti William Raveis Real Estate

Opportunity awaits to pre purchase these 2 luxurious condos. Rear unit with a spacious yard. Totally customize your home for your liking! Just steps to Penfield Beach. What a location! Great opportunity for homeowner or investors

Bette Gigliotti William Raveis Real Estate

Opportunity awaits to pre purchase these 2 luxurious condos. Totally customize your home for your liking! Just steps to Penfield Beach. What a location! Great opportunity for homeowner or investors

Bette Gigliotti William Raveis Real Estate

This Luxury Townhouse/Condo with 4000+ square feet offers an exceptional living experience in its spacious layout. Upon entering, you'll immediately notice the white oak flooring, wide hallways and elegant antique brass fixtures. You'll enjoy 4 generously sized bedrooms each with their own en suite bathroom. An additional office space gives the WFH owner a separate place to conduct business. A

Sara Santos Coldwell Banker Realty

A Luxury Townhouse with nearly 4000 square feet offers an exceptional living experience in every detail. With its spacious layout and carefully crafted design, this townhouse boasts a perfect blend of elegance and comfort. Upon entering, you'll immediately notice the thoughtfully designed interior that exudes sophistication. The townhouse features 4-5 generously sized bedrooms. Each bedroom is

Sara Santos Coldwell Banker Realty