Houses for Sale near Great Beginnings Montessori School

/40
$2,995,000
- 5 Beds
- 5.5 Baths
- 5,965 Sq Ft
2015 Redding Rd, Fairfield, CT 06824

Majestically sited on 2 private acres of professionally landscaped grounds, this exceptional SMART modern farmhouse surpasses new construction standards with uncompromising attention to detail. This 5,500+ SF estate exemplifies architectural integrity with handcrafted millwork and bespoke finishes throughout. Superior craftsmanship shines in every detail-from rich white oak hardwood floors to

Susan Lieberman

The Riverside Realty Group

(475) 252-9450

2015 Redding Rd, Fairfield, CT 06824
Explore Great Beginnings Montessori School
/34
$749,000
- 3 Beds
- 2 Baths
- 1,665 Sq Ft
274 High St, Fairfield, CT 06824

Welcome to 274 High Street, Fairfield, CT-where timeless elegance meets modern convenience. This beautifully renovated home boasts a fresh and inviting open-concept design, with a stunning new Trex deck just off the kitchen, perfect for relaxing or entertaining. The spacious kitchen features a large island with extra seating, complemented by a stylish design table for additional dining space.

Karly Worth Call It Closed Realty

274 High St, Fairfield, CT 06824
/40
$1,849,000
- 3 Beds
- 3.5 Baths
- 2,760 Sq Ft
1001 Hulls Farm Rd, Southport, CT 06890

Situated on 2 manicured acres in Southport and surrounded by multi-million-dollar estates, this gated, European-inspired country home blends timeless charm with modern elegance. A white-pebble drive, stone walls, and sweeping lawns with mature trees create a private estate feel. Inside, the home balances warmth with sophistication. Offering 3 bedrooms on the main level and a 4th bedroom option in

Ken Banks William Raveis Real Estate

1001 Hulls Farm Rd, Southport, CT 06890
/40
$4,200,000
- 4 Beds
- 3.5 Baths
- 4,038 Sq Ft
174 Sunnieholme Dr, Fairfield, CT 06824

Nestled on one of Fairfield's most coveted streets where the beach, town, & coastal charm are just steps away- this extraordinary 1944 farmhouse is a rare offering that blends timeless New England character w/ every modern luxury. Once part of the Annie B. Jennings estate, this completely reimagined 4,038 sq. ft. residence sits on nearly 3/4 of an acre, an unheard-of expanse in the beach area.

Susan Tortora William Raveis Real Estate

174 Sunnieholme Dr, Fairfield, CT 06824
/40
$2,498,000
- 5 Beds
- 8 Baths
- 8,136 Sq Ft
88 Merry Meet Center, Fairfield, CT 06824

Modern elegance meets estate living at 88 Merry Meet Circle, set on 3+ manicured acres in Fairfield's premier gated community, The Ridge. Perfectly positioned where Fairfield meets Westport, this gracious colonial manor offers 5+ bedrooms, 6 full and 2 half baths, and 4 beautifully finished levels-just minutes from vibrant downtowns, beaches, dining, and trains. A grand two-story foyer with a

Erin Bremen melson The Agency

88 Merry Meet Center, Fairfield, CT 06824
/40
$3,750,000
- 7 Beds
- 9 Baths
- 10,104 Sq Ft
249 Greens Farms Rd, Westport, CT 06880

Storied and superbly restored, 'The Lookout' at 249 Greens Farms Rd blends the grandeur of a 1907 Colonial Revival with todays modern luxury. Privately set among perennial gardens and antique copper beeches, this iconic 16-room residence offers a gracious floor plan with elegant formal spaces, a chefs eat-in kitchen, media room, wine cellar, and inviting family areas. Original architectural

Kim Harizman Compass Connecticut, LLC

249 Greens Farms Rd, Westport, CT 06880
/40
$2,785,000 Open Sat 10AM - 12PM
- 4 Beds
- 3.5 Baths
- 5,434 Sq Ft
6 Nutcracker Ln, Westport, CT 06880

A rare Westport retreat blending serenity, sophistication & resort-style living. Privately set at the end of a quiet cul-de-sac off Bayberry Lane, this elegant four-bedroom, three-and-a-half-bath home offers over 4,600 sq ft of sun-filled living space surrounded by beautifully landscaped grounds. The property's two private acres feel like a personal park-complete with mature trees, curated

Michelle Sperry Coldwell Banker Realty

6 Nutcracker Ln, Westport, CT 06880
/40
$3,888,000 Open Sun 1PM - 4PM
- 6 Beds
- 5.5 Baths
- 4,307 Sq Ft
944 Pequot Ave, Southport, CT 06890

Step into history in the heart of Southport Village, where this location doesn't get any better! On Pequot Ave, and just a short stroll to the beach, village shops, dining, library, and train to New York City, this beautifully restored 1853 Colonial was once home to Miss Augusta Smith's Seaside Seminary. The residence has been reimagined for today with warmth, elegance, and every modern

Elizabeth Tritschler William Raveis Real Estate

944 Pequot Ave, Southport, CT 06890
/12
$1,589,000 Open Sun 12PM - 3PM
- 4 Beds
- 5 Baths
- 3,224 Sq Ft
419 Valley Rd, Fairfield, CT 06825

Luxurious, like new construction home located in the desirable Stratfield Village neighborhood of Fairfield. Total interior renovation, including full second floor and additional two car garage was finished in 2025. This gorgeous property sits on 1.3 acres and features a modern, open-concept kitchen, four spacious bedrooms, three full bathrooms, two half bathrooms, and two dedicated home offices.

Danielle Baleeiro Realty ONE Group Connect

419 Valley Rd, Fairfield, CT 06825
/30
$1,749,000
- 4 Beds
- 6 Baths
- 4,000 Sq Ft
345 Reef Rd Unit B6, Fairfield, CT 06824

Approximately 4,000 square feet townhouse feels like a single family home with thoughtfully designed living space and featuring four bedrooms, four en-suite bathrooms, and two half baths, and private elevator. This residence offers ample room to accommodate a variety of household needs. The primary suite boasts a luxurious en-suite bathroom with a dual vanity, walk-in shower, soaking tub, and

Sara Santos Coldwell Banker Realty

345 Reef Rd Unit B6, Fairfield, CT 06824
/39
$1,949,000
- 4 Beds
- 5 Baths
- 4,400 Sq Ft
345 Reef Rd Unit C9, Fairfield, CT 06824

This luxury End unit new construction Townhouse feels like a single family home with over 4,400 square feet offering an exceptional living experience with a spacious and thoughtfully designed layout. Undeniably the best location in the entire complex with a private patio and yard. Upon entering, you'll notice the 7" white oak flooring, wide hallways, and modern fixtures. The home features four

Sara Santos Coldwell Banker Realty

345 Reef Rd Unit C9, Fairfield, CT 06824
/39
$2,200,000
- 6 Beds
- 2 Baths
- 2,180 Sq Ft
2142 Fairfield Beach Rd, Fairfield, CT 06824

OPPORTUNITY KNOCKS TWICE - A unique investment awaits with the only two-family home on the Fairfield Beach Road Peninsula featuring private beach access. This fully furnished property offers excellent rental income during the academic season and serves as a relaxing summer retreat for owners-or an additional rental opportunity. Unit 2142 is a spacious four-bedroom residence, each room furnished

Michael Menillo Collage Realty

2142 Fairfield Beach Rd, Fairfield, CT 06824
/40
$2,218,000
- 4 Beds
- 3 Baths
- 3,377 Sq Ft
4 Burr Farms Rd, Westport, CT 06880

Welcome to this captivating expanded cape retreat in the heart of Westport on a sought after, centrally located, walk to school street. Every aspect speaks the language of artistry and elevated attention to detail. This custom built sanctuary is an artist's haven nestled admist nature's finest tapestry. The residence boasts a thoughtfully designed living space harmoniously arranged on a

Susan Vanech Compass Connecticut, LLC

4 Burr Farms Rd, Westport, CT 06880
/40
$1,650,000
- 4 Beds
- 4.5 Baths
- 3,200 Sq Ft
264 Harvester Rd, Fairfield, CT 06825

Stunning modern new construction offering high-end finishes and sophisticated design throughout. Exterior showcases white Hardie board siding, galvanized metal roof accents, oversized grey windows, and a sleek modern glass garage door. The large windows and an 8-foot slider flood the interior with natural light and provide seamless access to the backyard. Inside, white oak floors run throughout

Basil Amso RE/MAX Right Choice

264 Harvester Rd, Fairfield, CT 06825
/11
$1,699,900
- 3 Beds
- 2 Baths
- 3,171 Sq Ft
40 Maple Ave N, Westport, CT 06880

Prime location a few houses down from the Hunt Club three bedrooms with two additional bounus rooms and two bathrooms home with a fully finished walkout on a level one acre of land surrounded by multi million dollars homes.

Sayed Ibrahim Nationwide Homes

40 Maple Ave N, Westport, CT 06880
/34
$1,899,000
- 4 Beds
- 4.5 Baths
- 4,515 Sq Ft
254 Sherwood Farm Rd, Fairfield, CT 06824

254 Sherwood Farm Road, tucked away at the end of a cul-de-sac in the desirable lower Greenfield Hill section of Fairfield, this stately brick Colonial blends timeless curb appeal with a flexible floor plan and rare amenities. Mature plantings, stone walkways, and professional landscape lighting frame the home with elegance from the moment you arrive. Inside, the first level offers remarkable

Aaron Goldberg Coldwell Banker Realty

254 Sherwood Farm Rd, Fairfield, CT 06824
/14
$1,890,000
- 5 Beds
- 3.5 Baths
- 3,780 Sq Ft
210 Pansy Rd, Fairfield, CT 06824

Welcome to 210 Pansy Road, a stunning new construction in Fairfield, CT offering nearly 4,000 sq. ft. of thoughtfully designed living space with 5 bedrooms and 3.5 baths. What truly sets this home apart is its rare setting-backing up to 8.5 acres of serene open nature preserve, providing a peaceful backdrop that's both private and unique. Inside, you'll find high-end finishes throughout: a chef's

Anthony Gigliotti Keller Williams Realty

210 Pansy Rd, Fairfield, CT 06824
/40
$1,695,000
- 5 Beds
- 6 Baths
- 5,136 Sq Ft
101 Brambley Hedge Cir, Fairfield, CT 06824

Move-in ready and freshly updated, this expansive 5,000+ sq ft Colonial is located in the prestigious Ridge of Greenfield Hill-a 24-hour guard-gated community situated on the border of Fairfield and Westport. The Ridge offers a resort-style lifestyle with amenities including a heated pool, lighted tennis courts, pickle ball, playground, and a private recreation center-all set among 96 luxury

Akenmisire Musa The Agency

101 Brambley Hedge Cir, Fairfield, CT 06824
/39
$1,539,000 Open Sun 1PM - 3:30PM
- 5 Beds
- 4.5 Baths
- 4,073 Sq Ft
1207 Stillson Rd, Fairfield, CT 06824

Come home to your own private retreat tucked away in the sought after University area location and settle right in to enjoy the holidays! Over 4,000 sq ft of living area along with an exceptionally designed flexible floor plan featuring 5 bedrooms, 4.5 bathrooms, custom culinary kitchen including quartz countertops, Z Line appliances, butler's pantry and dining area with fireplace. Open concept 2

John Hackett William Raveis Real Estate

1207 Stillson Rd, Fairfield, CT 06824
/40
$1,600,000
- 5 Beds
- 4.5 Baths
- 3,159 Sq Ft
226 Ruane St, Fairfield, CT 06824

Welcome to your dream come true lifestyle in the heart of Fairfield's coveted beach/town community-where coastal charm meets everyday convenience. This brand-new modern Colonial is more than a home, it's an upgraded living experience. Imagine morning walks to South Pine Creek Beach, afternoons on the tennis courts or golf course & evenings dining at vibrant restaurants, live music & theatres

Julie Vanderblue Higgins Group Real Estate

226 Ruane St, Fairfield, CT 06824
/40
$2,195,000
- 5 Beds
- 3.5 Baths
- 3,000 Sq Ft
17 Clover Ln, Westport, CT 06880

SOPHISTICATED CONTEMPORARY RETREAT - CLOVER LANE Exciting opportunity to own a beautifully reimagined Contemporary home on an expansive 1.27 acres at the end of a peaceful Westport cul-de-sac. This thoughtfully renovated 3000 square-foot residence features open concept living areas with streaming natural light and captivating views of mature lush greenery. A sleek, designer kitchen serves as the

Lisa Hartmann William Pitt Sotheby's Int'l

17 Clover Ln, Westport, CT 06880
/31
$2,065,000
- 4 Beds
- 3.5 Baths
- 4,255 Sq Ft
158 Coventry Ln, Fairfield, CT 06824

Discover this Connecticut Colonial, now with a dramatic price improvement, nestled on a peaceful cul-de-sac. This gem sits on two acres of meticulously landscaped, flat grounds, free from wetlands, showcasing vibrant gardens, stone walls & bluestone walkways. Indulge in the heated saltwater pool and spa with a waterfall feature, and unwind in the inviting cabana/pool house. A full house generator

Veronica Monahan Compass Connecticut, LLC

158 Coventry Ln, Fairfield, CT 06824
/40
$1,900,000 Open Sun 1PM - 4PM
- 4 Beds
- 4.5 Baths
- 5,283 Sq Ft
305 S Gate Ln, Southport, CT 06890

Tucked away on a serene street in the heart of Southport, this 4-bedroom, 4-bath Colonial invites you to experience the perfect balance of elegance, comfort, and privacy. From the moment you arrive, the home's setting feels special - an expansive property framed by mature trees, offering a sense of peace and seclusion. Step inside, and natural light floods the main level, where formal living and

Elizabeth Tritschler William Raveis Real Estate

305 S Gate Ln, Southport, CT 06890
/36
$1,795,000
- 6 Beds
- 4.5 Baths
- 5,325 Sq Ft
212 Fence Row Dr, Fairfield, CT 06824

Set on over two private acres in the gated community of The Ridge, this stunning estate combines modern comfort with timeless design. Residents enjoy resort-style amenities including a clubhouse, pool, tennis courts, playground, basketball court, private recreation facilities, and 24/7 gate security. Step inside through a soaring vaulted foyer that opens to a sun-filled living room framed by a

Adele Higgins Higgins Group Real Estate

212 Fence Row Dr, Fairfield, CT 06824
/31
$1,999,000
- 4 Beds
- 3.5 Baths
- 3,000 Sq Ft
137 Millard St, Fairfield, CT 06824

Stunning NEW construction the desirable Fairfield Beach neighborhood. This gorgeous home is crafted by premier 43 year Fairfield County builder. Premium materials, thoughtful design, and masterful workmanship are showcased throughout. Step inside to find a clean lined, open living space with 9' ceilings. The inviting living room, featuring a captivating 54" cool wall gas fireplace, seamlessly

Katie O'Grady Compass Connecticut, LLC

137 Millard St, Fairfield, CT 06824
/18
$1,800,000
- 4 Beds
- 2 Baths
- 1,925 Sq Ft
20 Ermine St, Fairfield, CT 06824

Endless opportunities await at this property-whether a buyer envisions their ideal home, a buyer interested in constructing a multigenerational family residence, someone looking to renovate the current home or rebuild and take advantage of the surrounding land, or a builder looking for a new project, this is the perfect place for you, Three individual lots, totaling three secluded acres, are

Harriet Stone William Pitt Sotheby's Int'l

20 Ermine St, Fairfield, CT 06824
/31
$2,250,000
- 4 Beds
- 4.5 Baths
- 6,600 Sq Ft
342 Greens Farms Rd, Westport, CT 06880

Historic Character Meets Modern Elegance Nestled in the storied Greens Farms enclave, this distinguished Victorian estate was originally constructed in 1861 and thoughtfully expanded with a high-quality rear addition in 2008, delivering over 6,600 sq ft of refined living space . Set on a serene 2.02-acre parcel with sweeping lawns and lush landscaping, the property invites outdoor enjoyment

Frank Zilinyi William Raveis Real Estate

342 Greens Farms Rd, Westport, CT 06880
/39
$1,299,999 Open Sat 12PM - 2PM
- 4 Beds
- 3.5 Baths
- 4,024 Sq Ft
947 Galloping Hill Rd, Fairfield, CT 06824

Welcome to 947 Galloping Hill Road. This true mid-century modern home was designed by the important architect Victor Civkin in 1967. This well thought out ranch has 4 bedrooms and 3 1/2 baths and is perfectly situated on a flat, private acre. Step inside the large foyer that has curved walls and a skylight. The living room is spacious with a rounded wall of floor to ceiling windows which flood

Nancy Freedman William Pitt Sotheby's Int'l

947 Galloping Hill Rd, Fairfield, CT 06824
/40
$1,350,000 Open Sat 12PM - 2PM
- 5 Beds
- 2.5 Baths
- 2,354 Sq Ft
357 Oldfield Rd, Fairfield, CT 06824

Coastal Chic Meets Modern Living! Discover the idyllic Fairfield lifestyle in this fully renovated 5BR, 2.5BA home, perfectly located between sandy beaches and vibrant town center. Welcome to 357 Oldfield Road - thoughtfully remodeled and designed for style, comfort and ease, this charming home blends relaxed coastal vibes with privacy, space, and an unbeatable location. Step inside to

Carol Langeland William Pitt Sotheby's Int'l

357 Oldfield Rd, Fairfield, CT 06824
/37
$639,900 Open Sat 1:30PM - 3PM
- 3 Beds
- 2.5 Baths
- 2,600 Sq Ft
130 Brentwood Ave, Fairfield, CT 06825

Beautiful 3-bedroom 2.5 bath townhouse with a bonus room, perfect for extra living space or a home office. This home features central air, a gas stove, black stainless steel appliances, a tankless water heater, and beautiful hardwood floors throughout. Enjoy the convenience of a spacious 3-car garage and the benefit of no HOA fees - a fantastic opportunity for comfortable and affordable living!

Cristina Lu YellowBrick Real Estate LLC

130 Brentwood Ave, Fairfield, CT 06825
/30
$515,000 Open Sat 12PM - 2PM
- 3 Beds
- 1.5 Baths
- 1,409 Sq Ft
709 Tunxis Hill Rd, Fairfield, CT 06825

This beautiful home offers modern finishes and thoughtful details throughout. Featuring 9-foot ceilings accented by elegant crown molding, the home feels bright, open, and inviting. The kitchen includes stylish tile flooring, while hardwood floors flow seamlessly through the rest of the home, adding warmth and character. Custom built-ins have been added to maximize storage and make the best use

Joseph Muratori Coldwell Banker Realty

709 Tunxis Hill Rd, Fairfield, CT 06825
/36
$7,995,000
- 5 Beds
- 7 Baths
- 4,998 Sq Ft
775 Sasco Hill Rd, Fairfield, CT 06824

Exceptional listing at 775 Sasco Hill Road - a home that seamlessly blends timeless elegance with modern luxury. Completely updated and impeccably decorated by the current owners, this residence offers three full levels of sophisticated living. Upon entering, you're greeted by a stunning cathedral ceiling in the foyer, with 9-foot ceilings throughout the main levels that create an airy, open

Suzy Ryan William Raveis Real Estate

775 Sasco Hill Rd, Fairfield, CT 06824
/40
$1,500,000
- 4 Beds
- 2.5 Baths
- 3,900 Sq Ft
105 Charter Oak Rd, Fairfield, CT 06824

Tucked away at the end of a tranquil cul-de-sac in one of Fairfield's most desirable neighborhoods, this center-hall Colonial exudes timeless elegance with mature landscaping and wonderful curb appeal.On the main floor, you'll discover the heart of the home, a generously proportioned kitchen with custom cabinetry and granite countertops, overlooking peaceful grounds.It opens into the expansive

Julie Vanderblue Higgins Group Real Estate

105 Charter Oak Rd, Fairfield, CT 06824
/15
$240,000
- 3 Beds
- 2 Baths
- 1,106 Sq Ft
291 Stillman St, Bridgeport, CT 06608

East End Colonial style property for sale. Great opportunity for both owner occupant and investor buyers. The first floor provides a foyer entrance, living room, dining area and kitchen. The second floor provides 3 Bedrooms and 1 Full Bath. The basement area is part finished including den, 1 full bathroom and washer/dryer hookups. Fenced in small yard. Two car detached garage. Low property taxes.

Aileen O'Connell Coldwell Banker Realty

291 Stillman St, Bridgeport, CT 06608
/32
$950,000
- 3 Beds
- 2.5 Baths
- 2,609 Sq Ft
74 Westford Dr, Southport, CT 06890

Enjoy everything that Southport has to offer!!! This beautiful home is situated on a peaceful cul-de-sac just around the corner from the Pequot Library, Southport Beach, the Harbor and of course, the quaint Village. Whether you sail, swim or simply beach, this spot is perfect for you! Enter the front foyer of this beautiful home, hang up your coat and now you can relax. Step into the comfortable

Lauren Dunne Berkshire Hathaway NE Prop.

74 Westford Dr, Southport, CT 06890
/40
$349,500
- 3 Beds
- 2 Baths
- 1,308 Sq Ft
119 Madison Terrace, Bridgeport, CT 06606

Charming ranch-style home located in the Upper North End. This property features 3 bedrooms and 1 full bath on the main level, along with a bright living room enhanced by a bay window that fills the space with natural light. The electric fireplace will remain with the home. The seller is currently using the third bedroom as a dining room. Additional highlights include hardwood floors throughout,

Angela Morales Keller Williams Realty Prtnrs.

119 Madison Terrace, Bridgeport, CT 06606
/28
$19,800,000
- 8 Beds
- 8.5 Baths
- 9,995 Sq Ft
Unlisted Address

Once-in-a-Generation Historic Estate set on a most coveted stretch of Fairfield County's Gold Coast, with a remarkable provenance as a former Bedford family estate. This extraordinary property is a rare offering that blends timeless architecture with iconic waterfront living. With sweeping views of Long Island Sound, the home's stately presence is matched only by its stunning 3.55 acres of

Cyd Hamer William Pitt Sotheby's Int'l

Unlisted Address
/40
$879,999
- 4 Beds
- 2 Baths
- 1,961 Sq Ft
60 Winnepoge Dr, Fairfield, CT 06825

Now's the perfect opportunity to own in the idyllic Lake Hills neighborhood-a sought-after enclave offering residents access to five private lakeside beaches! This thoughtfully renovated Cape Cod features a spacious floor plan ideal for entertaining. Its inviting facade & stunning new entryway create a warm welcome the moment you arrive. Inside, the new mudroom showcases high ceilings, stylish

Andrea Viscuso Compass Connecticut, LLC

60 Winnepoge Dr, Fairfield, CT 06825
/40
$1,099,000
- 4 Beds
- 3 Baths
- 2,648 Sq Ft
53 Eastfield Terrace, Fairfield, CT 06825

Filled with charm and curb appeal, this inviting 4-BR Colonial Split is perfectly sited on a quiet cul-de-sac just moments from Lake Mohegan's trails, playground, and beach. Original home was completely redesigned and expanded in 2010! A pretty front porch welcomes you home and sets the tone for the relaxed and comfortable vibe inside. Open main level features a spacious living room anchored by a

Tracie and Vicki Team William Raveis Real Estate

53 Eastfield Terrace, Fairfield, CT 06825
/17
$4,400,000
- 4 Beds
- 5 Baths
- 4,000 Sq Ft
2117 Fairfield Beach Rd, Fairfield, CT 06824

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

2117 Fairfield Beach Rd, Fairfield, CT 06824

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