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24 Tide Mill Ter, Fairfield

Rare opportunity in Fairfield's sought-after Sasco Hill/South Pine Creek neighborhood, ideally located between town and the beach. Set on a private, level 1/3-acre lot bordering the Sasco Hill estates, this beautifully expanded and renovated home offers stylish finishes and an easy, open layout designed for today's lifestyle. The custom kitchen flows seamlessly into the dining area and inviting living room, where a wood-burning fireplace and French doors open to the patio and backyard. A versatile first-floor bonus room currently serves as a home gym but is equally suited as a home office, playroom, or fifth bedroom. Upstairs, the spacious primary suite features a large walk-in closet and beautifully appointed ensuite bath. Three additional bedrooms and a convenient second-floor laundry room complete the upper level. The expansive backyard is a true retreat with a stone patio, custom pergola, and perennial gardens offering exceptional privacy. Recent improvements include newer mechanicals, a Generac generator, and fresh interior paint. Enjoy an unbeatable location less than a mile from Sasco and Pine Creek Beaches, Southport Harbor, the train, golf, tennis, Fairfield's vibrant town center, and top local amenities. A rare bonus for this beach area location: the home is outside the flood zone, so no flood insurance is required. A wonderful opportunity to enjoy coastal living in one of Fairfield's most desirable neighborhoods.

4 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24191108 MLS

Rare opportunity in Fairfield's sought-after Sasco Hill/South Pine Creek neighborhood, ideally located between town and the beach. Set on a private, level 1/3-acre lot bordering the Sasco Hill estates, this beautifully expanded and renovated home offers stylish finishes and an easy, open layout designed for today's lifestyle. The custom kitchen flows seamlessly into the dining area and inviting living room, where a wood-burning fireplace and French doors open to the patio and backyard. A versatile first-floor bonus room currently serves as a home gym but is equally suited as a home office, playroom, or fifth bedroom. Upstairs, the spacious primary suite features a large walk-in closet and beautifully appointed ensuite bath. Three additional bedrooms and a convenient second-floor laundry room complete the upper level. The expansive backyard is a true retreat with a stone patio, custom pergola, and perennial gardens offering exceptional privacy. Recent improvements include newer mechanicals, a Generac generator, and fresh interior paint. Enjoy an unbeatable location less than a mile from Sasco and Pine Creek Beaches, Southport Harbor, the train, golf, tennis, Fairfield's vibrant town center, and top local amenities. A rare bonus for this beach area location: the home is outside the flood zone, so no flood insurance is required. A wonderful opportunity to enjoy coastal living in one of Fairfield's most desirable neighborhoods.

114 Lee Dr, Fairfield

$2,595,000

Newly renovated in 2026, this extraordinary designer-inspired Modern Colonial presents a rare opportunity to own a turnkey luxury residence in Fairfield's coveted Sasco Hill. Offering 3,625 square feet of impeccably designed living space, this four-bedroom, five-bath home masterfully blends timeless architecture with exceptional craftsmanship and sophisticated contemporary design. Every detail has been meticulously curated, from the custom white oak millwork and hardwood flooring to the spectacular chef's kitchen featuring Taj Mahal quartzite countertops, premium Thermador appliances, custom cabinetry, and an oversized waterfall island. The thoughtfully designed first floor offers a gracious living room with fireplace, formal dining room, private office, family room, and a sun-filled eat-in kitchen that opens to an expansive bluestone terrace for seamless indoor-outdoor living. Upstairs, the luxurious primary suite features a cathedral ceiling, dual walk-in closets, separate sitting room and a spa-inspired bath. Three additional en-suite bedrooms provide outstanding comfort and privacy. Additional highlights include a beautifully finished lower level, 3-car garage, custom built-ins, four-zone HVAC, Generac generator, and designer finishes throughout. Ideally located minutes from downtown Fairfield, Southport Village, Metro-North, beaches, parks, shopping, and dining, this exceptional home offers luxury living in one of Fairfield's most prestigious neighborhoods.

4 Beds ⋅ 5 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24191170 MLS

Newly renovated in 2026, this extraordinary designer-inspired Modern Colonial presents a rare opportunity to own a turnkey luxury residence in Fairfield's coveted Sasco Hill. Offering 3,625 square feet of impeccably designed living space, this four-bedroom, five-bath home masterfully blends timeless architecture with exceptional craftsmanship and sophisticated contemporary design. Every detail has been meticulously curated, from the custom white oak millwork and hardwood flooring to the spectacular chef's kitchen featuring Taj Mahal quartzite countertops, premium Thermador appliances, custom cabinetry, and an oversized waterfall island. The thoughtfully designed first floor offers a gracious living room with fireplace, formal dining room, private office, family room, and a sun-filled eat-in kitchen that opens to an expansive bluestone terrace for seamless indoor-outdoor living. Upstairs, the luxurious primary suite features a cathedral ceiling, dual walk-in closets, separate sitting room and a spa-inspired bath. Three additional en-suite bedrooms provide outstanding comfort and privacy. Additional highlights include a beautifully finished lower level, 3-car garage, custom built-ins, four-zone HVAC, Generac generator, and designer finishes throughout. Ideally located minutes from downtown Fairfield, Southport Village, Metro-North, beaches, parks, shopping, and dining, this exceptional home offers luxury living in one of Fairfield's most prestigious neighborhoods.

131 Sasco Hill Rd, Fairfield

$3,500

Enjoy Southport Woods - community lifestyle with pool, clubhouse, paddle tennis and beautifully landscaped grounds in the heart of Southport. Convenient to Fairfield and Southport train stations, I-95, shopping, restaurants, schools and miles of beautiful shoreline, this location offers much. Privately located end unit features slate patio/yard area, two bedrooms (primary with full bath), sizeable living room and dining area off of the galley style Kitchen. Newly painted, furnace replaced in 2024. Hot Water Heater replaced in 2023. Turn the key to care-free living in 2026. One reserved parking space- # 76.

2 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24192631 MLS ⋅ Southport Woods BLDG.

Enjoy Southport Woods - community lifestyle with pool, clubhouse, paddle tennis and beautifully landscaped grounds in the heart of Southport. Convenient to Fairfield and Southport train stations, I-95, shopping, restaurants, schools and miles of beautiful shoreline, this location offers much. Privately located end unit features slate patio/yard area, two bedrooms (primary with full bath), sizeable living room and dining area off of the galley style Kitchen. Newly painted, furnace replaced in 2024. Hot Water Heater replaced in 2023. Turn the key to care-free living in 2026. One reserved parking space- # 76.

49 Southport Woods Dr Unit 49, Fairfield

$1,799,000

Customize your own beautifully crafted new construction in Fairfield's highly desirable Sasco Hill/South Pine Creek neighborhood, perfectly positioned between town and the beach. Enjoy an exceptional lifestyle just minutes from Pine Creek and Sasco Beaches, Southport Harbor, golf, tennis, the train, and Fairfield's vibrant town center-all within approximately one mile or less. Thoughtfully designed and built by respected local builder Associated Development, this home blends timeless architecture with quality craftsmanship and sophisticated finishes throughout. The flexible floor plan is designed for easy licing. The ground level features a garage, spacious mudroom, and a covered loggia that creates the perfect setting for outdoor entertaining. The sun-filled main level offers 9-foot ceilings, a beautifully appointed custom kitchen that opens seamlessly to the living and dining spaces, a welcoming family room with a fireplace and custom built-ins, and a private study ideal for working from home. Upstairs, the serene primary bedroom features a luxurious bath and generous walk-in closet, accompanied by two additional bedrooms. The third floor expands the home's versatility with a fourth bedroom, full bath, and bonus room-perfect for guests, a playroom, fitness space, or media room. Offering the rare opportunity to enjoy brand-new construction in one of Fairfield's most sought-after coastal neighborhoods, this duplex. Act now, still time to customize finishes!

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24192571 MLS ⋅ South Pine Creek Duplex BLDG.

Customize your own beautifully crafted new construction in Fairfield's highly desirable Sasco Hill/South Pine Creek neighborhood, perfectly positioned between town and the beach. Enjoy an exceptional lifestyle just minutes from Pine Creek and Sasco Beaches, Southport Harbor, golf, tennis, the train, and Fairfield's vibrant town center-all within approximately one mile or less. Thoughtfully designed and built by respected local builder Associated Development, this home blends timeless architecture with quality craftsmanship and sophisticated finishes throughout. The flexible floor plan is designed for easy licing. The ground level features a garage, spacious mudroom, and a covered loggia that creates the perfect setting for outdoor entertaining. The sun-filled main level offers 9-foot ceilings, a beautifully appointed custom kitchen that opens seamlessly to the living and dining spaces, a welcoming family room with a fireplace and custom built-ins, and a private study ideal for working from home. Upstairs, the serene primary bedroom features a luxurious bath and generous walk-in closet, accompanied by two additional bedrooms. The third floor expands the home's versatility with a fourth bedroom, full bath, and bonus room-perfect for guests, a playroom, fitness space, or media room. Offering the rare opportunity to enjoy brand-new construction in one of Fairfield's most sought-after coastal neighborhoods, this duplex. Act now, still time to customize finishes!

615 S Pine Creek Rd, Fairfield

$950,000

Nestled on approximately 1.1 acres in Southport, this classic 1941 Colonial offers a rare opportunity to create something truly special. Set in a picturesque, lightly wooded setting, the property combines privacy with a beautiful natural backdrop. The gently sloping lot opens to a spacious backyard, providing plenty of room to enjoy the outdoors. Inside, you'll find three bedrooms and one full bath, with timeless character ready to be re-imagined. Whether you're looking to restore its original charm or renovate to suit your own style, this home presents an exciting opportunity to bring your vision to life. A peaceful setting, generous acreage, and endless potential make this Southport property one not to miss. Highest & Best by Tuesday July 21st 5pm.

3 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24188073 MLS

Nestled on approximately 1.1 acres in Southport, this classic 1941 Colonial offers a rare opportunity to create something truly special. Set in a picturesque, lightly wooded setting, the property combines privacy with a beautiful natural backdrop. The gently sloping lot opens to a spacious backyard, providing plenty of room to enjoy the outdoors. Inside, you'll find three bedrooms and one full bath, with timeless character ready to be re-imagined. Whether you're looking to restore its original charm or renovate to suit your own style, this home presents an exciting opportunity to bring your vision to life. A peaceful setting, generous acreage, and endless potential make this Southport property one not to miss. Highest & Best by Tuesday July 21st 5pm.

600 Cedar Rd, Fairfield

$4,950

Beautifully maintained 3-bedroom, 2.5-bath half duplex offering the comfort and feel of a single-family home. Recently refinished hardwood floors extend throughout the entire home, creating a warm and inviting atmosphere. The spacious kitchen features stainless steel appliances, ample cabinetry, and a cozy breakfast nook. Step outside to a rear deck overlooking a generous backyard, perfect for entertaining, relaxing, or outdoor activities. The primary suite offers a private retreat complete with a full en-suite bathroom, walk-in closet, and a versatile sitting area ideal for a home office or reading nook. A full attic provides excellent storage. Ideally located just a short walk to Fairfield's beaches, vibrant town center, restaurants, shops, and the train station, with quick access to I-95, this home offers the perfect blend of coastal charm and convenience.

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24189339 MLS

Beautifully maintained 3-bedroom, 2.5-bath half duplex offering the comfort and feel of a single-family home. Recently refinished hardwood floors extend throughout the entire home, creating a warm and inviting atmosphere. The spacious kitchen features stainless steel appliances, ample cabinetry, and a cozy breakfast nook. Step outside to a rear deck overlooking a generous backyard, perfect for entertaining, relaxing, or outdoor activities. The primary suite offers a private retreat complete with a full en-suite bathroom, walk-in closet, and a versatile sitting area ideal for a home office or reading nook. A full attic provides excellent storage. Ideally located just a short walk to Fairfield's beaches, vibrant town center, restaurants, shops, and the train station, with quick access to I-95, this home offers the perfect blend of coastal charm and convenience.

405 S Pine Creek Rd, Fairfield

$4,395

Recently UpdatedSouthport Townhouse Duplex! This well-maintained 3 bedroom 1.5 bath in the heart of Southport has central air. The townhouse includes a private outdoor space with a deck and shed for extra storage. Close to shopping, highway and trains.

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24188907 MLS

Recently UpdatedSouthport Townhouse Duplex! This well-maintained 3 bedroom 1.5 bath in the heart of Southport has central air. The townhouse includes a private outdoor space with a deck and shed for extra storage. Close to shopping, highway and trains.

32 Sherwood Pl Unit 32, Fairfield

$1,495,000

Welcome to 85 Osborne Place - this beautifully updated 5-bedroom, 2.5-bath Colonial tucked away on a peaceful street, yet just a stroll from the train, shops, and dining is what makes Southport living so desirable. Step inside this turn-key gem to find a bright, flowing floor plan anchored by an updated kitchen that opens seamlessly into a spacious great room - perfect for everyday living and effortless entertaining. A formal dining room and separate living room with fireplace offer classic charm and flexibility, while a dedicated office makes working from home a breeze. The first-floor primary suite gives main-floor living its name with a layout for everyday ease that's hard to find. Upstairs you will find 4 additional bedrooms and an updated hall bath that provide room for everyone. Head down to the finished lower level, where a large rec/playroom awaits - easily reimagined as a home gym, media room, or man/she cave to suit your lifestyle. Outside, your own private retreat: a lovely, fenced yard offers space to play and garden, while the patio with option for shade by a charming awning - is made for morning coffee or evening unwinding. With its unbeatable location, versatile living spaces, and move-in-ready updates, this Southport Colonial checks every box. Don't miss your chance to make it home.

5 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24186094 MLS

Welcome to 85 Osborne Place - this beautifully updated 5-bedroom, 2.5-bath Colonial tucked away on a peaceful street, yet just a stroll from the train, shops, and dining is what makes Southport living so desirable. Step inside this turn-key gem to find a bright, flowing floor plan anchored by an updated kitchen that opens seamlessly into a spacious great room - perfect for everyday living and effortless entertaining. A formal dining room and separate living room with fireplace offer classic charm and flexibility, while a dedicated office makes working from home a breeze. The first-floor primary suite gives main-floor living its name with a layout for everyday ease that's hard to find. Upstairs you will find 4 additional bedrooms and an updated hall bath that provide room for everyone. Head down to the finished lower level, where a large rec/playroom awaits - easily reimagined as a home gym, media room, or man/she cave to suit your lifestyle. Outside, your own private retreat: a lovely, fenced yard offers space to play and garden, while the patio with option for shade by a charming awning - is made for morning coffee or evening unwinding. With its unbeatable location, versatile living spaces, and move-in-ready updates, this Southport Colonial checks every box. Don't miss your chance to make it home.

85 Osborne Pl, Fairfield

$599,000

Pristine 3 Bedroom, 2 Full Bath Main Level End Unit. Newer Kitchen. Private Patio off Kitchen and Living Room. Walk to Southport Village, Train, Harbor, Library. Great Complex that offers Underground Heated Pool & Clubhouse.

3 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24184740 MLS ⋅ Southport Woods BLDG.

Pristine 3 Bedroom, 2 Full Bath Main Level End Unit. Newer Kitchen. Private Patio off Kitchen and Living Room. Walk to Southport Village, Train, Harbor, Library. Great Complex that offers Underground Heated Pool & Clubhouse.

18 Southport Woods Dr Unit 18, Fairfield

$950,000

Rare opportunity in Fairfield's highly sought-after Beach Area! This 3-bedroom, 1,400 SF ranch offers an exceptionally rare combination of location, lot, and future potential. Just a short walk to South Pine Creek Beach and only a quarter mile from the prestigious Sasco Hill neighborhood, you'll also enjoy easy access to downtown Fairfield, the train station, restaurants, shops, and beaches. According to MLS history, 3-bedroom ranches with attached 2-car garages in both the Beach Area and Fairfield Center have been virtually nonexistent over the past decade, and this home's generous footprint makes it an ideal candidate for a second-story addition, with architectural plans included showing approximately 3,700 SF upon completion, along with a remodeled first floor. (see all photos for exterior front and back ) Based on recent neighborhood sales, expanded homes have exceeded $2 million. Partially finished lower level, private fenced yard, and no reported storm-related issues during recent major coastal storms. Renovate, expand, or enjoy as is. An outstanding value-add opportunity in one of Fairfield's most desirable neighborhoods. It's time for your new beach area home!

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24182336 MLS

Rare opportunity in Fairfield's highly sought-after Beach Area! This 3-bedroom, 1,400 SF ranch offers an exceptionally rare combination of location, lot, and future potential. Just a short walk to South Pine Creek Beach and only a quarter mile from the prestigious Sasco Hill neighborhood, you'll also enjoy easy access to downtown Fairfield, the train station, restaurants, shops, and beaches. According to MLS history, 3-bedroom ranches with attached 2-car garages in both the Beach Area and Fairfield Center have been virtually nonexistent over the past decade, and this home's generous footprint makes it an ideal candidate for a second-story addition, with architectural plans included showing approximately 3,700 SF upon completion, along with a remodeled first floor. (see all photos for exterior front and back ) Based on recent neighborhood sales, expanded homes have exceeded $2 million. Partially finished lower level, private fenced yard, and no reported storm-related issues during recent major coastal storms. Renovate, expand, or enjoy as is. An outstanding value-add opportunity in one of Fairfield's most desirable neighborhoods. It's time for your new beach area home!

102 Geneva Ter, Fairfield

$8,000

New England Modern Classic for lease in the heart of Southport! Walkable to picturesque Southport Harbor & Village - just a 5-minute stroll to the harbor. Available mid-to-end June. This beautifully maintained Center Hall Colonial offers hardwood floors, detailed trim work, and timeless millwork throughout. The expansive open-concept kitchen and dining area create the perfect gathering space, centered around a large island with seating for 6+. A gracious living room with a classic wood-burning fireplace flows into an oversized sunroom lined with walls of windows, offering abundant natural light and exceptional privacy. The home features 3 bedrooms plus a heated bonus space ideal for a home office, playroom, workout studio, yoga room, or guest space. Photos shown are of the previous tenant's furniture. Every room includes individual temperature zones for personalized comfort. The primary suite offers an en-suite bath and a mini walk-in closet. Outside, enjoy a bluestone patio and grassy backyard - perfect for relaxing or entertaining. A coastal classic with modern upgrades, all just moments from the charm of Southport Village.

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24185509 MLS

New England Modern Classic for lease in the heart of Southport! Walkable to picturesque Southport Harbor & Village - just a 5-minute stroll to the harbor. Available mid-to-end June. This beautifully maintained Center Hall Colonial offers hardwood floors, detailed trim work, and timeless millwork throughout. The expansive open-concept kitchen and dining area create the perfect gathering space, centered around a large island with seating for 6+. A gracious living room with a classic wood-burning fireplace flows into an oversized sunroom lined with walls of windows, offering abundant natural light and exceptional privacy. The home features 3 bedrooms plus a heated bonus space ideal for a home office, playroom, workout studio, yoga room, or guest space. Photos shown are of the previous tenant's furniture. Every room includes individual temperature zones for personalized comfort. The primary suite offers an en-suite bath and a mini walk-in closet. Outside, enjoy a bluestone patio and grassy backyard - perfect for relaxing or entertaining. A coastal classic with modern upgrades, all just moments from the charm of Southport Village.

146 Oxford Rd, Fairfield

$1,899,000

Wonderful waterfront oasis offers direct access to Long Island Sound via a private dock and includes deeded Fairfield beach access. The home features a bright, open floor plan, creating an inviting coastal atmosphere. The primary bedroom boasts a sitting room, a walk-in closet, and a balcony overlooking the waterfront, providing stunning views of LI Sound & Pine Creek. The property promises breathtaking vistas of coastal sunrises and tranquil sunset views over the salt marsh. Enjoy boating, kayaking, and paddleboarding are from the private dock on Pine Creek with access to Long Island Sound. There is also a private association dock and gated path to Fairfield beach just across the creek. Nature enthusiasts can enjoy exploring the area's abundant open space and walking trails, including paths through Pine Creek marsh leading to Pine Creek beach. Additionally, the location offers convenient walkable access to amenities including beaches, par-3 golf course, and tennis facilities, providing a perfect blend of outdoor recreation and relaxation in a beautiful coastal setting. Minutes to vibrant Fairfield town center as well as scenic Southport village & harbor. Waterfront community 50 miles from NYC offering coastal charm, historic preservation, wonderful dining, shopping & arts.

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24184277 MLS

Wonderful waterfront oasis offers direct access to Long Island Sound via a private dock and includes deeded Fairfield beach access. The home features a bright, open floor plan, creating an inviting coastal atmosphere. The primary bedroom boasts a sitting room, a walk-in closet, and a balcony overlooking the waterfront, providing stunning views of LI Sound & Pine Creek. The property promises breathtaking vistas of coastal sunrises and tranquil sunset views over the salt marsh. Enjoy boating, kayaking, and paddleboarding are from the private dock on Pine Creek with access to Long Island Sound. There is also a private association dock and gated path to Fairfield beach just across the creek. Nature enthusiasts can enjoy exploring the area's abundant open space and walking trails, including paths through Pine Creek marsh leading to Pine Creek beach. Additionally, the location offers convenient walkable access to amenities including beaches, par-3 golf course, and tennis facilities, providing a perfect blend of outdoor recreation and relaxation in a beautiful coastal setting. Minutes to vibrant Fairfield town center as well as scenic Southport village & harbor. Waterfront community 50 miles from NYC offering coastal charm, historic preservation, wonderful dining, shopping & arts.

23 Old Dam Road Unit 23, Fairfield

$3,850,000

This is why so many people fall in love with Southport. Set on an extraordinary .83-acre parcel in the heart of the Village, this circa 1874 residence captures the charm, character, and lifestyle that have made Southport one of New England's most treasured coastal communities. Approached by a long drive and set well back from Harbor Road, the home enjoys a level of privacy rarely found in the Village. Hidden from the road, it offers a sense of seclusion that is increasingly difficult to find. Rich with period details and timeless architectural character, the 5 bedroom, 4 full and 1 half bath home sits at one of the highest points on Harbor Road, where cooling summer breezes are a welcome feature. The property also includes a classic antique barn, pool, pool house, attached one-car garage, and detached two-car garage, creating a setting ideal for both everyday living and entertaining. While the home presents an exceptional opportunity for renovation and enhancement, its greatest assets cannot be replicated: its setting, scale, history, and location. For the next steward, it offers the chance to reimagine a treasured Southport property while preserving its authenticity and charm. Enjoy a quintessential Southport lifestyle with easy access to the Village, train station, Pequot Yacht Club, and the soon-to-open Southport General Store and Rose Hill Kitchen. Last offered for sale in 1989, opportunities like this rarely come to market. A true Southport gem ready for its next chapter

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24181784 MLS

This is why so many people fall in love with Southport. Set on an extraordinary .83-acre parcel in the heart of the Village, this circa 1874 residence captures the charm, character, and lifestyle that have made Southport one of New England's most treasured coastal communities. Approached by a long drive and set well back from Harbor Road, the home enjoys a level of privacy rarely found in the Village. Hidden from the road, it offers a sense of seclusion that is increasingly difficult to find. Rich with period details and timeless architectural character, the 5 bedroom, 4 full and 1 half bath home sits at one of the highest points on Harbor Road, where cooling summer breezes are a welcome feature. The property also includes a classic antique barn, pool, pool house, attached one-car garage, and detached two-car garage, creating a setting ideal for both everyday living and entertaining. While the home presents an exceptional opportunity for renovation and enhancement, its greatest assets cannot be replicated: its setting, scale, history, and location. For the next steward, it offers the chance to reimagine a treasured Southport property while preserving its authenticity and charm. Enjoy a quintessential Southport lifestyle with easy access to the Village, train station, Pequot Yacht Club, and the soon-to-open Southport General Store and Rose Hill Kitchen. Last offered for sale in 1989, opportunities like this rarely come to market. A true Southport gem ready for its next chapter

406 Harbor Rd, Fairfield

$24,500

July & August in Fairfield never looked so good. Ideally located on historic Old Post Road, this beautifully updated 1756 antique home places you right in the heart of all the summer fun. Grab your morning coffee, stroll downtown for lunch al fresco, enjoy gelato after dinner, catch summer concerts at the gazebo, or hop on the train for a quick day trip into NYC-no car or parking permit needed. When beach days beckon, Fairfield's spectacular beaches, marina, and Audubon Preserve are just a quick bike ride away. Known as the historic C.W. Thorpe House, this stunning home beautifully blends antique charm with modern comfort, featuring a gorgeous Chef's Kitchen, sun-filled entertaining spaces, and breathtaking outdoor living. Enjoy beautifully landscaped and manicured grounds, mature flowering trees, expansive lawn space, and a spacious flagstone patio perfect for summer dining, entertaining, or relaxing after a day at the beach. The ultimate in-town summer retreat with the perfect mix of charm, convenience, and coastal living.

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24178004 MLS

July & August in Fairfield never looked so good. Ideally located on historic Old Post Road, this beautifully updated 1756 antique home places you right in the heart of all the summer fun. Grab your morning coffee, stroll downtown for lunch al fresco, enjoy gelato after dinner, catch summer concerts at the gazebo, or hop on the train for a quick day trip into NYC-no car or parking permit needed. When beach days beckon, Fairfield's spectacular beaches, marina, and Audubon Preserve are just a quick bike ride away. Known as the historic C.W. Thorpe House, this stunning home beautifully blends antique charm with modern comfort, featuring a gorgeous Chef's Kitchen, sun-filled entertaining spaces, and breathtaking outdoor living. Enjoy beautifully landscaped and manicured grounds, mature flowering trees, expansive lawn space, and a spacious flagstone patio perfect for summer dining, entertaining, or relaxing after a day at the beach. The ultimate in-town summer retreat with the perfect mix of charm, convenience, and coastal living.

1005 Old Post Rd, Fairfield

$6,499,000

775 Sasco Hill Road is an extraordinary estate where timeless elegance meets modern luxury. Impeccably renovated and beautifully curated by the current owners, this sophisticated residence offers three full levels of refined living set across five private, park-like acres. A dramatic cathedral foyer and soaring 9-foot ceilings create an immediate sense of scale and light, while the thoughtfully designed floor plan balances grand entertaining with everyday comfort. Formal living and dining rooms, a private library, and a stunning open-concept kitchen seamlessly connect to the expansive family room with vaulted ceilings. Luxurious accommodations include a private guest suite, an elegant primary retreat with dual walk-in closets and a spa-inspired bath, plus additional ensuite bedrooms and a versatile third-floor bonus level ideal for recreation, guests, or a home office. Outdoors, a large stone patio overlooks meticulously landscaped grounds and a spectacular gunite pool, creating a true private oasis. Extensive upgrades throughout the home and property elevate both style and functionality, offering an exceptional lifestyle in one of Fairfield's most coveted locations. Furnishings available for purchase ~ Negotiable.

5 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24175742 MLS

775 Sasco Hill Road is an extraordinary estate where timeless elegance meets modern luxury. Impeccably renovated and beautifully curated by the current owners, this sophisticated residence offers three full levels of refined living set across five private, park-like acres. A dramatic cathedral foyer and soaring 9-foot ceilings create an immediate sense of scale and light, while the thoughtfully designed floor plan balances grand entertaining with everyday comfort. Formal living and dining rooms, a private library, and a stunning open-concept kitchen seamlessly connect to the expansive family room with vaulted ceilings. Luxurious accommodations include a private guest suite, an elegant primary retreat with dual walk-in closets and a spa-inspired bath, plus additional ensuite bedrooms and a versatile third-floor bonus level ideal for recreation, guests, or a home office. Outdoors, a large stone patio overlooks meticulously landscaped grounds and a spectacular gunite pool, creating a true private oasis. Extensive upgrades throughout the home and property elevate both style and functionality, offering an exceptional lifestyle in one of Fairfield's most coveted locations. Furnishings available for purchase ~ Negotiable.

775 Sasco Hill Rd, Fairfield

$1,799,900

Ideally located in the highly sought-after Sasco Hill neighborhood, this exceptional coastal home offers the rare advantage of beach-area living outside the flood zone-no flood insurance required. Perfectly positioned between town and shoreline, the property features a stunning second-floor addition completed in 2025 with over $200,000 invested, including a rooftop deck with beautiful Long Island Sound views. The open kitchen with granite counters and updated commercial-grade Thermador appliances flows into a sunny family room with built-ins and glass doors leading to the expansive fenced yard and deck. The living room showcases an authentic and working original fireplace crafted with Long Island Sound stone, adding historic charm and warmth. The main level offers 2 bedrooms and a full bath, while upstairs features a spacious primary suite with en-suite bath, 2 additional bedrooms, full bath, and laundry. Unfinished lower level with 9' ceilings and plumbing for future bath offers excellent expansion potential. Plenty of room for a pool. Additional features include new HVAC, hot tub, sprinkler system, shed, and backyard entertaining space. Walk to Sasco Beach, Pine Creek Beach, golf, tennis, scenic Southport Village, harbor, dining, shopping, and vibrant downtown Fairfield. Exceptional coastal lifestyle only 50 miles from New York City. Move in Ready

5 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24174607 MLS

Ideally located in the highly sought-after Sasco Hill neighborhood, this exceptional coastal home offers the rare advantage of beach-area living outside the flood zone-no flood insurance required. Perfectly positioned between town and shoreline, the property features a stunning second-floor addition completed in 2025 with over $200,000 invested, including a rooftop deck with beautiful Long Island Sound views. The open kitchen with granite counters and updated commercial-grade Thermador appliances flows into a sunny family room with built-ins and glass doors leading to the expansive fenced yard and deck. The living room showcases an authentic and working original fireplace crafted with Long Island Sound stone, adding historic charm and warmth. The main level offers 2 bedrooms and a full bath, while upstairs features a spacious primary suite with en-suite bath, 2 additional bedrooms, full bath, and laundry. Unfinished lower level with 9' ceilings and plumbing for future bath offers excellent expansion potential. Plenty of room for a pool. Additional features include new HVAC, hot tub, sprinkler system, shed, and backyard entertaining space. Walk to Sasco Beach, Pine Creek Beach, golf, tennis, scenic Southport Village, harbor, dining, shopping, and vibrant downtown Fairfield. Exceptional coastal lifestyle only 50 miles from New York City. Move in Ready

82 Lee Dr, Fairfield

$2,050,000

Set on a level and flat .24-acre lot in the highly sought-after Sasco Hill area of Fairfield, this charming home offers endless opportunities to customize and create your dream living space. Boasting 2,500 square feet of versatile living area, plus a full unfinished basement, a deck, and an outdoor shed, this property perfectly balances comfort and potential. Enjoy a unique dual-street frontage, enhancing privacy and offering multiple access possibilities. The fabulous location is just minutes from the train station, Southport Center, town amenities, shopping, and dining, with quick and convenient access to I-95. Equipped with town water, town sewer, and oil heat, this home provides the perfect foundation for your next chapter in one of Fairfield's most desirable neighborhoods. Don't miss the chance to make this wonderful property your own, combining convenience, space, and endless potential in the heart of Sasco Hill.

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24174341 MLS

Set on a level and flat .24-acre lot in the highly sought-after Sasco Hill area of Fairfield, this charming home offers endless opportunities to customize and create your dream living space. Boasting 2,500 square feet of versatile living area, plus a full unfinished basement, a deck, and an outdoor shed, this property perfectly balances comfort and potential. Enjoy a unique dual-street frontage, enhancing privacy and offering multiple access possibilities. The fabulous location is just minutes from the train station, Southport Center, town amenities, shopping, and dining, with quick and convenient access to I-95. Equipped with town water, town sewer, and oil heat, this home provides the perfect foundation for your next chapter in one of Fairfield's most desirable neighborhoods. Don't miss the chance to make this wonderful property your own, combining convenience, space, and endless potential in the heart of Sasco Hill.

79 Fairfield Pl, Fairfield

$1,825,000

Welcome to refined, like-new construction luxury in the heart of Southport Village. This private enclave is just minutes to the gorgeous beach & harbor, train, library, restaurants & shops, ideally located close to commute & downtown Village living. A lifestyle is what you find, with every high-end amenity, proximity, efficiency and easy, maintenance-free living, yet surrounded by 6-acres of open space and tranquil nature trails. This particular unit was customized from the ground up, with sophisticated, designer-curated finishes throughout. Elevator-ready on all levels. The main living level features a custom kitchen with inset cabinetry, a striking Hale Navy center island, and an abundance of storage, flowing seamlessly into elegant living and dining spaces highlighted by coffered ceilings, detailed focal walls, and oversized windows that flood the home with natural light. Three generously sized bedrooms including a spacious primary suite with a spa-inspired bath and walk-in closet. The finished lower level adds a versatile, apartment-style flexible space complete with a full bath, walk-in closet, and sliding barn doors, offering ideal accommodations for guests, a home office, or additional living area. Note the 2-bay garage and abundance of customized storage on every level. Quality abounds in this more than ready to move in, new energy/feel/vibe, all with location, location, location.

3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24173387 MLS ⋅ Village At Southport BLDG.

Welcome to refined, like-new construction luxury in the heart of Southport Village. This private enclave is just minutes to the gorgeous beach & harbor, train, library, restaurants & shops, ideally located close to commute & downtown Village living. A lifestyle is what you find, with every high-end amenity, proximity, efficiency and easy, maintenance-free living, yet surrounded by 6-acres of open space and tranquil nature trails. This particular unit was customized from the ground up, with sophisticated, designer-curated finishes throughout. Elevator-ready on all levels. The main living level features a custom kitchen with inset cabinetry, a striking Hale Navy center island, and an abundance of storage, flowing seamlessly into elegant living and dining spaces highlighted by coffered ceilings, detailed focal walls, and oversized windows that flood the home with natural light. Three generously sized bedrooms including a spacious primary suite with a spa-inspired bath and walk-in closet. The finished lower level adds a versatile, apartment-style flexible space complete with a full bath, walk-in closet, and sliding barn doors, offering ideal accommodations for guests, a home office, or additional living area. Note the 2-bay garage and abundance of customized storage on every level. Quality abounds in this more than ready to move in, new energy/feel/vibe, all with location, location, location.

491 Westway Rd Unit 491, Fairfield

$814,999

76 Geneva Terrace is a sweet 1,008-square-foot Ranch that delivers effortless one-level living on a peaceful, tree-lined side street. Situated just off the main road, this location provides exceptional access to Fairfield's renowned beaches, the train station, and the vibrant town center. Recently renovated throughout, including floors, the bathroom, and kitchen - cabinets, countertops and appliances. The Primary bedroom and walk in closet allow for luxury space, and high end finishes. The living room features a large bow window that fills the home with natural light, a theme that continues into the expansive 224-square-foot three-season porch. This additional space, boasting rich wooden paneling and a colorful slate floor, overlooks a private backyard and serves as a perfect spot for relaxation. The kitchen includes oak cabinetry and a gas cooktop, positioned conveniently next to the porch entrance. Below the main level, discover approximately 1,000 square feet of semi-finished basement space, complete with a half bath, a walk-in cedar closet, and a built-in bar area. This versatile lower level provides an ideal setup for a home office, playroom, or additional family room space. Outside, the property includes a storage shed and a fenced yard.

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24173204 MLS

76 Geneva Terrace is a sweet 1,008-square-foot Ranch that delivers effortless one-level living on a peaceful, tree-lined side street. Situated just off the main road, this location provides exceptional access to Fairfield's renowned beaches, the train station, and the vibrant town center. Recently renovated throughout, including floors, the bathroom, and kitchen - cabinets, countertops and appliances. The Primary bedroom and walk in closet allow for luxury space, and high end finishes. The living room features a large bow window that fills the home with natural light, a theme that continues into the expansive 224-square-foot three-season porch. This additional space, boasting rich wooden paneling and a colorful slate floor, overlooks a private backyard and serves as a perfect spot for relaxation. The kitchen includes oak cabinetry and a gas cooktop, positioned conveniently next to the porch entrance. Below the main level, discover approximately 1,000 square feet of semi-finished basement space, complete with a half bath, a walk-in cedar closet, and a built-in bar area. This versatile lower level provides an ideal setup for a home office, playroom, or additional family room space. Outside, the property includes a storage shed and a fenced yard.

76 Geneva Ter, Fairfield

$505,000

This first-floor, 2BR, 2-bath unit is in a quiet Southport complex with in-ground pool. Just a short walk to the grocery store, shopping, train, public bus line, bank, and more. The updated unit features a living room with vinyl plank flooring, ceiling fan, wood-burning fireplace with raised marble hearth, plus attractive millwork. Sliding glass doors open to a covered porch with lawn space for gardening and grilling. Dining area has space for a table for 6 or 8. This unit features a full-sized washer and dryer (new in 2017), newer gas HVAC, and water heater in 2022, remodeled hall bath (2019), ample storage, and central air. Updated, fully-applianced eat-in kitchen with tile floor. If you are looking for a place to call home that is warm, inviting, tidy, with neutral paint colors, and ready to just move in- you have found it. Lots of visitor spaces near the unit. Pretty, well maintained grounds as well.

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24163133 MLS ⋅ Quincy At Southport BLDG.

This first-floor, 2BR, 2-bath unit is in a quiet Southport complex with in-ground pool. Just a short walk to the grocery store, shopping, train, public bus line, bank, and more. The updated unit features a living room with vinyl plank flooring, ceiling fan, wood-burning fireplace with raised marble hearth, plus attractive millwork. Sliding glass doors open to a covered porch with lawn space for gardening and grilling. Dining area has space for a table for 6 or 8. This unit features a full-sized washer and dryer (new in 2017), newer gas HVAC, and water heater in 2022, remodeled hall bath (2019), ample storage, and central air. Updated, fully-applianced eat-in kitchen with tile floor. If you are looking for a place to call home that is warm, inviting, tidy, with neutral paint colors, and ready to just move in- you have found it. Lots of visitor spaces near the unit. Pretty, well maintained grounds as well.

12 Hulls Highway Unit 12, Fairfield

$1,497,000

Beautiful End Unit, Perfectly situated in Southport, this beautifully appointed 3-bedroom, 3.5-bath Colonial townhouse end unit offers an exceptional lifestyle just moments from village shops, restaurants, Southport Harbor, and the Metro-North train. Thoughtfully updated, the remodeled kitchen features quartz countertops, a sleek backsplash, and premium Bosch appliances, centered around a generous island-opening seamlessly to a private deck, ideal for entertaining. The open living and dining areas are anchored by a striking double-sided gas fireplace and hardwood floors. The walk-out lower level provides versatile additional space with a full bath and sliders to a private bluestone patio-ideal for relaxing or entertaining. Upstairs, the primary suite offers vaulted ceilings, a spacious walk-in closet, and a beautifully appointed marble bath. Recent updates include new carpet in the primary bedroom and freshly stained upper-level hallway floors. Extensive improvements include a brand-new Electrolux central vacuum system, new washer and dryer, new HVAC system, and a new hot water heater-delivering true turnkey living. Additional features include natural gas heat, central air, main-level laundry, and a 2-car attached garage, with the option to add an elevator. A rare opportunity to experience living in one of Fairfield County's most sought-after coastal communities.

3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24161254 MLS ⋅ Pequot Landing BLDG.

Beautiful End Unit, Perfectly situated in Southport, this beautifully appointed 3-bedroom, 3.5-bath Colonial townhouse end unit offers an exceptional lifestyle just moments from village shops, restaurants, Southport Harbor, and the Metro-North train. Thoughtfully updated, the remodeled kitchen features quartz countertops, a sleek backsplash, and premium Bosch appliances, centered around a generous island-opening seamlessly to a private deck, ideal for entertaining. The open living and dining areas are anchored by a striking double-sided gas fireplace and hardwood floors. The walk-out lower level provides versatile additional space with a full bath and sliders to a private bluestone patio-ideal for relaxing or entertaining. Upstairs, the primary suite offers vaulted ceilings, a spacious walk-in closet, and a beautifully appointed marble bath. Recent updates include new carpet in the primary bedroom and freshly stained upper-level hallway floors. Extensive improvements include a brand-new Electrolux central vacuum system, new washer and dryer, new HVAC system, and a new hot water heater-delivering true turnkey living. Additional features include natural gas heat, central air, main-level laundry, and a 2-car attached garage, with the option to add an elevator. A rare opportunity to experience living in one of Fairfield County's most sought-after coastal communities.

71 Aberdeen Way Unit 71, Fairfield

$2,200,000

Rare opportunity in sought-after Southport Green-just steps to Southport Village and Metro-North. One of only two stand-alone residences in this 24-unit enclave, this home offers the privacy of a single-family lifestyle with the ease of condominium living. The townhouse-style residence spans three levels and features 3 bedrooms, 3 renovated full and 1 half baths, plus a coveted attached two-car garage. Thoughtfully designed with flexibility for a future elevator (quote available upon request), it also includes a private patio-an uncommon amenity within the community. Ideal for downsizers or anyone seeking a true "lock-and-leave" lifestyle, this property pairs luxury with everyday convenience. Enjoy dining, shopping, and wellness just moments away at the Delamar Southport, Gray Goose Tavern, and Equinox Health Club.

3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24150747 MLS ⋅ Southport Green BLDG.

Rare opportunity in sought-after Southport Green-just steps to Southport Village and Metro-North. One of only two stand-alone residences in this 24-unit enclave, this home offers the privacy of a single-family lifestyle with the ease of condominium living. The townhouse-style residence spans three levels and features 3 bedrooms, 3 renovated full and 1 half baths, plus a coveted attached two-car garage. Thoughtfully designed with flexibility for a future elevator (quote available upon request), it also includes a private patio-an uncommon amenity within the community. Ideal for downsizers or anyone seeking a true "lock-and-leave" lifestyle, this property pairs luxury with everyday convenience. Enjoy dining, shopping, and wellness just moments away at the Delamar Southport, Gray Goose Tavern, and Equinox Health Club.

2 Elmwood Dr Unit 2, Fairfield

$25,000,000

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 drive, revealing a breathtaking landscape of curated gardens, rolling lawns, and panoramic water views. Designed for both grand entertaining and intimate gatherings, the estate features a newly built multi-car garage with a second-floor art studio and play space, a new pool, birch garden, and an expansive patio, all seamlessly integrated with the natural beauty of the surroundings. A private dock with stairs to the secluded beach provides direct waterfront access, while a newly added wine cellar and lower-level suite with a full bathroom enhance the home's luxurious amenities. Recent upgrades, including advanced irrigation, outdoor lighting, new A/V system, ensure modern convenience without compromising the estate's historic charm.Featured in Architectural Digest as "a new house with an old soul," the interiors are a masterclass in refined elegance. Every space is thoughtfully curated with serene color palettes, exquisite craftsmanship, and breathtaking water views from nearly every room. Sasco Point is truly one of America's most distinguished waterfront estates. Luxury Perfected!

6 Beds ⋅ 11 Baths ⋅ ACTIVE Status ⋅ 24084663 MLS

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 drive, revealing a breathtaking landscape of curated gardens, rolling lawns, and panoramic water views. Designed for both grand entertaining and intimate gatherings, the estate features a newly built multi-car garage with a second-floor art studio and play space, a new pool, birch garden, and an expansive patio, all seamlessly integrated with the natural beauty of the surroundings. A private dock with stairs to the secluded beach provides direct waterfront access, while a newly added wine cellar and lower-level suite with a full bathroom enhance the home's luxurious amenities. Recent upgrades, including advanced irrigation, outdoor lighting, new A/V system, ensure modern convenience without compromising the estate's historic charm.Featured in Architectural Digest as "a new house with an old soul," the interiors are a masterclass in refined elegance. Every space is thoughtfully curated with serene color palettes, exquisite craftsmanship, and breathtaking water views from nearly every room. Sasco Point is truly one of America's most distinguished waterfront estates. Luxury Perfected!

1131 Sasco Hill Rd, Fairfield