Tour 4 Breathtaking Historic Mansions Worth Millions in Connecticut

Written By

Mathew Abraham

Updated on

Mathew Abraham

Mathew Abraham, editor of Century Homes America, brings his passion for architectural history to explore the stories behind America’s most iconic homes.

Jennifer Leahy @ Douglas Elliman of Connecticut

Step into a world where timeless elegance meets modern luxury, as we explore a collection of historic estates that capture the very essence of New England’s rich architectural heritage. From the stately Georgian Colonials and charming Victorian waterfront retreats in Greenwich to the majestic Tudor Revival in Branford, these homes offer not just a place to live, but a journey through history, with each residence meticulously renovated to preserve its storied past while embracing contemporary comforts. Set against the backdrop of lush gardens, sparkling waterways, and scenic coastal vistas, these properties invite you to discover the art of refined living where every detail tells a story. Read on to uncover the secrets behind these architectural masterpieces and experience a legacy of luxury that transcends time.

1. 1900 Georgian Colonial in Greenwich

Joseph Barbieri @ Sotheby’s International Realty

Nestled on 7.37 acres of meticulously landscaped grounds, this distinguished Georgian Colonial dates back to 1900 and once served as the private residence of the late Mary Tyler Moore. Expanded and renovated by architect Stephen Wang, the estate boasts 13,825 square feet of refined living space, complete with a 2,000+ square foot primary suite, a striking 23′ x 23′ glass conservatory, and a 65-foot pool. Listed at $16,900,000, the stone-built home has been thoughtfully modernized while preserving its storied heritage. Lush gardens, a meandering stream, and over five acres of conservation land ensure a secluded retreat that exemplifies Greenwich’s rich architectural history.

Where is Greenwich?

Where is Greenwich?
Bing Maps

Greenwich is located in southwestern Connecticut, along the state’s Gold Coast in Fairfield County. Just 30 miles from Manhattan, this historic town has long been a desirable suburb for those seeking proximity to New York City. Known for its maritime heritage, upscale shopping on Greenwich Avenue, and cultural institutions such as the Bruce Museum, Greenwich also features numerous conservation areas and scenic coastlines. Its storied past includes colonial settlements and a long tradition of estate homes that reflect New England’s architectural evolution.

Back Exterior

Back Exterior
Joseph Barbieri @ Sotheby’s International Realty

An elegant stone façade rises behind a manicured lawn and topiary gardens, framing a pristine rectangular pool in the foreground. Low stone walls and neatly trimmed hedges surround the pool area, creating an intimate outdoor setting. The home’s expansive rear windows and turreted conservatory allow ample sunlight to flood interior spaces, while mature trees in the background offer privacy and a sense of tranquility.

Living Room

Living Room
Joseph Barbieri @ Sotheby’s International Realty

A grand black fireplace centers this serene, neutrally toned living area. Recessed lighting and a coffered ceiling enhance the sense of height and openness. Zebra-patterned accent chairs sit opposite a comfortable sofa, providing stylish seating around the hearth. Modern artworks punctuate the walls with vivid color, creating a balanced blend of traditional elegance and contemporary flair.

Dining Room

Dining Room
Joseph Barbieri @ Sotheby’s International Realty

Rich crimson walls envelop a spacious, light-filled dining room anchored by a round wooden table. Plush, patterned chairs circle the table, complemented by warm-toned sideboards on either side. Tall windows dressed in elegant drapes let in natural light, highlighting the ornate gold ceiling medallion and chandelier. The polished hardwood floors and traditional rug complete the room’s sophisticated yet inviting ambiance.

Bedroom

Bedroom
Joseph Barbieri @ Sotheby’s International Realty

A gently curved headboard and matching wooden furniture define this tranquil bedroom. Soft, muted blue walls and plush carpeting with playful polka-dot accents lend a calming atmosphere. Light streams in from large windows, while tasteful lamps and subtle wall sconces offer warm, ambient lighting. An upholstered armchair and side tables add comfort and functionality to this serene personal haven.

Conservatory

Conservatory
Joseph Barbieri @ Sotheby’s International Realty

A sunlit, circular conservatory showcases soaring arched windows and a domed glass roof. Tropical plants and tall potted palms thrive in this greenhouse-like setting, where a soft green palette complements the lush foliage. A grand chandelier hangs overhead, illuminating a cozy seating arrangement with plush cushions. The warm, natural light and panoramic garden views create a tranquil retreat for relaxation.

Gym

Gym
Joseph Barbieri @ Sotheby’s International Realty

Bright and spacious, this home fitness center features light blue tile floors and walls. State-of-the-art equipment, including treadmills, a rowing machine, and various strength-training stations, are neatly arranged for easy movement. Large windows provide natural light, while overhead fixtures ensure the space remains well-lit. Adjacent spa facilities, including a jacuzzi, steam shower, and sauna, complete this luxurious wellness area.

Source: Greenwich MLS, Inc via Zillow

2. 1920 Victorian Home in Greenwich

1920 Victorian Home in Greenwich
Eva Penson @ Sotheby’s International Realty

Built in 1920, this historic Victorian residence sits on nearly 0.70 acres of beautifully landscaped waterfront property in Greenwich, Connecticut. With 9,200 square feet of living space, it showcases classic architectural elements such as a wraparound porch, steeply pitched rooflines, and charming ornamental details reminiscent of early 20th-century design. Recently renovated to include a brand-new Italian kitchen, this home seamlessly blends its original character with modern amenities. Listed at $10,995,000, the estate features 6 bedrooms, 7 full bathrooms, and 2 half bathrooms. Additional highlights include a deep-water dock suitable for boats over 30 feet, an infinity pool, a 2-bedroom guest cottage, a private gym, and a wine cellar—offering resort-style living in a coveted location with easy access to New York City.

Where is Greenwich?

Where is Greenwich?
Bing Maps

Greenwich is located in southwestern Connecticut, along the Long Island Sound, just north of the New York state border. Founded in 1640, it is one of the oldest towns in the state and has long been known for its maritime heritage and affluent coastal estates. The town is approximately 30 miles northeast of Manhattan, making it a popular residential choice for those who commute to New York City. Notable attractions include its scenic shorelines, cultural institutions such as the Bruce Museum, and a vibrant downtown area featuring upscale shops and dining.

Backyard

Backyard
Eva Penson @ Sotheby’s International Realty

A sweeping view of the estate’s waterfront backyard reveals a multi-level design cascading down to the rocky shoreline. At the center, a sleek infinity pool overlooks the water, its edge seemingly merging with the Long Island Sound. A spacious wooden deck extends toward a private deep-water dock, offering panoramic vistas of the surrounding islands. Manicured gardens with lush greenery frame the property, creating a serene outdoor retreat for entertaining and relaxation.

Patio

Patio
Eva Penson @ Sotheby’s International Realty

This covered veranda features stately columns and a classic beadboard ceiling, echoing the home’s Victorian roots. Comfortable lounge seating and plush cushions invite relaxation, all while enjoying unobstructed water views. Soft neutral tones in the furnishings complement the light gray shingle exterior. Gentle breezes flow through the open sides, creating a breezy, resort-like atmosphere perfect for alfresco dining or sunset cocktails.

Kitchen

Kitchen
Eva Penson @ Sotheby’s International Realty

A sleek, newly renovated Italian kitchen that blends minimalism with natural warmth. A large center island features wood-grain paneling, contrasted by smooth white countertops. High-gloss cabinetry in neutral tones lines the walls, concealing ample storage and top-of-the-line appliances. A glass-front pantry section showcases dinnerware and adds visual interest. Recessed lighting and a skylight above the island ensure a bright, inviting workspace. The overall style is contemporary yet welcoming, perfect for both everyday cooking and entertaining.

Dining Room

Dining Room
Eva Penson @ Sotheby’s International Realty

An airy, sophisticated room anchored by a rustic wooden table and six contemporary chairs in soft cream upholstery. The walls are painted a soothing pale beige, allowing an abstract artwork in bold brushstrokes to serve as a focal point. Large windows and French doors bathe the space in natural light, offering glimpses of the waterfront. White columns subtly separate the dining area from the living room, maintaining an open-concept feel. A modern pendant light hangs above the table, providing warm illumination.

Living Room

Living Room
Eva Penson @ Sotheby’s International Realty

A bright and welcoming space with tall windows that allow sunlight to stream across polished hardwood floors. At the far end, a white mantel frames a warm fireplace, flanked by decorative columns that open to an adjacent sunroom. The seating arrangement includes a modern sofa, sleek swivel chairs, and a glass-topped coffee table, all in light neutral hues. Accents of color, including throw pillows and fresh flowers, add a lively touch. The overall ambience is both elegant and comfortable—perfect for relaxed gatherings.

Bedroom

Bedroom
Eva Penson @ Sotheby’s International Realty

A spacious, light-filled bedroom with expansive water views through a large bay window. The room features soft cream walls and dark hardwood floors, creating a soothing contrast. A low-profile bed with crisp white linens rests at the center, flanked by matching bedside tables and lamps. A built-in window seat runs along the bay window, offering a cozy spot to admire the scenic shoreline. Neutral-colored rugs and upholstery maintain a calm, serene atmosphere, while ample natural light highlights the room’s open layout and elegant simplicity.

Source: Greenwich MLS, Inc. via Zillow

3. 1902 Tudor Revival in Branford

1902 Tudor Revival in Branford
Jennifer Leahy @ Douglas Elliman of Connecticut

This grand estate, known as Rogers Island, exemplifies early 20th-century craftsmanship with its steeply pitched gables, half-timbering, and ornate detailing characteristic of the Tudor Revival style. Built in 1902 and meticulously renovated, the 8,746-square-foot main residence stands on 7.65 acres of pristine shoreline in Branford, Connecticut. Listed at $35,000,000, it offers 10 bedrooms, 8 baths, and an array of luxurious amenities—among them a four-bedroom waterfront guest house, a pool house, tennis court, koi pond, putting green, greenhouse, and three private beaches. Modern comforts blend seamlessly with historic charm, making this an incomparable legacy property on Long Island Sound.

Where is Branford?

Where is Branford?
Bing Maps

Branford is a coastal town in southern Connecticut, part of the New England region of the United States. Situated along the scenic shores of Long Island Sound, it lies just east of New Haven and approximately 80 miles northeast of New York City. With roots tracing back to the 17th century, Branford boasts a rich maritime heritage, charming town greens, and proximity to cultural hubs like Yale University. Visitors and residents alike enjoy the area’s picturesque coastline, historic Thimble Islands, and vibrant community events.

Aerial View

Aerial View
Jennifer Leahy @ Douglas Elliman of Connecticut

An expansive overhead perspective reveals the entirety of Rogers Island, surrounded by the shimmering waters of Long Island Sound. The 7.65-acre estate unfolds with manicured lawns, formal gardens, and winding pathways that connect the main residence to the tennis court, pool house, and guest house. From this vantage, you can also see the private beaches, docks, and lush foliage that give the property its secluded, resort-like atmosphere.

Exterior

Exterior
Jennifer Leahy @ Douglas Elliman of Connecticut

A closer outdoor vantage highlights the home’s Tudor-inspired architecture, with tall chimneys, decorative timbering, and multiple gabled roofs. The landscaped grounds feature neatly trimmed hedges, mature trees, and bursts of colorful foliage. Bay windows and a stately entrance hint at the refined interior awaiting beyond the stone walkway, while the surrounding lawns gently slope toward the water’s edge.

Kitchen

Kitchen
Jennifer Leahy @ Douglas Elliman of Connecticut

A bright, airy kitchen bathed in natural light streams through a series of tall windows. Crisp white cabinetry is accented by gold trim and hardware, while a marble backsplash and matching countertops add a sense of luxury. A spacious island, outfitted with gleaming bar stools, provides both prep space and casual seating. Warm hardwood floors contrast the white-and-gold palette, creating an inviting atmosphere perfect for both everyday cooking and elegant entertaining.

Dining Room

Dining Room
Jennifer Leahy @ Douglas Elliman of Connecticut

A pair of long wooden tables, flanked by sleek metal-framed chairs, anchor this cheerful dining space. The walls are painted a lavender hue above classic white wainscoting, lending both charm and modern flair. Simple brass sconces provide gentle lighting along the perimeter, while a large window allows natural daylight to stream in. The open, airy design makes it ideal for formal dinner parties or casual family meals with an elegant twist.

Living Room

Living Room
Jennifer Leahy @ Douglas Elliman of Connecticut

This bright, welcoming living area centers around a white fireplace with a traditional mantel, where a gentle fire casts a warm glow. Neutral-toned armchairs and a sofa are arranged around a sleek, low-profile coffee table, while large windows frame views of the surrounding greenery. Built-in shelving and a discreet wet bar add convenience, and soft textures—from the rug underfoot to the cushions—create a cozy yet sophisticated retreat for conversation or relaxation.

Bedroom

Bedroom
Jennifer Leahy @ Douglas Elliman of Connecticut

This spacious bedroom features a plush, white-upholstered bed with a tall, contemporary headboard. Soft blue carpeting adds a tranquil touch, complemented by two bold art pieces that lend a pop of color to the neutral walls. A comfortable armchair and low wooden table form a cozy seating nook near the large windows, allowing abundant natural light to illuminate the space. The overall ambiance is calm and refined, ideal for rest and relaxation.

Game Room

Game Room
Jennifer Leahy @ Douglas Elliman of Connecticut

A vibrant space designed for leisure, the game room showcases a classic pool table topped with emerald-green felt. Modern pendant lights with sculptural shades hang above, creating a focal point. The hardwood floors are partially covered by patterned rugs that echo the playful card-themed artwork on the walls. A comfortable seating area with plush cushions completes the inviting environment, perfect for gatherings and friendly competition.

Source: Greenwich MLS, Inc. via Zillow

4. 1900 Georgian Colonial in Greenwich

1900 Georgian Colonial in Greenwich
Joann Erb @ Brown Harris Stevens CT, LLC

Built in 1900, this magnificent Georgian Colonial in Greenwich, Connecticut, offers a glimpse into America’s architectural heritage. With only two previous owners, the estate is steeped in history and has been carefully maintained and expanded over the years. Priced at $30,000,000, it sits on 6.38 acres of lush greenery, complete with a circular driveway flanked by a guest house and caretaker’s cottage. The home’s 18,068 square feet reflect multiple additions, including a major 1991 expansion that nearly doubled its size. Inside, you’ll find classic wood paneling, original fireplaces, and intricate detailing, seamlessly blended with modern comforts for a timeless yet luxurious living experience.

Where is Greenwich?

Where is Greenwich?
Bing Maps

Greenwich is located in southwestern Connecticut, about 30 miles from Manhattan. Founded in 1640, this coastal town has a rich colonial history and is part of Fairfield County’s renowned “Gold Coast.” Known for its affluent neighborhoods, scenic waterfront, and vibrant cultural scene, Greenwich offers world-class shopping, art galleries, and museums. Its proximity to New York City makes it an attractive enclave for commuters seeking both urban convenience and the charm of a historic New England town.

Aerial View

Aerial View
Joann Erb @ Brown Harris Stevens CT, LLC

From above, the estate’s grandeur is fully revealed. The main residence, designed in the Georgian Colonial style, extends in a graceful layout around a brick-paved courtyard. Multiple gables, a slate roof, and mature trees accentuate the property’s historic charm. Manicured lawns, hedges, and additional outbuildings—including a guest house and caretaker’s cottage—underscore the estate’s expansive footprint and ensure privacy amid lush greenery.

Kitchen

Kitchen
Joann Erb @ Brown Harris Stevens CT, LLC

Bright and spacious, this gourmet kitchen features crisp white cabinetry, stainless-steel appliances, and a central island topped with dark stone. Crown molding and hardwood floors add an elegant touch. A wall of windows bathes the space in natural light, making it ideal for casual breakfasts or formal culinary endeavors. Modern lighting fixtures and ample countertop space emphasize functionality, while retaining a sense of timeless sophistication.

Dining Room

Dining Room
Joann Erb @ Brown Harris Stevens CT, LLC

A formal dining space adorned with paneled walls in a soft neutral finish. A large, ornate table anchors the room, surrounded by high-backed chairs with intricate detailing. Overhead, a crystal chandelier reflects light onto the hardwood floors, and a grand fireplace adds warmth. French doors open to the manicured grounds, seamlessly blending indoor elegance with the natural beauty beyond.

Living Room

Living Room
Joann Erb @ Brown Harris Stevens CT, LLC

A stately yet welcoming living area painted in a rich green hue. Floral-patterned armchairs and plush sofas surround a large wooden coffee table, creating a comfortable conversation space. A marble fireplace with an ornate mantel provides a focal point, while a chandelier sparkles overhead. Sunlight streams in through tall windows, highlighting decorative artwork and patterned drapes, giving the room a warm, inviting glow.

Bedroom

Bedroom
Joann Erb @ Brown Harris Stevens CT, LLC

A tranquil retreat with hardwood floors and softly painted walls, this expansive bedroom features a plush bed centered against an elegant headboard. A seating area with comfortable sofas is arranged near a fireplace for added warmth. Light pours in through tall windows, illuminating the space and highlighting the room’s understated décor. The combination of classic architectural elements and modern amenities creates a restful sanctuary.

Source: Greenwich MLS, Inc. via Zillow

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