luxury real estate for rent Old Greenwich, United States

DIRECT WATERFRONT in OLD GREENWICH Enjoy western facing views and gorgeous sunsets on this expansive 1 ACRE property close to Greenwich Point, schools, train, and Village of OG. Enjoy year round carefree living at this updated 4 bedroom home. Open floor plan with spectacular natural light throughout. Spacious gourmet kitchen w/adjoining family room w/fireplace and French doors opening to the oversized soccer field size back yard directly to the water. A large Living room w/fireplace, lovely dining room and office on first floor complete this ideal family retreat. A perfect home and location! Owner pays for Landscaping. Updated dock pending approval. Rental Terms: Annual: $25,000 Per Month

Have you ever fantasized about living in a charming coastal village with your very own access to a quiet cove? Here is a slice of heaven where you can enjoy this year 'round, convenient to everything! Direct Riverside waterfront with newly expanded views across Greenwich Cove. There is picture perfect space for entertaining on large deck with lovely views off kitchen/family room. Kitchen and baths are refreshed, bedrooms are generously sized and there is extra space up a separate staircase over garage that is a great office, playroom or guest suite. Filled with light and great grounds outside to enjoy year' round Convenient to Old Greenwich on a very quiet cul-de-sac close to Riverside School and EMS. Kayak or paddle board out to the cove from the base of the long back lawn.. go to more Show times week of May 24th are Hours this week: Weds 11 - 1 Friday 4 - 6 Sat 11 -2 Rental Terms: Annual: $14,000 Per Month

Summer rental in Riverside, available Memorial day through Labor day, (flexible into September) Beautifully furnished and privately set, this serene retreat features a heated pool, expansive terrace, and charming screened in porch overlooking lush gardens-ideal for effortless summer living. The open floor plan offers exceptional entertaining spaces, including a dining room with fireplace and a generous family room with a second fireplace. The gourmet eat-in kitchen is thoughtfully designed for both everyday living and hosting. Recent updates include a new primary bath and custom closet, along with a first floor bath. Enjoy close proximity to the village of Old Greenwich, train station and Tod's Point Beach with its miles of scenic nature trails and shoreline. Rental Terms: Annual: $28,000 Per Month

Located on one of the most picturesque streets in Riverside and part of the Willowmere Waterfront Association. This classic center hall colonial offers over 3200 square feet with generous living spaces including a formal dining and living room, sunroom and family room adjacent to the well-appointed galley kitchen. 4 bedrooms and 3 full bath. An oversized bluestone terrace overlooks a beautiful level half acre with western exposure. You'll love going home to this special neighborhood. Rental Terms: Annual: $16,000 Per Month

Casual coastal living with a vacation vibe all year long here at Dolphin Cove. Set on the border of Old Greenwich close to Innis Arden Golf Club, the residents of the private Dolphin Cove waterfront community enjoy over 3 acres of lush green lawns, sandy beach, in ground heated pool, tennis and pickle ball courts, clubhouse, boat slips and yacht club. Open concept, bright and crisp interiors enjoy sparkling water views from just about every room. The primary bedroom has a wall of glass overlooking the water, with sliders out to the deck. Two additional second floor bedrooms share a bath. A private ensuite makes for the perfect home office or weekend guest space. An oasis to soothe the soul.

Charming renovated farmhouse set on a beautiful level acre in one of Riverside's most sought-after locations. A heated pool surrounded by expansive terraces and mature gardens offers a private outdoor retreat . Thoughtfully updated interiors feature an open-concept eat-in kitchen and family room, an oversized sun-filled living room adjoining the formal dining room, and a cozy den ideal for a home office or library. The second floor offers a spacious primary suite, three additional bedrooms, a full bath, and a nursery or second office. Approximately 800 additional square feet in the finished third floor playroom, the detached garage with a gym and full bath and a second floor office or playroom. Two garage bays with storage. Offered furnished or unfurnished. Rental Terms: Annual: $24,000 Per Month

Charming home in the coveted Dundee school district convenient to schools, restaurants and shopping. An updated country kitchen with huge island is a great place for entertaining. While the flexible floor plan has a first floor guest or aupair suite, spacious second floor primary and wonderful lower level media and exercise rooms. Enjoy the private backyard with terrace and safety of a quiet cul-de-sac. Offered furnished or unfurnished. Weekly maid service available. 24 hr notice for showings if possible. (King bed and dresser in primary suite excluded if leased furnished). Flexible term 9 mo - 1 year. Perfect for buyers needing more time to look! Rental Terms: Annual: $13,000 Per Month

WATER WATER WATER, mesmerizing panoramic views across historic harbor. DIRECT waterfront property. End of cul de sac. High ceilings, nice moldings, beautiful floors, updated kitchen with fabulous countertops, state-of-line appliances & updated baths. Spacious rooms. Wonderful front & back verandas with 2 awnings. Big backyard for entertaining & warm weather pleasures. Kayaks, canoes, paddleboards, fishing or a small boat. Square footage does not include 905+/- on third floor. Close to train, schools, and shops. ''You will never want to leave home!'' FUN FUN FUN Rental Terms: Annual: $25,000 Per Month

Welcome to Harbor Points Luxury Penthouse Collection. Elevate your experience to the Beacon lifestyle. This single story 2,204 sq ft. Penthouse offers breathtaking 180-degree views across the Long Island Sound. With this 3 bedroom unit enjoy spacious open concept, NYC views, Quartz countertops and terrific amenity accommodations such as, 24/7 health club, Yoga studio with on-demand classes, resort-style heated pool, fireside lounge, gas grill stations and more! Experience waterfront luxury living in the most coveted community of the fastest-growing city in Connecticut. Stamford's Harbor Point sits along the Long Island Sound with luxury marina access and views stretching to NYC. This thriving community features award-winning restaurants, nightlife, dock and dine access, acres of parks, boardwalks, retail, and 200+ curated community events a year. Floor Plan, amenity & fees sheet attached. Bldg runs credit/criminal on all applicants. The BR/LR picture is a stage mode.

Fantastic rental opportunity in one of Greenwich's most popular neighborhoods. Located on a quiet cul-de-sac street, this sunny three-bedroom, two-full-bath ranch features a private backyard and is ready for occupancy on June 1st, 2026. Key features include: An open floor plan-family room and eat-in kitchen, updating with new quartz countertops. Large primary bedroom with an en-suite full bath, plus an additional den/office ideal for working from home. Nicely proportioned secondary bedrooms-full bath. Laundry Room. A detached two-car garage with walk-up storage. Situated right around the corner from the Cos Cob Train Station for an easy city commute. The home is central to everythingGreenwich has to offer, including Cos Cob Park, Mill Pond shopping, Bruce Park, Todds Point Beach and local schools both private and public.

Fully Furnished Millbrook Lakefront Rental!!! 4 month minimum Term. Privacy abounds as you enter over the bridge to your in-town private peninsula. This Gorgeous lakefront setting is truly a rare with oversized 1.11 acres in the R-20 Zone. The 5 bed 5 bath Manor Styled home has been recently renovated to include New appliances, new hardwood flooring, landscaping, paint and more. Rental Terms: Annual: $35,000 Per Month

Pristine townhome close to town, train and Bruce Park. A 5/6 bedroom light filled, custom built condominium of the highest quality. Gourmet kitchen adjacent to family room. Custom stone fireplace in expansive living room. Primary suite with private deck, then 4 additional bedrooms. Ten ft celings throughout. A lower level exercise room next to media room, or au pair suite. Outside a covered terrace with fireplace, and built in grill with open air seating. Two car garage. Rental Terms: Annual: $19,000 Per Month

Overlooking a picturesque golf course, this beautifully updated three-level townhouse offers a rare blend of space, light, and privacy in a prime Stamford location. The home is filled with natural light and features a clean, modern aesthetic with new flooring, fresh paint, and thoughtfully curated updates throughout. The main level is designed for both everyday living and entertaining, with a seamless flow between the living and dining areas and a recently renovated kitchen with stainless steel appliances. A private back deck provides a quiet outdoor retreat. Upstairs, two generously sized bedrooms offer a comfortable and serene escape, complemented by a well-appointed full bath. The fully finished lower level adds exceptional versatility, ideal as a recreation room, home office, or guest space, and includes a second full bath. Additional features include in-unit laundry, two assigned parking spaces, and ample guest parking, all within a well-maintained and peaceful community setting. Ideally located near the Greenwich border, moments from downtown Stamford, Metro-North, Old Greenwich and Scalzi Park, this home offers both convenience and a sense of retreat. Available for one-year or longer-term lease. Rental Terms: Annual: $4,500 Per Month

Beautifully updated and move-in ready, this bright 3-bed, 2-bath home offers a prime in-town location moments from shops, parks, and train. Available both short term minimum 3 months. Features include a sun-filled living room, modern kitchen with stainless appliances, spacious bedrooms, and a private backyard perfect for entertaining. Enjoy ease of living close proximity to all Greenwich amenities. A rare opportunity for convenience, comfort, and value in a sought-after neighborhood. Rental Terms: Annual: $16,000 Per Month

The ideal country House for your unforgettable Summer/Fall In Greenwich. Available from June 21st - September 13th. This amazing shingle style home was custom built in 2010 and offers 8482 square feet of beautifully detailed interior spaces with high ceilings Throughout. Offering graciously scaled public rooms, a private study, gorgeous formal dining room, a gourmet kitchen with breakfast room, access to a deck as well as a terrace for alfresco dining, fun filled third floor game room, 6 wonderful family bedroom suites, a walkout lower level with exercise room and a gorgeous brand new pool with spa! Rental Terms: Annual: $39,500 Per Month

Space, space, space - closets, closets, closets. More than you'll see in any other two bedroom. This freshly painted unfurnished unit offers an effortless lifestyle in a highly sought-after high-rise building. Immerse yourself in deluxe amenities, including 24-hour front door concierge security, a workout center, sauna, sparkling pool, and versatile Library/conference room. Entertain guests in the community/party room, complete with a full kitchen, TV, and ping pong table. This sun-drenched apartment boasts a terrace, ample storage space, and the convenience of an in-unit washer and dryer. Stay comfortable year-round with individual heating and cooling in each room. Step into a welcoming foyer with double closets, leading to a spacious living room/dining area perfect for hosting gatherings. The generously sized master bedroom features two double closets, while the sunny second bedroom/den also includes a double closet. With one assigned parking spot in a secure garage, parking is never a hassle. Moving permitted on weekdays between 9 AM and 4 PM. To secure this exceptional living experience, please submit an application along with a credit report. Lease signing requires one month's rent and two months' security deposit. Explore the convenience of the location, with shops, movies, and restaurants just a stroll away, and easy access to the Metro North bus line.

In-town living at its best! Incredible luxury apartment, with private rooftop terrace. Natural light bathes this 1,700 sq ft 2 bedroom 2.5 bath unit. Gourmet kitchen. High ceilings. Wide Plank floors. Views of Long Island Sound. Great location. Seconds from shopping, restaurants, Metro North and more. Rental Terms: Annual: $11,000 Per Month

Downtown Greenwich Living. Experience ultimate convenience in this bright 2-bedroom, 1-bath apartment, perfectly situated on the first floor of a charming multi-family home. Located in the absolute heart of downtown Greenwich, you are just minutes away from the premier shopping and dining on Greenwich Avenue, Whole Foods and an effortless commute to the train station. The interior boasts hardwood floors throughout, a spacious layout, and the ultimate rental luxury--an in-unit washer and dryer. Skip the street parking hassle with ample dedicated spaces with more parking in the back lot. Don't miss this rare opportunity for premium downtown living with every amenity at your doorstep. Unit is being painted and new kitchen appliances are being installed. Rental Terms: Annual: $3,950 Per Month

Located just moments from town, this classic turn-of-the-century Victorian in the North Street School district has been meticulously gut-renovated for modern living. The home features a bright, airy open floor plan with gleaming hardwood floors and an abundance of natural light throughout. Functional highlights include a convenient laundry room off the kitchen and a flexible layout offering either 4 bedrooms or 3 bedrooms plus a dedicated office. The third-floor primary suite provides a private retreat (not included in official square footage). Enjoy summer days on the charming sitting porch or cooling off in the above-ground pool. 2-car garage. Rental Terms: Annual: $6,950 Per Month

Charming 3-4 Bedroom Rental in Desirable Darien Water Community - $5,800/month Welcome to this inviting 3-4 bedroom, 2 full bathroom home in a sought-after Darien water community. Perfect for families or anyone seeking a blend of comfort and coastal living, this well-maintained residence offers flexible space to suit your lifestyle. The private, fenced-in backyard provides a safe haven for the family and pets to play, while also creating the perfect setting for outdoor dining and relaxation. Enjoy easy access to Holly Pond-just a short walk from your door-where you can embrace the waterfront lifestyle that makes Darien so special. This home combines practical living spaces with the lifestyle you've been dreaming of, all in one of Fairfield County's most desirable communities

New flooring and fresh paint throughout. Updated kitchen cabinets and countertops, new bathroom vanities and light fixtures. Adorable three bedroom, two full bath ranch style home with walk up attic for unlimited storage on a beautifully landscaped corner property in a convenient location minutes to everything. Cozy living room with oversized window and built in shelving. Large dining room plus a den with sliders to patio and a terrific rear yard. City water/sewer and all landscaping included. Strong credit is an absolute must. A cozy gem completely refreshed and ready for immediate occupancy.

FLEXIBLE TERM FURNISHED RENTAL WITH POOL. This timeless brick Georgian offers privacy, proximity to town, and ease. The home features updated top-of-the-line stainless steel appliances and updated systems. Designed for both relaxed living and effortless entertaining, gracious formal living and dining rooms are complemented by an expansive open kitchen and family room with doors to the greenhouse, flagstone terrace and pool. Additional first-floor spaces include a sitting room, private office, and laundry. The sun-lit primary suite offers a generous spa-like bath and ample closet space. Five additional bedrooms and three full baths complete this level. Fully equipped and turnkey, this is an exceptional opportunity to enjoy turnkey Greenwich living. Available short or long term. Rental Terms: Annual: $25,000 Per Month Other / Short Term - : $25,000

Live and experience Rye from this turn key rental property ~ Nestled between Rye and Greenwich, this stunning 5+ bedroom Colonial in the coveted waterfront enclave Greyrock on the Sound, blends quality craftsmanship with modern luxury. Tucked away at the end of a cul-de-sac, the home's wraparound porch, many windows and resort-inspired salt water pool, seamlessly integrate indoor and outdoor spaces providing a luxurious sanctuary whether you work from home or a city nearby. Step into the main level and be greeted by a double height entry foyer where adjacent formal living and dining rooms, each with coffered ceilings, make for easy living and gracious entertaining. Walk down the entry hall to an open-concept kitchen equipped with top-of-the-line stainless steel appliances (including a gas cooktop, dual wall ovens, and a wine fridge), custom cabinetry, marble counters, a large center island, a breakfast area, and a walk-in pantry. The kitchen opens to a family room with 3 exposures and a wood-burning fireplace with a sleek marble surround. An adjoining office with ensuite bathroom, and close by mudroom/laundry room and 0.5 bathroom, complete the main floor. Take the front or rear stairs to the second level which features a large primary suite with a sitting area, spa-like bathroom, and spacious walk-in closets. Three additional bedrooms are well proportioned, each with its respective ensuite bathroom. The second floor also includes a large bonus room which is perfect for movie and game nights. The finished lower level boasts a gym on one side, and an apartment-style renovation on the other, complete with a kitchen and full bathroom. A walkout staircase leads you from the lower level to the flat backyard. The perfectly sized backyard is outfitted with a tv, outdoor speakers, a patio, and a saltwater pool (with heating, LED lighting and fountain options). Your home, with a 3-car heated garage, sits on 0.5 acre of manicured lawns bound by mature evergreen trees. Stroll down to Greyrock's private beach, kayak on the Sound, enjoy sitting on the dock... experience it all. Conveniently located to downtown Rye and the Metro North train station (38 minutes to NYC). 15 min stroll to the Rye train station. Greyrock on the Sound is a hidden gem that can be found off of Grace Church Street where the City of Rye welcomes you. 16 Hilltop Drive is the one you've been waiting for! Enjoy this waterfront community :)